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CHEBI:143825 - ravuconazole

Default Structure
ChEBI IDCHEBI:143825
ChEBI Nameravuconazole
Stars
DefinitionA 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 Modified1 June 2022
SubmitterKalpana P
DownloadsMolfile
FormulaC22H17F2N5OS
Net Charge0
Average Mass437.475
Monoisotopic Mass437.11219
SMILESC[C@@H](c1nc(-c2ccc(C#N)cc2)cs1)[C@](O)(Cn1cncn1)c1ccc(F)cc1F
InChIInChI=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
InChIKeyOPAHEYNNJWPQPX-RCDICMHDSA-N
Wikipedia
Roles Classification
Biological Roles:
antileishmanial agent  An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
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 14α-demethylase (EC 1.14.14.154).
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
ergosterol biosynthesis inhibitor  Any compound that inhibits one or more steps in the pathway leading to the synthesis of ergosterol.
Applications:
antileishmanial agent  An antiprotozoal drug used to treat or prevent infections caused by protozoan parasites that belong to the genus Leishmania.
antifungal drug  Any antifungal agent used to prevent or treat fungal infections in humans or animals.
ChEBI Ontology
Outgoing Relation(s)
ravuconazole (CHEBI:143825) has role antifungal agent (CHEBI:35718)
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
ravuconazolWHO MedNet
ravuconazoleWHO MedNet
ravuconazoleWHO MedNet
ravuconazolumWHO MedNet
Synonyms  Source
BMS-20714ChEBI
BMS 207147ChemIDplus
BMS-207147ChEMBL
ER 30346ChemIDplus
ER-30346ChEBI
Manual XrefsDatabases
D02556KEGG DRUG
DB06440DrugBank
HMDB0257114HMDB
RavuconazoleWikipedia
US2011087030Patent
WO2011042827Patent
Registry NumbersSources
CAS:182760-06-1KEGG DRUG
CAS:182760-06-1ChemIDplus
Citations