CONFUSING ELEMENT SYMBOLS REPRESENTATIVE ELEMENTS

INORGANIC Element Latin Etymology

PHARMACEUTICAL & Sodium (Na) Natrium “Natrun”(A.) -
“Nitron”(Gk.)
Group IA: Alkali Metals
Potassium (K) Kalium “Al Qualiy” (A.) Group IIA: Alkaline Earth Metals
MEDICINAL Iron (Fe) Ferrum Sword or Iron
Group IIIA: Boron Group aka ?
Copper (Cu) Cuprum
CHEMISTRY
“Kypros” (Gk.) - Cyprus
Silver (Ag) Argentum Argentina
Group IVA: Carbon Group aka?
Gold (Au) Aurum “Aurora” -Dawn; Yellow Group VA: Nitrogen Group aka ?
Mercury (Hg) Hydrargyrum Hydrargyros(Gk.) -Liquid Ag Group VIA: Oxygen Group aka ?
Bart David A. Quibod, RPh, CPS Lead (Pb) Plumbum “Plumbing”-Pb in H2O pipes Group VIIA: Halogen Group
Antimony (Sb) Stibum “Stibi”-Eye paint/cosmetics
Group VIIIA/O: Noble/Inert Gas
Tin (Sn) Stannum “Stag”(Indo-Euro.)-
Tungsten (W) Wolfrum 2 Dripping Rahm/
Wolframite-Wolf 3
1
Foam

1 2 3

TRANSITION ELEMENTS BRIDGE ELEMENTS

• Diagonal Relationship
Group IB: Coinage Metals
Group IIB: Volatile Metals
IA IIA IIIA IVA VA VIA VIIA
Group IIIB: Sc & Y
Group IVB: Ti & Zr
Li Be B C N O F
Group VB: Ta, V
Group VIB: Cr, Mo, W, and U Na Mg Al Si P S Cl
Group VIIB: Mn, Tc
Group VIIIB: 1st, 2nd, 3rd Triads
4 5 6

4 5 6
GROUP IA: ALKALI METALS GROUP IA: ALKALI METALS GROUP IA: ALKALI METALS
MOST REACTIVE GROUP HYDROGEN (1783)
Valence electron: 1 HYDROGEN
aka Inflammable air (Cavendish, 1766)
Activity w/ atomic number Cation: Hydronium or Protium
Lightest Element
Anion: Hydride
Alkalinity w/ atomic number Most Abundant Element in the
Universe (74%) Isotopes:
Degree of Solvation ➡ w/ atomic 1H- Most Abundant; Protium
Production:
number Lane Process & Messerschmidt 2H- Heavy Hydrogen; Deuterium
Hydroxides are STRONG bases (e.g. Process - produces 99% pure H2 3H- Radioactive; Tritium
NaOH, KOH) blue water gas
7 8 9

7 8 9

WATER WATER NATURAL WATER

aka “Universal” Solvent CHARACTERISTICS
Types of Water: ALKALINE H2O
Contain appreciable amounts of Na2SO4,
MgSO4, and NaHCO3
Chemical Name: _______?________
Natural Water CARBONATED Contains CO2 under pressure;
H2O Effervescence; contain CaCO3 & MgCO3
Other “Universal” terms?? Potable Water CHALYBEATE Contain Fe in Sol. or Susp., Ferruginous
H2O Taste, Forms Fe(OH)3 and Fe2O3 in air
Universal Antidote Hard Water LITHIA H2O
Do not contain appreciable quantities of
Li2CO3 or LiCl

Universal Local Anaesthetic Official Water SALINE/ Contain relatively high amounts of MgSO4,
PURGATIVE H2O Na2SO4 and NaCl
Heavy Water SULFUR H2O
Contains dissolved H2S and deposit S upon
Universal Disinfectant exposure to the atmosphere
10 11 SILICEOUS H2O Water that 12
contain soluble alkali silicates

10 11 12
 POTABLE WATER TYPES OF WATER BASED WATER HARDNESS
ON HARDNESS
Water that is fit to drink Soft H2O TEMPORARY PERMANENT
Free from coliforms organisms Hard H2O - 2 types Soluble SO42-,
Ca(HCO3)2 &
Presence of minerals contributes CAUSE
Mg(HCO3)2
Cl-, and OH- of
to water hardness 1. Temporary Hardness Ca2+ & Mg2+
Boiling, lime Ion-Exchange
2. Permanent Hardness
process, Resin/
REMOVAL
Alkalinification, Deionization,
Purification Desalination
13 14 15

13 14 15

OFFICIAL WATERS HEAVY WATER HYDROGEN PEROXIDE

Purified Water (PW)
Water for Injection (WFI)
Sterile Water for Injection (SWFI)
Bacteriostatic Water for Injection
Sterile Water for Irrigation
Sterile Water for Inhalation
16
Aka Agua oxigenada, agua oxinada,
Oxygenated acid, Oxygenated Water, Hydrogen
Deuterium Oxide, D2O Dioxide
Use: Treatment of Vincent’s Stomatitis
Solvent for NMR studies (Trenchmouth)
Prolong use results to: Hypertrophied
Filiform Papillae or “Hairy Tongue
Syndrome”
Availability:
3% w/v solution - [BEQ]Volume; Red label
17
6% w/v solution - ?18Volume; Blue label

16 17 18
IMPORTANT CONCEPTS
Amphoteric property
An element or compound that
exhibit both acidic and basic
properties
e.g. Aluminum, Zinc, H2O
Auto-protolytic/Auto-ionisation
of H2O
H2O + H2O —> H3O+ + OH-
19
19
PHARMACEUTICALLY
IMPORTANT INORGANIC ACIDS
1. Boric Acid (H3BO3)
2. Hydrochloric Acid (HCl)
Diluted HCl
3. Nitric Acid (HNO3)
4. Sulphuric Acid (H2SO4)
5. Phosphoric Acid (H3PO4)
Diluted H3PO4 Acid
22
22
Acidity of Hydrogen Halides
HF < HCl < HBr < HI
As atomic size , Acidity
Basicity of Metal Hydroxides
LiOH < NaOH < KOH
As atomic size , Basicity
20
20
BORIC ACID
aka Sal Sedativum Hombergi, Sal
Sativum, Boracic acid
H3BO3 (Weak Acid)
ID Test:
1. Turmeric Paper Test
(+) Result: Brownish-Red
+NH3 / NaOH: Olive Green
2. Ignition Test aka MethylBorate
Test
(+) Result: Green-Bordered Flame
23
23
7 STRONG ACIDS
Hydrochloric Acid (HCl)
Hydrobromic Acid (HBr)
Hydriodic Acid (HI)
Nitric Acid (HNO3)
Sulfuric Acid (H2SO4)
Phosphoric Acid (H3PO4)
Perchloric Acid (HClO4)
21
21
BORIC ACID USES
Tonicity Adjusting Agent (E method)
Antiseptic (Borofax®)
Solutions (5%), Ointment, Dusting
Powder
Skin Toxicity? Boiled Lobster
Appearance
Used in ophthalmic preparations
Buffer component
Bacteriostatic Eyewash (2%)
24
24
 BORIC ACID
Buffer Component:
Standard pH Buffer: Alkaline
Borate Buffer (pH 8-10)
Pharmaceutical Buffer Systems
1. Feldman’s Buffer (pH 7—8.2)
2. Atkins and Pantin Buffer (pH
7.6-11)
3. Gifford’s Buffer (pH 6-7.8)
4. Sorensen’s Buffer (pH 5.9-8)
25
HYDROCHLORIC ACID DILUTED HYDROCHLORIC ACID
36-38% w/w conc. HCl solution
aka Spirits of Salt 10% w/v HCl solution
Muriatic Acid Uses:
Technical grade HCl Acidifying agent
+ Impurities - Cl2, Sulfurous & For gastric achlorydia (parietal
Arsenous Acid and Fe cells of stomach)
Skin: Coagulative/Caseous
Necrosis (White Burns)
Use: Acidifying agent
26 27

25 26 27

NITRIC ACID NITRIC ACID PHOSPHORIC ACID

68-70% w/w HNO3 in water
ID Test: 85% w/w H3PO4
aka Eau Forte, Aqua Fortis
1. Brown Ring Test Strong Triprotic Acid
Uses:
• (+) Result: Brown junction bet. 2 Phosphates nomenclature?
Nitrating Agent layers.
For Pyroxylin, USP production Uses:
2. Lunge/Diphenylamine Test
Xanthoproteic test - yellow stains/ • Reagents: Diphenylamine + conc.
Buffer component (Sorensen’s)
burns (e.g. Aromatic Amino Acids) H2SO4 Acidifying agent
Oxidising Agent • (+) Result: Blue junction bet. 2
Aqua Regia/Royal Water - 3 parts layers.
HCl & 1 part HNO3
28 29 30

28 29 30
HYPOPHOSPHOROUS ACID SULFURIC ACID GLACIAL ACETIC ACID
aka Oil of Vitriol
H3PO2 100% w/w CH3COOH
96-98% w/w conc. H2SO4 solution
aka Phosphinic Acid Strong Diprotic Acid solution
31% w/w H3PO2 Exothermic Diluted CH3COOH sol’n: 6%
Powerful Reducing Agent Uses: w/v solution
Used as an Antioxidant Dehydrating Agent
Has a glassy appearance when
Oxidizing Agent
congealed
Sulfonating or Sulfating Agent
Toxicity: Ground coffee vomitus & Use: Ingredient in Burrow’s
brown-black burns solution
31 32 33

31 32 33

HYDROFLUORIC ACID HYDRIODIC ACID LITHIUM

Used in glass etching test
Test for Fluoride:
1. NaF/NaMFP + Glass = Etching
2. Glass Etching due to
H2SiO3➡(Silicic Acid)
Use: Expectorant Lightest of all Metals
Best expectorant? Gk. Lithos - “Earth”, Rock, Stone
Discoverer: J.A. Arfvedson
ID Test: Flame Test
(+) Result: Carmine Red under non-
luminous Flame

34 35 36

34 35 36
 FLAME TEST LITHIUM LITHIUM COMPOUNDS
Metal Non-Luminous Flame Cobalt Glass
Pharmacologic actions: Lithium Bromide - as depressant, sedative
Sodium Golden Yellow Nil or no
Mood Stabilizing Agent Lithium Carbonate
Potassium Violet/Purple/Lilac Crimson
changeRed DOC for treatment & prevention of Bipolar Brand Names: Eskalith®, Quilonium-R®,
Lithium Carmine Red Purple Disorder (Hypomanic-Manic states) & Mania Lithase®
Calcium Brick Red Light Green Clinically relevant salt forms of Li? Lithium Citrate
Strontium Crimson Red Purple/Lilac Primary excretion occurs in the kidney Lithium Hydroxide
Barium Yellow Green Blue Green Diuretic (similar w/ Na+) Lithium Oral Solution
Borates, Green - Toxic (e.g. Hyponatremia)
Cu+, Tl Patient Counselling points: Do not restrict
Pb, As, Sb, Blue Yellow sodium intake
Bi, Cu2+
Al3+, Ti, Brilliant White/
37 - 38 39

Mg2+ Silver
37 38 39

TOUGH TEN QUESTIONS TOUGH TEN QUESTIONS

Water free of Pyrogens ______________
________ water
Water for manufacture of
Parenterals
Sulfuric Acid other name ______________
Acid found in stomach ______________
Test for Aromatic Amino
______________ Test
Acids
Isotonic Buffer ______________
Use of Boric Acid ______________
3% w/v H2O2 solution ____ volume O2 H2O2
Nitrate Test ________ _______ Test
Iron in solution with
_________ Water 40
Ferruginous taste
DOC Bipolar Disorder
______________ SODIUM
_________ acid aka Aqua Fortis The Cation of Choice to optimise
Hard water Cation/s ______________ the pharmaceutical utility of
___________ effect H2O + H2O —> H3O+ + OH- organic medicaments
Removal of Permanent D________________
Hardness D________________
Major/Primary Extracellular
Isotonic Buffer ______________ Cation INTRA (In) EXTRA (Out)
Amphoteric metals ____ & ____ PISO? CATION K+ (1o) Na+ (1o)
Mg+2 (2o) Ca+2 (2o)
3% w/v H2O2 solution ____ volume O2 H2O2 MICO? Cl- (1o)
ANION HPO4+2 (1o)
Diagonal partner of Be ______ PICO? HCO3- (2o)
_________ Water Water that is fit to drink
41 42

Promotes Water Retention (edema)

40 41 42
 SODIUM SODIUM SODIUM ACETATE
The Cation of Choice to optimise the
pharmaceutical utility of organic
Test for Sodium: Urinary and Systemic Alkalizer
medicaments (therapeutic action due to 1. Triple Acetate Test: Golden Yellow (why?)
anion, except NaCl) precipitate Diuretic, Antacid
Major/Primary Extracellular Cation • Cobalt Uranyl Acetate
INTRA (In) EXTRA (Out)
Test for Acetate Ion?
PISO? • Zinc Uranyl Acetate
MICO? CATION K+ (1o) Na+ (1o) Esterification
Mg +2 (2o) Ca +2 (2o) • Magnesium Uranyl Acetate
PICO?
ANION HPO4+2 (1o)
- o
Cl (1 )
HCO3- (2o)
Promotes Water Retention (edema)
C/I: HTN, HF, and Kidney Disease
43 44 45

43 44 45

SODIUM BICARBONATE SODIUM BICARBONATE SODIUM CARBONATE

aka Baking Soda Side Effect: Na2CO3
Uses: Systemic Alkalosis (Metabolic or Production: ____________ Process
1. Systemic Alkalizer (Preferred) Respiratory?) Forms & Other names
and Antacid Rebound Hyperacidity (also Ca2+) Decahydrate - ____________, Sal
2. Urinary Alkalizer (Preferred) Flatulence Soda, Soda Crystal
3. Antidote for Zn poisoning (oral) Sesquihydrate - Trona, Urao
Test for HCO3-: Anhydrous - Soda Ash, calcined Soda
Phenolphthalein Test Efflorescence

46 47 48

46 47 48
 SODIUM CARBONATE SODIUM DIHYDROGEN SODIUM MONOHYDROGEN
Highly alkaline reaction w/ water PHOSPHATE Na HPO
PHOSPHATE
2 4
NaH2PO4
Uses: aka Sodium Phosphate, Phosphate
Other chemical names?
1. Primary Std. of Soda
Uses:
2. Manufacture of “Soda Lime 1. Saline/Osmotic Laxative as Fleet®
Uses:
Glass” Enema 1. Saline/Osmotic Laxative as
Test for CO32-: 2. Urinary Acidifier - Methenamine Fleet® Enema
:Phenolphthalein Test (Cystitis) 2. Hypercalcemia
3. Hypercalcemia 3. Buffer
49 4. Buffer 50 51

49 50 51

SODIUM METABISULFITE SODIUM CHLORIDE SODIUM CITRATE

Na2S2O5
Sodium Pyrosulfite
Good Reducing Agent, used as?
Powerful preservatives
52
aka Table salt, rock salt, solar salt, Na3C6H5O7
sea salt, dendritic salt
Sequestering agent (Benedict’s
Electrolyte replenisher
Reagent)
NSS (___% w/v NaCl)
In vitro: ____-coagulant
Ringer’s Solution
Blood extraction
Lactated Ringer’s Solution(aka?)
Darrow’s solution In vivo: (parenteral): ____-coagulant
ORS Expectorant (What is the best
expectorant?)
53 54

52 53 54
 SODIUM CITRATE
Test for Citrate: _______ Test
(+) Result:
Carmine Red - ________
Emerald Green - ________
SODIUM FLUORIDE
Chemical Formula: NaF
Protoplasmic poison
Skin Toxicity: Painful, slow-
healing burns (Antidote: ?)
Formation of Fluoroapatite
Anticariogenic agent (2%)
SODIUM FLUORIDE
Side effect: Dental Fluorosis
(children) or mottling of teeth
enamel; Skeletal Fluorosis
(Premature calcification)

55 56 57

55 56 57

SODIUM HYDROXIDE SAPONIFICATION SODA LIME

NaOH
Aka Caustic Soda, Sosa, Liquid Sosa
NaOH + Vegetable Oil = Bar Soap / aka Calx Sodica
Hard Soap Use: CO2 absorber
Ingestion: Saponification/
KOH + Vegetable Oil = Liquid Soap /
Liquefactive Necrosis
Soft Soap
Mixture of Ca(OH)2 + NaOH
Very Deliquescent - easily absorb
H2O & CO2
NaOH/KOH + Olive Oil = Castile Soap®
Leaching - store in?
NaOH/KOH + Coconut Oil = Perla®
Use in titrimetry? Alkalimetric
Titrant NaOH/KOH + Palm Oil + Olive Oil =
58
PalmOlive® 59 60

58 59 60
SODIUM HYPOCHLORITE NaClO SOLUTIONS SODIUM IODIDE
NaClO Dakin’s Solution (5% / 4.0 - 6.0% NaClO) NaI
NaClO solution - aka Household Labarraque’s solution (approx. 2.5% I-- is required for synthesis of
bleach, Chlorox®, Zonrox®, Dakin’s NaClO) thyroid hormones (e.g. T3 and T4)
Solution Use: Disinfectant, and Bleaching Agent Source of Iodine (Essential trace
Use: Modified Dakin’s Solution (0.45-0.5%
element)
NaClO)
Bleaching agent Lack of Iodine?
Use: Antiseptic
Disinfectant - due to Hypothyroidism:
NaClO Topical Solution (0.025% NaClO)
Hypochlorous acid Use: Antiseptic Hyperthyroidism
61 62 63

61 62 63

SODIUM IODIDE SODIUM LACTATE SODIUM NITRITE

Uses:
aka Philippine Salitre
Expectorant (oral) Provides raw material for the Chemical Formula: NaNO2
Solubilizer of Iodine in Iodine Toxicity: Methemoglobinemia
regeneration of bicarbonate in the
tincture and Iodine solution (Antidote: Methylene Blue)
(Lugol’s Solution) body Antidote for CN- poisoning w/ Na2S2O3
Anti-fungal For curing meats & fish
Antacid (management of acidosis)
Preservative
Diuretic A/E: Carcinogenic to brain & GIT
(Nitrosoamines production)
64 65 66

64 65 66
 CYANIDE POISONING SODIUM NITRATE SODIUM SULFATE
Antidotes for cyanide poisoning:
NaNO3 aka __________ Salt, Sal Mirabile
Amyl Nitrite - Functional Antidote
aka _______ Saltpeter Chemical Form?
Sodium Nitrite - Functional
Antidote Use: Use: Saline Laxative
Sodium Thiosulfate - Chemical Meat preservative - _____________
SO42- poorly absorbed in the
Antidote production
intestinal tract
Other drugs used for CN- poisoning Production: ______________ process
Methylene Blue - Chemical Antidote
Hydroxocobalamin (Cyanide kit®) -
Chemical Antidote67 68 69

67 68 69

SODIUM TARTRATE SODIUM TARTRATE SODIUM/POTASSIUM

Primary standard for Karl Fischer
Test for Tartrate: Denige’s Test
THIOCYANATE
Reagent
Karl Fischer Titration: Water content (+) Result: NaSCN/KSCN
determination Carmine Red - Citrate _____________ agent
Method I = Titrimetric, KFR Emerald Green - Tartrate
Method II = Azeotropic/Toluene
Distillation
Method III = Gravimetric
Saline Laxative (Internal
administration)
(+K+) = ___________ Salt
70 71 72

70 71 72
SODIUM THIOSULFATE SODIUM PERBORATE SODIUM BORATE
Chemical Formula: Na2S2O3●5H2O
aka Sodium Hyposulfite, Prismatic Use: Mild Disinfectant
Rice, “______”, _______________, aka Borax
Antichlor Hypo Readily releases O2 Dobell’s Solution
Good Reducing Agent Alternative treatment for Use: Astringent, Antiseptic
susceptible to air oxidation Vincent’s Stomatitis (Trench wash (throat & nose)
____________ Antidote for CN- poisoning mouth) Not used internally
Management of I2 toxicity (Best
Antidote?)
Used in Iodometry?
Remove stains of ?73 74 75

73 74 75

SODIUM SODIUM NITROPRUSSIDE SODIUM SACCHARIN

MONOFLUOROPHOSPHATE
Chemical Formula:
Colgate™ Na2[Fe(CN)5NO]●2H2O Artificial Sweetener
Na2PFO3 Hypotensive agent - DOC for Linked to bladder tumors in animal
_____________________________ tests
Use: Anti-cariogenic Agent
S/E: Cyanide toxicity Test for Saccharin? ___________ Test
NaF (+) Result: Fluorescent Green
SnF2 Liquid

76 77 78

76 77 78
 SODIUM ASCORBATE
Brand names: Fern-C®, Euro-C®
Antioxidant, Vitamin supplement
(Vitamin C/Ascorbic Acid/
__________________)
Antiscorbutic agent (Scurvy)
SODIUM _____________
________________
BEST antidote for Hg poisoning
particularly for HgCl2 (“Corrosive
sublimate”)
SODIUM STARCH GLYCOLATE
Explotab®
Rapid Tablet Disintegrant - aka
____________________

79 80 81

79 80 81

MONOSODIUM GLUTAMATE SODIUM CYCLAMATE SODIUM LAURYL SULFATE

aka MSG, Vetsin, Ajinomoto® aka “Magic Sugar” aka SLS
Flavor enhancer: “Umami/6th Use: Artificial Sweetener Anionic Surfactant
taste”) It is ___________ by the FDA for Use:
S/E: ____________________ distribution, export and trade Foaming agent & Surfactant:
Syndrome Can cause colon cancer? Toothpaste
Light-headedness Shampoo
Headache Shaving cream
Uncomfortable sense of warmth Bubble bath
Dyspnea 82 83
Shark Repellant84

82 83 84
 OTHERS POTASSIUM POTASSIUM ACETATE
Principal/Primary/Major Intracellular Cation
Sodium Stearate - tablet lubricant aka Kalium, Potash (Same as Sodium acetate)
Sodium Alginate (Gaviscon®) Deficiency state:
Hypokalemia
Due to severe burns, diarrhea, etc.
S/Sx: Muscle weakness & muscle paralysis
Toxicity state:
Hyperkalemia - Cardiac arrest
Pharmacologic action:
Diuretic; Muscle contraction; Maintains
resting membrane potential
85 K in Glass: Makes glass86brown & light-resistant 87

85 86 87

POTASSIUM BICARBONATE POTASSIUM CARBONATE POTASSIUM DIHYDROGEN

PHOSPHATE
(Same as Na Bicarbonate) K2CO3 KH2PO4
aka Carbonate of Potash, Pearl Ash, aka Sorensen’s Potassium phosphate
Salt of Tartar, Salt of Wormwood Cathartic
Saponifying agent

88 89 90

88 89 90
POTASSIUM CHLORIDE POTASSIUM CHLORIDE POTASSIUM CITRATE
Kalium Durules® Component of Ringer’s & Systemic and urinary alkalizer
Electrolyte replenisher for Darrow’s Solution Acalka®
Hypokalemic states (SLOW IV Ringer’s Sol’n- Triple Cl- sol’n Osmotic Diuretic
drip) (Na+, K+, Ca2+)
Expectorant
Source of K+ Darrow’s Sol’n- NaCl, KCl, Na
Diaphoretic
IMPORTANT NOTE: Never give by Lactate, WFI; used in Fluid
Rapid IV push/ IV bolus therapy for K+ deficit
Final Drug in __________ Injection
91 92 93

