LECTURE 4

PHARMACEUTICAL CHEMISTRY
IHS 2016
09/02/2016

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

 The use of antifungal drugs in

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

CHEMICAL ANTIFUGAL AGENTS

A number of chemical agents have
antibacterial- antifungal properties .
The simplest are aromatic acid
Benzoic acid
Salicylic acid

BENZOIC ACID

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. On the above
structure The chemical structure of
carboxylic acid on the left indicates all
the carbon and hydrogen atoms on the
benzene ring.

 Benzoic acid is an organic compound

because it contains carbon,
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.
It's classified as a carboxylic acid
because it has a carboxyl group in its
structure, which is the COOH group
boxed in red.

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, ether and
alkali hydroxide .
A natural source of benzoic acid is gum
benzoin, which comes from certain tree
barks; however, benzoic acid can also be
made by synthetic means.
it is stable and gives a buff colored
precipitate with ferric salt ,

 It forms insoluble salts with heavy

metals like silver, led ,mercury etc.
Use
Benzoic acid is used externally as
antiseptic in lotions , 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

SALYCYLIC ACID

is a monohydroxybenzoic acid- a type of

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

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

It contains both a hydroxyl and a

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

 Phenyl salicylate is formed with phenol,

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

CLOTRIMAZOLE

An imidazole derivative with a broad

spectrum of antimycotic activity. It inhibits
biosynthesis of the sterol ergostol, an
important component of fungal cell
membranes. Its action leads to increased
membrane permeability and apparent
disruption of enzyme systems bound to the
membrane.

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

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.
Amphoterin B is large ring of atoms
with a cyclicester ring, containing
multiple conjugated carbon-carbon
double bonds on one side of the ring
and multiplehydroxyl.

PROPERTIES
Is a Crystalline Yellow-orange powder
with a faint odour and is water soluble.
It is amphoteric in nature.
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.

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

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

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

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