Chemical Entities of Biological Interest Ontology

Last uploaded: January 1, 2025
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Id http://purl.obolibrary.org/obo/CHEBI_6076
http://purl.obolibrary.org/obo/CHEBI_6076
Preferred Name

itraconazole
Definitions
An N-arylpiperazine that is cis-ketoconazole in which the imidazol-1-yl group is replaced by a 1,2,4-triazol-1-yl group and in which the actyl group attached to the piperazine moiety is replaced by a p-[(+-)1-sec-butyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]phenyl group. A potent P-glycoprotein and CYP3A4 inhibitor, it is used as an antifungal drug for the treatment of various fungal infections, including aspergillosis, blastomycosis, candidiasis, chromoblastomycosis, coccidioidomycosis, cryptococcosis, histoplasmosis, and sporotrichosis.
Synonyms
Itrizole (TN)
Sporanox (TN)
Oriconazole
2-(butan-2-yl)-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-2,4-dihydro-3H-1,2,4-triazol-3-one
Itraconazole
itraconazole
Type http://www.w3.org/2002/07/owl#Class

All Properties

definition

An N-arylpiperazine that is cis-ketoconazole in which the imidazol-1-yl group is replaced by a 1,2,4-triazol-1-yl group and in which the actyl group attached to the piperazine moiety is replaced by a p-[(+-)1-sec-butyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]phenyl group. A potent P-glycoprotein and CYP3A4 inhibitor, it is used as an antifungal drug for the treatment of various fungal infections, including aspergillosis, blastomycosis, candidiasis, chromoblastomycosis, coccidioidomycosis, cryptococcosis, histoplasmosis, and sporotrichosis.
label
itraconazole
prefLabel
itraconazole
database_cross_reference
Patent:US4267179
PMID:11219548
CAS:84625-61-6
KEGG:D00350
Patent:EP6711
PMID:11403818
VSDB:1853
PMID:15521894
PMID:19025521
PMID:25326091
Wikipedia:Itraconazole
DrugBank:DB01167
PMID:20400651
PMID:11422002
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notation
CHEBI:6076
in_subset
inchi
InChI=1S/C35H38Cl2N8O4/c1-3-25(2)45-34(46)44(24-40-45)29-7-5-27(6-8-29)41-14-16-42(17-15-41)28-9-11-30(12-10-28)47-19-31-20-48-35(49-31,21-43-23-38-22-39-43)32-13-4-26(36)18-33(32)37/h4-13,18,22-25,31H,3,14-17,19-21H2,1-2H3/t25?,31-,35-/m0/s1
has_related_synonym
Itrizole (TN)
Sporanox (TN)
Oriconazole
id
CHEBI:6076
charge
0
has_obo_namespace
chebi_ontology
formula
C35H38Cl2N8O4
subClassOf
inchikey
VHVPQPYKVGDNFY-ZPGVKDDISA-N
mass
705.63300
monoisotopicmass
704.23931
type
smiles
CCC(C)n1ncn(-c2ccc(cc2)N2CCN(CC2)c2ccc(OC[C@H]3CO[C@@](Cn4cncn4)(O3)c3ccc(Cl)cc3Cl)cc2)c1=O
has role
has_exact_synonym
2-(butan-2-yl)-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-2,4-dihydro-3H-1,2,4-triazol-3-one
Itraconazole
itraconazole
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