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LECTURE 4

PHARMACEUTICAL CHEMISTRY
IHS 2016
09/02/2016

ANTIFUNGALS
• Classification and nomenclature;
• Structures of selected antifungal
agents;
• Physical and chemical properties
• Pharmaceutical applications

some topically as ointments . lotions and suspensions Classification They can be broadly classified into two categories • Chemical antifungal agents • Antibiotics . cream. • There are used in a lot of infections • Some are active orally .• The use of antifungal drugs in treatment of infections are common.

antifungal properties .CHEMICAL ANTIFUGAL AGENTS A number of chemical agents have antibacterial. The simplest are aromatic acid • Benzoic acid • Salicylic acid .

BENZOIC ACID .

On the above structure The chemical structure of carboxylic acid on the left indicates all the carbon and hydrogen atoms on the benzene ring.CHEMICAL STRUCTURE • The chemical formula of benzoic acid is C7H6O2: • it has seven carbon (C) atoms hydrogen (H) atoms and two oxygen (O) atoms. . • This chemical formula can also be written as C6H5COOH.

• Benzoic acid is an organic compound because it contains carbon. . • It's classified as a carboxylic acid because it has a carboxyl group in its structure. which is the COOH group boxed in red. • it is also an aromatic carboxylic acid. It is aromatic because it has a benzene ring in its chemical structure. • Benzene is aromatic because it has alternating double bonds between each carbon.

ether and alkali hydroxide . benzoic acid can also be made by synthetic means. . • A natural source of benzoic acid is gum benzoin.PROPERTIES • Benzoic acid is a solid that is crystalline in appearance. similar to white needles. • It is sparingly soluble in cold water and more soluble in hot water. • Soluble in chloroform. alcohol. • it is stable and gives a buff colored precipitate with ferric salt . however. which comes from certain tree barks.

• It forms insoluble salts with heavy metals like silver. mouth washes etc. • It can be used in combination with salicydic acid to act as a antifungal agents • It is officially known as Whitefield's ointment . led .mercury etc. Use • Benzoic acid is used externally as antiseptic in lotions .

• Salicylic acid has the formula C6H4(OH)COOH.a type of phenolic acid and a beta hydroxy acid.SALYCYLIC ACID • is a monohydroxybenzoic acid. where the OH group is ortho to the carboxyl group. It is also known as 2-hydroxybenzoic acid .

Coloured compounds are produced with oxidizing agents . It has a strong antiseptic properties.• • • • • • • PROPERTIES It occurs as a white crystalline or fluffy powder with sweetish taste.lotion. It is slightly soluble in water and soluble in organic solvent and alkali hydroxides. . It forms salts with heavy metals. It produces violet colour with ferric salts. cream . It acts as an antifungal in 3% to 5 % in concentration form of ointment .

which used in food flavorings and preservatives.• It contains both a hydroxyl and a carboxyl group. e.g. menthyl salicylate is formed with methanol. • The hydroxyl group reacts with acetic acid to form acetylsalicylic acid (called aspirin) which is the most widely . which is used in suntan lotions. methyl salicylate is formed with methanol. which react with either an acid or an alcohol. • The carboxyl group forms esters with alcohols.

. Use Salicylic acid is a keratolytic. It works by increasing the amount of moisture in the skin and dissolving the substance that causes the skin cells to stick together. Salicylic acid does not affect the virus. Warts are caused by a virus.• Phenyl salicylate is formed with phenol. This makes it easier to shed the skin cells. which is also used as an antiseptic and antipyretic agent SALYCYLIC ACID . It belongs to the same class of drugs as aspirin (salicylates).

CLOTRIMAZOLE An imidazole derivative with a broad spectrum of antimycotic activity. Its action leads to increased membrane permeability and apparent disruption of enzyme systems bound to the membrane. It inhibits biosynthesis of the sterol ergostol. . an important component of fungal cell membranes.

PROPERTIES • It is a yellow odorless powder • It is insoluble in water . . soluble in alcohol and chloroform • It is stored in a closed container . protected from light Use It is used as cream and pessaries in the treatment tinea infections and candidiasis by candida abicans .

MICONAZOLE • Miconazole is a synthetic antifungal agent belonging to the imidazole group. • C18H14Cl4N20 .

PROPERTIES • It is a white micro crystalline powder. • Odourless or almost odourless. . Use It is used in 2% creams to be applied topically for treatment of fungal infections. • Slightly water soluble and more soluble in acetone.

ANTIBIOTICS These are substances that are effective orally as antifungal agents. • Amphoterin B • Candicin • Nystatin • Griseoflulvin .

GRISEOFLULVIN Formula:C17H17ClO6 .

PROPERTIES • Griseofulvin is an antifungal agent used in the treatment of TINEA infections • It is a macrolide antibiotic • White to pale cream crystalline powder. odourless or nearly odourless but bitter tasting. • Practically insoluble in water and sparingly soluble in alcohol. .

AMPHOTERIN B • Is a mixture containing amphoteric A and B which the B component is more active. containing multiple conjugated carbon-carbon  double bonds on one side of the ring and multiple hydroxyl. • Amphoterin B is large ring of atoms with a cyclic ester ring. .

PROPERTIES Is a Crystalline Yellow-orange powder with a faint odour and is water soluble. It is unstable in aqueous medium and deteriorates rapidly Amphotericin B is poorly water soluble . . Amphotericin B acts by binding sterols in the cell membrane leading to the formation of transmembrane channels and subsequent ion leakage. It is amphoteric in nature.

It is given parentally and topically for treatment of fungal infection CANDICIDIN Properties :Is a yellow powder . It is kept in a air-tight container away from light Use: it is used to treat viginal fungal . Antifungal.Use Polypeptide antibiotic active against gram positive bacteria. almost odourless and it is insoluble in water.

Increases the permeability of the cell membrane of sensitive fungi by binding to sterols.NYSTATIN Nystatin is a Polyene antifungal antibiotic complex containing 3 biologically active components. A2. . A3. A1.

. binds to sterols in the fungal cell membrane leading to formation of ion channels in the wall. ion imbalance and cell death. Nystatin. A2 and A3 from Streptomyces noursei .PROPERTIES Brown solid Nystatin is polyene antifungal containing a conjugated tetraene and a diene. like most polyene antifungals. isolated as a complex of three components A1.

LECTURE 5 ANTITUBERCULOSIS AGENTS • -Antiamoebics & anthelmintic • Antimalarials STERIODS • NON Steroidal anti-inflammatory • analgesics and antipyretic .