Compound Detail
CHEMBL64391
ITRACONAZOLE 💊 Approved Drug
Enter ChEMBL ID:
Free Research Context
This compound will appear in recent viewed items on the research home for this browser.
Research home
View demo workspace
💊 Approved Drug
CCC(C)n1ncn(-c2ccc(N3CCN(c4ccc(OCC5COC(Cn6cncn6)(c6ccc(Cl)cc6Cl)O5)cc4)CC3)cc2)c1=O
Basic Information
| ChEMBL ID | CHEMBL64391 |
| Name | ITRACONAZOLE |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | VHVPQPYKVGDNFY-UHFFFAOYSA-N |
| Therapeutic | ✓ Yes |
41
Targets
104
Activities
4
Assay Types
30
PK Parameters
20
Publications
24
Known Names
20
Indications
1
Mechanisms
Molecular Properties
705.6
MW (Da)
5.58
ALogP
12
HBA
0
HBD
104.7
PSA (Ų)
0.17
QED
3
Ro5 Violations
11
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| First Approval | 1992 |
| Availability | Prescription |
| Chirality | Racemic |
Mechanism of Action
| Mechanism | Action Type | Target | Direct | Efficacy |
|---|---|---|---|---|
| Cytochrome P450 51 inhibitor | INHIBITOR | Lanosterol 14-alpha demethylase | ✓ | ✓ |
Indications
Aspergillosis Blastomycosis Candidiasis Lung Diseases Mycoses Onychomycosis Onychomycosis Aspergillosis, Allergic Bronchopulmonary Bronchiectasis Cryptococcosis Histoplasmosis Neoplasms Neoplasms Burns Carcinoma, Basal Cell Carcinoma, Basal Cell Carcinoma, Non-Small-Cell Lung Coccidioidomycosis Crohn Disease Hematologic Diseases
ATC Classification
J02AC02
itraconazole
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIMYCOTICS FOR SYSTEMIC USE
Drug Warnings
Black Box Warning
cardiotoxicity
Activity Summary
IC50 88 meas. best 8.4
Kd 7 meas. best 7.51
Ki 6 meas. best 7.39
EC50 3 meas. best 7.0
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Trypanosoma cruzi CHEMBL368 | IC50 | 8.4 | 8.4 | 4.0 | 1 |
| ATP-dependent translocase ABCB1 CHEMBL4302 | IC50 | 7.52 | 6.054 | 30.0 | 5 |
| 14-alpha sterol demethylase CHEMBL1681624 | Kd | 7.51 | 7.51 | 31.0 | 1 |
| Cytochrome P450 3A4 CHEMBL340 | IC50 | 7.49 | 7.0071 | 32.6 | 7 |
| ADMET CHEMBL612558 | Ki | 7.39 | 7.14 | 41.0 | 5 |
| NON-PROTEIN TARGET CHEMBL3879801 | IC50 | 7.26 | 6.1967 | 55.0 | 3 |
| Molecular identity unknown CHEMBL612546 | IC50 | 7.2 | 6.655 | 63.0 | 4 |
| Leishmania amazonensis CHEMBL612877 | IC50 | 7.1 | 6.73 | 80.0 | 2 |
| Unchecked CHEMBL612545 | Kd | 7.0 | 6.098 | 100.0 | 5 |
| Unchecked CHEMBL612545 | EC50 | 7.0 | 5.65 | 100.0 | 2 |
| C-X-C chemokine receptor type 1 CHEMBL4029 | IC50 | 7.0 | 5.63 | 100.0 | 6 |
| Unchecked CHEMBL612545 | IC50 | 6.9 | 6.1792 | 125.0 | 12 |
| HUVEC CHEMBL613979 | IC50 | 6.8 | 6.785 | 160.0 | 2 |
| C-C chemokine receptor type 4 CHEMBL2414 | IC50 | 6.7 | 5.6257 | 200.0 | 7 |
| ATP-dependent translocase ABCB1 CHEMBL2573 | IC50 | 6.7 | 6.7 | 200.0 | 2 |
| Chikungunya virus CHEMBL4296563 | EC50 | 6.5 | 6.5 | 320.0 | 1 |
| Trichophyton mentagrophytes CHEMBL613162 | IC50 | 6.43 | 6.43 | 370.0 | 1 |
| Leishmania major CHEMBL612879 | IC50 | 6.4 | 6.1667 | 400.0 | 3 |
| Kluyveromyces marxianus CHEMBL612842 | IC50 | 6.4 | 6.4 | 400.0 | 1 |
| Toxoplasma gondii CHEMBL612888 | IC50 | 6.3 | 6.3 | 500.0 | 1 |
| Trichophyton rubrum CHEMBL612649 | IC50 | 6.25 | 6.13 | 560.0 | 2 |
| ATP-dependent translocase ABCB1 CHEMBL3467 | IC50 | 6.16 | 6.16 | 700.0 | 2 |
| Vasopressin V2 receptor CHEMBL1790 | IC50 | 6.1 | 5.4067 | 794.3 | 6 |
