itraconazole
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.
Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.
Classification
triazole antifungalARO:3007499
-
CHEBI:23697 -
CHEBI:35618 -
CHEBI:35727 -
CHEBI:39430 -
CHEBI:46848 -
CHEBI:59779 - conazole antifungal drug
CHEBI:87071 - triazole antifungal drug
CHEBI:87101 - triazole antifungal
ARO:3007499
Chemical structure
| Molecular formula | C35H38Cl2N8O4 |
|---|---|
| Charge | 0 |
| Average mass | 705.647 Da |
| Monoisotopic mass | 704.23931 Da |
| Source | ChEBI |
| InChIKey | VHVPQPYKVGDNFY-ZPGVKDDISA-N |
CCC(C)n1ncn(-c2ccc(N3CCN(c4ccc(OC[C@H]5CO[C@](Cn6cncn6)(c6ccc(Cl)cc6Cl)O5)cc4)CC3)cc2)c1=O
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
Also called
- 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
- Itrizole (TN)
- Oriconazole
- Sporanox (TN)
Cross-references
Drug registries
Patents and articles
Activity roles
- antifungal agent
CHEBI:35718 - antifungal drug
CHEBI:86327
Source concepts
| Source | Native ID | Label | Minted CURIE | Version |
|---|---|---|---|---|
| ARO | ARO:3007511 |
itraconazole | antibioticmech:aro-47bcb54181 |
2026-08-30 |
| CHEBI | CHEBI:6076 |
itraconazole | antibioticmech:chebi-126890f8e2 |
2026-08-30 |
Mechanism summary
- Mode of action
- ERGOSTEROL_PATHWAY_INHIBITION host shared target
- Clinical status
- APPROVED
Resistance mechanisms
ANTIBIOTIC_TARGET_ALTERATION 24
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| Aspergillus awamori Cyp51a with mutations conferring resistance to itraconazole | ARO:3009507 | — | ||
| Aspergillus flavus Cyp51A with mutations conferring resistance to itraconazole | ARO:3009495 | — | ||
| Aspergillus flavus Cyp51c with mutations conferring resistance to itraconazole | ARO:3009282 | — | ||
| Aspergillus fumigatus Hmg1 with mutations conferring resistance to itraconazole | ARO:3009236 | — | ||
| Aspergillus fumigatus Hmg2 with mutations conferring resistance to itraconazole | ARO:3009368 | — | ||
| Aspergillus fumigatus ase1 with mutations conferring resistance to itraconazole | ARO:3009273 | — | ||
| Aspergillus fumigatus cyp51a with mutations conferring resistance to itraconazole | ARO:3009202 | — | ||
| Aspergillus spp. Hmg1 with mutations conferring resistance to triazoles antibiotics | ARO:3007670 | — | ||
| Aspergillus spp. cyp51A with mutations conferring resistance to triazoles antibiotics | ARO:3007565 | — | ||
| Aspergillus terreus cyp51a with mutations conferring resistance to itraconazole | ARO:3009206 | — | ||
| Aspergillus tubingensis Cyp51a with mutations conferring resistance to itraconazole | ARO:3009509 | — | ||
| Candida albicans Cyp51 with mutations conferring resistance to itraconazole | ARO:3009527 | — | ||
| Candida albicans Cyp51a with mutations conferring resistance to itraconazole | ARO:3009505 | — | ||
| Candida albicans Erg11 with mutations conferring resistance to itraconazole | ARO:3009219 | — | ||
| Candida auris ERG11 lanosterol 14-alpha-demethylase with mutations conferring resistance to itraconazole | ARO:3009393 | — | ||
| Candida orthopsilosis ERG11 lanosterol 14-alpha-demethylase with mutations conferring resistance to itraconazole | ARO:3009580 | — | ||
| Candida spp. ERG11 with mutations conferring resistance to azole antibiotics | ARO:3007524 | — | ||
| Candida spp. cyp51A1 with mutations conferring resistance to triazoles and imidazole antibiotics | ARO:3007666 | — | ||
| Candida tropicalis Erg11 lanosterol 14-alpha-demethylase with mutations conferring resistance to itraconazole | ARO:3009583 | — | ||
| Colletotrichum truncatum cyp51a with mutations associated with resistance to itraconazole | ARO:3009217 | — | ||
| Cryptococcus neoformans Erg11 lanosterol 14-alpha-demethylase with mutations conferring resistance to itraconazole | ARO:3009586 | — | ||
| Nakaseomyces glabratus FKS1 beta-1,3-glucan synthase with mutations associated with resistance to itraconazole | ARO:3009614 | — | ||
| Nakaseomyces glabratus FKS2 beta-1,3-glucan synthase with mutations associated with resistance to itraconazole | ARO:3009618 | — | ||
| Saccharomyces cerevisiae ERG11 lanosterol 14-alpha-demethylase with mutations conferring resistance to itraconazole | ARO:3009589 | — |
UNKNOWN 21
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| Aspergillus fumigatus HapE with mutations associated with resistance to itraconazole | ARO:3009294 | — | ||
| CYP51A transformant(CM2627-CYP51Apromoter(2x34bp tandem repeat) and CM2627-CYP51A(L98H)) (transformant) [Overexpression] associated with resistance to itraconazole |
— | Aspergillus fumigatus NCBITaxon:746128PHIPO:0000675 |