91 92 93

POTASSIUM HYDROXIDE POTASSIUM BROMIDE POTASSIUM IODIDE

aka Caustic Potash, Potash Lye Depressant Iodide of Choice
Strong Base; Very corrosive Oldest anti-seizure Agent Stable in air
Used in manufacture of soft soaps Can cause allergic reaction
(Iodism)
Use in titrimetry? Antidote: NSS (NaCl)
Koettsdorfer Number /
Saponification Value
94 95 96

94 95 96
 POTASSIUM IODIDE POTASSIUM IODIDE SULFURATED POTASH
Uses: Uses:
Expectorant “Liver of Sulfur”
Component of Alkaloidal
prevention of goiter “Hepar Sulfur”
reagents:
Hyperthyroidism “Potassa sulfurata”
Wagner’s Reagent Necessity for the production of White
Anti-fungal: KISS (1g/mL) - DOC Mayer’s Reagent (Most Lotion
for Sporotrichosis (Rose sensitive) Sulfurated Potash + ZnSO4 ➡ ZnS
Gardener’s Thorn); Sporotrix Valser’s Reagent (White Sulfide) ➡ Anti-Psoriasis
schenckii
Dragendorff Reagent
97 98 99

97 98 99

POTASSIUM PERMANGANATE
POTASSIUM CHLORATE POTASSIUM NITRATE aka Mineral Chameleon
aka Saltpeter, Salitre, Salt prunelle Chemical Formula: KMnO4
KClO3 Oxidation state of Mn?
Use: MnO4- - +7
Oxidising agent Meat preservative MnO42- - +6 (unstable ➡ Disproportionation)
component of gargle and mouthwash Manufacture of explosive (e.g. MnO2 - +4 (Masks blue-green of Fe2O3 in
Gunpowder) glass)
Tooth-Desensitising agent MnS - +2 (Only salmon-pink sulfide)
MOA: Strong Oxidising Agent (pH-dependent)
Sensodyne® - 5% KNO3 Permanganometry: Self-indicating VS
Endpoint: pink solution persist for 15-30 sec
Produces brown stain on the skin
100 101
Use: Antiseptic(1:5000),102disinfectant

100 101 102

POTASSIUM PERMANGANATE
aka Mineral Chameleon POTASSIUM SODIUM POTASSIUM BITARTRATE
Chemical Formula: KMnO4 TARTRATE
aka Rochelle Salt, Sal Seignette
Oxidation state of Mn? KHC4H4O6
MnO4- - +7 Uses: aka Cream of Tartar, Argol, Acid
MnO42- - +6 Potassium Tartrate, Creamor
1. Saline Laxative
MnO2 - +4
2. Sequestering Agent - Fehling’s Saline laxative/Cathartic
MnS - +2
MOA: Strong Oxidising Agent (pH-dependent) Reagent The only insoluble salt of K+; Official
Permanganometry: Self-indicating VS Test for Tartrate: ID test
Endpoint: pink solution persist for 15-30 sec __________ Test
Produces brown stain on the skin (+) Result: Deep Violet or Blue
Use: Antiseptic(1:5000), disinfectant
103 coloration 104 105

103 104 105

AMMONIUM ION AMMONIUM SALTS AMMONIUM CARBONATE

Aka “Hypothetical” or “Pseudo”- Ammoniated Mercury - aka Sal Volatile, Preston’s Salt, Hart’s
alkali metal HgNH2Cl; “White Precipitate”; Horn
Preparation: Haber Process Topical Anti-Infective
Ammonium Iodide - Source of I2; Uses:
Pharmacologic action:
Anti-fungal; Expectorant Expectorant (NH4+); Antacid (CO32-)
Diuretic
Respiratory Stimulant: “Smelling
Buffer Salts”
Expectorant Ammonium Acetate - Spirit of
Minderesus; styptic Leavening agent hence aka
Anti-cariogenic “Baker’s Ammonia”
106 107 108

106 107 108

 AMMONIUM CHLORIDE 16O AMMONIA RUBIDIUM & CAESIUM
Caesium & Rubidium :Very similar in
NH4Cl behaviour to K+
aka Muriate of Ammonia, Sal Aqueous NH3: Mild Alkalizer Caesium (Cs)
Ammoniac, Muriate of Hart’s Horn Household NH3: 10% NH3 aka 16o Catalyst in polymerisation of resin
By-product of NaHCO3 production (degrees Baume) NH3 forming material
(Solvay Process) 1st element discovered by the use of
Uses: spectroscope in 1860
1. Osmotic Diuretic Caesium Spectral Line: BLUE
2. Systemic & Urinary Acidifier - DOC Rubidium (Rb)
or Antidote for Amphetamine 2nd element discovered by the use of
Toxicity (“Ion Trapping”) spectroscope in 1861
3. Expectorant Rubidium Spectral Line: RED
109 110 111

109 110 111

COPPER COPPER
GROUP IB: Syn: Cuprum (Gk.)
Protein precipitant (Heavy Metal)
Only Reddish Metal
COINAGE 3rd most malleable & ductile metal Important Alloys
METALS 2nd best conductor of electricity Bronze - Cu and Sn (“BronSS”)
Function of Cu as metalloenzyme: Brass - Cu and Zn (“BraZZ”)
Properties: Component of Hemocyanin(Only seen in Essential Trace Element
animals): respiratory pigment in
• Can occur free metal Cu Overload/Toxicity? Antidote:
state Cytochrome Oxidase (ETC)
Involve in activation of Tyrosinase
Penicillamine (Cuprimine®)
• Complexes/Chelates
• Very Malleable Needed by Lysyl oxidase for production of Cu Deficiency?
• Easy to recover from Ore connective tissues
112 113 114

112 113 114

 CUPRIC SULFATE CUPROUS CITRATE CUPRIC HYDROGEN
aka Blue Vitriol, Roman Vitriol, Salzburg
Vitriol, Blue Stone, Chalcanthite ARSENITE
CuSO4●5H2O Hatchett’s Brown “Scheele’s Green”
Component in Benedict’s, Fehling’s, and Cu3(C6H5O7) aka?
Barfoed’s Reagent
Test for Reducing Sugars?
Astringent (8%) CuHAsO3
Test to differentiate Mono vs Disaccharide?
(+) Result: Brick-Red precipitate
Powerful Emetic
Antidote for Phosphorous toxicity
Ingredient in Bordeaux mixture
115 116 117

115 116 117

CUPRIC SALTS SILVER SILVER NITRATE

Mountain Green aka Argentum, Shining, Bright, aka Lunar caustic, Argenti Nitras,
Copper Carbonate (Native) Seolfor, Noble metal, & Luna Lapiz infernulariz(caustic pencil),
Brunswick Green 2nd Most malleable & ductile of all indelible ink
Copper carbonate with chalk metals
Best Conductor of electricity & heat Treatment of Warts
Paris Green/Schweinfurt’s Green
Copper Aceto-arsenate Pharmacologic action: As 1% ophthalmic solution:
[Cu3(AsO3)2●Cu(C2H3O)2] Protein precipitant (Heavy Metal) Prophylaxis for Gonorrhea
Insecticide Oligodynamic property (Germicidal Ophthalmia Neonatorum (can
Bordeaux mixture action) cause blindness to the newborn )
Cupric sulfate and lime (CaO) Toxicity: Argyria
Wet dressing for 3rd degree burn
Algaecide & fungicide in swimming pools Antidote - NSS
118 119 (0.5%) 120

118 119 120

 SILVER NITRATE AMMONIACAL SILVER
NITRATE
SILVER IODIDE
Component of Tollen’s Reagent
Composition? Ammoniacal AgNO3 + aka Howe’s Solution AgI
NaOH Ag(NH3)2NO3 Insoluble
Tollen’s Test Use: Poisonous
Test to detect aldohexoses/ 1. Dental protective when mixed with Use: Disinfectant(Surfacine®),
aldehyde-containing sugar 10% formaldehyde or eugenol Germicide
(+) Result: Involves formation of 2. Desensitising agent
Silver Mirror

121 122 123

121 122 123

SILVER PROTEINATES SILVER SULFADIAZENE GOLD

aka Aurum, King of all metals,
TYPES OTHER GENERAL USE Shining Dawn, Noble Metal
NAME aka Flammazine® (micronized),
Mild Silver Eye antiseptic, for Silvadene®(1% cream), Flammacerium® Most malleable and ductile metal
Proteinate Argyrol 3rd Best conductor of electricity
vaginitis (+2.2% Cerium Nitrate)
Strong Silver Combines Oligodynamic property of Ag 2nd Best conductor of heat
Proteinate
Protargol Germicide for ear & throat
& antibacterial property of SDZ Precious metal - Jewellery (Carats)
Colloidal Silver For Pseudomonas aeruginosa Dissolved by:
Proteinate
Collargol General Germicide
Topical Use: For prophylaxis of wound Aqua Regia (3 HCl : 1 HNO3)
Colloidal Silver Lunosol/ *silver proteinate
sepsis in 2o & 3o burns Selenic Acid (H2SeO4) > the only
Chloride Neosilvol stabiliser: Disodium EDTA
124 125
single acid that can dissolve gold
126

124 125 126

 GROUP IIA: ALKALINE
GOLD GOLD PREPARATIONS EARTH METAL
Toxicity: Gold Dermatitis COMPOUN BRAND GOLD BY
USES 2 Valence electrons
D NAME WEIGHT
Antidote: BAL/Dimercaprol Forms Divalent Ions
Aurothio- Treatment of gout & R.A.
Purple of Cassius (Test for Au) glucose Solganal®
50% Felty’s Syndrome (RA,
Colloidal Gold with Stannic Gold Nuetropenia,
(IM) Splenomegaly)
Hydroxide(Au + Sn(OH)2) Gold Na
Myo- 50% Treatment of gout &
Thiomalat
chrisine® Gold R.A.
e (IM)
Auranofin 29% Given orally for R.A.
Ridaura® DOC for Felty’s
(PO) Gold
Syndrome
127 128 129

127 128 129

BERYLLIUM MAGNESIUM MAGNESIUM

aka Glucinum
Bridge element - resembles Al
The most toxic metal
Tends to replace Ca & Mg in the
body
Never employed in medicine, all
compounds of Be are toxic as
well.
Found in fluorescent lamp
130
Lightest of all structurally important
metals Pharmacologic Action:
Mg2+: 2nd Most abundant Intracellular Saline Laxative/Cathartic
cation
Depressant
Found in chlorophyll (Photosynthesis)
Present in Grignard’s Reagent (R-Mg-X)
Natural calcium channel blocker
used for synthesis of alcohols Anti-Convulsant
Natural Sources: Antidote for Mg2+ toxicity: Ca2+
As silicates (Talc, Asbestos) gluconate
As carbonate (Magnesite, Dolomite) Other use: Flares
As sulfate (Kieserite)
131 132

130 131 132

MAGNESIUM CARBONATE MAGNESIUM OXIDE MAGNESIUM SULFATE
MgO MgSO4●7H2O
aka Magnesia aka Calcined Magnesia, Magnesia aka Epsom Salt, Bitter Salt
(MgCO3)4●Mg(OH)2●5H2O Usta(Burnt) PO: Cathartic
Antacid Use: IM: Anti-convulsant (DOC for seizures
in eclampsia)
Laxative Antacid, Saline Laxative/Cathartic
Pre-Eclampsia Triad = HTN,
Curing agent - mask bitterness of Proteinuria, Edema
Sacred Bark Eclampsia = Pre-Eclampsia Triad +
Component of Universal Antidote Seizure
133 134 Antidote for Barium toxicity
135

133 134 135

MAGNESIUM HYDROXIDE TALC MAGNESIUM CITRATE

Mg(OH)2
Native Hydrated Magnesium Silicate
aka Milk of Magnesia(7-8.5%), Philips®,
3MgO●4SiO2●H2O
Magnesia Magma, Maalox® (with Al(OH)3) Mg3(C6H5O7)2
aka Talcum, French Chalk, Purified Talc,
Buzz: Milk of Amnesia? aka Lemonada Purgante,
Soapstone, Steatite
Antacid Softest Mineral (Moh’s Scale of Hardness) Purgative Lemon
+ Citric acid = gives a milder & less Uses:
chalky taste; also it➡ alkalinity of Use: Saline cathartic (Both Mg2+ &
Dusting Powder -protective
Citrate)
magma Can cause granulomas or sterile abscess on broken skin
➡ Alkalinity: ➡ leaching in glass Clarifying Agent PO
Filtering Aid
Dispensed in Blue glass containers -
Adsorbent
enhances the white character of magma
136 137 138

136 137 138

MAGNESIUM CHLORIDE MAGNESIUM STEARATE CALCIUM
2nd most abundant extracellular
MgCl2●6H2O BEST Tablet Lubricant cation
Preferred salt as electrolyte Major constituent of bones & teeth
replenisher (also Magnesium (Calcium Hydroxyapattite/ Ca5(OH)
gluconate) (PO4)3)
Vitamin D = required for max.
Deliquescent
absorption of Ca2+
Vitamin C = Fe absorption
Vitamin E = Se absorption
139 140 141

139 140 141

CALCIUM CALCIUM CALCIUM BROMIDE

Calcium Deficiency
Pharmacologic Action:
Osteomalacia (adults)
For Blood coagulation: Rickets (children) Sedative
Ca2+ is needed for the conversion Bones fail to calcify Depressant
of prothrombin to thrombin Calcium salts not deposited
For muscle contraction Bones becomes soft & rubbery, easily
Important for release of deformed
Neurotransmitter Osteoporosis
Porous bones
Structural material for bones &
More calcium is lost than absorbed
teeth
Bones susceptible to fracture
142 143 144

142 143 144

CALCIUM CARBONATE CALCIUM CARBONATE CALCIUM CARBONATE
CaCO3
aka Limestone, calcite, marble 2 Crystal Forms: Uses:
2 Important Forms: Aragonite Antacid - Tums®
Precipitated CaCO3 (Precipitated Calcite - Natural Birefringent Ingredient in toothpaste
Chalk) Crystal Dentifrice
Pharmacologically relevant form Iceland Spar - - very pure form
Prepared CaCO3 (Prepared Chalk) of Calcite
Impure form Polarimeters - (Nicol’s Prism)
Exhibit optical birefringence
145 146 147

145 146 147

CALCIUM CHLORIDE CALCIUM GLUCONATE CALCIUM HYDROXIDE

Slaked Lime
aka “Muriate of Lime” Calsan® Milk of Lime
CaCl2●2H2O Most commonly used calcium Calcium Hydrate
Deliquescent salt as supplement & electrolyte Hydrated Lime
Use: replenisher Uses:
Calcium Replenisher Less irritating than CaCl2 Antacid
Ca Citrate - electrolyte Saponifying agent
Component of Ringer’s
replenisher Prevention of milk curdling -
Solution, LRR
promote digestibility
148 149 150

148 149 150

 DIBASIC CALCIUM
CALCIUM LACTATE PHOSPHATE
CALCIUM OXIDE
Oral treatment of calcium deficiency CaHPO4●2H2O CaO
Prevention and retardation of PO: source of Ca and P in aka Lime, Quicklime, Calx, Apog
osteoporosis pregnancy, lactation, and Ca Component of Bordeaux mixture
Ideal for geriatric patients deficiency (insecticide)
Brand Name: Calactate®, Caltrate Provides optimum ratio of Ca to Ingredient in Vleminckx’s Solution
Plus® P = 1:1
Dental abrasive in toothpaste
formulations
151 152 153

151 152 153

TRIBASIC CALCIUM
PHOSPHATE
CALCIUM HYPOCHLORITE CHLORINATED LIME
Precipitated Calcium Phosphate Ca(ClO)2 aka Bleaching powder, Chloride of
Bone Ash Bleaching agent Lime, Calx Chlorinata
Antacid (PO) Disinfectant CaClO(Cl)●H2O
Sanitation of swimming pools Disinfectant/Antiseptic - Ignaz
Semmelweis
Bleaching Agent

154 155 156

154 155 156

 GROUP IIA: ALKALINE
CALCIUM SULFATE EARTH METALS
STRONTIUM CHLORIDE
(CaSO4)2●H2O of CaSO4●1/2H2O Strontium Sensodyne®
Plaster Paris (Hemi-hydrate) Radioactive strontium is used Use: Temperature Desensitising
Use: preparation of surgical casts as bone scanner Agent
& dental impression Strontium has an affinity for Sensodyne® Rapid Relief
CaSO4●2H2O bones and useful in studying Active Ingredient: Strontium
Gypsum, Terra Alba (Dihydrate) bone lesions Acetate
Use: Tablet Diluent, binding agent in Use: Manufacture of flares
TLC chromatogram
157 158 159

157 158 159

BARIUM BARIUM SULFATE BARIUM HYDROXIDE

“Barium Meal” - Radiopaque for
“Heavy” imaging of GIT
BEQ: Found in GREEN Stops passage of X-rays due to
pyrotechnic high MW
Toxicity by inhalation: Baritosis Doesn’t dissociate in water & HCl
(Digitalis-like toxicity) - cannot be absorbed - The only
Antidote: Magnesium Sulfate Non-Toxic Ba compound
Side effect: Constipation
160 161
Ba(OH)2●8H2O
Baryta water - saturated solution
of Barium hydroxide in water
Component of Barium hydroxide
Lime
Similar to soda lime - used as
CO2 absorber
162

160 161 162

 GROUP IIB - VOLATILE
RADIUM METALS
ZINC
Discovered by Marie Curie Zinc Family 2nd most important trace
Metals have relatively low melting points
Radioactive element in the body
Zinc
Radioactive element use for: Cadmium (Most important trace element?)
Cancer radiotherapy Mercury Present in Insulin - stabilises and
Diagnostic purpose Property: shelf-life
Exhibit auto-complexation
Only Zn is amphoteric Essential component of Carbonic
Anhydrase & other enzymes
163 164 165

163 164 165

ZINC ZINC CHLORIDE ZINC OXIDE

Deficiency states:
Parakeratosis of skin
Important in immune system
Deficiency state leads to impaired
immunity
Toxicity: Metal Fume Fever
Antidote for poisoning by
ingestion of H2O-soluble salts of
Zinc: Baking Soda
166
aka Butter of Zinc, Burnett’s
Pharmaceutical: Flowers of Zinc,
Disinfecting Fluid
ZnCl2 - Deliquescent
Zinc White
Use: Component of Lassar’s Paste
Antiseptic found in mouthwashes Mild antiseptic, astringent,
topical protectant
Astring-O-Sol® (Original
Formula) Physical Sunblock (Opacity) ➜
Dentin desensitising agent Refractive Index
Lucas Reagent component (ZnCl2 in
HCl)
167 168

166 167 168

 ZINC SULFIDE ZINC SULFATE HYDRATED ZINC SILICATE
white lotion ingredient ZnSO4●7H2O Natural Calamine
Zinc sulfate + Sulfurated potash aka White Vitriol, Zinc Vitriol Use: Topical protectant
Only “white sulfide”
Lithopone : 30% ZnS, 70% BaS Used as ophthalmic astringent
Uses Emetic
Parasiticide Ophthalmic astringent (only
topical protectant FDA-approved OTC
Antiseptic ophthalmic astringent) - 0.25%
169 170 171

169 170 171

ZINC-EUGENOL CEMENT CADMIUM CADMIUM COMPOUNDS

Pharmacologic action: CADMIUM CHLORIDE
Dental protective Astringent Emetic
Source of Eugenol: Clove oil Used for Tinea/Ring Worm infections
Other use: Manufacture of Stink
Toothache drops; Dental CADMIUM SULFIDE
Bomb
Only yellow sulfide
Analgesic Cd Toxicity: Itai-Itai disease (Japan)
Anti-seborrheic agent
Common source of cadmium: Capsebon® = CdS + CaCl2
Cigarette smoking CADMIUM SULFATE
Antidote: BAL/Dimercaprol or Topical astringent
EDTA Ophthalmic antiseptic
172 173 174

172 173 174

 MERCURY (Hg) MERCURY (Hg) MERCUROUS CHLORIDE
aka Quicksilver, Messenger of gods,
Liquid Silver All mercury salts are poisonous. aka Calomel, Mild Mercury
Hg Diseases - Pink’s Disease, Acrodynia, The best antidote is SODIUM Chloride
Hydrargyria or Erethism
FORMALDEHYDE SULFOXYLATE. Hg2Cl2
Organic Hg Toxicity - Minamata Disease
Most toxic (Crosses BBB ➜ Brain Cathartic
Damage); Mutagenic Question: How to remove mercury Black Lotion: Calomel + Lime
The only metal that exists as a liquid at that falls into cracks? Cover with Water
room temperature sulfur
Toxicity: Organic Hg > Inorganic Hg
175 176 177

175 176 177

MERCURIC CHLORIDE MERCURY IODIDES MERCURIC OXIDE

aka Corrosive sublimate, Mercurous Iodide “Yellow precipitate”
Mercury Bichloride Treatment of Syphilis Ophthalmic anti-infective
HgCl2 Mercuric Iodide
Disinfectant Stimulant of indolent/painless
Antisyphilitic ulcers
Mercury Potassium Iodide
Mayer’s Reagent
178 179 180

178 179 180

AMMONIATED MERCURY BORON BORIC ACID
aka Mercuric amidochloride, Industrial Use: Vulcanising H3BO3
non-fusible white precipitate rubber sal sativum
HgNH2Cl Boron (as borate) ➡coefficient Toxicity: lobster appearance
Mild topical antiseptic Uses:
of expansion of glass Germicide eyewash (ophthalmic
soln 2%)
Antiseptic
Tonicity adjusting agent
181 182 183

181 182 183

BORAX ALUMINUM ALUMINUM CHLORIDE

Most Abundant Metal
AlCl3●6H2O
Na2B4O7. 10H2O 3rd most abundant element
Lewis Acid
Borax Amphoteric
Uses: Astringent, Antiseptic,
Thin Al foil used to treat burns
Dobell’s solution Deodorant
Al compounds - antacid,
Uses: Antiperspirant:
antiperspirant, deodorant
Antiseptic Driclor®- 25% AlCl3 ➜ for
Toxicity (Inhalational): Shaver’s Disease
Hyperhidrosis
Throat and nose wash Neurotoxin (brain)
“Perspirant stain” = Sweat + Al3+
Wet dressing for wounds Exposure to Bauxite fumes: Bauxite
Removal: Na2CO3, (×) Iron,
Pneumoconiosis
184 185 Washing 186

184 185 186

 ALUM ALUMINUM HYDROXIDE ALUMINUM PHOSPHATE
Alum - double salts with formula
M+2M3+2(SO4)4●24H2O Gastric antacid & protectant Phosphagel®
M+ = monovalent ion (Na+, K+, Amphogel® Cremalin Gel Uses:
Rb+, NH4+, Tl+) Side effects: Gastric antacid
M3+ = trivalent ion (Al3+, Tl3+, Constipation Demulcent
Cr3+, Fe3+ phosphate deficiency Astringent
[AlNH4(SO4)2. 12H2O] – NH4 salt Advantage: Do not interfere with
[AlK(SO4)2. s12H2O] – K salt phosphate
187 188 189