| Sterol 14-alpha demethylase cyp51A CHEMBL1681623 | Kd | 6.0 | 6.0 | 1010.0 | 1 |
| Madurella mycetomatis CHEMBL6066062 | IC50 | 5.96 | 5.96 | 1100.0 | 1 |
| Candida albicans CHEMBL366 | IC50 | 5.86 | 5.855 | 1390.0 | 2 |
| Plasmodium falciparum CHEMBL364 | IC50 | 5.86 | 5.86 | 1370.0 | 1 |
| PBMC CHEMBL613107 | IC50 | 5.82 | 5.82 | 1530.0 | 1 |
| Broad substrate specificity ATP-binding cassette transporter ABCG2 CHEMBL5393 | IC50 | 5.7 | 5.7 | 2000.0 | 1 |
| Microsporum canis CHEMBL612335 | IC50 | 5.7 | 5.7 | 2020.0 | 1 |
| Unchecked CHEMBL612545 | Ki | 5.63 | 5.63 | 2351.0 | 1 |
| Leishmania donovani CHEMBL367 | IC50 | 5.62 | 5.62 | 2420.0 | 1 |
| Trichophyton quinckeanum CHEMBL612334 | IC50 | 5.53 | 5.53 | 2930.0 | 1 |
| Cruzipain CHEMBL3563 | IC50 | 5.52 | 5.52 | 3000.0 | 1 |
| A549 CHEMBL392 | IC50 | 5.52 | 5.52 | 3000.0 | 1 |
| Lanosterol 14-alpha demethylase CHEMBL3849 | IC50 | 5.44 | 5.44 | 3600.0 | 1 |
| Nakaseomyces glabratus CHEMBL612647 | IC50 | 5.43 | 5.43 | 3740.0 | 1 |
| Tyrosine-protein kinase Fyn CHEMBL1841 | IC50 | 5.41 | 5.41 | 3890.0 | 1 |
| Pichia kudriavzevii CHEMBL612841 | IC50 | 5.38 | 5.38 | 4210.0 | 1 |
| 7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase CHEMBL4523494 | IC50 | 5.33 | 5.33 | 4700.0 | 1 |
| HepG2 CHEMBL395 | IC50 | 5.1 | 5.1 | 7870.0 | 1 |
| Trypanosoma brucei rhodesiense CHEMBL612348 | IC50 | 5.07 | 5.07 | 8530.0 | 1 |
| NIH3T3 CHEMBL614822 | IC50 | 4.86 | 4.86 | 13700.0 | 1 |
| Bile salt export pump CHEMBL6020 | IC50 | 4.75 | 4.75 | 18000.0 | 2 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| AUC | 4922.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 2121.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 9510.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 3765.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 2669.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 3811.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 4155.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 4249.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 4166.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 3133.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 20500.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 34400.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 7400.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 101000.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 27.5 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 343.0 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 3340.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 2270.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 905.09 | ng.hr.mL-1 | Homo sapiens |
| AUC | 9046.81 | ng.hr.mL-1 | Homo sapiens |
| AUC | 6134.92 | ng.hr.mL-1 | Homo sapiens |
| AUC | 23000.0 | ng.hr.mL-1 | Homo sapiens |
| CL | 11.71 | mL.min-1.kg-1 | Homo sapiens |
| CL | 19.05 | mL.min-1.kg-1 | Homo sapiens |
| CL | 8.817 | mL.min-1.kg-1 | Homo sapiens |
| CL | 10.35 | mL.min-1.kg-1 | Homo sapiens |
| CL | 12.95 | mL.min-1.kg-1 | Homo sapiens |
| CL | 5.1 | mL.min-1.kg-1 | Homo sapiens |
| CL | 5.1 | mL.min-1.kg-1 | Homo sapiens |
| CL | 5.1 | mL.min-1.kg-1 | Homo sapiens |
Activity Data Samples
Top measurements by pChEMBL value
Literature References
Data from ChEMBL 36 via Core Engine