loading...| Preferred Name | itraconazole | |
| Synonyms |
Oriconazole Itrizole (TN) Sporanox (TN) itraconazole Itraconazole 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 |
|
| 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. |
|
| ID |
http://purl.obolibrary.org/obo/CHEBI_6076 |
|
| charge |
0 |
|
| database_cross_reference |
PMID:11219548 DrugBank:DB01167 PMID:11422002 Patent:EP6711 PMID:15521894 PMID:20400651 PMID:19025521 PMID:11403818 PMID:25326091 CAS:84625-61-6 Patent:US4267179 KEGG:D00350 Wikipedia:Itraconazole VSDB:1853 |
|
| 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. |
|
| formula |
C35H38Cl2N8O4 |
|
| has characteristic |
http://purl.obolibrary.org/obo/CHEBI_50183 |
|
| has role |
http://purl.obolibrary.org/obo/CHEBI_50183 |
|
| has_exact_synonym |
itraconazole Itraconazole 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 |
|
| has_obo_namespace |
chebi_ontology |
|
| has_related_synonym |
Oriconazole Itrizole (TN) Sporanox (TN) |
|
| id |
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 |
|
| inchikey |
VHVPQPYKVGDNFY-ZPGVKDDISA-N |
|
| label |
itraconazole |
|
| mass |
705.63300 |
|
| monoisotopicmass |
704.23931 |
|
| notation |
CHEBI:6076 |
|
| prefLabel |
itraconazole |
|
| smiles |
CCC(C)n1ncn(-c2ccc(cc2)N2CCN(CC2)c2ccc(OC[C@H]3CO[C@@](Cn4cncn4)(O3)c3ccc(Cl)cc3Cl)cc2)c1=O |
|
| subClassOf |
http://purl.obolibrary.org/obo/CHEBI_35618 http://purl.obolibrary.org/obo/CHEBI_39430 http://purl.obolibrary.org/obo/CHEBI_46848 http://purl.obolibrary.org/obo/CHEBI_87101 http://purl.obolibrary.org/obo/CHEBI_23697 |