Fluconazole

  • 2 - (2,4 -difluorophenyl ) -1,3 -bis ( 1H-1 ,2,4-triazol- 1-yl) -2-propanol
  • Latin: Fluconazolum
  • D01AC15
  • J02AC01

Antifungal

Inhibition of the biosynthesis of ergosterol for fungi

138-140 ° C

Attention

1273 mg · kg -1 ( LD50, mouse, ip)

Template: Infobox chemical / molecular formula search available

Fluconazole is a drug from the group of antifungal agents, one of the triazole derivatives.

Mechanism of Action

Fluconazole acts fungistatic in therapeutic doses usually, but can - depending on the dose - also show fungicidal activity in some organisms. Like other imidazole and triazole derivatives inhibits the fluconazole 14 -alpha demethylase cytochrome P450 system of the fungal cell. Characterized the transformation of lanosterol to ergosterol is interrupted, which leads to membrane defects, the fungal cell. The human demethylase is significantly weaker inhibited by fluconazole.

Spectrum of activity

Fluconazole is effective against a broad spectrum of pathogenic fungi, including against Candida spp. (except Candida krusei and Candida glabrata ), Cryptococcus neoformans, Epidermophyton spp., Microsporum spp. Histoplasma capsulatum and.

Adverse effects

Most common side effects of fluconazole are nausea, vomiting and diarrhea as well as the increase of certain enzymes such as aminotransferases and alkaline phosphatase, rarely leads to serious liver damage. Fluconazole is a potent inhibitor of CYP2C9 and a weak inhibitor of CYP3A4. This results in a risk of interactions with numerous substances that are often also metabolized by these enzymes.

In animal studies, reproductive toxicity has been found in humans, there are reports on the occurrence of congenital malformations in children whose mothers (400 to 800 mg / day) treated over a long period with high doses of fluconazole. A study to review the teratogenicity of fluconazole showed up on on the rare tetralogy of Fallot no increased incidence of malformations.

Indications

Fluconazole is used for the topical and systemic treatment of fungal infections, including:

  • Schleimhautcandidosen
  • Serious fungal infections of the skin and mucous
  • Systemic fungal infections

Trade names

Canifug - Fluco (D), Diflucan (D, A, CH), Difluzol (A), Flucazol (CH), Fluconax (CH), Flucosept (A), Flucozal (A), Flunazul (D), Fungata (D, A), various generics (D, A, CH)

CAS registry number PubChem Anatomical Therapeutic Chemical Classification System DrugBank Dangerous Substances Directive (67/548/EEC) Intraperitoneal injection Active ingredient Fungicide Candida (fungus) Epidermophyton floccosum Transaminase Congenital disorder Digital Object Identifier
240034
de