187 188 189

ALUMINUM CARBONATE ALUMINA ALUMINUM SILICATE

Basal Gel® Aluminum Oxide Kaolin
Treatment of phosphatic calculi Use: Treatment of silicosis aka Porcelain clay, Bolus alba,
Promotes elimination of Al2O3 China Clay or White bole
phosphate via fecal route Native Hydrated Aluminum
Silicate
Use: Adsorbent
Treatment diarrhea
190 191 192

190 191 192

 ALUMINUM SILICATE
Bentonite
aka Soapclay, Mineral soap,
WILHINITE
Native colloidal hydrated
aluminum silicate
Suspending agent
193
193
THALLIUM
Thallus (budding twig, Green
spectral lines)
2nd Most toxic metal
Used formerly as ant poison,
insecticide
196
196
ALUMINUM SILICATES GALLIUM
Pumice Eka-Aluminum
Substance of volcanic origin Melts at near body temperature
Abrasive (29.75oC)
Ga3+ similar to Fe3+
Feldspar Treatment of cancer-related
Potassium Aluminum Silicate - hypercalcemia by binding with
Most common rock transferrin (as Gallium nitrate)
194 195
194 195
GROUP IVA - CARBON CARBON
FAMILY / CRYSTALLOGEN The only element that can form
Non-metallic in character multiple bonds with itself
Organic Chemistry: Chemical basis
of life?
CATENATION (Chain-
formation)
aka “King of All Elements”,
Charcoal (Latin)
197 198
197 198
 CARBON CARBON DIOXIDE CARBON DIOXIDE
2 Allotrope:
Crystalline aka After-damp, Aer Fixus, Dry Ice (solid CO2) - destroy
Diamond Carbonic Acid Gas unwanted tissues by freezing
Graphite Use: Respiratory stimulant (with acne, korns, callouses, eczema,
Amorphous 5-7% O2); Hiccups moles, psoriasis, and warts
Bituminous coal (soft coal) Stored in GRAY container
and Anthracite (hard coal) Toxicity through suffocation
Coke (impure form of carbon)
199 200 201

199 200 201

GERMANIUM SILICON SILICON DIOXIDE

Possess immune system enhancing 2nd most abundant element Glidant - prevents inter-particle
anti-tumor effects
Silicosis adhesion in granules
Eka silicon – Germanium
Lung condition resembling TB
Eka aluminum – Gallium
developing after long exposure
Eka boron – Scandium (7 years or more)
Eka manganese – technetium
Germanium dioxide
increases RBC production
202 203 204

202 203 204

 GLASS TYPES & LIMIT TESTS KAOLIN SILICEOUS EARTH
TYPE
GENERAL
TYPE OF TEST USE
aka Porcelain clay, Bolus alba, Fuller’s earth
DESCRIPTION
China Clay or White bole Diatomaceous Earth
I
Highly Resistant,
Borosilicate Glass
Powdered Glass Parenteral Native Hydrated Aluminum Kieselguhr
Treated Soda Lime Silicate Celite
II Water Attack Parenteral
Glass
Adsorbent
III Soda Lime Glass Powdered Glass Parenteral Treatment of mild diarrhea
NP
General Purpose
Powdered Glass Non-Parenteral
(Kaopectate®)
Soda Lime Glass
205 206 207

205 206 207

BENTONITE ATTAPULGITE SIMETHICONE

aka Soapclay, Mineral soap, Polymagma®, Quintess® Antiflatulent
WILHINITE Native Hydrated Magnesium Anti-foaming agent
Native colloidal hydrated Aluminum Silicate Disflatyl® & Kremil-S®
aluminum silicate Adsorbent for Diarrhea
Suspending agent
Most Abundant of all clays
naturally occuring aluminium
silicate
208 209 210

208 209 210

 DIMETHICONE, NF SILICA GEL FUME SILICA GEL
Dimethyl siloxane polymer condensation of silica vapour hydrolysis of orthosilicates
Protective and emollient
Simeco

211 212 213

211 212 213

TIN ALLOYS OF TIN TIN COMPOUNDS

aka Stannum
Used in production of cans
Test for Au: Purple of Cassius
Reagent: Stannous chloride
214
Babbit metal: 80% Sn, 20% Sb Stannous fluoride
Gun metal: 10% Sn, 90% Cu SnF2
Anti-cariogenic agent (8%)
Pewter metal Old: 80% Sn, 20% Pb
Pewter metal New: 85% Sn, Cu, Sb, Bi Stannic Oxide
Rose metal: 25% Sn, 25% Pb, 50% Bi SnO2
Solder metal Old: 50% Sn, 50% Pb Germicide
Solder metal New: 90% Sn, Ag, Cu
Plumber’s solder: 33% Sn, 67% Pb
215 216

214 215 216

 LEAD LEAD LEAD ACETATE
aka Plumbum Source of Poisoning aka Sugar of Lead
Pharmacologic use: Lead pipes Component of burrow’s solution
Astringent Paints (+ Aluminum sulfate)
Protein precipitant Burrow’s = Aluminum acetate
Batteries
Poisoning: Plumbism/Saturnism solution
Antidote:
Used for the preparation of Lead
EDTA
Subacetate Solution
Ca Versenate
217 218 219

217 218 219

LEAD SUBACETATE
LEAD MONOXIDE SOLUTION
LEAD SULFIDE
aka Litharge® aka Goulard’s Extract Black Sulfide
PbO Skin inflammation Galena (most common ore)
Astringent (Lead (II) acetate + PbO)
Lead (II) oxide

220 221 222

220 221 222

GROUP IVB - TITANIUM
FAMILY
ZIRCONIUM NITROGEN
Titanium Antiperspirant aka Azote, Mephitic air
aka: Titan (Sons of the Earth) Deodorant Meaning: “Without life”
Use: Powerful Reducing Agent Toxicity: causes skin granuloma Most abundant gas in air : 71 %
Titanium (IV) oxide N2, 25% O2
Titanium dioxide
Opaquant (Ocusert®)
UV Ray protectant
223 224 225

223 224 225

NITROGEN NITROGEN DIOXIDE NITROGEN TRIOXIDE

Inert Air pollutant Oxidizing agent
Very Stable vs nitrite - vasodilator; For (vs) Nitrate - preservative
Provides an inert atmosphere cyanide poisoning
for readily oxidisable
pharmaceuticals
stored in BLACK containers
Liquid N2: Refrigerant
226 227 228

226 227 228

 AROMATIC SPIRIT OF
AMMONIA
NITROUS OXIDE
spirit of hartshorn, spirit of sal N2O
volatile Laughing Gas or Dinitrogen monoxide
respiratory stimulant Used as general anaesthetic
Dental procedure
weakest but probably the safest
inhalational anesthetic
S/E: diffusion hypoxia
Stored in BLUE container
229 230
PHOSPHORUS
aka Bringer of Light, Light-
carrier, St. Elmo’s Fire
Three main allotropic forms:
White/Yellow Phosphorus -
Poisonous
Red Phosphorus - Non -
Poisonous
231

229 230 231

ARSENIC ARSENIC DETECTION OF ARSENIC?

King of All Poisons; Choice of
Professional Poisoners
Component of Salvarsan/
Compound 606/Arsphenamine/
Private 606
1st anti-syphilis drug
Paul Ehrlich
232
Aka: Lewisite metal MARSH TEST
Insecticide: Copper Aceto Arsenate
Toxicity: Aldrich-Mee’s Line
Antidote: BAL or dimercaprol As
Test in As detection
Marsh Test (Modified form of
this test is GUTZEIT TEST)
Fleitmann’s Test (+) Arsine Gas (AsH3)
233 234

232 233 234

 ARSENIC TRIOXIDE
aka Arsenious oxide, white
arsenic, arsenic (III) oxide,
arsenicum album, Inheritance
Powder
Amphoteric oxide
Treatment of leukaemia, IV
(Trisenox®)
235
ARSENICALS
Paris Green - Cupric Aceto-Arsenite
Cupric sulfate and arsenic trioxide
Cu(C2H3O2)2●3Cu(AsO2)2
Rodenticide, insecticide, pigment,
blue colorant of fireworks
Scheele’s Green - Cupric Hydrogen
Arsenite
Fowler’s Solution - 1% Potassium
Arsenite Solution (KAsO2); Anti-
Leukemics; For Psoriasis and asthma
Donovan’s Solution - AsI3 & HgI2
236
ARSENIC POISONING
General Protoplasmic Poison
Acute Poisoning:
Digestive Problems - Vomiting, abdominal
pains, diarrhoea accompanied by bleeding
Aldrich Mee’s lines - Characteristic white
lines on nails (nail growth arrest)
Alopecia - Hair loss
Chronic Poisoning: Arsenicosis
Found in smelters, patients treated w/
arsenicals [e.g. Melarsoprol(Mel-B)],
drinking water with levels of As
Blackfoot Disease & 237
CANCER

235 236 237

ANTIMONY POTASSIUM
ANTIMONY ANTIMONY TARTRATE
Antimony Glance Pharmacologic action of water- SbKC4H4O6
soluble compounds:
Most important source of Astringent More exact: C8H4K2O12Sb2●3H2O
antimony Emetic aka Tartar Emetic, Brown mixture
Sb2S3 Expectorant Emetic
Red-Orange in color Anthelminthic (For Schistosomiasis) Expectorant
Kills and expels intestinal worms For treatment of
(vs vermifuge - only expels Schistosomiasis (Liver Fluke)
worms)
238 239 240

238 239 240

 OTHER COMPOUNDS OF
BISMUTH MILK OF BISMUTH BISMUTH
aka “Beautiful Meadow” Bismuth Cream, Bismuth Magma Bismuth citrate
Uses: Contains bismuth hydroxide & bismuth Bismuth Subcarbonate
Astringent subcarbonate in suspension in water Bismuth Subgallate
Antiseptic/Antimicrobial Composition:
Astringent, mildly germicidal, antacid
Triple and Quadruple Therapy Bismuth subcarbonate
HNO3
Bismuth subsalicylate (“Pink Bismuth”)
Gastric Protectant Active Ingredient in Pepto-Bismol®
Ammonium Carbonate
Compound are poisonous Anti-Inflammatory, bactericidal,
Strong Ammonia solution & Purified H2O
Side effect of bismuth compounds used Protective for gastric ulcers antacid
internally: Black stools (Bi2S3➡) Inhibit growth of H. pylori (antiseptic) Colloidal Bismuth Subcitrate
Antidote: Dimercaprol Astringent Tx of PUD
241 242 243

241 242 243

GROUP VIA -
GROUP VB CHALCOGENS
OXYGEN
Oxygen
Tantalum aka Dephlogisticated Air(Priestly), Three Allotropes:
Unaffected by body fluids - Empyreal air(Scheele), Acid- Nascent
Former(Lavoisier), Yne
inert [O]
3rd MostAbundant Element in
Sheet form - surgical repair of Universe Atmospheric/Molecular
bones Most abundant Element in Earth’s O2
crust Ozone
Most Essential Element in humans
Exist as a diatomic molecule under O3
244
ordinary conditions (O2)
245 246

244 245 246

 OXYGEN OZONE SULFUR
Therapeutic gas in the treatment Powerful Oxidising Agent aka Brimstone, Shulbari
of conditions involving hypoxia Disinfectant, bleach (industrial) (Sanskrit: Enemy of Copper),
Stored in GREEN containers Bluish irritant gas Asupre / Azufre

Occurs in free state and in

combination, mainly as sulfides
and sulfates
247 248 249

247 248 249

PHARMACEUTICAL
FORMS OF SULPHUR
SULFUR SULFURATED LIME
Used as scabicide (precipitated S)
PRECIPITATED SUBLIMED WASHED
Keratolytic effect - Sulfur Vleminckx’s Solution
SULFUR SULFUR SULFUR
MILK OF Stimulant in alopecia Prepared from lime and
FLOWERS OF
SULFUR, LAC SULFUR Stimulant cathartic (Sublimed S) sublimed sulfur and water
SULFUR
Very fine, pale Fumigation (when burned) Ca(OH)2 + S ➜ 2CaS5 + CaS2O3
Fine, yellow,
yellow, Fine, yellow,
crystalline Depilatories (Sulfides) - Remove + H2O
amorphous or crystalline
microcrystalline powder, with faint
powder, with unwanted hair
faint odour &
powder, odourless odour & taste
taste Reduction in sulfide link in cystine Used as scabicide, treating acne,
& tasteless
in highly alkaline media and other skin diseases
Used in ointments Used as cathartic e.g. Sodium thioglycolate (Veet®)
& lotions (irritant
250 laxative) 251 252

250 251 252

 SELENIUM SULFIDE
SeS2 (Selsun Blue®)
2.5% suspension used for the topical
treatment of seborrheic dermatitis
(Cytostatic effect)
Hands should be washed off - Se
is toxic
Should not come in contact in eyes
and mouth
Cadmium sulfide, in the past, was
also used for this purpose
253
SELENIUM GROUP VI-B
Selene (Gk.) - moon Chromium and Molybdenum
Toxic in large doses Important trace elements
Prolonged contact with skin:
contact dermatitis
Important trace element:
Deficiency? Keshan Disease
Absorbed very slowly on the skin
Promotes absorption of vitamin E
254 255

253 254 255

CHROMIUM MOLYBDENUM MOLYBDENUM OXIDE

Chromous Ion - (Cr2+) - Good RA
Chromic Ion - (Cr3+) Essential Trace Element With ferrous sulfate - hematinic
Glucose Tolerance Factor Cofactor for enzymes associated Brand name? Mol-Iron®
Essential Trace Element (Cr3+) with flavin-dependent enzymes
Hexavalent Chromium (Cr+6)
Poisonous form
Cr2O72- + H2O ➜ 2CrO42- + 2H+
Dichromate e.g. Potassium dichromate
(K2Cr2O7) - Strong OA
Chromate - Good Precipitant; Orange-
Red 256 257 258

256 257 258

 URANIUM GROUP VIIA - HALOGENS
Radioactive element Halogen = Sea-salt producer
Discovered by Becquerel and Fluorine - Colorless gas
Curie from Pitchblende ore Chlorine - Yellow-green gas
Bromine - Reddish-brown
Becquerel = discovered fuming liquid
radioactivity, together with Pierce Iodine - Violet solid w/c easily
and Marie Curie sublimes
259 260
259 260
PHARMACEUTICALLY IMPORTANT OTHER COMPOUNDS
COMPOUNDS OF FLUORINE
OF FLUORINE
Sodium Fluoride Chlorofluorocarbons (Freon)
Stannous Fluoride Used as aerosol propellant
Sodium Monofluorophosphate refrigerant
e.g. dichlorofluoromethane
Used as prophylaxis for dental Effect on environment?
caries “Greenhouse effect” ➜ Global
Fluorides also used for tx of Warming
osteoporosis Destroy O3 (ozone) layer
262 263
262 263
FLUORINE
Most electronegative element
(EN)
Least EN?
Strong Oxidizing agent
Linus Pauling’s Superhalogen
261
261
CHLORINE
aka Dephlogisticated muriatic acid
Universal Water disinfectant
“Chloros” - greenish yellow
Most abundant extracellular anion
Used as water disinfectant
Chlorides are precipitated with
Silver Nitrate
264
264
 CHLORINE
BROMINE
COMPOUNDS Dark reddish brown fuming liquid
Hydrochloric acid, Dil. HCl with suffocating odor
Sodium Chloride, Potassium Powerful caustic (quickly attacks the
skin to cause burn that is hard to
Chloride, Calcium Chloride
heal) and germicide
Ammonium Chloride
Skin exposure: area washed by a
Hypochlorites solution of baking soda and treated
with glycerin
Used as a chemical reagent:
265
Ex: Bromine Water (1% Br2 in H2O)
266
BROMIDES
Poisoning: Bromism/Brominism
Long term use of bromides
Somnolence, psychosis, seizures, and
delirium, skin eruption, weakness,
Headache
Antidote: NaCl + Ammonium
Chloride
Oldest known anaesthetic
Bromide ion internally acts as a sedative
(depressant)
Three Bromides Elixir (Na+, K+, NH4+)
Bromine 10th N solution - Koppeschar’s
solution 267

265 266 267

IODINE IODIDES IODINE PREPARATION

Heaviest Non-metallic element
Oldest antiseptic
Easily undergoes sublimation ➜
violet vapours
Solid with metallic sheen
Poisoning: Iodism
Acute rhinitis, acneform eruption,
weakness, salivation and foul
breath
Antidote: Starch solution, Sodium
thiosulfate (ingestion)
268
Pharmacologic effect:
Expectorant
Antiseptic
Essential trace element necessary
for synthesis of thyroid hormones
Deficiency state: Simple Goiter
Dangerous for pregnant women -
Cretinism
Prevention? Iodised Salt (NaI)
269
Iodine Tincture - NaI, 2% I2 in 50% EtOH
Iodine Topical Solution - NaI, 2% I2 in
water
Strong I2 Solution (Lugol’s Solution) - KI,
5% I2
Strong Iodine Tincture - KI, 7.5% I2, 50%
EtOH
Phenolated Iodine Solution
Boulton's Solution ➜ antibacterial &
irritant 270

268 269 270

IODINE PREPARATION ASTATINE GROUP VII-B
Iodophors
The only synthetic, metallic, & Manganese (Mn)
Iodine complexed with an organic Pyrolusite (MnO2) - principal ore
complexing agent as solubilizer radioactive halogen
of manganese
Povidone/PVP-I2 solution The rarest element
Essential trace element
(Betadine®) Cofactor involved in protein
Skin Cleanser - 7.5% I2 w/ synthesis, phosphorylation, fatty
surfactant acid, and cholesterol synthesis
Solution - 10% I2 Toxicity: similar to parkinsonism
Muscle rigidity & tremors
Vaginal Wash - 7.5% I2
271 272 273

271 272 273

GROUP VIII-A/O -
TECHNETIUM (Tc) HELIUM
NOBLE / INERT GASES
“Technetos” - Artificial _____?______ Helium (Gk. - Sun)
First element produced artificially Inert Gases 2nd lightest gas
Used in radiopharmaceutical: Noble Gases 2nd Most Abundant Element in
Technetium 99m Universe
___?___ Gases
Inhalation produces Donald Duck-
Most Commonly Used like Sound
Radiopharmaceutical “Mobile” Gas
Production: Decay of Mo-99 Component of Artificial Air
Stored in BROWN container
80% He and 20% O2
274 275 276

274 275 276

 NEON ARGON KRYPTON
Gk. - New Most abundant noble gas Gk. - Hidden
Use: Advertising purposes (Neon Gk. - Idle Least abundant noble gas
lights)
Substitute for nitrogen as inert Discoverer: Ramsay and Travers
atmosphere for pharmaceuticals isolated Krypton from liquid
residues of Argon
Inhalational Anaesthesia, also Xenon

277 278 279

277 278 279

GROUP VIII-B - IRON

XENON RADON
TRIAD
Gk. - Stranger aka Niton
Investigated as General Anaesthesia Inert gas emitted by Radium salts
Treatment of certain types of cancer
(Cervical CA) First Triad: Fe, Co, Ni
_____?_____ Noble Gas 2nd Triad: Rh, Ru, Pd
3rd Triad: Os, Ir, Pt

280 281 282

280 281 282

 IRON IRON IRON FORMS
Hemoglobin Most important element in
engineering Pig Iron or Cast Iron
Oxygen transport
Transferrin Iron is best absorbed in the From blast furnace (92-94% Fe)
Transport from of iron in the body duodenum White Cast Iron - aka?; Solution of
hard, brittle iron carbide
Ferritin
Gray Cast Iron - aka? Liquid Fe run
Storage form of Iron in the body into sand molds & allowed to cool
Cytochrome Oxidase Wrought Iron - removal of
Enhance absorption of Iron: Vit C & impurities of cast irons (99.9% Fe)
Copper
283 284 285

283 284 285

IRON IRON IRON COMPOUNDS

Common ores
Pyrite/“Fool’s Gold” (FeS2)
is a native iron sulfide
Chalybeate water
Iron in solution with ferruginous
taste
Misch Metal: 70% Cerium + 30% Iron
286
Iron Toxicity/Overload:
Hemochromatosis
Antidote: Deferoxamine Mesylate (IV);
Desferasirox (PO)
Physiologic role of Fe2+
Hematinic - Stimulates production
of RBC (Most important therapeutic
use of Fe)
For correction of Iron Deficiency
Anemia
Side effect: causes GI constipation
287
Ferrous Sulfate - green vitriol
aka Green Vitriol (FeSO4●7H2O)
Ferrous Gluconate (Fergon®, Sangobion®)
Produces less gastric irritation than
FeSO4
Ferrous fumarate (Toleron®)
More stable; less air [O] than FeSO4
Ferrous Carbonate
aka Chalybeate Pills, and Ferruginous
Pills
288

286 287 288

 IRON COMPOUNDS IRON COMPOUNDS IRON COMPOUNDS
Ferric Chloride
Use: Astringent, Styptic, Ferrous Ferricyanide - Fe3[Fe(CN)6]2 Ferric Ferrocyanide - Fe4[Fe(CN)6]3
Detection of Tannin aka Turnbull’s blue aka Prussian Blue

Prussian blue and turnbull’s blue

have different chemical formula,
yet they are identical
289 290 291

289 290 291

IRON COMPOUNDS IRON COMPOUNDS IRON COMPOUNDS

Ferric Subsulfate solution
Ferric Ammonium Sulfate Iron Sorbitex (complex of Iron w/ aka Monsel’s Solution
Mohr Salt Sorbitol, & Citric Acid)
Used in analytical chemistry For poor absorption of Iron
Ferric Oxide
Makes Calamine pink (aesthetic
purpose)

292 293 294

292 293 294

 COBALT COBALTOUS CHLORIDE NICKEL
Development of erythrocytes & aka Lover’s Ink or Sympathetic Ink aka Old Nick’s Copper
hemoglobin CoCl2 Fancy Jewelries
As Co2+: Central metal ion in Vit B12 Use: Desiccator’s Indicator in silica Nickel’s itch - contact dermatitis
(Cyanocobalamin) gel beads Product of fossil fuel combustion
Deficiency: Megaloblastic Anemia Anhydrous form - Blue
Hydrous form - Pink
Cobalt Meta-aluminate
“Thenard’s Blue”
295 296 297

295 296 297

SECOND TRIAD THIRD TRIAD THIRD TRIAD

Rh Osmium, Iridium, Platinum Platinum
Ru complexes Catalyst
investigated for its anticancer Osmium low reactivity ➜ Noble Metal
properties Heaviest and most dense metal
Palladium Cisplatin, Carboplatin
Osmium tetroxide, Osmic acid
Catalyst in organic reactions Cis-
Staining of specimens for
Catalyst in finely divided steel electron microscopy diamminedichloroplatinum

298 299 300

298 299 300

 TECHNETIUM 99M- OTHER RADIOPHARMACEUTICAL
RADIOPHARMACEUTICAL USES
RADIOPHARMACEUTICAL Sodium Chromate - 52 Scanning of the Spleen
RADIO PHARMACEUTICAL USES Gold Au-198 Scanning of the Liver
Tc 99m - Phytate Liver imaging & potency
studies
Sodium Rose Bengal I-131 Tracer for Liver Function ORGANIC
Kidney imaging,
CHEMISTRY
Tc 99m - Heptagluconate Human Serum Albumin NaI Blood volume & Cardiac Output
Determining renal I-131 Determination
Tc 99m - IDA (IminoDiacetic function Sodium Iodide I-131 Scanning of the Thyroid
Acid)
Hepato-Biliary studies
Sodium Iodide I-125 Diagnosis of Thyroid Function
Tc 99m - Etidronate/
Bone Imaging/Scanning
Phosphonates Sodium Iodohippurate Diagnosis of Liver Function By Bart David A.
Tc 99m - Sestamibi /
Methoxy Isobutyl Isonitrile
Myocardial Perfusion Chlormerodrin Hg-197
Scintillating scans of kidney &
brain
Quibod, RPh, CPS
agent
Tc 99m - pertechnetate Thyroid Scanning Sodium Phosphate P-32 Treatment of Polycythemia Vera
Tc 99m - Macroaggregated Cyanocobalamin Co-57 Diagnosis of Pernicious Anemia
Albumin
Lung Scanning
301 Selenomethionine Se-75 Diagnosis
302 of Pancreatic Tumors 303

301 302 303

ORGANIC CHEMISTRY QUESTION CARBON: CHEMICAL

BASIS OF LIFE
• Study of CARBON and its compound What is the Chemical Basis of Life? • aka “King of all Elements”, Charcoal
• Is the branch of chemistry which deals  A. Oxygen
 • Carbon - Group IV, Period II
w/ carbon-containing compounds.  B. Hydrogen

 C. Sodium

• Formerly defined as the branch of  D. Carbon
science concerned with substances
derived from living things.

