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
-
conazole antifungal drugView Class →
CHEBI:87071
-
dichlorobenzeneView Class →
CHEBI:23697
-
DichlorobenzeneView Class →
CHEBI:23697
-
N-arylpiperazineView Class →
CHEBI:46848
-
triazole antifungal drugView Class →
CHEBI:87101
-
aromatic etherView Class →
CHEBI:35618
-
dioxolaneView Class →
CHEBI:39430
-
cyclic ketalView Class →
CHEBI:59779
-
t254915
-
t255343
-
t255670
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
🔍 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
- 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
- application_number
- ANDA205724
- RO_0000087
- http://purl.obolibrary.org/obo/CHEBI_77748
- oboInOwl#inSubset
- http://purl.obolibrary.org/obo/chebi#3_STAR
- 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
- 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
- package_description
- 150 mL in 1 BOTTLE (10147-0150-1)
- 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
- has_treatment
- http://purl.obolibrary.org/obo/DOID_12053
- rdf-schema#domain
- https://w3id.org/def/predibionto#has_side_effect29852
- owl#annotatedSource
- t256080
- owl#someValuesFrom
- t1049732