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Collage of pharmacy
Pharmaceutical Chemistry dept.
Prepared by:
Mohamed Saad
Gad
Mohamed Rabee
Supervised by:
Dr. Soaad Hawash
:Fungi is
• Eukaryotic – a true nucleus
• Do not contain chlorophyll
• Have cell walls
• Produce filamentous structures
• Produce spores
• Contain ergosterol
• The Term mycosis (plural:
mycoses) refers to conditions in
which fungi pass the resistance
barriers of the human or animal
body and establish infections.
Classification of antifungals
Polyene anti fungals:-
A polyene is a circular molecule consisting of
.a hydrophobic and hydrophilic region
The polyene antimycotics bind with sterols
in the fungal cell membrane, principally
ergosterol. As a result, the cell's contents
leak out (usually the hydrophilic contents)
and the cell dies. Animal cells contain
cholesterol instead of ergosterol and so they
are much less susceptible. (Note: as
polyene's hydrophobic chain is reduced, its
sterol binding activity is increased.
Therefore, increased reduction of the
hydrophobic chain may result in it binding to
Classification of antifungals
Examples:
* Natamycin -- 33 Carbons, binds well to
ergosterol
* Rimocidin
* Nystatin
* Amphotericin B
Classification of antifungals
Allylamines
Allylamines inhibit the enzyme squalene
epoxidase, another enzyme required for
:ergosterol synthesis
"Terbinafine - marketed as "Lamisil*
Amorolfine*
Naftifine - marketed as "Naftin*
:Classification of antifungals
Echinocandins
Echinocandins inhibit the synthesis of glucan
in the cell wall, probably via the enzyme 1,3-β
:glucan synthase
Anidulafungin
Caspofungin
Micafungin
Polyene antifungal:
Structure activity relationship (SAR):
hydropho
bic
hydrophil
ic
Amphtericin B
Nystatin
:Polyene antifungal
:(Structure activity relationship (SAR
The polyene antibiotic produced by
actinomycetes contain a large lactone ring with
4 to 7 unsubstituted conjugated double bond .
Mechanism of action :
Binds to keratin
disrupts the cell's mitotic spindle
structure
cause defective DNA synthesis
interferes with tubulin polymerization
Resistance:
is due to alteration of the drug's target
site, by mutation of ribosome sequences.
Griseofulvin
Uses:
is effective against dermatophytes but yeast-like
fugi are less susceptible.
Tinea capitis (ringworm of the scalp)
Tinea cruris (ringworm of the high)
Tinea corporis (ringworm of the body(
Tinea unguium (onychomycosis)
Tinea barbae (barber's itch)
Tinea :
species of fungus that causes ringworm
Butenafine hydrochloride
Pharmacology
Odorless white crystalline powder that
, is freely soluble in methanol , ethanol
and chloroform , and slightly soluble in
.water
structure-activity relationships
Efficacy may be related to an interaction with cell
membrane phospholipids and permeabilization of
the fungal cell wall.
High lipophilicity could account for the long
duration of action
Indications
Butenafine is indicated for the topical •
treatment of tinea (pityriasis)
versicolor due to M. furfur, as well as
athlete’s foot (Tinea pedis), ringworm
(Tinea corporis) and jock itch (Tinea
cruris) due to E. floccosum, T.
mentagrophytes, T. rubrum, and T.
.tonsurans
:Some Trade Names
• Lotrimin ultra®
Anidulafungin
• Anidulafungin is an anti-fungal
drug manufactured by Pfizer.
• Cancidas ®
Ciclopirox
Ciclopirox olamine is a•
synthetic antifungal agent for
topical dermatologic
treatment of superficial
.mycoses
Mechanism of action
It acts by inhibiting the membrane
transfer system by interrupting the
Na+ K+ ATPase.
:Some Trade Names
• Ezon-T ®
• Tineacure ®
Haloprogin
Haloprogin is an antifungal drug
used to treat athlete's foot and
other fungal infections. It is
marketed in creams under the
trade names Halotex, Mycanden,
Mycilan, and Polik.
Action
It was marketed over the counter
primarily to treattinea infections
of the skin. The mechanism of
. action isunknown
Uses
Is used to treat skin infections
such as athlete's foot, jock itch,
ringworm, and other fungal skin
.(infections (candidiasis
• It is structurally related to
the cytostatic fluorouracil
and to floxuridine .
Mechanisms of action
The drug is intrafungally converted
into the cytostatic fluorouracil that
undergoes further steps of
activation and finally interacts as 5-
fluorouridinetriphosphate with RNA
biosynthesis and disturbs the
building of certain essential
proteins.
Mechanisms of action
Is the conversion into 5-
flourodeoxyuridinemonophosph
ate which inhibits fungal DNA
synthesis.
resistance