304 305 306

304 305 306

 CARBON: CHEMICAL BEQ HISTORY OF ORGANIC
BASIS OF LIFE CHEMISTRY
• Hardest form of Carbon? What is the major element present in Jon Jacob Berzelius ➜ “Organic”
organic compounds? made “Vital Force / Life Force Theory”
• Softest form? organic compounds ONLY originate
 A. Carbon
 from LIVING things
• C-14: Useful in radiocarbon dating  B. Hydrogen
 Friedrich Wholer
• Pure C is non-toxic e.g. activated  C. Nitrogen
 Disabuse the Vital Force Concept (1828)
charcoal (Universal antidote)  D. Sulfur Ammonia + Cyanic Acid ➜ Urea
Tobers Bergman
Diff. Organic vs Inorganic (see table)
307 308 309

307 308 309

PROPERTY ORGANIC INORGANIC

CHEMICAL BONDING OCTET RULE
Flammability Flammable Not Flammable
Boiling Point Low High
Forces that hold atoms together
Solubility in Water Insoluble Soluble All elements try to achieve the
Solubility in Non- configuration of the NOBLE GASES
Soluble Insoluble
Polar solvents
Octet Rule - atoms become stable when the
Types of Bonding ___?___ bonding Ionic Bonding
valence electron will complement fully the
Isomerism Exhibit Does not Exhibit valence shell
Atoms per Several Few Types of Chemical Bonding:
molecules
1. IONIC BOND
Structure Complex Simple
2. COVALENT BOND
Electrical
Poor Good
Conductivity 310 311 312

310 311 312

 INTRAMOLECULAR CHEMICAL BONDING INTERMOLECULAR FORCES
FORCES (FORCES WITHIN) (“FORCES BETWEEN”)
2 Types: Types of Chemical Bonding: Van der Waals Forces of
IONIC Bonding 1. IONIC BOND (Complete electron transfer) Attraction
Bond formed by a metal & a non-metal
COVALENT Bonding 1. Ion - Dipole
ELECTROSTATIC BOND
2. COVALENT BOND (Sharing of electrons) 2. Dipole - Dipole
2 Non-polar (similar atoms) ➜ equal
electron sharing (e.g. I2)
3. Dipole - Induced Dipole
2 Polar (dissimilar atoms) ➜ unequal 4. Instantaneous Dipole -
electron sharing Induced Dipole
313 314 315

313 314 315

ION-DIPOLE KEESOM FORCES HYDROGEN BOND

Strongest IMFA / Van der Waals
Force
Polar molecules are attached to either
positive or negative charges
Ex: KI and Iodine
aka: Dipole-Dipole forces
Occurs between POLAR molecules
special type of dipole-dipole?
aka?
attraction of a hydrogen atom for a
strongly ELECTRONEGATIVE atom
Oxygen, Nitrogen, Flourine (BEQ),
Chlorine and Sulfur

316 317 318

316 317 318


DEBYE FORCES LONDON FORCES
aka: Dipole - Induced Dipole forces aka: Instantaneous Dipole -
Occurs between POLAR & NON- Induced Dipole forces
POLAR molecules Occurs between POLAR, NON-
aka? POLAR & NON-POLAR molecules
aka?
PROPERTIES OF CARBON-
CONTAINING STRUCTURE
STABLE
Due to the ___?___ rule
When forming
covalent bond, the
carbon atom must have
8 valence electron or a
total __?__ bonds

319 320 321

319 320 321

PROPERTIES OF CARBON- PROPERTIES OF CARBON-

CONTAINING STRUCTURE
CATENATION
Chain Formation or the formation
of multiple bonds with itself
322
CONTAINING STRUCTURE
HYBRIDIZATION
mixing of 2 or more non-
equivalent atomic orbitals,
involving redistribution of energy,
to form a new set of equivalent
hybrid orbital or degenerate
orbitals
323 324

322 323 324

 TYPES OF HYBRIDISATION TYPES OF HYBRIDISATION

Sp3 - 4 hybrid orbitals - Tetrahedral

Sp2 - 3 hybrid orbitals - Trigonal
Planar
Sp - 2 hybrid orbitals _____?______

325 326 327

325 326 327

PROPERTIES OF CARBON- ISOMERS

CONTAINING STRUCTURE
_______?________
STRUCTURAL STEREOISOMERS
Existence of 2 or more compounds
having the same molecular formula
ISOMERS aka _____?______ CONSTITUTIONAL /
aka _________?_________ (Diff. in spatial orientation)
but different in structure (diff. in order of bonding) STRUCTURAL ISOMERS
May be due to:
CHAIN GEOMETRIC
ORDER of Bonding
SPATIAL ORIENTATION ➜ ___?___ POSITIONAL CONFORMATIONAL

328 _____?_____ 329 OPTICAL 330

328 329 330

 POSITIONAL ISOMERS
CHAIN ISOMERS CHAIN ISOMERS Differ in the position of the
unsaturated bonds (C = C or C ≡ C)
Differ in the arrangement of C or functional groups
atoms
Usually exhibited by alkanes due to
_____?_______

331 332 333

331 332 333

POSITIONAL ISOMERS POSITIONAL ISOMERS FUNCTIONAL ISOMERS

Differ in functional groups
e.g. C2H6O (Ethanol & Methyl
Ether)

334 335 336

334 335 336

FUNCTIONAL ISOMERS FUNCTIONAL ISOMERS FUNCTIONAL ISOMERS
Functional isomers ALWAYS occur in Functional isomers ALWAYS occur in Functional isomers ALWAYS occur in
pairs pairs pairs
Ether and Ethanol Aldehyde and Ketone Carboxylic Acid and Ester

337 338 339

337 338 339

FUNCTIONAL ISOMERS INDEX OF HYDROGEN IHD INTERPRETATION

DEFICIENCY (IHD) if IHD is equal to ZERO ➜ Fully saturated
(Alkane)
if IHD is equal to ONE ➜ Double bond / Ring
if IHD is equal to TWO ➜
IHD = (2C + 2) - H - X + N 1 Triple Bond OR
2 2 rings OR
2 double bonds OR
MEMORIZE!!!
1 Double bond and 1 Ring

340 341 342

340 341 342

 IHD SAMPLE IHD SAMPLE
COMPUTATIONS COMPUTATIONS
IHD value of C4H8 is ONE, Hence:
Double bond or Ring
There are four possible isomers: SPATIAL ISOMERS /
Compute for the IHD value of C6H14
Cyclobutane STEREOISOMERS
Compute for the IHD value of C4H8
Methyl-1-cyclopropane
1-Butene
2-Butene
343 344 345

343 344 345

STEREOISOMERS GEOMETRIC ISOMERISM CIS & TRANS

Configurational or Inversional STEREOISOMERISM
Isomers compound must be double bond
(alkene); ring / cyclic CISame side TRANS ➜ Opposite
compounds that can be
interconverted by the breaking of Cis and Trans Nomenclature
chemical bond. E and Z Nomenclature
Conformational Isomers aka
Rotamers
interconvert easily at room
temperature through rotation
about a single bond
346 347 348

346 347 348

 CAHN-INGOLD
Z and E ISOMERISM GEOMETRIC ISOMERS
PRELOG SEQUENCE
Z ➜ Zame side E ➜ Epposite side Increase ___?___ ; Increase Priority

349 350 351

349 350 351

CONFORMATIONAL SAWHORSE DASH & WEDGE /

ISOMERS aka? PROJECTION PERSPECTIVE FORMULA
involves rotation Tetrahedral
along a single bond
only e.g. CH3CH3
(Ethane)
Sawhorse projection
Dash & Wedge aka
Perspective formula
Ball and stick model
aka ______?_______
352 353 354

352 353 354

 FACTORS AFFECTING CONFORMATIONAL
BALL & STICK MODEL CONFORMATIONAL ISOMERS
ISOMERS
STABILITY
1. Torsional Energy Example: Cyclobutane
energy needed to Planar & Puckered/“Butterfly”
resist rotation conformation
TE ➜ ___?___
Stability
2. Steric Effect aka
____?____
presence of bulky
groups
Crowding ➜ ___?___
Instability: Eclipsed > Gauche > Anti
355 Stability 356 357

355 356 357

CONFORMATIONAL CONFORMATIONAL CONFORMATIONAL

ISOMERS ISOMERS ISOMERS
Example: Cyclopentane Example: Cyclohexane Example: Cyclohexane
Flat, Envelope, & Twist Boat & Chair conformation Boat & Chair conformation
conformation

358 359 360

358 359 360

 ________?________ aka REQUIREMENTS FOR
1) CHIRAL CENTER
OPTICAL ISOMERS OPTICAL ACTIVITY
Optical Activity Sp3 carbon with ___?___
The ability of a compound to rotate different groups attached to it
a plane polarised light either to the 1. Chirality Center/_____?_____
right or left Carbon
Instrument which measures optical
activity: _______?________ 2. NO Symmetry element/Line of
Symmetry

361 362 363

361 362 363

1) CHIRAL CENTER 1) CHIRAL CENTER 1) CHIRAL CENTER

All amino acids have chiral No. of Stereoisomers = 2n
properties except: ____BEQ____ where n = # of Chiral Carbon Absolute Configuration
Structure: Example: Tartaric Acid R & S configurational isomers
H No. of Stereoisomers = 22 = 4! R - rotate to the Right (Clockwise)
S - rotate to the Left (Counter-
NH2 C COOH HOOC CH CH COOH Clockwise)

H OH OH
364 365

364 365 366

 2) NO SYMMETRY
1) CHIRAL CENTER _____?______
ELEMENT
RACEMIC MIXTURE Mirror images; Non-
Equal amount or concentration of R Enantiomers superimposable
& S or D & L isomers
Optically _____?______ Diastereomers Always occur in pair hence same
e.g. 50% R(+) & 50% S(-) Meso Compounds ____?_____ physicochemical
50% D(+) & 50% L(-) properties
Thalidomide Crisis (?) D vs L
368 369

367 368 369

D vs L ISOMERISM
Position of the OH on the LAST CHIRAL
center
Dextrorotatory: toCLOCKWISE
the Right, d or (+)
Levorotatory: COUNTER-CLOCKWISE
to the Left, l or (-)

370 371 372

370 371 372

 DIASTEREOMERS MESO COMPOUNDS TAUTOMERIZATION
Non-mirror images Mirror images, Tauto / “Same”; Meros / “Part”
Non-superimposable Superimposable Special kind of Isomerism
Same compound Rapid interconversion between 2
Optically substances
_____?______ aka KETO-ENOL TAUTOMERS
E.g. Propanone to 2-Propenol

373 374 375

373 374 375

TAUTOMERIZATION LINEAR VS CYCLIC EPIMERS “C2

Carbohydrates can exist as either Glucose Epimers:
GulaMann”
linear (open chain) or as cyclic Carbon 2 (C2) - Mannose
structures. Carbon 4 (C4) - Galactose
Equilibrium exist between the open/
linear chain and the two cyclic
projections of carbohydrates
Fischer projection: _________ Form
Haworth projection: ________ Form
376 377 378

376 377 378

FISCHER & HAWORTH MUTAROTATIONS ANOMERS
PROJECTION Defined as the change in specific Carbonyl Carbon in Linear or acyclic
optical rotation representing the form undergoes cyclisation with the OH
interconversion bet. 𝛂 & β anomer of of the 6th carbon to form the Anomeric
carbohydrates Carbon (Chiral Center)

379 380 381

379 380 381

ISOMER DESCRIPTION
ANOMERS ANOMERS Enantiomers
MIRROR Image; NON-
Superimposable
2 cyclic forms: Meso MIRROR-Image;
𝛂 anomer: If the OH group at the Compound Superimposable
anomeric carbon is on the opposite Diastereomers
NON-MIRROR Image;
side of the ring as the CH2OH group NON-Superimposable
Isomers that are rapidly
β anomer: If the OH group at the Tautomers interconverted (Keto-Enol Formation)
anomeric carbon is on the same Epimers Differ in chirality @ 1 carbon (C2 or
side of the ring as the CH2OH group C4)
Anomers Differ in the carbonyl carbon (𝛂 or β)
Cis- Same Side
Cis-Trans 384
382 383 Trans - Opposite Side

382 383 384

 FUNCTIONAL GROUP FUNCTIONAL GROUP
FUNCTIONAL GROUP
DETERMINATION DETERMINATION
The Chemistry of every molecule is Functional group in Vanillin: [BEQ] Functional group in Ibuprofen:
determined by the functional group it [BEQ]
IUPAC name: [BEQ]
contains
Use: Flavorant

The pharmacologic and PK

(absorption, solubility etc) activity of your
drugs is dependent on the functional
group/s attached.
385 386 387

385 386 387

FUNCTIONAL GROUP FUNCTIONAL GROUP

DETERMINATION DETERMINATION
Functional group in Aspirin: [BEQ] Functional group in Penicillin: [BEQ]

388 389 390

388 389 390

 HYDROCARBONS HYDROCARBONS
I. Simple Hydrocarbons II. Hydrocarbon Derivatives
A. Alkane A. Oxygen-containing
B. Alkene i. Alcohols, Phenols, Ether
C. Alkyne ii. Aldehyde, Ketone
II. Hydrocarbon Derivatives (X, N, iii. Carboxylic Acid, Ester
O, P) B. Nitrogen-containing
i. Amines and Amides
391 392 393

391 392 393

HYDROCARBONS HYDROCARBONS
II. Hydrocarbon Derivatives A. Aliphatic - single chain, no ring/s
involved
C. Halogen-containing
SIMPLE 1. Saturated - Single bonds only,
i. Alkyl halide
Alkane family
ii. Aryl halide HYDROCARBONS
2. Unsaturated - has multiple
D. Sulfur-containing bonds, Alkenes & Alkynes
i. Thiols or _______
ii. Thioethers & Thiophenols
394 395 396

394 395 396

 HYDROCARBON HYDROCARBON
B. Aromatic - presence of ring/s, B. Aromatic
specifically Benzene Ring & its Pleasant odour
derivatives
Benzene is the parent substance
Isolated by _________ in 1825
Who discovered its structure?
Orbital Hybridisation in
aromatics?
397 398 399

397 398 399

MONOSUBSTITUTED
HYDROCARBON
BENZENE
B. Aromatic (Monosubstituted
Benzene)
Nitrobenzene
Ethylbenzene
Chlorobenzene

400 401 402

400 401 402

😂 😁HUE HUE HUE 😅😆 HYDROCARBON
B. Aromatic (Disubstituted Benzene)
The prefixes ortho-, meta-, para-
(o-,m-,p-) are used as prefixes
Ortho - adjacent
Meta - one carbon apart
Para - opposite
HYDROCARBON
B. Aromatic (Polysubstituted
Benzene)
Mono substituted compounds will
serve as a parent name, + the
principal substituents assumed to
be carbon 1
e.g. 1,3,5-trinitrobenzene

403 404 405

403 404 405

RULES OF AROMATICITY HUCKEL’S RULE AROMATIC OR ANTI-AROMATIC

OR NON-AROMATIC?
used to determine if a compound is
Four Criteria of Aromaticity
aromatic or not
Molecule is Cyclic (ring) 4n + 2 = Pi e- / 𝛑 electrons (e- in
Molecule is Planardoes
If the compound (all atoms
not meet in the
double bond)
molecule
all the lie in the same
following plane)
criteria, it is Note: If n = whole number (AROMATIC)
Molecule
likely NOT is Fully Conjugated (p-
AROMATIC
orbitals at every atom in the ring)
Anthracene
Molecule must follow 4n + 2 = 𝛑 Phenanthrene
electrons
Benzene is AROMATIC!
406 407 408

406 407 408

AROMATIC OR ANTI-AROMATIC AROMATIC OR ANTI-AROMATIC AROMATIC OR ANTI-AROMATIC
OR NON-AROMATIC? OR NON-AROMATIC? OR NON-AROMATIC?
Cyclobutadiene Azulene Cyclopentadienyl Cyclopentadienyl
Anion Cation

Naphthacene
Cyclopentadiene
409
Naphthalene
410 411

409 410 411

AROMATIC OR ANTI-AROMATIC
OR NON-AROMATIC? ALKANES
aka __________
Cyclooctatetraene
contain C-C SINGLE BOND ONLY
General Formula: ________
Suffix: -ane
Alkyl Group (R Group)
Removal of 1 H; ends with -yl
e.g. Methane (when 1 H is removed:
412 413
_________) 414

412 413 414

IUPAC SYSTEM PREFIXES IUPAC SYSTEM PREFIXES IUPAC SYSTEM PREFIXES
# of C Name # of C # of C Name # of C # of C
Name Name Name
Atoms Atoms Atoms Atoms Atoms
Methane 1 Heptane 7 Tridecane 13 Nonadecane 19
Hentriacontane 31
Ethane 2 Octane 8 Tetradecane 14 Eicosane 20
Dotriacontane 32
Propane 3 Nonane 9 Pentadecane 15 Heneicosane 21
Tritriacontane 33
Butane 4 Decane 10 Hexadecane 16 Doeicosane 22
Undecane 11 Trieicosane 23 Tetracontane 40
Pentane 5 Heptadecane 17
Hexane 6 Dodecane 12 Octadecane 18 Triacontane 30 Hectane 100
415
se 416 417

415 416 417

SYSTEMS OF
ALKANES IUPAC
Little chemical affinity for other
NOMENCLATURE aka “International Union of Pure
1. COMMON NAME
substances and Applied Chemistry”
Uses the name given when it was
Inert to most laboratory reagents discovered Most systemic
Show regular increase in boiling point e.g. Formic acid (Formica ➜ ____) Based:
& melting point as weight increases Uses: Prefixes (n-, iso-, neo-) (A)Longest continuous C chain or
2. DERIVED NAMES parent chain
Derived from a parent compound (B)Use of n numbers
3. IUPAC NAME
418 419
(C)Use of C # prefixes
420

418 419 420

 IUPAC RULES
1. Identify the parent or __?__ C
chain
2. Assign lowest position number for C
3. Identify the substituents
4. If > 1 substituent, indicate the # of
groups using prefixes (di-, tri-, tetra-,
etc)
5. Arrange substituent in alphabetical
order 421
IUPAC RULES PARENT CHAIN
1. Identify the parent or __?__ C chain Determine the longest possible chain
2. # C atoms from one end so that the and name the corresponding alkane
branch or substituents are given the name
lowest position numbers
3. Identify the substituents and indicate
the positions by using numbers
4. If > 1 substituent, indicate the # of
groups using prefixes (di-, tri-, tetra-, etc)
5. Arrange substituent in alphabetical
order 422 423

421 422 423

SUBSTITUENTS COMPLEX SUBSTITUENTS COMPLEX SUBSTITUENTS

Substituents are numbered with the
lowest position number
composed of a substituent on a
substituent
Isopropyl - __?__ R-groups
Isobutyl - __?__ R-groups
Sec-butyl - __?__ R-groups
Tert-Butyl - __?__ R-groups

424 425 426

424 425 426

 NAMING ACTIVITY NAMING ACTIVITY NAMING ACTIVITY

427 428 429

427 428 429

COMMON MISTAKES SATURATED

COMMON MISTAKES
Substituents are numbered with the
HYDROCARBONS
lowest position number Cycloalkanes
Carbon rings; can be written in
geometric figures
General Formula: ________
Named with the prefix _____ - in
front of the corresponding alkane
name
430 431 432

430 431 432

 NOMENCLATURE COMMON MISTAKES NAME THE STRUCTURE
Additional Rule in Naming Cycloalkane
Step 1: Use the cycloalkane name as the
parent chain
Step 2: Number the substituents
starting at the group that has
alphabetical priority & proceed
around the ring in the direction that
gives the 2nd substituent the lower
possible number
433 434 435

433 434 435

UNSATURATED
NAME THE STRUCTURE ALKENES
HYDROCARBONS
Alkenes or ______
at least 1 DOUBLE DOND
General Formula: ________
Same nomenclature as alkane but
change -ane to -ene

436 437 438

436 437 438

 UNSATURATED UNSATURATED OTHER FUNCTIONAL
HYDROCARBONS HYDROCARBONS GROUPS
Alkadienes Cycloalkenes Halides
Carbon ring w/ DOUBLE DOND Carbon ring w/ Halogenation
2 carbon-carbon DOUBLE DOND
General Formula: ________ Formation of an alkyl or aryl halide
indicate the position of double bond
Alkynes or ________ e.g. of organic halides are -F, -Cl, -Br, -I
+ prefix + diene
at least 1 Triple bonds Functional group: R—X
e.g. 1,3-butadiene & Isoprene General Formula:__________
Same nomenclature as alkane but change
-ane ➜ -yne
439 440 441

439 440 441

TYPES OF BOND
REACTION MECHANISM REACTION MECHANISM
Reaction Mechanism
CLEAVAGE
Reaction Mechanism Homolytic Cleavage
Detailed course of overall reaction
a process by which a chemical A + B ➜ [C] ➜ D + E Equal electron fission or splitting
reaction occurs stepwise results to format of free radicals
A - Substrate
Electron movement B - Reagent
Bond breaking C - Intermediate
Bond making D - Main product
Timing E - Side product
442 443 444

442 443 444

 TYPES OF BOND
CLEAVAGE
Heterolytic Cleavage
Unequal electron fission or splitting
due to difference in EN
ADDITION REACTION ELIMINATION REACTION
2 reactants react together to form a opposite of addition reaction
single new product with no atoms “left single reactant splits into 2 products
over”
e.g. chloroethane ➜
e.g. Ethylene + HCl

445 446 447

445 446 447

SUBSTITUTION REARRANGEMENT
REACTION REACTIONS
2 reactants exchange parts to give 2 single product undergoes a
new products reorganisation of bonds and atoms to
e.g. methane + chlorine ➜
yield a single isomeric products ALCOHOLS, PHENOLS,
e.g. Phenol + Br2 ➜
e.g. conversion of cis-butene to THIOLS, ETHERS
trans-butene

