How does fluconazole work


FluconazoleDrug groupsAntifungal drugsAzole Antifungal Drugs Fluconazole is an active ingredient in the triazole antifungal group that is used to prevent and treat fungal infections. The effects are based on the inhibition of the enzyme lanosterol-14α-demethylase, whereby the ergosterol synthesis in the mushrooms is blocked. Fluconazole has a long half-life of about 30 hours and is taken once a day with or without food. Some diseases can be treated with a single dose. Fluconazole is an inhibitor of CYP450 isoenzymes and can cause drug interactions. The most common possible adverse effects include abdominal pain, diarrhea, nausea, vomiting, elevated liver values, rashes and headaches.

synonym: FluconazolumPhEur

Products

Fluconazole is available in the form of capsules, as a powder for the preparation of a suspension and as an infusion solution (Diflucan®, generics). It has been approved in Switzerland since 1989.

Structure and properties

Fluconazole (C.13H12F.2N6O, Mr = 306.3 g / mol) is a fluorinated triazole derivative. It exists as a white, crystalline and hygroscopic powder that is sparingly soluble in water.

Effects

Fluconazole (ATC J02AC01) has antifungal (fungistatic) properties. The effects are based on the inhibition of the enzyme lanosterol-14α-demethylase in the fungal cells. This interrupts the conversion of lanosterol to ergosterol. This leads to an accumulation of 14α-methylsterols and a disruption in the structure of the fungal cell membrane.

Indications

Fluconazole is used to prevent and treat fungal infections. This includes:

dosage

According to the medicinal product information. The capsules are taken once a day with or without meals. The dosage interval depends on the indication. Some infections can be treated with a single dose (e.g. vaginal thrush).

Depending on the area of ​​application, daily or weekly intake may also be necessary. Fluconazole has a long half-life of about 30 hours (range: 20-50 hours). The usual dose range is 50 to 400 mg (adults). A suspension is available for children.

Contraindications
  • Hypersensitivity
  • Fluconazole must not be combined with medicinal products which are metabolised by CYP3A4 and which at the same time prolong the QT interval.

The complete precautionary measures can be found in the medicinal product information sheet.

Interactions

Fluconazole has a high potential for interaction. It is a substrate for CYP3A4 and an inhibitor of CYP2C9, CYP2C19 and CYP3A4 and can cause drug interactions.

unwanted effects

The most common possible adverse effects include abdominal pain, diarrhea, nausea, vomiting, elevated liver values, rashes, and headaches. Very rarely, serious side effects such as a prolongation of the QT interval, liver damage and severe skin damage can occur.

Checklist for advising patients

Download: Checklist_Fluconazole.pdf

see also

Azole antifungal drugs

literature
  • Pharmaceutical product information (CH, USA)
  • European Pharmacopoeia PhEur
  • Kowalsky S.F., Dixon D.M. Fluconazole: a new antifungal agent. Clin Pharm, 1991, 10 (3), 179-94 Pubmed
  • Lazar J.D., Wilner K.D. Drug interactions with fluconazole. Rev Infect Dis., 1990, 12 (3), 327-33 Pubmed
  • Richardson K., Cooper K., Marriott M.S., Tarbit M.H., Troke P.F., Whittle P.J. Discovery of fluconazole, a novel antifungal agent. Rev Infect Dis, 1990, 12 Suppl 3, S267-71 Pubmed
  • Washton H. Review of fluconazole: a new triazole antifungal agent. Diagn Microbiol Infect Dis, 1989, 12 (4), 229-233 Pubmed
  • Zervos M., Meunier F. Fluconazole (Diflucan): a review. Int J Antimicrob Agents, 1993, 3 (3), 147-70 Pubmed
author

Conflicts of Interest: None / Independent. The author has no relationships with the manufacturers and is not involved in the sale of the products mentioned.

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