voriconazole (CHEBI:10023)

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ChEBI Name	voriconazole

ChEBI ID	CHEBI:10023

Definition	A triazole-based antifungal agent used for the treatment of esophageal candidiasis, invasive pulmonary aspergillosis, and serious fungal infections caused by Scedosporium apiospermum and Fusarium spp. It is an inhibitor of cytochrome P450 2C9 (CYP2C9) and CYP3A4.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:127308

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Formula

C16H14F3N5O

Net Charge

Average Mass

349.31050

Monoisotopic Mass

349.11504

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

InChIKey

BCEHBSKCWLPMDN-MGPLVRAMSA-N

SMILES

C[C@@H](c1ncncc1F)[C@](O)(Cn1cncn1)c1ccc(F)cc1F

Roles Classification
Biological Role(s):	P450 inhibitor An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances. antifungal drug Any antifungal agent used to prevent or treat fungal infections in humans or animals. (via triazole antifungal drug ) (via conazole antifungal drug ) antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. (via triazole antifungal agent ) (via conazole antifungal agent ) ergosterol biosynthesis inhibitor Any compound that inhibits one or more steps in the pathway leading to the synthesis of ergosterol. (via conazole antifungal agent )

Application(s):	antifungal drug Any antifungal agent used to prevent or treat fungal infections in humans or animals. (via triazole antifungal drug ) (via conazole antifungal drug )

ChEBI Ontology
Outgoing	voriconazole (CHEBI:10023) has role P450 inhibitor (CHEBI:50183) voriconazole (CHEBI:10023) is a conazole antifungal drug (CHEBI:87071) voriconazole (CHEBI:10023) is a difluorobenzene (CHEBI:38582) voriconazole (CHEBI:10023) is a pyrimidines (CHEBI:39447) voriconazole (CHEBI:10023) is a tertiary alcohol (CHEBI:26878) voriconazole (CHEBI:10023) is a triazole antifungal drug (CHEBI:87101)

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	Sources
(αR,βS)-α-(2,4-difluorophenyl)-5-fluoro-β-methyl-α(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol	ChemIDplus
(R-(R,S))-alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol	ChEBI
VCZ	DrugBank
voriconazole	UniProt

Brand Name	Source
Vfend	ChEBI

Last Modified

15 October 2019