448 449 450

448 449 450

 ALCOHOLS
Classification
A. Based on the # of R bonded to C bearing
-OH group (C-OH, Carbinol group)
a. Primary - _?_ R-group
b. Secondary - _?_ R-group
c. Tertiary - _?_ R-group
B. Based on the # of -OH groups
a. Monohydric - _?_ OH-group
b. Dihydric - _?_ OH-group
c. Trihydric - _?_ OH-group
d. Polyhydric - _?_ OH-group
451
NOMENCLATURE
Common Names
Name of alkyl group + alcohol
CH3OH = Methyl Alcohol
Derived Name: Carbinol (an old name of
methanol)
CH3CH2OH = Methyl Carbinol
IUPAC rules: similar to alkanes
Include -OH group in the parent chain
-OH is given the lowest possible #
Name ending in -ol
452 453

451 452 453

NOMENCLATURE REACTIONS OF ALCOHOL

IUPAC naming of Alcohol
Position of -OH group + Rootword
(# of C) + -ol (suffix for alcohol)
e.g.
CH3—OH CH3CH2—OH

CH3CH2CH2—OH CH3CH—OH

454
CH3 455 456

454 455 456

REACTIONS OF ALCOHOL REACTIONS OF ALCOHOL
Oxidation Dehydration
Reagents used? Alcohol + HCl/H2SO4 ➜ Alkene +
Alkanes ➜ Alcohols ➜ Aldehydes/ H2O
Ketone ➜ Carboxylic Acids ➜ CO2 Type: Elimination reaction
Primary(1°) Alcohol ➜ Aldehyde ➜
Carboxylic Acid
Secondary(2°) Alcohol ➜ Ketone
Tertiary(3°) Alcohol ➜ No Reaction
457 458 459

457 458 459

REACTIONS OF ALCOHOL REACTIONS OF ALCOHOL REACTIONS OF ALCOHOL

Dehydration Esterification Lucas Test
Alcohol + HCl/H2SO4 ➜ Alkene + Reaction between Carboxylic acid Lucas Reagent: ZnCl2 (Catalyst) in
and Alcohol ➜ Ester & Water concentrated HCl (reactant)
H2O
Involves double displacement
Type: Elimination reaction 3° Alcohols are the MOST reactive
Zaitsev’s rule 1° Alcohols do not undergo the
Alkene w/ the greatest # of R reaction easily >> needs heat
groups is the MAJOR product of Order of reactivity: 3°>2°>1°>CH3OH
reactions (+) VR: 2 immiscible layes
460 461 462

460 461 462

 LUCAS TEST
REACTIONS OF ALCOHOL
Reaction with active Metals
Williamson’s Reagent: Alkoxide used in
synthesis of ethers
Involves single displacement
1° Alcohols are the MOST reactive
3° Alcohols do not undergo the
reaction
Order of reactivity: CH3OH>1°>2°>3°
THIOLS
aka Mercaptan
Nomenclature: same as alcohol
except the -ol suffix is replaced by -
thiol
e.g. methanethiol, 2-butanethiol
Properties: Foul odor, oxidized to
disulfide

463 464 465

463 464 465

PHENOLS
Hydroxyl group attached to an
aromatic ring
Properties
Form Ion-dipole & H-bonds
Enhance water solubility
Susceptible to oxidation
e.g. Ortho(Catechol),
Meta(Resorcinol), Para(Hydroquinone)
e.g. 1-Naphthol, 2-Naphthol, Eugenol
466 467 468

466 467 468

NAPHTHALENE / NAPHTHOL TEST FOR POLYSACCHARIDES TEST FOR POLYSACCHARIDES
Test Species Responsible (+) Result Test Species (+) Result
Responsible
Molisch General Test Purple ring @ junction
Iodine Polysaccharide Starch - Blue
Anthrone General Test Blue-Green Glycogen - Red
Osazone Aldehyde/Ketone Maltose = Sunflower; Lactose =
Bial’s Pentoses
Hedgehog; Glucose/Fructose/ Blue-Green
Reducing Sugars Mannose = Needle like
Tauber’s Pentoses Cherry Red
Moore Reducing Sugars Yellow-Orange Benzidine
Nylander Reducing Sugars Black precipitate
Picric Acid Reducing Sugars Mahogany Red
Barfoed Mono vs Di Brick-Red
Seliwanoff Ketoses Deep-Red
469 Mucic Acid Galactose 470 Crystal Formation 471

469 470 471

IMPORTANT ALCOHOLS
ALCOHOLS ALCOHOLS
& PHENOLS Methanol - aka? CH3—OH Glycerol - aka? OH OH OH
Methanol Cresol oxidised into _________ & _________ Use: Humectant
Ethanol Resorcinol (Blindness)
Test for Glycerol?
Ethanol - aka? CH3CH2—OH CH2CH2CH2
Isopropyl Eugenol
Alcohol Thymol oxidised into _________ (“Hangover” H H
Effect) Ethylene Glycol - aka?
Cholesterol Hydroquinone Isopropyl Alcohol - aka? CH3CH—OH Nephrotoxicity HO C C OH
Glycerol Hexylresorcinol oxidised into _________ Hypocalcemia
Ethylene Glycol Menthol (Nail Polish Remover) CH3 H H
Seizures & Paralysis
Phenol Geraniol Cholesterol - found in animals
Catechol 472 Glucose Basic Ring structure:
473
CPPP 474

472 473 474

 PHENOLS PHENOLS ETHERS
Phenol - aka? Eugenol -
Discovered by _________ (Father of IUPAC: 4-Allyl-2-methoxyphenol Contain an -O- between Carbon
Antiseptic Surgery) Use: Dental analgesic (Toothache Drops) groups
Source: Eugenia caryophyllus
Standard for all antiseptics & disinfectants
Thymol
Common Name: Simple ethers
(Phenol Coefficient) named from -yl names of the attached
IUPAC: 2-Isopropyl-5-methylphenol
Catechol - Ring structure for endogenous
Use: Anti-Fungal agent groups and adding ether
catecholamines
Source: Thymus vulgaris IUPAC: Use “oxy” + parent alkane
e.g. Norepinephrine, Epinephrine, Dopamine Hydroquinone - (MaxiPeel®)
Cresol (Lysol®) name
Use: Depigmenting agent [BEQ]
combination of ortho-, meta-, para-cresol Tretinoin + Hydroquinone = Treatment of CH3-O-CH3 aka ?
Resorcinol - Keratoytic
475
agent for Warts Acne 476 477

475 476 477

ETHERS ETHERS IMPORTANT ETHERS

aka ORGANIC OXIDES Classification Diethyl ether aka?
R—O—R Open-chain (symmetric or most widely used anesthetic
Ar — O — Ar asymmetric) safe in long surgical procedures
Ar — O — R Explosive ➜ Nitrous oxide
Ring/Cyclic (Epoxides)
Ethylene Oxide - Gas sterilant
Examples: Monobenzone - a _____?_____ agent
Diethyl ether in excessive melanin formation e.g. Freckling
Ethylene Oxide Eugenol - forms ZnO-Eugenol cement used
Monobenzone as temporary fillings
478 479 480

478 479 480

 ETHER DRUGS ETHER DRUGS EPOXIDES/CYCLIC
ETHERS
Compounds that contain an oxygen
atom incorporated in a ring
Simplest epoxide?

481 482 483

481 482 483

CARBONYL
FUNCTIONAL GROUP
A functional group composed of a Aldehydes & Ketones
carbon atom double-bonded to an General Formula: ___________
CARBONYL GROUP & oxygen atom Functional Isomers
CARBONYL CONTAINING Aldehydes have at least 1 H atom
bonded to carbonyl group
COMPOUNDS Ketones have only alkyl or aryl
(denoted as Ar) groups bonded to
carbonyl carbon
484 485 486

484 485 486

 NOMENCLATURE OF
IMPORTANT ALDEHYDES
ALDEHYDES
Aldehydes IUPAC: Select longest continuous chain Formaldehyde / Formalin
Oxidised to _________ and reduced having the aldehyde group (aldehyde Acetaldehyde
to ____________ group is automatically C #1). Change -e Benzaldehyde
Ketones of the alkane with -al
Cinammaldehyde
Reduced to ___________ Common Names
# of Carbon + aldehyde Vanillin
Derived Name: Alkyl group + Chloral ➜ Chloral Hydrate
aldehyde Citral
487
Examples: Formaldehyde
488 489

487 488 489

IMPORTANT ALDEHYDES IMPORTANT ALDEHYDES IMPORTANT ALDEHYDES

Formaldehyde / Formalin (_?_%) Acetaldehyde Benzaldehyde
IUPAC name: Methanal (1C) IUPAC name: Ethanal (2C) Synthetic Bitter Almond Oil
Use: responsible for “Hangover effect”
Urinary Tract Antiseptic of alcohol
(Urotropin/Methenamine) Use: Preservative
Embalming Agent - Harden the Disulfiram ➜ (×) Aldehyde DH ➜ Cinnamaldehyde
skin and body acetaldehyde ➜ S/Sx alcohol Chief constituent of the oil of
Carcinogenic toxicity Cinnamon Bark
490 491 492

490 491 492

IMPORTANT ALDEHYDES IMPORTANT ALDEHYDES IMPORTANT ALDEHYDES
Vanillin CHLORAL HYDRATE CITRAL
IUPAC Name: 4-Hydroxy-3- aka Mickey Finn / Knockout Drops Odor and flavour of
MethoxyBenzaldehyde [BEQ] Active metabolite: [BEQ] lemon oil
Use: Flavorant (fragrant component A/E: CNS depression (Metabolic Source:
of vanilla beans) acidosis) Citrus limon
Cymbopogon
citratus - Lemon
Grass / Tangled
493 494 495

493 494 495

NOMENCLATURE OF
IMPORTANT ALDEHYDES IMPORTANT ALDEHYDES
KETONES
Paraldehyde Metaldehyde IUPAC: Parent chain has the ketone
trimer of acetaldehyde pesticide against snails, group (given the lower number) Change
CNS depressant slugs -e to -one
hypnotic cyclic tetramer of Derived Name: Alkyl name + ketone
anti-convulsant acetaldehyde Examples: CH3COCH3
sedative IUPAC Name: ?
Derived Name: ?
Use: ?
496 497 498

496 497 498

IMPORTANT KETONES IMPORTANT KETONES IMPORTANT KETONES
Acetone Acetone Methylethyl Ketone (MEK)
Muscone Solvent; nail polish remover Solvent for paints, lacquers & plastics
Acetophenone
Testosterone Muscone
Hypnotic agent; replaced by new drugs
Methylethyl Ketone (MEK) Odorous component of musk deer, a
sex attractant; enhance fragrance Chloroacetophenone
Acetophenone
(fixative agent); expensive Lachrymator & used as tear gas
Chloroacetophenone
Testosterone Fructose
Fructose “Fruit sugar”; High Fructose Corn syrup
499
Male sex hormone
500 501

499 500 501

TEST FOR ALDEHYDE TEST FOR ALDEHYDES TEST FOR KETONES

AND KETONE IODOFORM TEST
Tollen’s Test (_______)
based on the ability of silver ions to
oxidise ALDEHYDES
(+) result: _____________
Fehling’s Test & Benedict’s Test
The ALDEHYDE group is [o] to an
acid by Cu2+ ions
(+) result: _____________
502 503 504

502 503 504

CARBOXYLIC ACID AND
DERIVATIVES
Contains _______ group
R-COOH
Ar-COOH
Nomenclature
IUPAC: Carboxyl group is ALWAYS C#1.
Change -e to -oic acid
Methane ➜ Methanoic acid
Common Name: Acetic Acid, Formic Acid
Use of Gk. prefixes (𝛂- carbon next to
COOH, β, Gamma, Epsilon)
505
CARBOXYLIC ACID AND CLASSIFICATION OF
DERIVATIVES CARBOXYLIC ACIDS
Benzoic Acid - anti-fungal agent Saturated COOH/ Monocarboxylic acid
(Whitefield’s ointment); Na salt is used Single bond, one carboxylic acid group
Unsaturated carboxylic acids/ Mono-
as preservative
carboxylic acid
GHB (Liquid Ecstasy) - “Rave” / party
Double bond/s, one carboxylic acid
drugs. “Date rape” drug
Beta-Hydroxybutyric Acid - ketone Examples:
Oleic acid
bodies
PABA - sunblock; precursor to Vit B9 Linoleic acid (________)
GABA - Major inhibitory NT Linolenic acid (________)
506
Arachidonic acid507
(found in animal fat)

505 506 507

LINOLEIC & CLASSIFICATION OF

LINOLENIC ACID # of
CARBON
NAME CARBOXYLIC ACIDS
1 Formic acid # of
NAME
Aromatic carboxylic acid
CARBON
2 Acetic acid e.g. Benzoic acid; o-toluic acid; m-
3 Propionic acid 10 Capric acid toluic acid; p-toluic acid
4 Butyric acid 12 Lauric acid Dicarboxylic acid
5 Valeric acid 14 Myristic acid 2 carboxyl groups
6 Caproic acid 16 Palmitic acid Simplest Dicarboxylic acid is ______
7 Enanthoic acid 18 Stearic acid
8 Caprylic acid Arachidonic
20
9 Pelargonic acid
508
acid 509 510

508 509 510

OH MY SUCH GOOD APPLE IMPORTANT CARBOXYLIC IMPORTANT CARBOXYLIC
PIE SWEET AS SUGAR ACIDS ACIDS
# of NAME
CARBON Formic Acid Formic Acid - Toxic (Blindness); gives
2 Oxalic acid Acetic Acid characteristic sting of ants
3 Malonic acid Propionic Acid Acetic Acid - Acetum (L.); sour taste
4 Succinic acid
Butyric Acid of vinegar
5 Glutaric acid
6 Adipic acid
Oxalic Acid Propionic Acid - natural anti-fungal
7 Pimelic acid Azelaic Acid in sweat
8 Suberic acid Undecylenic Acid Butyric Acid - gives rancid butter its
9 Azelaic acid Acetylsalicylic Acid putrid smell
10 Sebacic
511
acid 512 513

511 512 513

IMPORTANT CARBOXYLIC IMPORTANT CARBOXYLIC

ACIDS ACIDS
Oxalic Acid - stain remover (KMnO4) in Citric Acid - found in citrus fruits Hydroxy acids
clothing; affinity for Ca2+ (Toxic) Tartaric Acid - found in grapes, by- Examples:
Azelaic Acid - anti-acne principle of Castor product of wine production Lactic acid
Oil Salicylic acid
Lactic Acid - found in sour milk
Undecylenic Acid - anti-fungal principle of Tartaric acid
Castor oil Salicylic Acid - anti-fungal (Topical)
(Whitfield’s ointment), keratolytic Malic acid
Acetylsalicylic Acid - aka? Analgesic,
agent (Topical), Anti-RA (PO: Anti- Amino acids
Antipyretic, Anti-platelet A/E: GI bleeding,
Haemorrhage Inflammatory) examples: Essential amino acids
514 515 516

514 515 516

 CARBOXYLIC ACID CARBOXYLIC ACID LACTONE DRUGS
DERIVATIVES DERIVATIVES
ESTER ESTER
RCOOR Important Reaction
Nomenclature Esterification: RCOOH and ROH
IUPAC: Use the alkyl or aryl portion Hydrolysis: Reverse of
of the alcohol name as the first
esterification
name. Change -ic to -oate
Characteristic: Pleasant odor;
Ethanoic acid + Methanol ➜ Methyl
Methanoate Upon hydrolysis, acidic &
Salicylic acid + Methanol ➜ _______ unpleasant odor
517 518 519

517 518 519

CARBOXYLIC ACID
DERIVATIVES
Anhydrides Amine
Reaction between 2 COOH Organic compound that are derived from
Anhydride: “Without Water”
eg. Acetic Anhydride
ORGANIC NITROGEN ammonia
Order of Basicity: Secondary > Tertiary
Amides COMPOUNDS: AMINES > Primary
R-CO-NH2 (carbonyl group bonded to Quaternary - NOT basic, no lone pair
amine)
AND AMIDES electron; positively charged
e.g. Aniline, Epinephrine, Atropine,
Urea
Nicotine, Saccharin
Penicillin (B-Lactam Ring) Amides
Acetaminophen(Tylenol®):
520 (✕)NSAID 521 522

520 521 522

 ALKALOIDS AMINE NOMENCLATURE
Naturally Occurring Amines Primary: alkanamines
Ethylamine, Isopropylamine,
Cyclohexylamine
Aromatic amines
Aniline, Metachloroaniline
Secondary & Tertiary

523 524 525

523 524 525

ORGANIC MEDICINAL ORGANIC MEDICINAL

CHEMISTRY
Drug Discovery & Development
Purpose: To discover & develop new
drugs or improve pre-existing drug
CHEMISTRY
The discipline devoted to the
discovery and development of new
agents for treating diseases
Drug Discovery & Development

Purpose: To discover & develop new

drugs or improve pre-existing drug

526 527 528

526 527 528

 QUANTITATIVE-STRUCTURE
ACTIVITY RELATIONSHIP (QSAR)
Relationship bet. the quantity of the
drug that binds to the active site, its drug
structure, and pharmacologic activity
QSAR can be used to:
Predict the design of new
compounds, and
To reduce the types of chemical
process involved in the biological
activity
529
Organic Medicinal Organic Medicinal
Drug
Chemistry Chemistry
The practice of medicinal chemistry devoted to
An agent intended for use in the
diagnosis, mitigation, cure, or the discovery & development of new drugs
prevention of disease in humans or in Drug
An agent intended for use in the diagnosis,
other animals mitigation, cure, or prevention of disease in
Receptor humans or in other animals
A substance to w/c a drug needs to Receptor
interact w/ to elicit a pharmacological A substance to w/c a drug needs to interact w/
response to elicit a pharmacological response
Interaction leads to pharmacologic
The interaction of a drug to a specific receptor
may induce or inhibit a certain pharmacologic
effect 530 effect 531

529 530 531

Organic Medicinal
Chemistry
Affinity
Ability of a drug to bind to the
receptor
Four Fundamental
Intrinsic activity Pathways (ADME)
Ability of a drug to exert a
pharmacologic action

532 533

532 533 534

 Pathway Primary Organ / Major Site
Absorption DRUG ABSORPTION
• aka the transfer of a drug from its site of
administration to the systemic circulation (or
Absorption The transfer of a drug from its site of to the bloodstream)
administration to the systemic ★Chemical structure
Distribution circulation (or to the bloodstream) ★Variation in particle size
★Nature of the crystal form
Metabolism Site of ★Type
Blood Supply of the tablet coating
Applicatio
★Blood flow to the absorption site
Excretion
★Total surface area available for absorption surface
★Contact time at the absorption site
536 537

535 536 537

DRUG DRUG
DRUG ABSORPTION
DISTRIBUTION DISTRIBUTION
• the process by which a drug reversibly leaves
• Bioavailability the blood stream and enters the interstitium
(extracellular fluid) and/or the cell of the
• May limit access to certain body
✦ thefraction of administered drug
tissues compartment (e.g. placenta, bone,
that reaches the systemic circulation
PLASMA PROTEIN BINDING fats)
in a chemically unchanged form •

✦ Rate and extent of absorption

• Serve as a reservoir • PROLONGS drug duration of
!ALBUMIN: binds acidic drugs action
✦ Oral vs Intravenous
!α-acid glycoprotein: binds basic drugs

538 539 540

538 539 540

 DRUG METABOLISM Metabolism
aka Biotransformation
• to supply energy for body functions Formerly: Detoxification
and maintenance Major Organ: Liver
METABOLISM • plays central role in the elimination of Objective: Convert drugs into forms
the drugs and xenobiotics (foreign which are:
compounds) Less active or inactive
• converts drug into polar, water soluble, Less toxic or non-toxic
ionized form that are readily excreted Polar or water-soluble (to be easily
excreted)
541 542 543

541 542 543

Exemption to Metabolism Exemption to Metabolism Exemption to Metabolism

1. Prodrugs
An inactive parent drug that has
to be metabolised to the active
form
e.g. Enalapril ➜ Enalaprilat
Responsible for the
antihypertensive effect
Clopidogrel, Allopurinol
544
2. Active drug w/ active metabolites 3. Nontoxic drug metabolised to a
Diazepam (active) ➜ N- toxic drug
desmethyldiazepam Acetaminophen (non-toxic) ➜
(Nordiazepam) ➜ active Enzyme: CYP1A2
➜ Oxazepam (active) ➜ N-AcetylParabenzoQuinone
➜ Glucuronide (inactive) Imine (NAPQI) ➜ Hepatotoxic
Peripherally prolongs half-life Conjugation with GSH ➜
of drug Mercapturic acid form
(inactive/nontoxic)
545 546

544 545 546


Examples of Prodrugs
__________________➜ Chloramphenicol
Levodopa ➜ _____________
___________ ➜ Monoacetylmorphine ➜
Morphine
Prednisone ➜ _____________
___________ ➜ Morphine
Enalapril ➜ ______________
____________➜ Salicylic acid (Anti-RA)
547
Important Metabolising
Examples of Prodrugs
Organs
Liver - most important
GIT (Stomach, intestines) - MAO & COMT
Blood (plasma: portal, systemic) - Esterases /
Cholinesterase / pseudocholinesterase
Kidneys
Imipenem (dihydropeptidase enzyme in
kidney)
Cilastatin (Dihydropeptidase inhibitor)
Lungs, Placenta, Aqueous humor of eyes
548 549

547 548 549

First-Pass Effect /
Liver
Metabolism
Hepatic microsomal enzyme system aka: Pre-Systemic Metabolism

e.g. Cytochrome P450 superfamily
has several isoenzymes
CYP1A2, CYP2A6, CYP2C9,
CYP2D6, CYP2E1, CYP3A4
550
phenomenon where drugs are PHASES OF DRUG
metabolised initially following
absorption but before reaching the METABOLISM
systemic circulation
Significance - FPE can dec. oral BA of a
drug
551

550 551 552

 Phase I Metabolism Phase I Enzyme Substrate Phase I Metabolism
aka Functionalization phase Oxidation - ______________➜ Most
Oxidation Dominant reaction
Non-synthetic reactions (addition or Reduction - reductase
unmasking of a functional group) e.g. Chloral hydrate ➜
Reduction
______BEQ______ (CNS Depressant)
Hydrolysis - Hydrolases
Hydrolysis

553 554 555

553 554 555

Phase I Metabolism Phase I Metabolism Phase I Metabolism

Oxidative reactions: Reduction reactions: Hydrolysis reactions:
1. CYP - mediated 1. Nitro reduction ➜ Esters
e.g. CYP-450 mixed oxidase system Chloramphenicol Amides
aka? 2. Carbonyl reduction - Naloxone B-lactams
2. CYP - Independent (DOC for Opioid toxicity);
Monoamine oxidases (MAO), Methadone
Alcohol & Aldehyde Dehydrogenase, 3. Azo Dye Reduction - Prontosil
Flavin Mono-oxygenase
556 557 558

556 557 558

Phase II Metabolism
Phase II Enzyme Co-Substrate Substrate
Phase I Metabolism
Glucoronidation CYP FAMILIES SUBSTRATES
aka Conjugation reactions / Acetaminophen, Theophylline,
Synthetic phase or reactions Acetylation CYP1A2 Caffeine

