Classes Antifungal

1 classes

1.1 polyene antifungals
1.2 imidazole, triazole, , thiazole antifungals

1.2.1 imidazoles
1.2.2 triazoles
1.2.3 thiazoles


1.3 allylamines
1.4 echinocandins
1.5 others

classes
polyene antifungals

a polyene molecule multiple conjugated double bonds. polyene antifungal macrocyclic polyene heavily hydroxylated region on ring opposite conjugated system. makes polyene antifungals amphiphilic. polyene antimycotics bind sterols in fungal cell membrane, principally ergosterol. changes transition temperature (tg) of cell membrane, thereby placing membrane in less fluid, more crystalline state. (in ordinary circumstances membrane sterols increase packing of phospholipid bilayer making plasma membrane more dense.) result, cell s contents including monovalent ions (k, na, h, , cl), small organic molecules leak , regarded 1 of primary ways cell dies. animal cells contain cholesterol instead of ergosterol , less susceptible. however, @ therapeutic doses, amphotericin b may bind animal membrane cholesterol, increasing risk of human toxicity. amphotericin b nephrotoxic when given intravenously. polyene s hydrophobic chain shortened, sterol binding activity increased. therefore, further reduction of hydrophobic chain may result in binding cholesterol, making toxic animals.

amphotericin b
candicidin
filipin – 35 carbons, binds cholesterol (toxic)
hamycin
natamycin – 33 carbons, binds ergosterol
nystatin
rimocidin

imidazole, triazole, , thiazole antifungals

azole antifungal drugs (except abafungin) inhibit enzyme lanosterol 14 α-demethylase; enzyme necessary convert lanosterol ergosterol. depletion of ergosterol in fungal membrane disrupts structure , many functions of fungal membrane leading inhibition of fungal growth.

imidazoles

bifonazole
butoconazole
clotrimazole
econazole
fenticonazole
isoconazole
ketoconazole
luliconazole
miconazole
omoconazole
oxiconazole
sertaconazole
sulconazole
tioconazole

triazoles

albaconazole
efinaconazole
epoxiconazole
fluconazole
isavuconazole
itraconazole
posaconazole
propiconazole
ravuconazole
terconazole
voriconazole

thiazoles

abafungin

allylamines

allylamines inhibit squalene epoxidase, enzyme required ergosterol synthesis. examples include amorolfin, butenafine, naftifine, , terbinafine.

echinocandins

echinocandins may used systemic fungal infections in immunocompromised patients, inhibit synthesis of glucan in cell wall via enzyme 1,3-beta-glucan synthase:

anidulafungin
caspofungin
micafungin

echinocandins poorly absorbed when administered orally. when administered injection reach tissues , organs concentrations sufficient treat localized , systemic fungal infections.

others

aurones - have been shown possess antifungal properties
benzoic acid – has antifungal properties, must combined keratolytic agent such in whitfield s ointment
ciclopirox – (ciclopirox olamine) – hydroxypyridone antifungal interferes active membrane transport, cell membrane integrity, , fungal respiratory processes. useful against tinea versicolour.
flucytosine or 5-fluorocytosine – antimetabolite pyrimidine analog
griseofulvin – binds polymerized microtubules , inhibits fungal mitosis
haloprogin – discontinued due emergence of more modern antifungals fewer side effects
tolnaftate – thiocarbamate antifungal, inhibits fungal squalene epoxidase (similar mechanism allylamines terbinafine)
undecylenic acid – unsaturated fatty acid derived natural castor oil; fungistatic, antibacterial, antiviral, , inhibits candida morphogenesis
crystal violet – triarylmethane dye, has antibacterial, antifungal, , anthelmintic properties , formerly important topical antiseptic.
balsam of peru has antifungal properties.
orotomide (f901318) - pyrimidine synthesis inhibitor.




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