Voriconazole

Voriconazole

Clinical data
Pronunciation	vor-i-KON-a-zole
Trade names	Vfend
AHFS/Drugs.com	Monograph
MedlinePlus	a605022
License data	EU EMA: VFEND US FDA: Voriconazole
Pregnancy category	D
Routes of administration	IV, by mouth (tablets, oral suspension)
ATC code	J02AC03 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	96% (oral administration)
Protein binding	58%
Metabolism	Liver: CYP2C19 (significant involvement), also CYP2C9, CYP3A4
Metabolites	Voriconazole N-oxide (major; minimal antifungal activity)
Biological 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
Synonyms	(αR,βS)-α-(2,4-Difluorophenyl)-5-fluoro-β-methyl-α-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol
CAS Number	137234-62-9 Y
PubChem CID	71616
DrugBank	DB00582 Y
ChemSpider	64684 Y
UNII	JFU09I87TR
KEGG	D00578 Y
ChEBI	CHEBI:10023 Y
ChEMBL	CHEMBL638 Y
Chemical and physical data
Formula	C16H14F3N5O
Molar mass	349.311 g/mol
3D model (Jmol)	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 Y Key:BCEHBSKCWLPMDN-MGPLVRAMSA-N Y

Voriconazole (INN, brand name Vfend VEE-fend, manufactured by Pfizer) is a triazole antifungal medication that is generally used to treat serious, invasive fungal infections. These are generally seen in patients who are immunocompromised, and include invasive candidiasis, invasive aspergillosis, and certain emerging fungal infections.

Voriconazole is used to treat invasive aspergillosis, which may occur in immunocompromised patients, including allogeneic BMT, hematologic cancers, and solid organ transplants.

For multiple site or CNS aspergillosis a combination therapy of voriconazole and liposomal amphotericin B should be considered. It is also the recommended treatment for the CNS fungal infections transmitted by epidural injection of contaminated steroids.

Voriconazole has proven to be as effective as a regimen of intravenous amphotericin B followed by oral fluconazole in patients with culture-proven candidemia. Voriconazole cleared Candida from the bloodstream as quickly as amphotericin B (median 2 days) and showed a trend toward better survival. Voriconazole was also associated with fewer serious adverse events and cases of renal toxicity, but a higher incidence of visual disturbances.