Glycine/Glutamate
CYP2C19 Propranolol, PPI, Clopidogrel
Conjugation

Involves addition of a POLAR

CYP2C9 Phenytoin, Sulfonylureas, S-Warfarin
Glutathione
conjugate Conjugation Codeine, Dextromethorphan, Most
CYP2D6 antidepressant & anti-psychotics,
Methylation Debrisoquin (Most studied)
Macrolide, Amiodarone, CCB, Azole
Sulfation CYP3A4 Anti-fungals, Proteases inhibitor,
559 560 561
Antihistamine

559 560 561

Phase II Metabolism Glucuronidation Phase II Metabolism

Major/Dominant conjugation reaction
Glucuronidation among adults Acetylation
Enzyme involved: Glucuronosyl Acyl- Enzyme: NAT / N-acetyltransferase
Acetylation Transferase (poorly expressed in < 28 days) Drugs:
Glutathione conjugation Endogenous substrate: UDP-Glucuronic
Acid (UDP-GA)
S
Glycine & Glutamate H
a. ____BEQ_____ - DOC for typhoid fever
conjugation b. ______________ I
Sulfation c. Morphine P
Methylation Convulsant metabolite: ______BEQ______
Analgesic metabolite: ______BEQ______
562 563 564

562 563 564

Phase II Metabolism
Glutathione conjugation
Scavenger for ____________ ➜
electrophilic in nature
Detoxification of ROS
Anti-oxidant for NAPQI toxicity:
____________ ➜ Replenishes
glutathione in the body
Toxic APAP dose: ______ / day
565
Phase II Metabolism
Glycine conjugation
Most common endogenous amine
for conjugation with organic acids
Reduced in infants and the elderly
Glutamine conjugation
Enzymes localised in liver &
kidneys
566
Phase II Metabolism
Glycine / Glutamine conjugation
Amino acid conjugation
____________ Moieties
e.g. Benzoic acid + Glycine ➜
______BEQ_______
e.g. Salicylic acid + Glycine ➜
_________________
567

565 566 567

Chemotherapy
Phase II Metabolism Phase II Metabolism
Sulfate conjugation
Methylation Anti-Infective Anti-Neoplastic
Sulfate pool ➜ limited, easily
depleted Minor pathway
Enzyme: Methyltransferases Local Anti- Systemic Bactericidal
Dominant phase II in newborn
(easily saturated) e.g. COMT - Catecholamines Infective Anti-
Antiseptic • Antibiotic Bacteriostatic
Enzyme involved: _____________ Endogenous substrate: SAM Disinfectant • Antibacterial
Endogenous substrate: PAPS • Anti-TB
example: • Anti-Fungal
• Anti-Helminth
Paracetamol/Acetaminophen • Anti-Protozoal
570

Phenol 568 569

• Anti-Viral

568 569 570


LOCAL ANTI-INFECTIVES
571
571
LOCAL ANTI-INFECTIVES
I. ALCOHOL & RELATED COMPOUNDS
II. PHENOLS & DERIVATIVES
III. OXIDIZING AGENTS
IV. HALOGEN-CONTAINING
V. CATIONIC SURFACTANTS
VI. DYES
VII. HEAVY METALS
VIII. PRESERVATIVES
574
574
ANTI-INFECTIVES VS
GERMICIDES
Anti-infectives: are substances that
destroy or kill microorganisms
that cause infection.
Germicides: are compounds that
is used locally to kill
microorganism but not spores
aka “Local Anti-infectives”
572
572
ALCOHOL & RELATED
I. ALCOHOL & RELATED
COMPOUNDS
575
575
ANTISEPTIC VS
DISINFECTANT
Compounds that kill (Bactericidal)
or prevent the growth
(Bacteriostatic) of microbes when
applied to living tissues
Compounds that prevent infection
by destruction of pathogenic
organism when applied to
inanimate objects
573
573
COMPOUNDS
SAR: ___ #C, ___ antibacterial
property (limit up to ___ C only)
Beyond limit, #C, ➡water-
solubility, ➡potency
Branching: ___ antibacterial
property (1°>2°>3°)
except: ______
MOA: Protein denaturation
576
576
 1. ALCOHOL, USP
aka Ethanol, Grain Alcohol, Neutral
spirit, Wine Spirit, ______________)
Source: Fermentation of Grapes;
hydration of ethene
Absolute Alcohol - ____ %
Rubbing Alcohol - ____ %
Diluted Alcohol - ____ %
Dehydrated Alcohol - ____ %
577
1. ALCOHOL, USP
Alcohol in Pharmacy will always
pertain to ETHANOL, is a clear,
colorless, volatile liquid with a
BURNING taste and a
characteristic door
MOST WIDELY ABUSED
RECREATIONAL DRUG
578
DENATURED ALCOHOL
Denatured Alcohol - “Unfit for use”
Completely Denatured Alcohol -
Methanol + Ethanol + Benzene
Specially Denatured Alcohol -
Ethanol that is treated w/ 1 or more
substance to be used in tinctures,
MW, lotions and extraction purposes.
579

577 578 579

USES OF ALCOHOL 2. ETHYLENE OXIDE

Antiseptic 3. FORMALDEHYDE
Preservative EXTERNAL USE (C2H4O)
Mild counterirritant (Refrigerant/ Epoxide (Oxirane®, Carboxide®) Formalin (Thermodent®)
Coolant) Gas Sterilant: For Heat-labile Contains ___% of HCHO with
Solvent medicinal equipment and methanol added (Retard
Rubefacient pharmaceuticals that cannot be Polymerization in carcass)
Astringent RUBBING ALCOHOL autoclaved Use: Disinfectant, Embalming
Mild Local Anaesthetic MOA: Non-selective Alkylation of fluid, Tooth desensitising agent
Analgesic in neuralgias functional groups in Nucleic acid & MOA: Alkylation (Non-specific) of
Mild Sedative
proteins functional groups to form
Weak Vasodilator INTERNAL USE
VERY TOXIC & CARCINOGENIC carbinol derivatives
Carminative 580 581 582

580 581 582

4. GLUTARALDEHDYE
Cidex®
Glutaryl Disinfecting solution
For equipments and instruments
that cannot be sterilised
Ortho-phthalaldehyde (OPA)
Less irritating & more effective
than Glutaraldehyde
BEQ
Phenol Coefficient is the ratio of a
dilution of a given test disinfectant to
II. PHENOLS & the dilution of phenol required to kill
a given strain of _________________.
DERIVATIVES A. Pseudomonas aeruginosa
B. Mycobacterium leprae
C. Bacillus subtilis
D. Salmonella typhi

583 584 585

583 584 585

PHENOLS & PHENOLS & PHENOLS &

DERIVATIVES
Phenol - aka?
Discovered by? used as?
_____ ________ - Ratio of the
dilution of disinfectant to 5% ______
required to kill a strain of ______
_____. (a measure of disinfectant
potency)
________: Antibacterial property
DERIVATIVES
SAR: Substitution of alkyl, aryl,
halogen groups at the para position
increase antibacterial property
Straight chain alkyl > Branched
chain alkyl group
MOA: Protein precipitant (Low
conc.); Bacterial cell membrane
lysis (High conc.)
DERIVATIVES
Liquefied Phenol - ____ % water
Thymol(m-cresol) - fungicidal for
Tinea or _____ worm infections
Cresol or aka? (Lysol®) - Disinfectant
Resorcinol - Keratolytic for warts &
callouses; antiseptic
Eugenol - dentrifice, relieves
toothache

586 587 588

586 587 588

 BISPHENOLS OXIDIZING AGENTS
MOA: Injury to cell membrane ➜
leakage of cell contents (Cell lysis)
Derivatives of phenol that contain 2 MOA:
phenolic groups connected by a A. Liberation of nascent oxygen
bridge (peroxides)
1. Hexachlorophene (?®) - more potent III. OXIDIZING AGENTS H2O2 ➜ H2O + O
than monophenolic; easily absorbed Active against anaerobic organism
onto skin & sebaceous glands For cleaning contaminated wounds
2. Triclosan (?®) Poor penetration & transient action
S/E: Neurologic toxicity in infants & B. Denaturation of proteins
burn patients (permanganates)
589 590 591

589 590 591

OXIDIZING AGENTS
1. Carbamide peroxide ➜ Urea + H2O2
Use: Antiseptic, Disinfectant
2. Hydrous Benzoyl peroxide (Panoxyl®)
Use: Keratogenic & Keratolytic in
acne
MOA: induce proliferation of
epithelial cells ➜ sloughing off
( Cell Turnover)
HALOGENATED
AGENTS
Salt-formers
Strong Oxidising agents
A. Chlorine - water
IV. HALOGEN- Universal disinfectant (H2O disinfectant)
e.g. NaOCl (Zonrox®/Chlorox®)
CONTAINING Use: Bleaching agent, Disinfectant
Halazone - disinfectant for drinking H2O
MOA: Chlorination of amide moiety
in protein& oxidation of -SH group
(Irreversible bond)

592 593 594

592 593 594

 HALOGENATED HALOGENATED HALOGENATED
AGENTS AGENTS AGENTS
B. Iodine
1. Calcium Hypochlorite (aka?) MOA: I2 inactivates proteins by B. Iodine
2. Sodium Hypochlorite (BN?®) iodination, oxidation of -SH groups Iodophores - Non-Ionic surfactant
3. Chlorine Dioxide Bactericidal complexes of I2
4. Chloramines Iodine Tincture - __% I2 in __% e.g. Povidone-Iodine (?®)
5. Chlor-Floc® - aka? diluted alcohol with NaI Use of PVP / Polyvinylpyrollidone:
Iodine Solution - __% I2 in H2O w/ Solubilizer of Iodine
NaI Advantage over NaI & KI: Non-
Strong Iodine Solution / Lugol’s
staining, washable, less I2 volatility
Solution - __% I2 with KI
595 596 597

595 596 597

CATIONIC
BIGUANIDES
SURFACTANTS (Quats)
Quaternary (4°) Ammonium MOA: Injury to cell membrane ➜
Compounds leakage of cell contents (Cell lysis)
V. CATIONIC MOA: Surfactant - dissolves cell Broad spectrum of activity
1. Chlorhexidine (?®) - combined w/
SURFACTANTS membrane ➜ Cell lysis detergents, used for hand scrubs
1. Benzalkonium chloride (?®) & preoperative skin preparations
2. Methylbenzethonium chloride 2. Alexidine - more rapid action
(?®) 3. Hexetidine (?®)
3. Cetylpyridinium chloride (?®)
598 599 600

598 599 600

 1. GENTIAN VIOLET
aka Crystal Violet / Methyl Violet
Use: vaginal suppository for
VI. DYES treatment of yeast infection &
anti-helminthic for strongyloides
and oxyuriasis
Strongyloides stercuralis - feet
penetration
2. BASIC FUCHSIN
ingredient of Carbolfuchsin
(aka?)
Use: treatment of fungal
infections, ringworm and
athlete’s foot

601 602 603

601 602 603

3. METHYLENE BLUE 3. METHYLENE BLUE

Antidote for CN- poisoning
along w/ NaNO2 & Na2S2O4
Antidote for Methemoglobinemia
Counterstain in Acid-Fast
Staining
A/E: Blue-green stools and urine
604
In high concentrations, it
promotes the conversion of
hemoglobin to Methemoglobin,
which because of its high affinity VII. HEAVY METALS
for Cyanide ion diverts it from
inactivating Cytochrome oxidase
In low concentrations, it is used
to treat drug-induced
methemoglobinemia
605 606

604 605 606

 HEAVY METALS
MOA: Protein Denaturation
Oligodynamic action - ability of
very small amounts of heavy
metals to exert antimicrobial
activity.
607
1. SILVER
Antiseptic (__% AgNO3 solution)
OLD DOC for Gonorrhoea
Ophthalmia Neonatorum (NEW
DOC?)
Ag Sulfadiazene (Brand Name?)
DOC for burn wound to prevent
infection or sepsis
Topical cream
608
1. SILVER
Antiseptic (__% AgNO3 solution)
OLD DOC for Gonorrhoea
Ophthalmia Neonatorum (NEW
DOC?)
Ag Sulfadiazene (Brand Name?)
DOC for burn wound to prevent
infection or sepsis
Topical cream
609

607 608 609

2. MERCURY 3. COPPER 4. ZINC

Mercuric Chloride (aka?)
Thimerosal (Old Merthiolate®)
New Merthiolate® - ?
Limited use because of their
toxicity, corrosiveness &
ineffectiveness in organic matter
610
Copper sulfate (aka?) Zinc Chloride
Algicide for reservoirs, stock Common ingredient in
ponds, swimming pools, fish mouthwash (Old Astring-O-Sol
tanks formula)
Bordeaux mixture ➜ fungicide in Zinc Pyrithrone
plants Ingredient in anti-dandruff
Xgel® - relatively new hand shampoo
sanitiser that contains copper
611 612

610 611 612

 PRESERVATIVES
Added to an initially clean or
sterile env’t or object to preserve
or prevent microbial
VII. PRESERVATIVES contamination
SAR: Molecular Weight:
Preservative action
PARABENS
Esters of p-hydroxybenzoic acid
Anti fungal:
Methylparaben - For?
Propylparaben - For?
Butylparaben - not used
anymore! why?

613 614 615

613 614 615

OTHER OTHER
PRESERVATIVES PRESERVATIVES
Chlorobutanol
Bacteriostatic agent for injection,
Benzoic Acid
Low pH (optimum)
ophthalmic, intranasal administration
Benzyl Alcohol Sorbic Acid ANTI-TUBERCULOSIS
Preservative in vial of injectable drugs
In ointment & lotions as antiseptic in
Anti-fungal for food & syrups DRUGS
treatment of various pruritic
infections

616 617 618

616 617 618

 TUBERCULOSIS DOTS 1ST LINE AGENTS
Pulmonary Tuberculosis ➜ aka? Preferred core Remember this Mnemonic:
Causative agent: ? management strategy for P - yrazinamide (Z)
Gram Staining: appears as “ghost” ➜ TB treatment
impervious to GRAM staining (even R - rifampicin (R)
Ensure patient adherence I - soniazid (H)
though it has cell wall)
Cell Wall Anatomy:
to therapy E - thambutol (E)
Contains peptidoglycan (murein) but How: A trained designated
St - reptomycin (S) - (×)
60% of the cell wall is a complex lipid person watches a patient
swallow each dose of anti- RIPES
Complex lipid: MYCOLIC ACID, cord
factor & wax D TB drugs and documents it
619 620 621

619 620 621

1ST LINE: ISONIAZID

1ST LINE: RIFAMPICIN 1ST LINE: RIFAMPICIN
(H)
Isolated from: ?
Semi-synthetic derivative of A/E: Imparts a harmless orange aka Isonicotinic Acid Hydrazide,
Rifamycin to orange-red color to urine, Isonicotyl Hydrazide
MOA: Inhibits bacterial DNA- sweat, tears & contact lenses due Most active drug for TB
dependent RNA Polymerase ➜ (×) to its intense red color synthetic agent w/ a structural
RNA synthesis (transcription) Less common A/E: similarity to that of pyridoxine/
Used in prophylaxis of Neisseriae Thrombocytopenia vitamin?
meningitidis Jaundice A/E: Peripheral neuropathy /
Enzyme Inducer Hepatitis neuritis (Antidote?)
622 623 624

622 623 624

1ST LINE: ISONIAZID
(H)
MOA: inhibit synthesis of
MYCOLIC acid (major
component of M. tuberculosis
cell wall)
Other A/E: GI disturbance
(constipation & appetite loss) &
Hepatotoxicity
Safest TB drug in __________
625
625
1ST LINE:
PYRAZINAMIDE (Z)
Prodrug: Pyrazinamide ➜
Pyrazinoic acid (active)
MOA: inhibit incorporation of
MYCOLIC acid in cell wall
A/E: MOST Hepatotoxic of all TB
drugs; Hyperuricemia
1st line in short-term treatment
of TB
628
628
1ST LINE: 1ST LINE:
ETHAMBUTOL (E) ETHAMBUTOL (E)
MOA: inhibit incorporation of MYCOLIC A/E: Optic Neuritis /
acid in cell wall (inhibition of arabinosyl Retrobulbar neuritis
transferase enzymes that are involved in
biosynthesis of arabinogalactan portion Loss of visual acuity
of the cell wall) Red-Green color blindness
A/E: Optic Neuritis / Retrobulbar Requires periodic visual acuity
neuritis / Red-Green color blindness testing (Snellen Chart)
Not for Children whose clarity or
sharpness of vision cannot be
monitored.
626 627
626 627
1ST LINE: 1ST LINE:
PYRAZINAMIDE (Z) STREPTOMYCIN (S)
MOA:
PZA is pH dependent: BACTERICIDAL
4th drug in combination with H,
at acidic pH (5.5) & inactive at pH 7.0 R, & Z in patients w/ high risk
converted to it active form Pyrazinoic acid for drug resistance
(POA) by the mycobacterial enzyme Used in txt of MDR TB
Pyrazinamidase Most Vestibulotoxic
POA lowers the intracellular pH to a Aminoglycoside
suboptimal level w/c inactivates a vital
target enzyme e.g. Fatty Acid Synthase ➜ 1st Antibiotic effective in the txt
disruptiong plasma membrane & energy of TB (Discovered by?)
metabolism 629 630
629 630
 1ST LINE(?): 2ND LINE AGENTS 2ND LINE: P-AMINO
STREPTOMYCIN (S) Take note of these drugs! SALYCYLIC ACID (PAS)
Para - amino salicylic acid (PAS)
Source: ? E - thionamide Structural analogue of
MOA: irreversible inhibition of C - ycloserine p-aminobenzoic acid
mycobacterial protein synthesis C - apreomycin (PABA)
by binding to 30S ribosomal C - lofazimine (Last line drug MOA: Folate synthesis
subunit for MDR tuberculosis) antagonist that
Bacteriostatic Aminoglycoside (Amikacin/ interferes w/ the
Aminoglycoside antibiotic Kanamycin) incorporation of PABA
A/E? Respiratory Fluoroquinolones into folic acid
631 632 633

631 632 633

2ND LINE: P-AMINO 2ND LINE:

2ND LINE: CYCLOSERINE
SALYCYLIC ACID (PAS) ETHIONAMIDE
Derivatives of Isonicotinic acid & Isolated from the fermentation beer of 3
MOA: Inhibits INH different streptomyces species.
Folate Synthesis MOA: Inhibition of O2- Streptomyces orchidaceus
(Anti-metabolite) dependent mycolic acid synthesis Streptomyces garyphalus
A/E: Streptomyces lavendulus
To generate a -OH GI disturbances: N&V & MOA: acts through a competitive inhibition
dihydrofolate intense gastric irritation of the D-alanine that is involved in
antimetabolite, w/c Neurological disturbances: bacterial cell wall synthesis
in turn inhibits confusion, peripheral Toxicity: Dizziness, confusion, irritability,
DHFR enzyme neuropathy, psychosis & psychotic behavioural changes & suicidal
activity seizures tendency.
634 635 636

634 635 636

 2ND LINE: CAPREOMYCIN
2ND LINE: CYCLOSERINE
& VIOMYCIN
MOA: disrupts cell wall synthesis by Capreomycin
binding & inhibiting 2 key enzymes Isolated from S. capreolus
responsible for cross-linking of A/E: Ototoxic & Nephrotoxic
peptidoglycan: D-alanine racemase &
Resembles viomycin in activity
D-alanyl-D-alanine synthetase
Viomycin
D-alanine racemase: L-alanine ➜ D- MDR strains of TB
alanine No longer available
D-alanyl-D-alanine synthetase: D- 1st tuberactinomycin drug
alanyl-D-alanine peptides Isolated from S. puniceus
637 638
2ND LINE: AMIKACIN &
KANAMYCIN
It is considered in the treatment of
MDR tuberculosis after
streptomycin and capreomycin
Disadvantage: VERY EXPENSIVE
Cross-Resistance
If the organism is Kanamycin &
capreomycin-resistant, often it is
amikacin-resistant
Most Ototoxic aminoglycoside
639

637 638 639

2ND LINE: LAST LINE:

FLUOROQUINOLONE
Typical Mycobacteria:
Ofloxacin >> Ciprofloxacin
Atypical Mycobacteria:
Ciprofloxacin >> Ofloxacin
MOA:
Inhibits Topoisomerase II
Inhibits Topoisomerase IV
640
CLOFAZIMINE
Activity:
M. leprae >>> M. tuberculosis
Used as an agent of LAST-RESORT
for MULTI-DRUG RESISTANT TB ANTI-LEPROSY AGENTS
A/E(Most Common): Red-Brown
discolouration of the skin
641 642

640 641 642

 LEPROSY
aka?
Chronic infectious disease
Causative Agent:?
Types:
Tuberculoid Leprosy - (+) Lepromin
Skin Test; Intact cell-mediated
immunity; relative paucity of bacilli;
Granuloma Formation
Lepromatous Leprosy - ( - ) Lepromin
Skin Test; Depressed cell-mediated
immunity; numerous bacilli; NO
Granulomas
643
643
ACEDAPSONE
Long-acting IM repository form
of dapsone w/ half-life of 46
hours
It may prove useful in leprosy
patients who cannot tolerate long-
term oral dapsone therapy
646
646
SULFONES
MOA: similar to sulfonamides;
Folate synthesis inhibitor
DAPSONE / DDS
Used to treat leprosy
DOC for Leprosy
IUPAC: 4-[(4-
aminobenzene)sulfonyl] aniline
Diaminodiphenylsulfone
644
644
CLOFAZIMINE
Phenazine Dye
MOA: Unknown but involves
mycobacterial DNA binding
Treat sulfone-resistant leprosy or
to patients who are intolerant to
sulfones
Advantage: Has anti-
inflammatory effect w/c prevents
Erythema Nodosum Leprosum
647
647
SULFONES & DAPSONE
Structural analogues of PABA &
competitive inhibitors of folic acid
synthesis
Dapsone (Avlosulfon)
Most widely used sulfone for long-
term Leprosy treatment
Indicated for PCP in AIDS patient
who are allergic / intolerant to
SMZ-TMP (DOC for PCP)
A/E: Erythema Nodosum Leprosum
645
645
CLOFAZIMINE
For emphasis: Clofazimine is the
last line drug for MDR TB
MOST COMMON ADR: Red-
Brown skin discolouration,
especially in light-skinned
persons
648
648
 ETHIONAMIDE & ANTI-SCABIES & ANTI-
PROTHIONAMIDE PEDICULAR AGENTS
Alternatives to clofazimine in the Scabicides - kill mite, Sarcoptes
treatment of MDR leprosy
scabei, thrives under poor
ANTI-SCABIES & ANTI- personal hygiene
PEDICULAR AGENTS
Pediculicides - kill lice

649 650 651

649 650 651

SCABICIDES PEDICULICIDE ANTI-SCABIES & ANTI-

Permethrin Pediculosis - used to eliminate head,
PEDICULAR AGENTS
Benzyl Benzoate body, and genital / crab lice Malathion
Obtained from Peru balsam & Pyrethrin Permethrin (New Kwell®)
other resins Derived from Chrysanthemum For head lice only
plants Lindane (Old Kwell®)
Immediate relief from itching
MOA: Nerve poisoning Gamma-Benzene
Crotamiton Piperonyl Butoxide
Ivermectin Hexachloride
enhances the pediculicide effects
ADR: Neurotoxicity
of pyrethrins
652 653 654

