Voriconazole

Voriconazole
Clinical data
Pronunciation/vɒrɪˈkɒnəzl/ vorr-i-KON-ə-zohl
Trade namesVfend, others
AHFS/Drugs.comMonograph
MedlinePlusa605022
License data
Pregnancy
category
  • AU: B3
Routes of
administration
Intravenous, by mouth
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • US: ℞-only
  • EU: Rx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability96% (oral)
Protein binding58%
MetabolismLiver: CYP2C19 (significant involvement), also CYP2C9, CYP3A4
MetabolitesVoriconazole N-oxide (major; minimal antifungal activity)
Elimination half-lifeDose-dependent
ExcretionUrine (80–83%)
Identifiers
  • (2R,3S)-2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.157.870
Chemical and physical data
FormulaC16H14F3N5O
Molar mass349.317 g·mol−1
3D model (JSmol)
  • Fc1cncnc1[C@@H]([C@@](O)(c2ccc(F)cc2F)Cn3ncnc3)C
  • InChI=1S/C16H14F3N5O/c1-10(15-14(19)5-20-7-22-15)16(25,6-24-9-21-8-23-24)12-3-2-11(17)4-13(12)18/h2-5,7-10,25H,6H2,1H3/t10-,16+/m0/s1 Y
  • Key:BCEHBSKCWLPMDN-MGPLVRAMSA-N Y
  (verify)

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.

Common side effects include vision problems, nausea, abdominal pain, rash, headache, and seeing or hearing things that are not present. Use during pregnancy may result in harm to the baby. It is in the triazole family of medications. It works by affecting fungal metabolism and fungal cell membranes.

Voriconazole was patented in 1990 and approved for medical use in the United States in 2002. It is on the World Health Organization's List of Essential Medicines.