Compound Detail
CHEMBL157101
KETOCONAZOLE 💊 Approved Drug
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💊 Approved Drug
CC(=O)N1CCN(c2ccc(OCC3COC(Cn4ccnc4)(c4ccc(Cl)cc4Cl)O3)cc2)CC1
Basic Information
| ChEMBL ID | CHEMBL157101 |
| Name | KETOCONAZOLE |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | XMAYWYJOQHXEEK-UHFFFAOYSA-N |
| Therapeutic | ✓ Yes |
90
Targets
507
Activities
4
Assay Types
21
PK Parameters
20
Publications
20
Known Names
20
Indications
1
Mechanisms
Molecular Properties
531.4
MW (Da)
4.21
ALogP
7
HBA
0
HBD
69.1
PSA (Ų)
0.46
QED
1
Ro5 Violations
7
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| First Approval | 1981 |
| Availability | OTC |
| Chirality | Racemic |
Mechanism of Action
| Mechanism | Action Type | Target | Direct | Efficacy |
|---|---|---|---|---|
| Cytochrome P450 51 inhibitor | INHIBITOR | Lanosterol 14-alpha demethylase | ✓ | ✓ |
Indications
Adrenal Gland Diseases Blastomycosis Cushing Syndrome Dermatitis, Seborrheic Tinea Tinea Pedis Acne Vulgaris Candidiasis, Vulvovaginal Dermatitis Prostatic Neoplasms, Castration-Resistant Respiratory Distress Syndrome Vaginosis, Bacterial Breast Neoplasms Burns Hypogonadism Leukemia, Myelogenous, Chronic, BCR-ABL Positive Neoplasms Neoplasms Prostatic Neoplasms Prostatic Neoplasms
ATC Classification
D01AC08
ketoconazole
Level 1: DERMATOLOGICALS
Level 2: ANTIFUNGALS FOR DERMATOLOGICAL USE
G01AF11
ketoconazole
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
H02CA03
ketoconazole
Level 1: SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS
Level 2: CORTICOSTEROIDS FOR SYSTEMIC USE
J02AB02
ketoconazole
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIMYCOTICS FOR SYSTEMIC USE
Drug Warnings
Withdrawn
hepatotoxicity
Liver toxicity is more frequent and severe than with other antifungal treatments; Elevated risk of early onset liver damage
Withdrawn
hepatotoxicity
Liver toxicity is more frequent and severe than with other antifungal treatments; Elevated risk of early onset liver damage
Black Box Warning
hepatotoxicity
Black Box Warning
cardiotoxicity
Activity Summary
IC50 445 meas. best 9.15
Ki 43 meas. best 8.15
Kd 15 meas. best 9.66
EC50 4 meas. best 9.52
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Gonadotropin-releasing hormone receptor CHEMBL3066 | Kd | 9.66 | 8.3933 | 0.2 | 3 |
| Trypanosoma cruzi CHEMBL368 | EC50 | 9.52 | 9.52 | 0.3 | 1 |
| Unchecked CHEMBL612545 | IC50 | 9.15 | 5.7353 | 0.7 | 17 |
| Cytochrome P450 3A4 CHEMBL340 | IC50 | 9.05 | 7.2201 | 0.9 | 142 |
| Cytochrome P450 2D6 CHEMBL289 | IC50 | 8.73 | 6.558 | 1.9 | 5 |
| Unchecked CHEMBL612545 | Kd | 8.3 | 5.83 | 5.0 | 5 |
| Cytochrome P450 3A4 CHEMBL340 | Ki | 8.15 | 7.6267 | 7.0 | 9 |
| Candida albicans CHEMBL366 | IC50 | 8.0 | 7.63 | 10.0 | 4 |
| Trichophyton rubrum CHEMBL612649 | IC50 | 8.0 | 7.85 | 10.0 | 2 |
| Cytochrome P450 3A4/3A5 CHEMBL2111472 | IC50 | 7.9 | 7.8 | 12.5 | 2 |
| Sterol 14-alpha demethylase CHEMBL1075110 | IC50 | 7.85 | 7.85 | 14.0 | 1 |
| Cryptococcus neoformans CHEMBL365 | IC50 | 7.7 | 7.35 | 20.0 | 2 |
| Trypanosoma cruzi CHEMBL368 | IC50 | 7.64 | 5.5115 | 22.7 | 13 |
| Lanosterol 14-alpha demethylase CHEMBL3849 | Ki | 7.61 | 7.405 | 24.5 | 2 |
| Steroid 17-alpha-hydroxylase/17,20 lyase CHEMBL3522 | IC50 | 7.58 | 6.251 | 26.0 | 39 |
| 1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial CHEMBL4521 | Ki | 7.48 | 7.47 | 33.0 | 2 |
| Homo sapiens CHEMBL372 | IC50 | 7.43 | 7.43 | 37.0 | 1 |
| Steroid 17-alpha-hydroxylase/17,20 lyase CHEMBL3522 | Ki | 7.42 | 7.42 | 38.0 | 2 |