652 653 654

 ANTI-FUNGAL AGENT ANTI-FUNGAL AGENT
Cell Wall/Glucan CELL WALL/GLUCAN Synthesis
Synthesis Inhibitors
Inhibitors
Cell Membrane
(Ergosterol) Echinochandins
1. Polyene e.g. Caspofungin, Micafungin,
ANTI-FUNGAL AGENTS 2. Azole
3. Allylamine
Anidulafungin
MOA: Interferes with cell wall
synthesis/permeability via irreversible
Nuclear Division
inhibition of β-(1,3)-D-Glucan
/Anti-Mitotic synthesis effective against most
species of Candida but NOT
Nucleic Acid Synthesis Cryptococcus
655 656 657

655 656 657

ANTI-FUNGAL AGENT ANTI-FUNGAL AGENT ANTI-FUNGAL AGENT

Disruption of β-(1,3)-D-Glucan
synthesis leads to reduced cell wall
integrity, cell rupture and death
658
AZOLES Ketoconazole (Nizoral®)
only administered orally for systemic
MOA: interacts with C-14 𝛂-
infection
demethylase to block inhibits CYP450 (Hepatotoxic) and
demethylation of lanosterol to gonadal/steroid/adrenal hormone
ergosterol, the principal sterol of synthesis
fungal membranes. This inhibition has endocrine effects: gynecosmastia,
decreased libido, impotence, menstrual
disrupts membrane function & irregularities
increases permeability Itraconazole (Sporanox®)
FUNGI_______ it lacks the endocrinologic effects of
659 ketoconazole (MOST 660 POTENT AZOLE)

658 659 660

 ANTI-FUNGAL AGENT
Fluconazole (Diflucan®)
■administered orally and intravenously
■it has Excellent penetrability into the
CSF (Very Lipophilic)
■Drug of Choice for cryptococcal
meningitis (Cryptococcus neoformans)
Ketoconazole, Itraconazole,
Fluconazole, Voriconazole
■for SC & Systemic mycoses
Clotrimazole, Miconazole, Econazole
■for superficial mycoses
661
661
ANTI FUNGAL ANTIBIOTICS
Polyenes
Amphotericin B (Fungizone®)
A/E:
Renal toxicity
Acute febrile reaction
Anemia
Inflammation of vein (Phlebitis)
664
664
NUCLEOSIDES ANTI FUNGAL ANTIBIOTICS
Flucytosine Polyenes
■used only in combination with Amphotericin B (Fungizone®)
Amphotericin B for the treatment of naturally occurring produced by
systemic mycoses and meningitis Streptomyces nodosus
caused by Cryptococcus neoformans MOA: binds to ergosterol present in
the cell membrane disrupting
and Candida
membrane function, allowing
electrolytes to leak out from the cell
resulting in cell death
Drug of Choice for systemic mycoses
662 663
662 663
ANTI FUNGAL ANTIBIOTICS ANTI FUNGAL ANTIBIOTICS
Nystatin Griseofulvin
Streptomyces noursei obtained from the mold
cereal like odor Penicillium griseofulvum
used for the treatment of candida
infections
MOA: interacts with the
administered as an oral agent for the microtubule within the fungus to
treatment of oral candidiasis distrupt the mitotic spindle and
negligibly absorbed from the GIT tract inhibit mitosis ( arrests cell
so adverse effects are rare division in metaphase)
Natamycin absorption is increased by fats
obtained from Streptomyces natalensis
665 666
665 666
OTHER ANTI-FUNGAL AGENT DISCOVERY OF
FATTY ACIDS
SULFONAMIDE
all fatty acids and their salts have _____?_____
fungicidal properties First synthesised by Bayer chemist
Propionic acid: present in
SYNTHETIC Josef Klarer and Fritz Mietzsch
aka “Mietzsch-Klarer” Dye
perspiration in low concentrations ANTIBACTERIAL AGENTS Chemical name:
(around 0.01%) Sulfonamidechrysoidine
Undecylenic Acid: obtained from QUINOLONES, NITROFURANS,
________ Dye a “brilliant red dye”
the destructive distillation of SULFONAMIDES which was studied by Gerhard
castor oil Domagk
667 668 669

667 668 669

SULFONAMIDES MECHANISM OF ACTION

Large group of
compounds that are
structural analogs of
PABA
They differ primarily in
the substituents on either
the amido group (SO2-NH-
R) or the amino (-NH2) of
the sulfanilamide nucleus
670
Blocks PABA incorporation;
sulfonamides inhibit the enzyme
dihydropteroate synthase, which is
necessary for PABA to be
incorporated dihydropteroic acid, an
intermediate compound in formation
of folinic acid
Selectively toxic to bacteria not
humans
671 672

670 671 672

 NOMENCLATURE OF
SULFONAMIDE
Sulfonamides is a generic term that denotes 3
different cases:
Antibacterials - aniline substituted
sulfonamides (sulfanilamide)
Prodrugs that react to generate active
sulfanilamides (Sulfasalazine, Olsalazine)
Non-aniline sulfonamides (Mafenide acetate)
Other sulfonamide:
Tolbutamide (_______)
Furosemide (_____ Diuretics)
Chlorthalidone (_______ Diuretics)
673
SULFAMETHOXAZOLE-
TRIMETHOPRIM
TRIMETHOPRIM
Structural analog of the pteridine Bactrim®, Septra®, Cotrim®,
portion of dihydrofolic acid Septrim®
(×) Dihydrofolate reductase Prophylaxis & treatment for
Pneumocystis carinii Pneumonia
*Dihydrofolate reductase is an (PCP)
enzyme that catalyses the reduction of First attack of UTI
dihydrofolic acid to tetrahydrofolic Nocardiasis
acid (active form) of folate Severe traveller’s diarrhea
674 675

673 674 675

PYRIMETHAMINE- SULFADOXINE-
MAFENIDE ACETATE
SULFADIAZINE PYRIMETHAMINE
aka? Fansidar Sulfamylon®
DOC for Toxoplasmosis Treatment of chloroquine- Prevention of infection for burn
For Leishmaniasis resistant malaria caused by patients
Problem: Crystalluria Plasmodium falciparum Effective agains Pseudomonas
Prevention: Use triple sulfas aeruginosa (frequently colonizes
(Trisulfapyrimidine) burns)

676 677 678

676 677 678


CLINICAL USES
DOC for uncomplicated Urinary Tract infection
(Bactrim®)
DOC for PCP (Bactrim®); alternative:
Pentamidine)
Prevent and treat bacterial infection in burns
(Ag SDZ & Mafenide)
Treatment of conjunctivitis & related
superficial ocular infections (Na surfacetamide)
Treatment of chloroquine-resistant malaria (in
combination w/ Quinine, pyrimethamine +
sulfadoxine(Fansidar))
679
ADVERSE EFFECTS QUINOLONES: NALIDIXIC
C•H•R•A•N•K•S ACID & FLUOROQUINOLONE
Crystalluria ➜ Bleeding & Kidney Contain a carboxylic acid moiety
obstruction in the 3-position of the basic ring
Haemolytic anemia ➜ G6PD patients
structure (the 4-quinolones)
Rashes ➜ Hypersensitivity reaction
Agranulocytosis or Thrombocytopenia (×) DNA synthesis through specific
action on DNA gyrases.
N/V
Kernicterus ➜ Toxic encephalopathy
(brain damage caused by excessive
bilirubin)
Steven-Johnson Syndrome (SJS)
680 681

679 680 681

SOME IMPORTANT GENERATIONS OF

FLUOROQUINOLONE
NOTES
have less effect on the gamma-
aminobutyric acid (GABA) receptor
sites, and have less CNS toxicity
Extreme sunlight sensitivity
(phototoxicity)
Halogenation at 8th position ➜
highest phototoxicity
Methoxy group or amino group at 5th
or 8th position ➜ lowest phototoxicity
682 683
QUINOLONE
1st: Nalidixic acid & Cinoxacin ➜
limited Gram ( - ) activity
Proteus, E. coli, Klebsiella (PEcK)
2nd: Ciprofloxacin, Lomefloxacin
Ofloxacin, Norfloxacin, Enoxacin
Most reliable activity against
Gram ( - ) organisms
Anti-Pseudomonadal property
due to piperazine moiety
684

682 683 684

 GENERATIONS OF
1ST GENERATION 2ND GENERATIONS
QUINOLONE
3rd: Sparfloxacin, Levofloxacin, Nalidixic acid Poor activity in treating
Gatifloxacin For UTI caused by community-acquired pneumonia
Proteus
4th: Alatrofloxacin, Trovafloxacin, Bacterial resistance very
(CAP) because of their poor
Moxifloxacin common especially if activity against S. pneumoniae
Greater activity against gram- taken in long period of Norfloxacin
positive organisms, such as S. time Treatment of UTI
pneumoniae, is demonstrated by Cinoxacin Single 800-mg dose for uncomplicated
UTI caused by susceptible
the 3rd & 4th generations. gram negative bacteria
gonorrhoea
685 686 687

685 686 687

2ND GENERATIONS 2ND GENERATIONS 2ND GENERATIONS

Ciprofloxacin
DOC for gastroenteritis caused by
gram ( - ) bacilli
Also for complicated & uncomplicated
UTI
+ Ceftriaxone ➜ for disseminated
Gonorrhea
+ Doxycycline ➜ Gonococcal urethritis
Postexposure treatment of anthrax
Not effective against Syphilis
688
Ofloxacin Enoxacin
Same spectrum as ciprofloxacin, Acute & Chronic UTI
but greater oral BA STD (e.g. uncomplicated
Treatment of PID, Gonococcal & gonococcal urethritis)
Chlamydia, UTI
NOT effective against Syphilis
+Doxycycline ➜ Gonnococal
urethritis (accdg to Center for
Disease Control & Prevention)
689 690

688 689 690

 2ND GENERATIONS 3RD GENERATIONS ADVERSE EFFECTS
Levofloxacin
Enantiomeric form of ofloxacin
Lomefloxacin Once daily dosing Diarrhea
One of several quinolones for Sparfloxacin Nausea & Vomiting
Higher potency against gram (+) bacteria
which once-daily dosing suffices Also impressive against gram ( - ) bacteria Headache
Most phototoxic Once-daily dosing Dizziness
For chronic bronchitis caused by Gastroenteritis & Cholecystitis Nephrotoxicity
Least phototoxic due to 5-amino group that
Moraxella catarrhalis counteracts halogen at 8th position Arthropathy (Arthro-dysgenesis)
Prophylaxis prior to Gatifloxacin Tendinitis - risk for tendon rupture
transurethral prophylaxis only available in Canada & US as ophthalmic Phototoxicity
drops
691 S/E: Serious hypoglycaemia
692 693

691 692 693

URINARY ANTISEPTICS NITROFURAZONE FURAZOLIDONE

Nitrofurans
Nitrofurantoin (Macrodantin®)
treatment and/or prophylaxis of
microbial infections, primarily
in the urinary tract
Reduction of the 5-nitro group to
the nitro anion results in
bacterial toxicity
Txt of burns or skin grafts in w/c
bactericidal contamination may
cause tissue rejection
Relatively safe topical agent, but
skin sensitisation has been
reported
used to treat diarrhea and enteritis
caused by bacteria or protozoan
infections
also used for giardiasis (due to
Giardia lamblia), though it is not a
1st line agent
can inhibit aldehyde dehydrogenase
+alcohol ➜ Disulfiram-like effect

694 695 696

694 695 696

 METHENAMINE METHENAMINE PROTOZOAL INFECTION
Disease Causative Agent
Hydrolysed at an acidic pH (6.0) to Long-term prophylactic or Amebiasis
liberate ammonia and the active suppressive therapy of recurring Trichomoniasis
alkylating agent Formaldehyde, UTIs. It is not a primary drug for Giardiasis
w/c denatures protein, and is therapy of acute infections Leishmaniasis
bactericidal +sulfonamide ➜ antagonism African
administered as a salt of either 10 to 30% decomposes in the Trypanosomiasis
mandelic (Mandelamine®) or stomach ➜ irritation! / toxic! American
hippuric (Hiprex®, Urex®) acid Recommendation: Prepare the Trypanosomiasis
drug as ________________ Toxoplasmosis
697 698
Malaria 699

697 698 699

ANTI-PROTOZOAL METRONIDAZOLE
ANTIPROTOZOAL DRUGS
DRUGS (FLAGYL®)
Metronidazole Atovaquone Drug of Choice for infections Diloxanide
Diloxanide Eflornithine T - Trichomonas vaginalis asymptomatic E. histolytica
A - Entamoeba histolytica carriers
8- Nifurtimox 8-Hydroxyquinoline
Hydroxyquinoline Benznidazole G - Giargia intestinalis
S - Spore formers (C. difficile) Iodoquinol
Iodoquinol Melarsoprol DOC for asymptomatic amebiasis
an unpleasant metallic taste is often
Emetine & Sodium experienced Emetine & Dehydroemetine
Dehydroemetine stibogluconate if taken with alcohol, a disulfiram-like protoplasmic poison that (×)
Pentamidine Dimercaprol effect occurs protein synthesizing protozoal &
Isethionate Suramin Na mammalian cells by preventing
700 701 protein elongation
702

700 701 702

ANTIPROTOZOAL DRUGS
Pentamidine isethionate
alternative treatment of PCP
alternative treatment of visceral
leishmaniasis (esp. when
stibogluconate is unresponsive or
contraindicated)
S/E: cough & bronchospasm
(inhalation); HTN & Hypoglycemia
(injection)
Prophylaxis & treatment of
African Trypanosomiasis
703
703
ANTIPROTOZOAL DRUGS
Melarsoprol
prepared by reduction of a
corresponding pentavalent
arsanilate to the trivalent
arsenoxide followed by reaction of
the latter with BAL
OLD DOC for txt of latter stages of
African Trypanosomiasis
Adv: excellent penetration into the
CNS; therefore effective against
meningoencephalitis form
706
706
ANTIPROTOZOAL DRUGS
Atovaquone
Original: P. falciparum (tolerated rapidly)
Alternative: to TMP-SMX against PCP
(treatment & prophylaxis)
Absorption is increased by fatty food.
Eflornithine
West African Sleeping Sickness
(meningoencephalitic stage) (T. brucei var.
gambiense)
myelosuppressive: incidence of
anaemia, leukopenia & thrombocytopenia➜
CBC count monitoring
704
704
ANTIPROTOZOAL DRUGS
Sodium stibogluconate
Pentavalent antimonial compound
Schistosomiasis and other flukes
Pentavalent ➜ Trivalent
Anti-Leishmaniasis (DOC)
Dimercaprol
2,3-dimercapto-1-propanol
Developed by the british during
WWII; an antidote to German Nazi’s
Lewisite
Antidote for As, Sb, Hg, Au & Pb
toxicity
707
707
ANTIPROTOZOAL DRUGS
Nifurtimox
T. cruzi (South American Sleeping
Sickness) ➜ the only clinically proven
regimen for both acute & chronic
forms of the disease
Benznidazole
Treatment of Chaga’s disease
(similar effect with Nifurtimox)
705
705
ANTIPROTOZOAL DRUGS
Suramin Sodium
Prophylaxis for Trypanosomiasis
& Onchocerciasis
DOC for African Trypanosomiasis
early stage (but not Chaga’s disease)
not absorbed in the GIT & is given
parenterally
Early stage: Suramin alone; Late
Stage (CNS involvement)
poor penetration of suramin &
pentamidine, requires melarsoprol
708
708
 HELMINTHS ANTI-HELMINTHIC
INTESTINAL INFECTION
Ancyclostoma DRUGS
Nematodes duodenale Piperazine Albendazole
GIT Necator americanus Diethyl- Niclosamide
Blood or Tissue Ascaris lumbricoides carbamazine Bithionol
Flatworms Enterobius citrate Oxamniquine
Cestodes vermicularis Pyrantel Praziquantel
Trematodes Strongyloides pamoate Ivermectin
stercularis Thiabendazole
Trichuris trichuria Mebendazole
709 Trichinella spiralis
710 711

709 710 711

MEBENDAZOLE ALBENDAZOLE THIABENDAZOLE

Mebendazole irreversibly blocks
glucose uptake in susceptible
helminths, thereby depleting
glycogen stored in the parasite
KATZUNG: acts by selectively
inhibiting microtubule synthesis &
glucose uptake in nematodes
Arrest cell division in metaphase
by interfering w/ microtubule
assembly. They exhibit a high
affinity for tubular, the precursor
protein of microtubule synthesis
structural congener of
mebendazole and has a similar
action on microtubules
DOC for Threadworm infection
A/E:
Erythema multiforme and SJS
(Fatal)

712 713 714

712 713 714

 PYRANTEL PAMOATE PIPERAZINE FILARIAL INFECTION
stimulates nicotinic receptors MOA: blocks the response of the
present at neuromuscular Ascaris muscle to acetylcholine,
Wuchereria
junctions of nematodes ➜ causing flaccid paralysis
bancrofti
contraction of a muscle occurs, Paralyses ascaris by acting as an
Brugia malayi
followed by a depolarisation- agonist at GABA receptors
Onchocerca volvulus
induced tetanic paralysis Pyrantel + Piperazine =
Loa loa
The drug has no actions on flukes Antagonist effect
or ringworms
715 716 717

715 716 717

DIETHYLCARBAMAZINE TREMATODE INFECTION

CITRATE
Immobilises microfilariae by an
unknown mechanism, increasing
their susceptibility to host defence
mechanisms
DOC for Filariasis / Elephantiasis
Causative agent: ?
718
IVERMECTIN
Isolated from S. avermitilis
Intensifies GABA mediated
neurotransmission in nematodes &
causes immobilisation of parasites,
facilitating their removal by the
reticuloendothelial system
DOC for River blindness /
Onchocerciasis
A/E: Mazzotti reaction
719
Schistosoma japonicum
Schistosoma mansoni
Schistosoma haematobium
(bilharziasis)
Clonorchis sinensis (liver fluke);
Paragonimus westermani (lung
fluke)
Fasciola hepatica (sheep liver fluke)
Fasciolopsis buski (large intestinal
fluke) 720

718 719 720

CESTODES INFECTION
Taenia saginata (beef tapeworm)
Taenia solium (pork tapeworm)
Diphyllobothrium latum (fish
tapeworm);
Cysticercosis (pork tapeworm larval
stage)
Hymenolepis nana (dwarf
tapeworm)
Echinococcus granulosus (hydatid
disease); Echinococcus multilocularis
721
PRAZIQUANTEL
MOA: increases cell membrane
permeability of susceptible
worms, resulting in loss of
extracellular Ca2+ ions causing
massive contraction & ultimate
paralysis
722
NICLOSAMIDE
MOA: uncoupling oxidative
phosphorylation or by activating
ATPases
2nd line for Cestodes
For intestinal cestodes only:
Taenia saginata
Diphyllobotrium datum
Hymenolepsis nana
723

721 722 723

BITHIONOL OXAMNIQUINE
MOA: Unknown MOA: Unknown; causes
Co-Drug of Choice contraction-paralysis in worms
(Triclabendazole) for treatment of For S. mansoni
fascioliasis (Sheep liver fluke) Alternative to Praziquantel
ANTI-MALARIAL DRUGS
A/E: Red-orange urine

724 725 726

724 725 726

 CHEMISTRY MALARIA ANTI-MALARIAL AGENTS
Prevent
Acute Chemo- Radical
Caused by any of 5 species of protozoal Transmissio
have one common structural genus Plasmodium
Malaria prophylaxis Cure n
feature-a-quinoline ring or a Plasmodium falciparum Quinine Chloroquine Primaquine Quinine
Mefloquine Mefloquine Primaquine
“quinoline with an additional Plasmodium vivax Chloroquine Proguanil Proguanil
benzene added” (an acridine ring) Plasmodium ovale Halofantrine Pyrimethamine Pyrimethamin
Sulfones Dapsone e
Plasmodium malariae Pyrimethamin Doxycycline
Plasmodium knowlesi (zoonotic) e
Tetracycline
S/Sx: High fever, shaking chills, flu-like Doxycycline
symptoms and anemia Artemisinin &
Analogs
Vector: _____________
727 728 729

727 728 729

DRUGS USED TO TREAT

ACUTE ATTACK OF MALARIA
MOA: Blood Schizonticidal agents
act on the erythrocytic forms of
the plasmodium
Suppress the actual attack or
______________ Prophylaxis
(infections w/ P. vivax or P. ovale)
effect a cure (infections w/ P.
falciparum or P. malariae)
730
CINCHONA ALKALOIDS CINCHONA ALKALOIDS
QUININE (PO, IV, IM)
QUININE (PO, IV, IM) Dextrorotatory form of Quinine?
reserved for malarial strains Blood schizonticidal against 4
resistant to other agents species of human malarial parasites
General Protoplasmic Poison Gametocidal against P. vivax & P.
oval but NOT P. falciparum
Quinoclidine ring
1st-line therapy for Chloroquine-
resistant falciparum malaria
1st-line therapy in treatment of
infection with Babesia microti or
731
other Babesial infection
732

730 731 732

 QUININE (PO, IV, IM) QUININE (PO, IV, IM) QUININE (PO, IV, IM)
Adverse Effect:
MOA: Cinchonism: Contraindications & Cautions:
(✕) parasite Heme polymerase allowing Tinnitus, Visual disturbances, Flushing,
accumulation of cytotoxic substrate, Dizziness, Headache, Nausea patients w/ visual or auditory
Heme. Hypoglycaemia: problems
May poison parasite’s feeding mechanism Stimulation of __________ release patients w/ cardiac abnormalities
Toxic Heme: Glucose consumption of parasite
Differential diagnosis w/ coma is difficult
(use w/ great caution)
monomeric 𝛂-hematin
(ferriprotoporphyrin IX) QT prolongation: or ? (IV Quinidine)
catalyses production of ROS (pro-oxidant) Blackwater Fever:
bind & dispute cell membrane and cause Rare severe illness that includes marked
hemolysis & hemoglobinuria -
lysis of host RBC
(Hypersensitivity reaction)
733 734 735

733 734 735

7-CHLORO-4- 7-CHLORO-4-
8-AMINOQUINOLINES
AMINOQUINOLINES AMINOQUINOLINES
CHLOROQUINE (Aralen®) AMODIAQUINE PRIMAQUINE
DOC in txt of erythrocytic highly suppressive in P. vivax & The only drug effective against
_________ malaria (except falciparum exoerythrocytic stages of malaria
resistant strain) has curative activity against P. only agent that can lead to
Anti-inflammatory action explains falciparum “radical cures” of the P. vivax &
its occasional use in RA and SLE S/E: prolonged use pigmentation ovale
Prophylaxis (in areas with no of the palate, nail & skin, Gametocidal for all 4 plasmodia
resistance) agranulocytosis species
736 737 738

736 737 738


9-AMINOACRIDINES
QUINACRINE
primarily used in txt of Giardiasis,
but also effective against
tapeworm and malaria, and
topically against leishmaniasis
should not be given w/ primaquine
because of increased toxicity 
 DOC for malarial suppression
739
ARTEMISININ, ARTESUNATE,
9-AMINOACRIDINES
ARTEMETHER
MEFLOQUINE Artemisinin (Quinghaosu) (PO)
effective single agent for Artesunate (PO, IV, IM, Rectal)
suppressing and cutting multi- Artemether (PO, IM, Rectal)
drug resistant forms of P. Very rapidly acting blood
schizonticides against all malaria
falciparum
parasites
Most widely used anti-malarial Rapidly metabolised to the active
metabolite Dihydroartemisinin (PO)
A/E: N & V, Diarrhea
740 741

739 740 741

ARTEMISININ, ARTESUNATE, ARTEMISININ, ARTESUNATE,

ARTEMETHER ARTEMETHER
MOA:
Clinical Uses:
production of free radicals that follows the
iron-catalyzed cleavage of the artemisinin treatment of multidrug-resistant P.
endoperoxide bridge in the parasite food falciparum malaria
vacuole only drugs reliably effective against
Quinine-resistant strains
ANTI-VIRALS
Heme is released during digestion of human
hemoglobin by the parasite. The iron of the Artesunate
heme directly reduces the peroxide bond in treatment of severe malaria
artemisinin, generating high-valent iron-oxo treatment of uncomplicated & severe
species & resulting in a cascade of reactions falciparum malaria
that produce reactive oxygen radicals w/c treatment of highly resistant falciparum
damages the parasite742
& lead to its death malaria in Thailand
743
(with Mefloquine) 744

742 743 744

 HSV INFECTION HSV INFECTION HSV INFECTION
Sign: sore (near the area where the virus Chicken pox - extremely itchy
Herpes has entered the body) ➜ blisters (itchy & blisters all over the body
Types: painful) Shingles - a painful, blistering skin
HSV-1 or Oral Herpes rash
transmitted by kissing
HSV-2 or Genital herpes
affect the eyes, skin, brain or
other parts of the body.

