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PHARMACEUTICAL CHEMISTRY
IHS 2016
09/02/2016
ANTIFUNGALS
Classification and nomenclature;
Structures of selected antifungal
agents;
Physical and chemical properties
Pharmaceutical applications
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.
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 ,
SALYCYLIC 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.
CLOTRIMAZOLE
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