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.
OverviewAI-generated
Fluconazole is a chemical compound with the formula C₁₃H₁₂F₂N₆O. Its IUPAC name is 2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)propan-2-ol. The substance has a molecular mass of 306.104065444 and a weight of 306.27. It possesses a charge of 0, an xlogp of 0.4, and a topological polar surface area of 81.7.
The molecule contains one hydrogen bond donor and seven hydrogen bond acceptors. Its canonical SMILES representation is C1=CC(=C(C=C1F)F)C(CN2C=NC=N2)(CN3C=NC=N3)O. Fluconazole is the subject of 18786 PubMed entries and is referenced by 261 other encyclopedia articles.
Synthesized by Vinony from 17 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
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
~10 min read
Encyclopedic overview
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.
Excerpted from Wikipedia’s “fluconazole” article, available under the CC BY-SA 4.0 licence.