Voriconazole

Voriconazole
Clinical data
Pronunciation/vɒrɪˈkɒnəzoʊl/ 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
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%)[4]
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 Edit this at Wikidata
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 checkY
  • Key:BCEHBSKCWLPMDN-MGPLVRAMSA-N checkY
  (verify)

Voriconazole, sold under the brand name Vfend among others, is an antifungal medication used to treat a number of fungal infections.[5] This includes aspergillosis, candidiasis, coccidioidomycosis, histoplasmosis, penicilliosis, and infections by Scedosporium or Fusarium.[5] It can be taken by mouth or used by injection into a vein.[5]

Common side effects include vision problems, nausea, abdominal pain, rash, headache, and seeing or hearing things that are not present.[5] Use during pregnancy may result in harm to the baby.[5] It is in the triazole family of medications.[5] It works by affecting fungal metabolism and fungal cell membranes.[5]

Voriconazole was patented in 1990 and approved for medical use in the United States in 2002.[6][7] It is on the World Health Organization's List of Essential Medicines.[8]

  1. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  2. ^ "Product monograph brand safety updates". Health Canada. 6 June 2024. Retrieved 8 June 2024.
  3. ^ "Vfend EPAR". European Medicines Agency (EMA). 19 March 2002. Retrieved 14 August 2024.
  4. ^ Cite error: The named reference Vfend FDA label was invoked but never defined (see the help page).
  5. ^ a b c d e f g "Voriconazole". The American Society of Health-System Pharmacists. Retrieved 8 December 2017.
  6. ^ Kendig EL, Wilmott RW, Chernick V (2012). Kendig and Chernick's Disorders of the Respiratory Tract in Children. Elsevier Health Sciences. p. 539. ISBN 978-1437719840.
  7. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 503. ISBN 9783527607495.
  8. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.