Voriconazole

Voriconazole
Clinical data
Pronunciation	/vɒrɪˈkɒnəzoʊl/ vorr-i-KON-ə-zohl
Trade names	Vfend, others
AHFS/Drugs.com	Monograph
MedlinePlus	a605022
License data	US DailyMed: Voriconazole;
Pregnancy; category	AU: B3;
Routes of; administration	Intravenous, by mouth
ATC code	J02AC03 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	96% (oral)
Protein binding	58%
Metabolism	Liver: CYP2C19 (significant involvement), also CYP2C9, CYP3A4
Metabolites	Voriconazole N-oxide (major; minimal antifungal activity)
Elimination half-life	Dose-dependent
Excretion	Urine (80–83%)
Identifiers
	IUPAC name (2R,3S)-2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;
CAS Number	137234-62-9 ;
PubChem CID	71616;
DrugBank	DB00582 ;
ChemSpider	64684 ;
UNII	JFU09I87TR;
KEGG	D00578 ;
ChEBI	CHEBI:10023 ;
ChEMBL	ChEMBL638 ;
CompTox Dashboard (EPA)	DTXSID5046485 ;
ECHA InfoCard	100.157.870
Chemical and physical data
Formula	C16H14F3N5O
Molar mass	349.317 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Fc1cncnc1[C@@H]([C@@](O)(c2ccc(F)cc2F)Cn3ncnc3)C;
	InChI 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 ; Key:BCEHBSKCWLPMDN-MGPLVRAMSA-N ;
	(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 hallucinations.^[5] Use during pregnancy may result in harm to the fetus.^[5] It is in the triazole family of medications.^[5], and 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]

^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
^ "Product monograph brand safety updates". Health Canada. 6 June 2024. Retrieved 8 June 2024.
^ "Vfend EPAR". European Medicines Agency (EMA). 19 March 2002. Retrieved 14 August 2024.
^ Cite error: The named reference Vfend FDA label was invoked but never defined (see the help page).
^ ^a ^b ^c ^d ^e ^f ^g "Voriconazole". The American Society of Health-System Pharmacists. Retrieved 8 December 2017.
^ 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.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 503. ISBN 9783527607495.
^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.

[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.

[Vfend_FDA_label-4] Cite error: The named reference Vfend FDA label was invoked but never defined (see the help page).

[AHFS2017-5] ^ ^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.

[Fis2006-7] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 503. ISBN 9783527607495.

[WHO23rd-8] World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.

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