fluconazole (CHEBI:46081)

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ChEBI Name	fluconazole

ChEBI ID	CHEBI:46081

Definition	A member of the class of triazoles that is propan-2-ol substituted at position 1 and 3 by 1H-1,2,4-triazol-1-yl groups and at position 2 by a 2,4-difluorophenyl group. It is an antifungal drug used for the treatment of mucosal candidiasis and for systemic infections including systemic candidiasis, coccidioidomycosis, and cryptococcosis.

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

Secondary ChEBI IDs	CHEBI:46079, CHEBI:5099

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Formulae

C13H12F2N6O
C13H12F2N6O

Net Charge

Average Mass

306.27080

Monoisotopic Mass

306.10407

InChI

InChI=1S/C13H12F2N6O/c14-10-1-2-11(12(15)3-10)13(22,4-20-8-16-6-18-20)5-21-9-17-7-19-21/h1-3,6-9,22H,4-5H2

InChIKey

RFHAOTPXVQNOHP-UHFFFAOYSA-N

SMILES

OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F

Roles Classification
Chemical Role(s):	environmental contaminant Any minor or unwanted substance introduced into the environment that can have undesired effects.

Biological Role(s):	P450 inhibitor An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances. xenobiotic A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means. antifungal drug Any antifungal agent used to prevent or treat fungal infections in humans or animals. (via conazole antifungal drug ) (via triazole antifungal drug ) ergosterol biosynthesis inhibitor Any compound that inhibits one or more steps in the pathway leading to the synthesis of ergosterol. (via conazole antifungal agent ) antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. (via conazole antifungal agent ) (via triazole antifungal agent )

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

ChEBI Ontology
Outgoing	fluconazole (CHEBI:46081) has functional parent 1,3-difluorobenzene (CHEBI:38584) fluconazole (CHEBI:46081) has parent hydride 1H-1,2,4-triazole (CHEBI:35550) fluconazole (CHEBI:46081) has role environmental contaminant (CHEBI:78298) fluconazole (CHEBI:46081) has role P450 inhibitor (CHEBI:50183) fluconazole (CHEBI:46081) has role xenobiotic (CHEBI:35703) fluconazole (CHEBI:46081) is a conazole antifungal drug (CHEBI:87071) fluconazole (CHEBI:46081) is a difluorobenzene (CHEBI:38582) fluconazole (CHEBI:46081) is a tertiary alcohol (CHEBI:26878) fluconazole (CHEBI:46081) is a triazole antifungal drug (CHEBI:87101)

Incoming	Fosfluconazole (CHEBI:31634) has functional parent fluconazole (CHEBI:46081)

IUPAC Name

2-(2,4-difluorophenyl)-1,3-bis-(1H-1,2,4-triazol-1-yl)propan-2-ol

Synonyms	Sources
2,4-difluoro-α,α-bis(1H-1,2,4-triazol-1-ylmethyl)benzyl alcohol	ChemIDplus
2-(2,4-DIFLUOROPHENYL)-1,3-DI(1H-1,2,4-TRIAZOL-1-YL)PROPAN-2-OL	PDBeChem
Elazor	ChemIDplus
fluconazole	UniProt

Last Modified

15 October 2019

General Comment
2014-10-29	Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag