ravuconazole (CHEBI:143825)

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CHEBI:143825 - ravuconazole

ChEBI ID	CHEBI:143825
ChEBI Name	ravuconazole
Stars
Definition	A member of the class of triazoles that is 1-butyl-1H-1,2,4-triazole in which the butyl group is substituted at positions 2, 2, and 3 by hydroxy, 2,4-difluorophenyl, and 4-(p-cyanophenyl)-1,3-thiazol-2-yl groups, respectively (the R,R stereoisomer). It exhibits antifungal activity by inhibition of 14α demethylase, an enzyme involved in sterol synthesis, resulting in lysis of the fungal cell wall and fungal cell death. (NCIO4)
Last Modified	1 June 2022
Submitter	Kalpana P
Downloads	Molfile

Formula	C22H17F2N5OS
Net Charge	0
Average Mass	437.475
Monoisotopic Mass	437.11219
SMILES	C[C@@H](c1nc(-c2ccc(C#N)cc2)cs1)[C@](O)(Cn1cncn1)c1ccc(F)cc1F
InChI	InChI=1S/C22H17F2N5OS/c1-14(21-28-20(10-31-21)16-4-2-15(9-25)3-5-16)22(30,11-29-13-26-12-27-29)18-7-6-17(23)8-19(18)24/h2-8,10,12-14,30H,11H2,1H3/t14-,22+/m0/s1
InChIKey	OPAHEYNNJWPQPX-RCDICMHDSA-N

Wikipedia

Roles Classification

Biological Roles:

antifungal drug Any antifungal agent used to prevent or treat fungal infections in humans or animals.

antileishmanial agent An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.

ergosterol biosynthesis inhibitor Any compound that inhibits one or more steps in the pathway leading to the synthesis of ergosterol.

EC 1.14.14.154 (sterol 14alpha-demethylase) inhibitor Any EC 1.14.14.* (oxidoreductase acting on paired donors, incorporating of 1 atom of oxygen, with reduced flavin or flavoprotein as one donor) inhibitor that interferes with the action of sterol 14α-demethylase (EC 1.14.14.154).

Applications:

antifungal drug Any antifungal agent used to prevent or treat fungal infections in humans or animals.

antileishmanial agent An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.

ChEBI Ontology

Outgoing Relation(s)
	ravuconazole (CHEBI:143825) has role antifungal drug (CHEBI:86327)
	ravuconazole (CHEBI:143825) has role antileishmanial agent (CHEBI:70868)
	ravuconazole (CHEBI:143825) has role EC 1.14.14.154 (sterol 14α-demethylase) inhibitor (CHEBI:143828)
	ravuconazole (CHEBI:143825) has role ergosterol biosynthesis inhibitor (CHEBI:75282)
	ravuconazole (CHEBI:143825) is a 1,3-thiazoles (CHEBI:38418)
	ravuconazole (CHEBI:143825) is a fluorobenzenes (CHEBI:35496)
	ravuconazole (CHEBI:143825) is a nitrile (CHEBI:18379)
	ravuconazole (CHEBI:143825) is a tertiary alcohol (CHEBI:26878)
	ravuconazole (CHEBI:143825) is a triazoles (CHEBI:35727)

IUPAC Name
4-[2-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]-1,3-thiazol-4-yl]benzonitrile

INNs	Source
ravuconazol	WHO MedNet
ravuconazole	WHO MedNet
ravuconazole	WHO MedNet
ravuconazolum	WHO MedNet

Synonyms	Source
BMS-20714	ChEBI
BMS 207147	ChemIDplus
ER 30346	ChemIDplus
ER-30346	ChEBI

Manual Xrefs	Databases
D02556	KEGG DRUG
DB06440	DrugBank
HMDB0257114	HMDB
Ravuconazole	Wikipedia
US2011087030	Patent
WO2011042827	Patent

Registry Numbers	Sources
CAS:182760-06-1	ChemIDplus
CAS:182760-06-1	KEGG DRUG

Citations