745 746 747

745 746 747

FOR HERPES INFECTION RETROVIRAL INFECTIONS HIV

Cyclovir & congeners spread through body fluids
Acyclovir (PO, IV, Topical) - DOC for? HIV infection
HIV infection leads to AIDS.
Valacyclovir (PO) AIDS - Final stage of HIV
Famciclovir (PO) the human body cannot get
less than __?__ T-
Penciclovir (Topical) rid of HIV.
Cells / µL or mm3 of
Ganciclovir - DOC for CMV Can be controlled but no
blood
Cidofovir cure
Human T Cell Leukemia -
Foscarnet - DOC for? HIV-1 from gorillas and
CD4 or CD8? <14%
Docosanol (Topical) chimpanzees in West Africa
HAART
Trifluridine (Topical) HIV-2 from Sooty mangabey
748 749 750

748 749 750

 ANTI-RETROVIRAL
HAART NRTI
AGENTS (ANTI-HIV)
HAART
Backbone or foundation of any MOA:
(Highly Active Antiretroviral competitive inhibitors of reverse
ART combinations
Therapy) transcriptase, which leads to chain
“two scoops of rice” + chicken or
ART (Antiretroviral Therapy) termination when incorporated into
beef
COMBINATIONS OF CHOICE 2 NRTIs (rice) plus NNRTI the viral DNA chain.
2 NRTIs and 1 PI (chicken) or (PI) Beef Requires intracytoplasmic activation
2 NRTIs and 1 NNRTI via phosphorylation by cellular
2 NRTIs and 1 PI with enzymes to the triphosphate form.
Ritonavir
2 NRTIs and
751
Abacavir 752 753

751 752 753

NUCLEOSIDE REVERSE NUCLEOSIDE REVERSE NUCLEOSIDE REVERSE

TRANSCRIPTASE INHIBITORS TRANSCRIPTASE INHIBITORS TRANSCRIPTASE INHIBITORS
Didanosine (?) Zidovudine (AZT) Lamivudine (3TC)
Abacavir (?) Thymidine analog Cytosine analog
Zalcitabine (?) 1st line drug & 1st antiviral against Generally well tolerated
Zidovudine (?) HIV For treatment of HIV-1, HIV-2, &
Lamivudine (?) usually combined w/ Lamivudine HBV
Emtricitabine (?) (Combivir) + Interferon alpha
Stavudine (?) A/E Severe Bone Marrow MOA: Inhibits HBV replication
Suppression - treatment: ?
754 755 756

754 755 756

 NUCLEOSIDE REVERSE
TRANSCRIPTASE INHIBITORS
Didanosine (ddl)
deoxyadenosine analog
Black Box Warning: Acute
Pancreatitis (lethal)
unstable in acidic environment
Long half-life (8-24hrs)
NUCLEOSIDE REVERSE
TRANSCRIPTASE INHIBITORS
Zalcitabine (ddC)
Cytosine analog
active against HIV-1, HIV-2, and
HBV
Require acidic stomach - For
complete absorption
NUCLEOSIDE REVERSE
TRANSCRIPTASE INHIBITORS
Abacavir (ABC)
Guanosine analog
good CSF penetration
Approved for use only in
combination with other anti
retroviral agents
Black Box Warning: Life-threatening
hypersensitivity reaction

757 758 759

757 758 759

NUCLEOSIDE REVERSE NUCLEOSIDE REVERSE NON-NUCLEOSIDE REVERSE

TRANSCRIPTASE INHIBITORS TRANSCRIPTASE INHIBITORS TRANSCRIPTASE INHIBITORS
Emtricitabine (FTC) Stavudine (d4T) NNRTIs
Fluorinated analog of Lamivudine Thymidine analog Neivrapine (PO)
in vitro activity against HBV AZT reduces activation of d4T Efavirenz (PO)
A/E: Asthenia For HIV infection intolerant to Delaviridine (PO)
other antiviral therapies.

760 761 762

760 761 762

NON-NUCLEOSIDE REVERSE NON-NUCLEOSIDE REVERSE NUCLEOTIDE REVERSE
TRANSCRIPTASE INHIBITORS TRANSCRIPTASE INHIBITORS TRANSCRIPTASE INHIBITORS
Cidofovir - For Herpes
Nevirapine Efavirenz
Adefovir - For HIV
First NNRTI approved for use by Only NNRTI approved for once-
FDA in the treatment of HIV daily dosing Tenofovir - For HIV
infection A/E: CNS effects (52%), Rash
CYP450 inducer (25%), Teratogenic
Adverse Effects: potentially fatal Delaviridine
hepatic toxicity, skin reactions Auto inhibition (CYP450 inhibitor)
(Steven-Johnson Syndrome) A/E: Rash (most frequent)
763 764 765

763 764 765

PROTEASE INHIBITORS PROTEASE INHIBITORS

RECOMMENDED ALTERNATE
(PI) (PI) AGENTS AGENTS
Lopinavir-Ritonavir (PO) competitively inhibit the viral NRTIs
Indinavir (PO) protease enzyme, preventing the Zidovudine, Didanosine,
Nelfinavir (PO) enzyme from cleaving the gag pol lamivudine emtricitabine,
Protease polyprotein necessary for the stavudine, abacavir
“LOvirs IN PARIS”
Amprenavir (PO) production of the infectious virions. NNRTIs
Ritonavir (PO) Nevirapine
Inhibitor Active against HIV-1 protease Protease inhibitors (PIs)
Saquinavir (PO) Adverse effects: diarrhea, nausea and Lopinavir/ritonavir Indinavir, nelfinavir,
abdominal discomfort, hyperglycemia
ritonavir, saquinavir
766 767 768

766 767 768

 ANTI-INFLUENZA ANTI-INFLUENZA
FUSION INHIBITORS
AGENTS AGENTS Enfuvirtide (Fuzeon)
Amantadine (Symmetrel) formerly called T-20 or Pentafuside
Oseltamivir (Tamiflu) & Zanamivir
Rimantadine: α-methyl derivative of First representative of a new class of
(Relenza)
Amantadine antivirals
active against influenza A & B Maraviroc (Selzentry) - CCR5
active against influenza A only
DOC severe influenza infection antagonist
MOA: Inhibits viral uncoating after
MOA: Neuraminidase inhibitor Palivizumab
entering cell
A/E: Livedo reticularis MOA: neutralizes respiratory
syncytial virus (RSV) and inhibits its
ability to fuse with host cell
769 770
membranes 771

769 770 771

NAMING OF MAB OTHER ANTI-VIRAL

Last syllable is always –mab
Next to last syllable
AGENTS
-u- human (100%) : Panitumumab Ribavirin - for RSV
-zu- humanized (95%) : Trastuzumab Interferon alpha - For Hepatitis B
-xi- chimeric (65%) : Rituximab infection; Found in Liver unit or ANTIBACTERIAL
-o- mouse, -a- rat, -e- hamster, -i- primate
: Tositumomab
Hepatology or Hepato-Pancreato- ANTIBIOTICS
Previous syllable Biliary (HPB) unit in hospital
-tu(m)- for tumor in general [-ma(r)-
breast, -pr(o)- prostate, -co(l)- colon, etc.]
-vi - for viral infection
-ci(r)- for circulatory
772
: Bevacizumab 773 774

772 773 774

 ANTIBIOTICS PENICILLIN
substance produced by Penicillin nucleus
microorganism which has the BETA-LACTAM
capacity to inhibit the growth & COMPOUNDS
cause destruction of other
microorganism
Bactericidal or Bacteriostatic?

775 777

775 776 777

BETA-LACTAM
PENICILLIN
ANTIBIOTICS
PENICILLINS Penicillin nucleus
1929: Discovered by Alexander Fleming
serendipitously
MOA: Interfere w/ the last step of
bacterial cell wall synthesis
(transpeptidation or cross-linking of
peptidoglycan chains)
Beta-lactam attached to thiazolidine
ring
Nucleus: ___________?___________ acid
778 779

778 779 780

 Penicillin G
NATURAL PENICILLIN NATURAL BETA-LACTAM
DOC for infections caused by: ANTIBIOTICS
Penicillin G (Benzyl Penicillin)
available in the form of water- ✓streptococci
soluble salt or potassium, sodium ✓meningococci Penicillin V (Phenoxymethyl
and calcium ✓enterococci Penicillin)
poorly absorbed from the intestinal ✓penicillin-susceptible pneumococci Acid stable
tract, oral doses must be very large ✓non-β-lactamase-producing staphylococci Can be given via oral
Its rapid elimination from the ✓Treponema pallidum & many other spirochetes administration
bloodstream led to the development ✓clostridium species
of repository forms ✓actinomyces
Repository Forms (IM) ✓other g(+) rods & non-β-lactamase-producing
Pen G Procaine
g(-) anaerobic organisms
Pen G Benzathine
781 783

781 782 783

PENICILLINASE- PENICILLINASE- PENICILLINASE-

RESISTANT PENICILLINS
Anti staphylococcal Penicillins
METHICILLIN
2,6-dimethylphenylpenicillin
Prototype drug
Off the market due to high
incidence of interstitial
nephritis
784
RESISTANT PENICILLINS
Anti staphylococcal Penicillins
NAFCILLIN
2-ethoxyl-phenylpenicillin
relatively small amounts are
excreted through kidneys w/ the
major portion excreted in the bile
Can be given to patients with
renal problems
785
RESISTANT PENICILLINS
Anti staphylococcal Penicillins
ISOXAZOLYL PENICILLINS
Oxacillin, Cloxacillin,
Dicloxacillin
Best absorbed
Treatment of Staphylococcal
infections (e.g. impetigo)
786

784 785 786

AMINOPENICILLINS AMINOPENICILLINS AMINOPENICILLINS
Antibacterial spectrum is similar AMPICILLIN AMOXICILLIN
to Pen G but are more effective Poor GI absorption Better GI absorption than
against Gram ( - ) bacilli More frequently administered Ampicillin
aka? parenterally
Prodrugs:
HETACILLIN
BACAMPICILLIN
CYCLACILLIN
787 788 789

787 788 789

ANTI-PSEUDOMONAS BETA-LACTAMASE
PENICILLINS INHIBITORS
CARBOXYPENICILLINS inactivate beta-lactamases
Carbenicillin Clavulanic acid, Sulbactam, Tazobactam Cephalosporins & Cephamycins
Augmentin- Amoxicillin + Clavulanic
Ticarcillin
acid
UREIDOPENICILLINS Timentin - Ticarcillin + Clavulanic
Piperacillin - most potent acid
Azlocillin Unasyn- Ampicillin + Sulbactam
Mezlocillin PipTaz/Tazocin/Zosyn - Piperacillin +
Tazobactam
790 791

790 791 792

 %&LETS TRY THIS! '👊
CEPHALOSPORINS CEPHALOSPORINS Ceftibuten Cefpodoxime Ceftazidime
Cefadroxil Cefprozil Ceftidoxime
beta-lactam attached to Cefditoren
dihydrothiazine ring Cefixime Cefepime
Cefaclor
nucleus: 7-aminocephalosporanic Loracarbacef Cephradine
Cephalexin
acid Cefotetan Cefpirome
Cefazolin
Cross-sensitivity with Penicillin Cefoperazone Cefamandole
Cephalothin
Classified into 5 generations Moxalactam Ceftriaxone Cefdinir
Cefoxitin Cefuroxime Ceftizoxime
Cephapirin Cefotaxime Ceftobiprole
Cefonicid Cefmetazole Ceftaroline
793 794 795

793 794 795

First
Cefadroxil
Second
Cefaclor
Third Fourth
Cefoperazone Cefepime
Fifth
Ceftobiprole
FOR EMPHASIS!
Cefazolin Cefamandole Cefotaxime Cefpirome Ceftaroline
Cephalexin Cefonicid Ceftazidime P. aeruginosa
Cephalothin Cefuroxime Ceftizoxime Cefepime
Cephapirin Cefuroxime Ceftriaxone
Cephradine axetil Cefixime Cefoperazone
Cefprozil Cefpodoxime Ceftazidime (DOC) OTHER β-LACTAM DRUGS
Loracarbef proxetil
Cefoxitin Cefdinir Cefotaxime & Ceftriaxone
Cefmetazole Cefditoren Antibiotic of first choice for the
Cefotetan pivoxil
Ceforanide Ceftibuten empirical treatment of brain
Moxalactam abscess & meningitis
797

796 797 798

 CARBAPENEM CARBAPENEM MONOBACTAMS
differ with penicillin in that the S atom of
the thiazolidine ring has been externalized
the beta-lactam ring is not fused
& replaced by a Carbon atom
THIENAMYCIN (Prototype) to another ring
Source: Streptomyces cattleya AZTREONAM
IMIPENEM Source: ?
Broadest of all Beta-lactam antibiotics bactericidal
undergoes cleavage by dihydropeptidase “Magic Bullet” for Pseudomonas
(+) Cilastatin ➜ PRIMAXIN® active against many gram negative
A/E: Seizures (Imipenem)
organism including Enterobacter
MEROPENEM & ERTAPENEM
Resistant to dihydropeptidase and P. aeruginosa
799 800 801

799 800 801

AMINOGLYCOSIDES Aminoglycosides Structure

(Streptomycin, Amikacin, Gentamicin) • hexose ring
• most widely used against g(-) enteric bacteria
“mycin”- derived from Streptomyces ➢either streptidine
“micin”- derived from • Sreptomycin (Streptomycin) or 2-
Micromonospora • Neomycin
• Kanamycin deoxystreptamine (others)
• Amikacin
MOA: inhibit protein synthesis at the • Gentamicin ➢to w/c various amino sugars
30s ribosomal subunit • Tobramycin are attached by glycosidic
synergistic with B-lactam antibiotics • Sisomicin
• Netilmicin linkages
802 803

802 803 804

 AMINOGLYCOSIDES
BacteriCIDAL
the highly POLAR structure of
aminoglycosides prevents adequate
absorption after oral administration
all must be given PARENTERALLY
to achieve adequate serum levels
except neomycin (topical & oral only)
ADR: Nephrotoxicity & Ototoxicity
805
805
TETRACYCLINES
808
808
Adverse Effects
• Ototoxicity
➢auditory / cochlear damage
✓tinnitus & high-frequency
hearing loss initially
➢vestibular damage
✓vertigo, ataxia, & loss of balance
806
806
TETRACYCLINES
Doxycycline, minocycline,
tetracycline, demeclocycline
broadest spectrum antibiotic
has activity against gram (+) ,
gram (-) , spirochetes, Mycoplasma,
Rickettsia and Chlamydia
contain four fused rings with a
system of conjugated double bonds
809
809
NOTES
Cystic fibrosis: Tobramycin
Endocarditis
■Gentamicin + ampicillin:
prophylaxis before surgery
■Gentamicin + vancomycin:
alternative drug if sensitive to beta-
lactam antibiotics
■Gentamicin (or Streptomycin) +
Penicillin: treatment of endocarditis
807
807
MOA
bind reversibly to the 30S
subunit of the bacterial ribosome,
blocking the binding of
aminoacyl-tRNA to the acceptor
site on the mRNA-ribosome
complex
810
810
 Tetracyclines Classification Tigecycline
• Absorption is impaired by: Short-Acting Intermediate- Long-Acting • newly approved tetracycline analog
(6-8hrs) Acting (16-18hrs)
➢food (except Doxycycline & • glycylcycline
Minocycline) - Most Lipid Soluble (12hrs)
• semisynthetic derivative of minocycline
➢divalent cations (Ca2+, Mg2+, Fe2+) or Al3+ Chlortetracycline Demeclocycline Doxycycline
➢dairy products & antacids
➢alkaline pH Tetracycline Methacycline Minocycline

Oxytetracycline
• cross the placenta
• excreted in milk
811
Tigecycline has a half-life of 36 hours.
812

811 812 813

Tetracyclines Doxycycline Doxycycline

• DOC in infections with M. pneumoniae,
chlamydiae, rickettsiae, & some
spirochetes
• g(+) & g(-) bacterial infections, including
Vibrio infections
• combination therapy:
➢ulcer disease caused by H. pylori
➢plague, tularemia, & brucellosis
• DOC for the 1° stage of Lyme disease in
adults & children older than 8 years
• potential first-line agent in the prophylaxis
of anthrax after exposure
• popular choice for patients w/ preexisting
renal disease or those who are at risk for
developing renal insufficiency
• oral tetracycline of choice
• preferred parenteral tetracycline

814 815 816

 Minocycline, Demeclocycline,
Tigecycline
Adverse Effects Adverse Effects
Minocycline GI Effects Kidney Toxicity
• effective alternative to rifampin for eradication of • nausea, vomiting, & diarrhea • outdated tetracycline preparations
meningococci from the nasopharynx • renal tubular acidosis & other renal injury resulting
Bony Structures & Teeth in nitrogen retention
Demeclocycline
• inappropriate secretion of ADH or similar peptides • teeth: fluorescence, discoloration, & enamel
by certain tumors dysplasia Photosensitivity (Demeclocycline, Doxycycline)
• bone: deformity or growth inhibition, temporary
Tigecycline stunting of growth Vestibular Reactions
• skin & skin-structure infection & intraabdominal • dizziness, vertigo, nausea, & vomiting
infections Liver Toxicity • Doxycycline, Minocycline
• Hepatotoxicity

817 818 819

MACROLIDES MACROLIDES MACROLIDES

Common chemical characterictics: ERYTHROMYCIN ERYTHROMYCIN
■a large lactone ring ■Streptomyces erythreus ■Preferred drug for:
■a ketone group ■Formerly llotycin®
■a glycosidically linked amino sugar ■alternative to penicillin ■Legionnaires Disease
MOA: inhibit protein synthesis at the 50s ■Erythromycin base is inactivated by ■Mycoplasma pneumonia
ribosomal subunit gastric acid ■Campylobacter jejuni
Spectrum of activity: resembles PenG but ■Esters of erythromycin base (e.g stearate,
also effective against Mycoplasma, estolate, and ethlysuccinate) have ■Chlamydia infections
Chlamydia, Campylobacter, Legionella improved acid stability & their absorption ■Diphtheria
ADR: epigastric distress, cholestatic is less by food
jaundice (ESTOLATE form of erythromycin)
■Pertussis
A/E: GI upset
820 821 822

820 821 822

 MACROLIDES
CLARITHROMYCIN (Biaxin®)
more potent than erythromycin
against streptococci &
staphylococci
clarithromycin may be given w or
w/out food, but the extended-
release form, typically given once-
daily as a 1g dose, should be
administered w/ food to improve
bioavailability
823
Clarithromycin
• derived from Erythromycin by addition of a methyl
AZITHROMYCIN (Zithromax®)
group
• similar activity with Erythromycin except:
➢more active against M. avium complex
➢activity against H. pylori
➢activity against M. leprae & T. gondii
Advantages:
• improved acid stability & oral absorption
• lower incidence of GI intolerance
• less frequent dosing
824
MACROLIDES
extensive tissue distribution & high drug
concentrations within cells (including
phagocytes) resulting in much greater
concentrations of drugs in tissue or
secretions compared to simultaneous
serum concentrations (Depot)
once a day dosing
should not be administered with food
the elimination half-life, 40 to 68 hours, is
prolonged because of extensive tissue
sequestration and binding
825

823 824 825

LINCOSAMIDES POLYPEPTIDES POLYPEPTIDES

LINCOMYCINS
sulfur- containing antibiotics isolated from
Streptomyces lincolnensis
resembles MACROLIDES in antibacterial
spectrum and biochemical mechanism of
action
CLINDAMYCIN
one of the most potent agents available
against non-spore forming anaerobic
bacteria (Bacteroides fragilis)
adverse effect: pseudomembranous
enterocolitis
826
Their clinical use has been limited
by their undesirable side reactions,
particularly RENAL TOXICITY
most lack systemic activity (only
used topically ), except
VANCOMYCIN (systemic)
827
VANCOMYCIN
From Streptomyces orientalis
IV: effective against MRSE/MRSA
PO: used for potentially life-
threatening antibiotic-associated
colitis due to Clostridium difficile
slow intravenous infusion is employed
for treatment of systemic infections
ADR: flushing (Red Man Syndrome)
Infusion related & Histamine-
related
828

826 827 828

 Vancomycin MOA
• inhibits cell wall synthesis by
binding firmly to the D-Ala-D-Ala
terminus of nascent peptidoglycan
pentapeptide
• inhibits the transglycosylase,
preventing further elongation of
peptidoglycan & cross-linking
829
POLYPEPTIDES
BACITRACIN (Bacillus subtilis):
inhibits cell wall synthesis
POLYMXIN (Bacillus polymyxa)
GRAMICIDIN (Bacillus brevis)
830
UNCLASSIFIED ANTIBIOTICS
CHLORAMPHENICOL
From Streptomyces venezuelae
MOA: inhibits protein synthesis at
the 50sribosomal subunit
Drug of Choice for Typhoid fever
ADR:
Gray Baby Syndrome
Aplastic Anemia - ___?___ group
831

829 830 831

UNCLASSIFIED ANTIBIOTICS SUMMARY Activity

MUPIROCIN(Bactroban®) 50s Ribosome Inhibitors: Protein synthesis inhibitors are
from Pseudomonas fluorecens ■Chloramphenicol bacteriostatic with the exception of
used topically for impetigo, ■Streptogramins Aminoglycosides and
eczema, staphylococcal and beta ■Erythromycin Streptogramins.
hemolytic streptococcal infections ■Lincosamides, Linezolid
MOA: inhibition of RNA and DNA 30s Ribosome Inhibitors:
synthesis ■Aminoglycoside
■Tetracycline
832 833 834

832 833 834