voriconazole

Also known as (AlphaR,betas)-alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol, Voriconazolum, (R-(R*,s*))-alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol, Voriconazol, VCZ, UK-109496

Voriconazole, sold under the brand name Vfend among others, is an antifungal medication used to treat a number of fungal infections. This includes aspergillosis, candidiasis, coccidioidomycosis, histoplasmosis, penicilliosis, and infections by Scedosporium or Fusarium. It can be taken by mouth or used by injection into a vein.

In the Vinony graph

Vinony's link graph records 184 inbound references to voriconazole, and connects out to intravenous infusion and defusion, antifungal and World Health Organization.

Vinony files it under CYP2B6 inhibitors, CYP2C19 inhibitors and CYP2C9 inhibitors.

Vinony links it to 25 Wikipedia language editions.

Key facts

Drug.Watchedfields: changed
Drug.verifiedrevid: 470631790
Drug.image: Voriconazole structure.svg
Drug.image_class: skin-invert-image
Drug.image2: Voriconazole ball-and-stick model.png
Drug.image_class2: bg-transparent
Drug.tradename: Vfend, others
Drug.MedlinePlus: a605022
Drug.DailyMedID: Voriconazole
Drug.pregnancy_AU: B3
Drug.routes_of_administration: Intravenous, by mouth
Drug.ATC_prefix: J02
Drug.ATC_suffix: AC03
Drug.legal_AU: S4
Drug.legal_CA: Rx-only
Drug.legal_US: Rx-only
Drug.legal_EU: Rx-only
Drug.legal_status: Rx-only

via Wikipedia infobox

Chemical data

Formula: C16H14F3N5O
Molecular weight: 349.31 g/mol
IUPAC name: (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1,2,4-triazol-1-yl)butan-2-ol
SMILES: C[C@@H](C1=NC=NC=C1F)[C@](CN2C=NC=N2)(C3=C(C=C(C=C3)F)F)O
InChIKey: BCEHBSKCWLPMDN-MGPLVRAMSA-N
XLogP: 1.5
Polar surface area: 76.7 Å²
H-bond donors: 1
H-bond acceptors: 8
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 2002
Admin. routes: oral, parenteral
Indications: aspergillosis, infection, HIV infection, chronic lymphocytic leukemia

via ChEMBL · EBI

Research

10,369 papers

Pharmacokinetic/pharmacodynamic profile of voriconazole.Clinical pharmacokinetics · 2006
Voriconazole.Clinical therapeutics · 2003
Voriconazole-refractory invasive aspergillosis.The Korean journal of internal medicine · 2017
Voriconazole in the management of invasive pulmonary aspergillosis in patients with severe liver disease: balancing efficacy and hepatotoxicity.Journal de mycologie medicale · 2025
[Voriconazole-induced periostitis].Ugeskrift for laeger · 2019

via PubMed

Wikidata facts

Subclass of: azole
Mass: 349.115
Has use: medication

Show 9 more facts

chemical formula: C₁₆H₁₄F₃N₅O
NCI Thesaurus ID: C1707
medical condition treated: esophageal candidiasis
subject has role: essential medicine
canonical SMILES: CC(C1=NC=NC=C1F)C(CN2C=NC=N2)(C3=C(C=C(C=C3)F)F)O
World Health Organisation international non-proprietary name: voriconazole
isomeric SMILES: C[C@@H](C1=NC=NC=C1F)[C@](O)(CN2C=NC=N2)C3=CC=C(F)C=C3F
Commons category: Voriconazole
significant drug interaction: pimozide

Sources (6)

via Wikidata · CC0

~5 min read

Encyclopedic overview

11 sections

Contents

Medical uses
Contraindications
Side effects
Interactions
Pharmacology
Pharmacokinetics
History
Society and culture
Brand names
References
Further reading

Common side effects include vision problems, nausea, abdominal pain, rash, headache, and hallucinations. Use during pregnancy may result in harm to the fetus. It is in the triazole family of medications., and works by affecting fungal metabolism and fungal cell membranes.

Excerpted from Wikipedia’s “voriconazole” article, available under the CC BY-SA 4.0 licence.