CHEBI:6076 - itraconazole

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name itraconazole
ChEBI ID CHEBI:6076
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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information eMolecules:29541763, eMolecules:902000, eMolecules:36753603, Selleckchem:Itraconazole(Sporanox)
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C35H38Cl2N8O4
Net Charge 0
Average Mass 705.63300
Monoisotopic Mass 704.23931
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
SMILES CCC(C)n1ncn(-c2ccc(cc2)N2CCN(CC2)c2ccc(OC[C@H]3CO[C@@](Cn4cncn4)(O3)c3ccc(Cl)cc3Cl)cc2)c1=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): Hedgehog signaling pathway inhibitor
Any pathway inhibitor that inhibits the Hedgehog signalling pathway.
P450 inhibitor
An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.
EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor
An EC 3.6.3.* (acid anhydride hydrolase catalysing transmembrane movement of substances) inhibitor that interferes with the action of xenobiotic-transporting ATPase (EC 3.6.3.44).
antifungal drug
Any antifungal agent used to prevent or treat fungal infections in humans or animals.
(via conazole antifungal drug )
(via triazole antifungal drug )
ergosterol biosynthesis inhibitor
Any compound that inhibits one or more steps in the pathway leading to the synthesis of ergosterol.
(via conazole antifungal agent )
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
(via conazole antifungal agent )
(via triazole antifungal agent )
Application(s): antifungal drug
Any antifungal agent used to prevent or treat fungal infections in humans or animals.
(via conazole antifungal drug )
(via triazole antifungal drug )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing itraconazole (CHEBI:6076) has role EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor (CHEBI:77748)
itraconazole (CHEBI:6076) has role Hedgehog signaling pathway inhibitor (CHEBI:140921)
itraconazole (CHEBI:6076) has role P450 inhibitor (CHEBI:50183)
itraconazole (CHEBI:6076) is a N-arylpiperazine (CHEBI:46848)
itraconazole (CHEBI:6076) is a aromatic ether (CHEBI:35618)
itraconazole (CHEBI:6076) is a conazole antifungal drug (CHEBI:87071)
itraconazole (CHEBI:6076) is a cyclic ketal (CHEBI:59779)
itraconazole (CHEBI:6076) is a dichlorobenzene (CHEBI:23697)
itraconazole (CHEBI:6076) is a dioxolane (CHEBI:39430)
itraconazole (CHEBI:6076) is a triazole antifungal drug (CHEBI:87101)
itraconazole (CHEBI:6076) is a triazoles (CHEBI:35727)
IUPAC Name
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
Synonyms Sources
itraconazole UniProt
Itraconazole KEGG DRUG
Itrizole (TN) KEGG DRUG
Oriconazole ChemIDplus
Sporanox (TN) KEGG DRUG
Manual Xrefs Databases
1853 VSDB
D00350 KEGG DRUG
DB01167 DrugBank
EP6711 Patent
Itraconazole Wikipedia
US4267179 Patent
View more database links
Registry Numbers Types Sources
84625-61-6 CAS Registry Number KEGG DRUG
84625-61-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11219548 PubMed citation Europe PMC
11403818 PubMed citation Europe PMC
11422002 PubMed citation Europe PMC
15521894 PubMed citation Europe PMC
19025521 PubMed citation Europe PMC
20400651 PubMed citation Europe PMC
25326091 PubMed citation Europe PMC
Last Modified
15 October 2019