The Drug Ontology

Last uploaded: March 3, 2024
Preferred Name

Itraconazole

Synonyms

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

Oriconazole

Itrizole (TN)

Sporanox (TN)

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 role

http://purl.obolibrary.org/obo/CHEBI_50183

http://purl.obolibrary.org/obo/CHEBI_77748

http://purl.obolibrary.org/obo/CHEBI_140921

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)

has_RxCUI

28031

id

CHEBI:6076

in_subset

http://purl.obolibrary.org/obo/chebi#3_STAR

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

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

http://purl.obolibrary.org/obo/CHEBI_59779

http://purl.obolibrary.org/obo/CHEBI_87071

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