CHEBI:143825 - ravuconazole

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ChEBI Name ravuconazole
ChEBI ID CHEBI:143825
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)
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kalpana P
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Formula C22H17F2N5OS
Net Charge 0
Average Mass 437.470
Monoisotopic Mass 437.11219
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
SMILES C=1C(=C(C=C(C1)F)F)[C@@]([C@@H](C)C2=NC(=CS2)C=3C=CC(=CC3)C#N)(O)CN4C=NC=N4
Roles Classification
Biological Role(s): ergosterol biosynthesis inhibitor
Any compound that inhibits one or more steps in the pathway leading to the synthesis of ergosterol.
antifungal drug
Any antifungal agent used to prevent or treat fungal infections in humans or animals.
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 14alpha-demethylase (EC 1.14.14.154).
antileishmanial agent
An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
ravuconazol WHO MedNet
ravuconazole WHO MedNet
ravuconazole WHO MedNet
ravuconazolum WHO MedNet
Synonyms Sources
BMS 207147 ChemIDplus
BMS-20714 ChEBI
ER 30346 ChemIDplus
ER-30346 ChEBI
Manual Xrefs Databases
D02556 KEGG DRUG
DB06440 DrugBank
HMDB0257114 HMDB
Ravuconazole Wikipedia
US2011087030 Patent
WO2011042827 Patent
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Registry Numbers Types Sources
182760-06-1 CAS Registry Number ChemIDplus
182760-06-1 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
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Last Modified
01 June 2022