Discuss This Drug

Itraconazole

CHEBI: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.

Chemical Information

Molecular Formula
C35H38Cl2N8O4
Molecular Mass
705.63300
Charge
0
SMILES
CCC(C)n1ncn(-c2ccc(cc2)N2CCN(CC2)c2ccc(OC[C@H]3CO[C@@](Cn4cncn4)(O3)c3ccc(Cl)cc3Cl)cc2)c1=O
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

Alternative Names

  • 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
  • Itrizole (TN)
  • Oriconazole
  • Sporanox (TN)

Drug Classification

Important Medical Information

⚕️ This information is sourced from ChEBI (Chemical Entities of Biological Interest) database and is intended for educational purposes only.

  • Always consult with a healthcare professional before starting, stopping, or modifying any medication.
  • Side effects may vary and this list may not be comprehensive.
  • Drug interactions may occur with other medications.

Additional Identifiers

DRON_00010000
28031
oboInOwl#hasDbXref
Wikipedia:Itraconazole
core#notation
CHEBI:6076

Additional References

Wikipedia:Itraconazole

🔍 Click on any linked disease name to learn more about the conditions this medication is used to treat, or explore related drug classifications for more information about similar medications.

Additional Attributes

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chebi_ontology
DRON_00010000
28031
oboInOwl#hasDbXref
Wikipedia:Itraconazole
oboInOwl#id
CHEBI:6076
core#notation
CHEBI:6076
RO_0000087
http://purl.obolibrary.org/obo/CHEBI_77748
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http://purl.obolibrary.org/obo/chebi#3_STAR
22-rdf-syntax-ns#type
http://www.w3.org/2002/07/owl#Class
has_treatment
http://purl.obolibrary.org/obo/DOID_12053
rdf-schema#domain
https://w3id.org/def/predibionto#has_side_effect29852
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t256080
owl#someValuesFrom
t1049732