DIFFERENT CLASSES OF ANTIBIOTICS - AN OVERVIEW

Key: COMMONLY ACT AS BACTERIOSTATIC AGENTS, RESTRICTING GROWTH & REPRODUCTION COMMONLY ACT AS BACTERICIDAL AGENTS, CAUSING BACTERIAL CELL DEATH

-LACTAMS AMINOGLYCOSIDES chloramphenicol glycopeptides ansamycins streptogramins

MOST WIDELY USED ANTIBIOTICS FAMILY OF OVER 20 ANTIBIOTICS COMMONLY USED IN LOW INCOME COMMON DRUGS OF LAST RESORT CAN ALSO DEMONSTRATE TWO GROUPS OF ANTIBIOTICS THAT
IN THE NHS COUNTRIES OH ANTIVIRAL ACTIVITY ACT SYNERGISTICALLY
O
NH2
OCH3 O
R O O
OH
NH OH
H HO
HO O HO OH
N+
HO O
O NH2 OH H3CO OH
S O O- HO

O HO O O N
O
O
O
O
Cl

O O O
N NH2 Cl HO OH
O
O N O
HO HN N OH N Cl O O
O
O O O
H O
H
N
H
N HN H3CO NH2
N
O

OH H2N NH2 Cl OH O
NH
N
H
O
N
H
H2N O
N
H
HN O
O
HO

All contain a beta-lactam ring
EXAMPLES
Penicillins (shown) such as
amoxicillin and flucloxacillin;
Cephalosporins such as cefalexin.
MODE OF ACTION
Inhibit bacteria cell wall biosynthesis.
All contain aminosugar substructures
EXAMPLES
Streptomycin (shown), neomycin,
kanamycin, paromomycin.
MODE OF ACTION
Inhibit the synthesis of proteins by
bacteria, leading to cell death.
Distinct individual compound All contain an aromatic ring bridged by Combination of two structurally differing
HO OH OH
an aliphatic chain. compounds, from groups denoted A & B
MODE OF ACTION Consist of carbohydrate linked to a EXAMPLES EXAMPLES
Inhibit synthesis of proteins, peptide formed of amino acids Geldanamycin (shown), rifamycin, Pristinamycin IIA (shown),
preventing growth. EXAMPLES naphthomycin. Pristinamycin IA.
Vancomycin (shown), teicoplanin.
No longer a first line drug in any MODE OF ACTION MODE OF ACTION
developed nation due to increased MODE OF ACTION Inhibit the synthesis of RNA by Inhibit the synthesis of proteins by
resistance and worries about safety. Inhibit bacteria cell wall biosynthesis. bacteria, leading to cell death. bacteria, leading to cell death.

DISCOVERY 1930 1940 1950 1960 1970 1980

sulfonamides tetracyclines macrolides oxazolidinones quinolones lipopeptides

FIRST COMMERCIAL ANTIBIOTICS BECOMING LESS POPULAR DUE TO SECOND MOST PRESCRIBED POTENT ANTIBIOTICS COMMONLY RESISTANCE EVOLVES RAPIDLY INSTANCES OF RESISTANCE RARE
WERE SULFONAMIDES DEVELOPMENT OF RESISTANCE ANTIBIOTICS IN THE NHS USED AS DRUGS OF LAST RESORT HO O
O O
O
O O
N
OH O OH O O
O
H
OH O F O NH HN OH
F
H HO OH
O
OH H2N O
NH2 OH
NH O NH

H2N S N HO
N H
N
N
N N N
O O
O

C2H5 O O O CH3 O HN O HN

H OH O NH2 O OH
H H

O HO N
O O
OCH3
O
HN C9H19

O
N
N
H
O
N
N
H
OH O OO
HN O
OH
CH3 OH
O NH

All contain the sulfonamide group

O O NH O

All contain 4 adjacent cyclic All contain a 14-, 15-, or 16-membered All contain 2-oxazolidone somewhere All contain fused aromatic rings with a
hydrocarbon rings macrolide ring in their structure carboxylic acid group attached NH2

EXAMPLES
Prontosil, sulfanilamide (shown),
sulfadiazine, sulfisoxazole.
MODE OF ACTION
Do not kill bacteria but prevent their
growth and multiplication. Cause
allergic reactions in some patients.
EXAMPLES
Tetracycline (shown), doxycycline,
limecycline, oxytetracycline.
MODE OF ACTION
Inhibit synthesis of proteins by
bacteria, preventing growth.
EXAMPLES EXAMPLES All contain a lipid bonded to a peptide
EXAMPLES
Erythromycin (shown), Linezolid (shown), posizolid, Ciprofloxacin (shown), levofloxacin, EXAMPLES
clarithromycin, azithromycin. tedizolid, cycloserine. trovafloxacin. Daptomycin (shown), surfactin.
MODE OF ACTION MODE OF ACTION MODE OF ACTION MODE OF ACTION
Inhibit protein synthesis by bacteria, Inhibit synthesis of proteins by Interfere with bacteria DNA Disrupt multiple cell membrane
occasionally leading to cell death. bacteria, preventing growth. replication and transcription. functions, leading to cell death.

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