| Aromatase CHEMBL1978 | IC50 | 7.4 | 5.8267 | 40.0 | 15 |
| Candida parapsilosis CHEMBL612868 | IC50 | 7.4 | 7.4 | 40.0 | 1 |
| Candida tropicalis CHEMBL612870 | IC50 | 7.4 | 6.16 | 40.0 | 2 |
| Lanosterol 14-alpha demethylase CHEMBL4981 | IC50 | 7.33 | 7.125 | 47.0 | 2 |
| 25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial CHEMBL3329080 | Ki | 7.24 | 7.24 | 58.0 | 2 |
| Lanosterol 14-alpha demethylase CHEMBL4981 | Ki | 7.19 | 7.19 | 65.0 | 1 |
| Cytochrome P450 11B2, mitochondrial CHEMBL2722 | IC50 | 7.17 | 6.9533 | 67.0 | 15 |
| Liver CHEMBL613642 | IC50 | 7.09 | 7.09 | 80.6 | 1 |
| Trichophyton mentagrophytes CHEMBL613162 | IC50 | 7.0 | 6.85 | 100.0 | 2 |
| Lanosterol 14-alpha demethylase CHEMBL3849 | Kd | 6.96 | 6.34 | 110.0 | 3 |
| Cytochrome P450 11B1, mitochondrial CHEMBL1908 | IC50 | 6.94 | 6.79 | 116.0 | 11 |
| Cytochrome P450 3A5 CHEMBL3019 | IC50 | 6.92 | 6.6883 | 120.0 | 6 |
| 1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial CHEMBL4521 | IC50 | 6.9 | 6.426 | 126.0 | 10 |
| Lanosterol 14-alpha demethylase CHEMBL1780 | IC50 | 6.89 | 6.89 | 130.0 | 1 |
| Cytochrome P450 26B1 CHEMBL3713687 | IC50 | 6.85 | 6.85 | 140.0 | 1 |
| Cytochrome P450 11B1, mitochondrial CHEMBL2927 | IC50 | 6.82 | 6.52 | 152.0 | 2 |
| Lanosterol 14-alpha demethylase CHEMBL3849 | IC50 | 6.72 | 6.72 | 190.0 | 1 |
| Cytochrome P450 7A1 CHEMBL2339 | IC50 | 6.71 | 6.165 | 195.0 | 2 |
| Plasmodium falciparum CHEMBL364 | IC50 | 6.7 | 5.4111 | 200.0 | 9 |
| Steroid 17-alpha-hydroxylase/17,20 lyase CHEMBL4430 | IC50 | 6.69 | 5.5678 | 206.0 | 18 |
| Sodium-dependent serotonin transporter CHEMBL228 | Ki | 6.55 | 6.55 | 282.0 | 1 |
| Heme oxygenase 1 CHEMBL5035 | IC50 | 6.52 | 6.52 | 300.0 | 1 |
| Lanosterol 14-alpha demethylase CHEMBL6066821 | Kd | 6.5 | 6.5 | 320.0 | 1 |
| 25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial CHEMBL5993 | IC50 | 6.47 | 6.47 | 340.0 | 1 |
| 25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial CHEMBL3329080 | IC50 | 6.44 | 6.44 | 360.0 | 2 |
| Cytochrome P450 2A2 CHEMBL3705 | IC50 | 6.43 | 6.345 | 369.0 | 2 |
| Aromatase CHEMBL1978 | Ki | 6.4 | 5.6633 | 398.1 | 3 |
| Pichia kudriavzevii CHEMBL612841 | IC50 | 6.4 | 5.2 | 400.0 | 2 |
| Sodium-dependent serotonin transporter CHEMBL228 | IC50 | 6.28 | 6.28 | 531.0 | 1 |
| Leishmania donovani CHEMBL367 | IC50 | 6.26 | 5.4567 | 550.0 | 3 |
| Leishmania amazonensis CHEMBL612877 | IC50 | 6.26 | 5.3217 | 550.0 | 6 |
| Leishmania major CHEMBL612879 | IC50 | 6.26 | 6.26 | 550.0 | 1 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| AUC | 16600.0 | ng.hr.mL-1 | Homo sapiens |
| AUC | 11691.68 | ng.hr.mL-1 | Sus scrofa |
| AUC | 6908.72 | ng.hr.mL-1 | Sus scrofa |
| AUC | 16522.47 | ng.hr.mL-1 | Homo sapiens |
| Cmax | 7093.93 | nM | Homo sapiens |
| Cmax | 9000.0 | nM | Sus scrofa |
| Cmax | 3000.0 | nM | Sus scrofa |
| Cmax | 12507.0 | nM | Homo sapiens |
| Fu | 0.39 | - | Homo sapiens |
| Fu | 0.0068 | - | Rattus norvegicus |
| Fu | 0.0374 | - | Rattus norvegicus |
| Fu | 0.00345 | - | Rattus norvegicus |
| Fu | 0.00933 | - | Rattus norvegicus |
| Fu | 0.002 | - | Rattus norvegicus |
| Fu | 0.0091 | - | Rattus norvegicus |
| T1/2 | 3.1 | hr | Sus scrofa |
| T1/2 | 4.1 | hr | Sus scrofa |
| T1/2 | 0.75 | hr | Cavia porcellus |
| T1/2 | 0.6667 | hr | Cavia porcellus |
| Tmax | 0.7 | hr | Sus scrofa |
| Tmax | 1.8 | hr | Sus scrofa |
Activity Data Samples
Top measurements by pChEMBL value
Literature References
Data from ChEMBL 36 via Core Engine