ANTIMYCOTIC DRUGS Modes of Action

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1 ANTIMYCOTIC DRUGS Modes of Action Prapasarakul Nuvee, D.V.M., Ph.D. Department of Veterinary Microbiology, Faculty of Veterinary Science, Chulalongkorn University 1 What drugs act as antifungal agents? Generally present more difficult therapeutic problems than do bacterial infections. There are relatively few agents that can be used to treat fungal infections. The fungal cell wall may be considered to be a prime target for selectively toxic antifungal agents because of its chitin structure, absent from human cells. MOST COMMON FUNGAL PATHOGENS Dermatophytes Candida Aspergillus Cryptococcus Rhizopus... ANTIFUNGAL DRUGS --by structure POLYENES Amphotericin B, nystatin AZOLES Imidazoles: Ketoconazole.. Triazoles: Fluconazole, itraconazole, voriconazole, posaconazole, ravuconazole ALLYLAMINES Terbinafine, butenafine MORPHOLINE Amorolfine FLUORINATED PYRIMIDINE Flucytosine ECHINOCANDINS Caspofungin, anidulafungin, micafungin PEPTIDE-NUCLEOSIDE Nikkomycin Z TETRAHYDROFURAN DERIVATIVES Sordarins, azasordarins OTHER Griseofulvin 1

2 MODES of ACTION ANTIFUNGAL DRUGS by mode of action Membrane disrupting agents Amphotericin B, nystatin Ergosterol synthesis inhibitors Azoles, allylamines, morpholine Nucleic acid inhibitor Flucytosine Anti-mitotic (spindle disruption) Griseofulvin Glucan synthesis inhibitors Echinocandins Chitin synthesis inhibitor Nikkomycin Protein synthesis inhibitors Sordarins, azasordarins AMPHOTERICIN B generates pores in the membrane Incorporation of 5-FU in RNA 2

3 Ergosterol synthesis TERB Incorporation of 5-FU in RNA Terbinafine : a synthetic antifungal agent introduced into the UK in 1991 and is used to treat skin and nail infections. t inhibits ergosterol biosynthesis. Azoles, allylamines & morpholines inhibit specific ENZYMES Clin Microbiol Rev 1998; 11: 382 3

4 Butoconazole (Suppository, Topical) Clotrimazole (Topical) Econazole (Topical) Fluconazole (Oral, Topical)* Itraconazole (Oral) Ketoconazole (Oral, Topical)* Miconazole (IV, Intrathecal, Topical) Oxiconazole (Topical) Sulconazole (Topical) Terconazole (Suppository, Topical) RNA/EF3 (Nucleic acid/protein synthesis) Incorporation of 5-FU into RNA FLUCYTOSINE (5-fluorocytosine) Cytosine permease 5-FC cytosine deaminase 5-FU 5-fluorodeoxyuridine 5-FU monophosphate thymidylate synthase inhibitor inhibits DNA synthesis 5-FU uracil phosphoribosyl 5-fluorouridilic acid (FUMP) transferase (UPRTase) FUMP phosphorylation 5-fluoro-UTP incorporated into RNA disrupts protein synthesis Incorporation of 5-FU into RNA 4

5 SORDARINS, AZASORDARINS EF3: A target in protein synthesis machinery unique to FUNGI GM (sordarins) GW (azasordarins) Yet investigational Incorporation of 5-FU into RNA Inhibition of glucan / chitin synthesis ECHINOCANDINS Caspofungin is licensed Inhibition of β-(1-3) glucan synthesis (of glucan synthase??) Secondary reduction in ergosterol & lanosterol Increase in chitin Kills hyphae at their growth tips and branching points Buds fail to seperate from the mother cell Yields osmotically sensitive fungal cells Incorporation of 5-FU into RNA Inhibition of glucan / chitin synthesis 5

6 NIKKOMYCIN Miscellaneous types Competitive inhibition of chitin synthase Yet investigational Griseofulvin Haloprogin Ciclopirox olamine Tolnaftate Potassium iodide (KI) Griseofulvin A true antibiotic with antifungal properties. It binds to the proteins involved in microtubule formation and prevents separation of chromosomes at mitosis. Why griseofulvin does not affect human cells is not known. It is used in the treatment of ringworm and other fungal infections of the skin or nails. Miscellaneous types Haloprogin - a halogenated phenolic ether administered topically for dermatophytic infections. Ciclopirox olamine - a topical for the treatment of dermatophytic infections and Candida albicans. Tolnaftate - a thiocarbonate used to treat dermatophytic infections. Potassium iodide (KI) - Given orally for sporotrichosis 6

7 ANTIMYCOTIC DRUGS Have a guest? Systemic antifungal agents Polyene macrolide Flucytosine Azoles Morpholine derivatives Griseofulvin Topical antifungal agents Polyene macrolide Azole Griseofulvin Allyamines Thiocarbamate Aspergillus fumigatus Nystatin Amphotericin B, Itraconazole Candida albicans Nystatin, Clotrimazole Amphotericin B, Ketoconazole Cryptococcus neoformans Amphotericin B+Flucytosine, Fluconazole Histoplasma capsulatum Amphotericin B, Ketoconazole, Itraconazole Malassezia pachydermatis Nystatin, Miconazole Microsporum spp. Clotrimazole, Tolnaftate, Ketoconazole Griseofulvin Trichophyton spp. Clotrimazole, Tolnaftate Griseofulvin Sporothrix schenckii Zygomycetes KI (po), NaI (IV), Itraconazole, Amphotericin B Amphotericin B, Ketoconazole 7

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