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

listing_expiration_date
20241231
route
ORAL
marketing_start_date
20191124
labeler_name
Patriot Pharmaceuticals, LLC
spl_id
c8b8791d-eb13-a578-e053-2a95a90af9ed
package_ndc
59349-0012-0
application_number
ANDA205080
package_description
1 BAG in 1 DRUM (59349-0012-0) / 1 BAG in 1 BAG / 25 kg in 1 BAG
rxcui
833164
active_ingredient_strength
1 kg/kg
pharm_class_epc
Azole Antifungal [EPC]
pharm_class_moa
Breast Cancer Resistance Protein Inhibitors [MoA]
nui
N0000190113
package_marketing_start_date
24-NOV-19
manufacturer_name
Patriot Pharmaceuticals, LLC
active_ingredient_name
ITRACONAZOLE
unii
304NUG5GF4
spl_set_id
349ffcf4-b2cd-4c93-9411-13c39275b8f3
upc
0331722006316
has_treatment
http://purl.obolibrary.org/obo/DOID_12053
oboInOwl#hasOBONamespace
chebi_ontology
DRON_00010000
28031
oboInOwl#hasDbXref
Wikipedia:Itraconazole
oboInOwl#id
CHEBI:6076
generic_name
ITRACONAZOLE MICRONIZED
brand_name
Itraconazole Oral
brand_name_base
Itraconazole Oral
product_type
BULK INGREDIENT
marketing_category
BULK INGREDIENT FOR HUMAN PRESCRIPTION COMPOUNDING
dosage_form
CAPSULE, COATED PELLETS
product_ndc
59349-0012
RO_0000087
http://purl.obolibrary.org/obo/CHEBI_77748
oboInOwl#inSubset
http://purl.obolibrary.org/obo/chebi#3_STAR
core#notation
CHEBI:6076
pharm_class
Breast Cancer Resistance Protein Inhibitors [MoA]
pharm_class_cs
Azoles [CS]
22-rdf-syntax-ns#type
http://www.w3.org/2002/07/owl#Class
rdf-schema#domain
https://w3id.org/def/predibionto#has_side_effect29852
owl#annotatedSource
t256080
owl#someValuesFrom
t1049732