— | |
| Candida albicans TAC1 with mutations conferring resistance to itraconazole | ARO:3009428 | — | ||
| ERG11(Y132F F145L) (amino acid mutation) [Not assayed] associated with resistance to itraconazole |
— | Candida albicans NCBITaxon:5476PHIPO:0000675 |
— | |
| ERG3delta (deletion) associated with resistance to itraconazole |
— | Candida albicans NCBITaxon:5476PHIPO:0000675 |
— | |
| ERG3delta (deletion) associated with resistance to itraconazole |
— | Candida parapsilosis NCBITaxon:5480PHIPO:0000675 |
— | |
| HapE transformant(Isolate3-HapE(P88L)) (transformant) [Not assayed] associated with resistance to itraconazole |
— | Aspergillus fumigatus NCBITaxon:746128PHIPO:0000675 |
— | |
| algAdelta (deletion) associated with resistance to itraconazole |
— | Aspergillus fumigatus NCBITaxon:746128PHIPO:0000675 |
— | |
| cox10 transformant(W004-cox10(R243Q)) (transformant) [Not assayed] associated with resistance to itraconazole |
— | Aspergillus fumigatus NCBITaxon:746128PHIPO:0000675 |
— | |
| cyp51A transformant(H10-1-50A-cyp51A(N22D)) (transformant) [Not assayed] associated with resistance to itraconazole |
— | Aspergillus fumigatus NCBITaxon:746128PHIPO:0000675 |
— | |
| cyp51A transformant(H10-2-50A-cyp51A(M220I)) (transformant) [Not assayed] associated with resistance to itraconazole |
— | Aspergillus fumigatus NCBITaxon:746128PHIPO:0000675 |
— | |
| cyp51A transformant(W601-cyp51A(F219L)) (transformant) [Not assayed] associated with resistance to itraconazole |
— | Aspergillus fumigatus NCBITaxon:746128PHIPO:0000675 |
— | |
| cyp51A(G54E) (amino acid mutation) [Not assayed] associated with resistance to itraconazole |
— | Aspergillus fumigatus NCBITaxon:746128PHIPO:0000675 |
— | |
| cyp51A(G54E) (amino acid mutation) [Not assayed] associated with resistance to itraconazole |
— | Aspergillus fumigatus NCBITaxon:746128PHIPO:0000675 |
— | |
| cyp51A(G54K) (amino acid mutation) [Not assayed] associated with resistance to itraconazole |
— | Aspergillus fumigatus NCBITaxon:746128PHIPO:0000675 |
— | |
| cyp51A(G54R) (amino acid mutation) [Not assayed] associated with resistance to itraconazole |
— | Aspergillus fumigatus NCBITaxon:746128PHIPO:0000675 |
— | |
| cyp51A(G54R) (amino acid mutation) [Not assayed] associated with resistance to itraconazole |
— | Aspergillus fumigatus NCBITaxon:746128PHIPO:0000675 |
— | |
| cyp51A(G54W) (amino acid mutation) [Not assayed] associated with resistance to itraconazole |
— | Aspergillus fumigatus NCBITaxon:746128PHIPO:0000675 |
— | |
| cyp51A(M220K) (amino acid mutation) [Not assayed] associated with resistance to itraconazole |
— | Aspergillus fumigatus NCBITaxon:746128PHIPO:0000675 |
— | |
| cyp51A(M220T) (amino acid mutation) [Not assayed] associated with resistance to itraconazole |
— | Aspergillus fumigatus NCBITaxon:746128PHIPO:0000675 |
— | |
| cyp51A(M220V) (amino acid mutation) [Not assayed] associated with resistance to itraconazole |
— | Aspergillus fumigatus NCBITaxon:746128PHIPO:0000675 |
— |
ANTIBIOTIC_EFFLUX 9
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| Aspergillus fumigatus MDR3 with mutations conferring resistance to itraconazole | ARO:3009452 | — | ||
| Aspergillus fumigatus MDR4 with mutations conferring resistance to itraconazole | ARO:3009453 | — | ||
| Candida albicans MDR1 with mutations conferring resistance to itraconazole | ARO:3009448 | — | ||
| Cryptococcus neoformans AFR1 with mutations conferring resistance against itraconazole | ARO:3009434 | — | ||
| Trychophyton rubrum Mdr2 with mutations associated with resistance to itraconazole | ARO:3009253 | — | ||
| Trychophyton rubrum Mdr3 with mutations associated with resistance to itraconazole | ARO:3009255 | — | ||
| Trychophyton rubrum Mdr5 with mutations associated with resistance to itraconazole | ARO:3009259 | — | ||
| Trychophyton rubrum Mfs1 with mutations associated with resistance to itraconazole | ARO:3009262 | — | ||
| fungal MDR | ARO:3009425 | — |
Curation history
-
SEEDED_FROM_SOURCES
Seeded from data/raw/ inventories (ARO, CHEBI)
-
RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Applied 1 pinned subject-context reviews, retaining reference-locus grounding while withholding unverified experimental protein/strain identifiers. Source alterations, phenotypes, species, genes, and existing activities unchanged. Refreshed provenance checksums on any previously reviewed claims. ERG11 parent, replicate and clinical-donor contexts remain separate.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the whole-file PHI-base review checksum after Eddouzi subject reviews; all biological fields and prior decisions unchanged.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Scoped two imported ERG3 associations: reference proteins and strain TaxIDs are not experimental-subject identifiers. Retained source species, background labels, alterations and phenotypes; clinical isolates remain separate. Existing activities and curator claims unchanged; refreshed older review checksums.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the whole-file PHI-base review checksum after carboxin reference-context reviews; all biological fields, activities and previous decisions unchanged.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the whole-file PHI-base review checksum after two additional carboxin identifier-scope corrections; all biological fields, activities and previous decisions unchanged.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the whole-file PHI-base review checksum after eleven additional identifier-scope corrections; biological fields, activities and decisions unchanged.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Scoped imported associations to the reported parent background: Af293 reference protein and strain TaxID are not tested-subject identities. Source alterations, phenotypes, assays and clinical activities unchanged; no exact allele or genome inferred.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the whole-file PHI-base review checksum after one yeast identity-scope correction; biological fields, activities and prior decisions unchanged.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Scoped imported reference protein and strain TaxID to provenance, not tested-subject identity. Source parent labels, alterations, phenotypes and assays preserved; no experimental allele, genome or activity measurement inferred.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the shared PHI-base review checksum after nine identifier-scope corrections; previous decisions, biological fields and activities unchanged.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the shared PHI-base review checksum after six identifier-scope corrections; previous decisions, biological fields and activities unchanged.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the shared PHI-base review checksum after eight subject-identity corrections; previous decisions, biological fields and activities unchanged.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Darlington subject correction; prior review decisions, biological fields and activities unchanged.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Nakayama reference-scope review; prior decisions, biological fields and activities unchanged.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Duan reference-scope review; prior decisions, biological fields and activities unchanged.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Piotrowska parent-reference review; prior decisions, biological fields and activities unchanged.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Xu subject and species corrections; prior decisions, biological fields and activities unchanged.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Shima parent-reference review; prior decisions, biological fields and activities unchanged.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Mehrabi parent-reference review; prior decisions, biological fields and activities unchanged.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Huang parent-reference review; prior decisions, biological fields and activities unchanged.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the HDF1 subject-reference review; prior decisions, biological fields and activities unchanged.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Fouche parent-cohort review; prior decisions, biological fields and activities unchanged.
-
REVIEWED_RESISTANCE_REFERENCE_CONTEXT
Refreshed shared PHI-base review checksum after the SDH8 reference-alias correction; prior decisions, biological fields and activities unchanged.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the shared PHI-base review checksum after the Posteraro subject-context review; previous decisions, biological fields and activities unchanged.
-
REVIEWED_RESISTANCE_REFERENCE_CONTEXT
Refreshed the shared PHI-base review checksum after four reference-identifier scope corrections; previous decisions, biological fields and activities unchanged.
-
REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the shared PHI-base review checksum after one Neurospora subject-context correction; previous decisions, biological fields and activities unchanged.