Structure via PubChem · Public domain (PubChem)
fluconazole
Sign in to saveAlso known as 2-(2,4-difluorophenyl)-1,3-di(1H-1,2,4-triazol-1-yl)propan-2-ol, 2,4-difluoro-alpha,alpha-bis(1H-1,2,4-triazol-1-ylmethyl)benzyl alcohol
Fluconazole is an antifungal medication used for a number of fungal infections. These include candidiasis, blastomycosis, coccidioidomycosis, cryptococcosis, histoplasmosis, dermatophytosis, and tinea versicolor. It is also used to prevent candidiasis in those who are at high risk such as following organ transplantation, low birth weight babies, and those with low blood neutrophil counts. It is given either by mouth or by injection into a vein.
Key facts
- Drug.KEGG
- D00322
- Drug.KEGG2
- C07002
- Drug.ChEBI
- 46081
- Drug.ChEMBL
- 106
- Drug.legal_US
- Rx-only
- Drug.legal_EU
- Rx-only
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 456485284
- Drug.image
- Fluconazole skeletal formula.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 185
- Drug.image2
- Fluconazole ball-and-stick model.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 175
- Drug.tradename
- Diflucan, others
- Drug.MedlinePlus
- a690002
- Drug.DailyMedID
- Fluconazole
- Drug.pregnancy_AU
- D
via Wikipedia infobox
Chemical data
- Formula
- C13H12F2N6O
- Molecular weight
- 306.27 g/mol
- IUPAC name
- 2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)propan-2-ol
- SMILES
- C1=CC(=C(C=C1F)F)C(CN2C=NC=N2)(CN3C=NC=N3)O
- InChIKey
- RFHAOTPXVQNOHP-UHFFFAOYSA-N
- XLogP
- 0.4
- Polar surface area
- 81.7 Ų
- H-bond donors
- 1
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Research
18,786 papers- Candida albicans targets that potentially synergize with fluconazole.Critical reviews in microbiology · 2021
- Fluconazole: pharmacokinetics and indications.Archives of medical research · 1993
- Fluconazole: a new antifungal agent.Clinical pharmacy · 1991
- Fluconazole prophylaxis in high-risk neonates.The Annals of pharmacotherapy · 2010
- Efficacy of fluconazole for the treatment of onychomycosis.The Annals of pharmacotherapy · 2009
via PubMed
Wikidata facts
- Mass
- 306.104
Show 4 more facts
- chemical formula
- C₁₃H₁₂F₂N₆O
- Commons category
- Fluconazole
- canonical SMILES
- C1=CC(=C(C=C1F)F)C(CN2C=NC=N2)(CN3C=NC=N3)O
- World Health Organisation international non-proprietary name
- fluconazole
Sources (6)
via Wikidata · CC0
~10 min read
Article
12 sectionsContents
- Medical uses
- Resistance
- Combating resistance
- Contraindications
- Side effects
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- History
- References
- Further reading
Fluconazole is an antifungal medication used for a number of fungal infections. These include candidiasis, blastomycosis, coccidioidomycosis, cryptococcosis, histoplasmosis, dermatophytosis, and tinea versicolor. It is also used to prevent candidiasis in those who are at high risk such as following organ transplantation, low birth weight babies, and those with low blood neutrophil counts. It is given either by mouth or by injection into a vein.
Common side effects include vomiting, diarrhea, rash, and increased liver enzymes. Serious side effects may include liver problems, QT prolongation, and seizures. Use during pregnancy may increase the risk of miscarriage or birth defects. Fluconazole is in the azole antifungal family of medication. It is believed to work by affecting the fungal cellular membrane.