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Compound Detail

CHEMBL295698

LEVOKETOCONAZOLE
💊 Approved Drug
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💊 Approved Drug
CC(=O)N1CCN(c2ccc(OC[C@@H]3CO[C@@](Cn4ccnc4)(c4ccc(Cl)cc4Cl)O3)cc2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL295698
Name LEVOKETOCONAZOLE
Phase Approved
Structure Type MOL
InChI Key XMAYWYJOQHXEEK-ZEQKJWHPSA-N
Therapeutic ✓ Yes

Known Names

(-)-(2s,4r)-ketoconazole 2s,4r ketoconazole 2s,4r-ketoconazole COR-003 COR003 DIO-902 Ketoconazole, (2s,4r)- Levoketoconazol Levoketoconazole Normocort Recorlev
1
Targets
1
Activities
1
Assay Types
1
PK Parameters
13
Publications
11
Known Names
5
Indications
4
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 2021
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -conazole
USAN Year 2015

Extended Properties

Molecular Formula C26H28Cl2N4O4
MW 531.44
Aromatic Rings 3
Heavy Atoms 36
NP-Likeness -0.77

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cytochrome P450 11B1 inhibitor INHIBITOR Cytochrome P450 11B1, mitochondrial ✓ ✓
Cytochrome P450 11B2 inhibitor INHIBITOR Cytochrome P450 11B2, mitochondrial ✓ ✓
Cytochrome P450 17A1 inhibitor INHIBITOR Steroid 17-alpha-hydroxylase/17,20 lyase ✓ ✓
Cytochrome P450 11A1 inhibitor INHIBITOR Cholesterol side-chain cleavage enzyme, mitochondrial ✓ ✓

Indications

Adrenal Gland Diseases Adrenocortical Hyperfunction Cushing Syndrome Pituitary ACTH Hypersecretion Diabetes Mellitus, Type 2

ATC Classification

H02CA04
levoketoconazole
Level 1: SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS
Level 2: CORTICOSTEROIDS FOR SYSTEMIC USE

Drug Warnings

Black Box Warning
cardiotoxicity
Country: United States
Black Box Warning
hepatotoxicity
Country: United States

Activity Summary

IC50 1 meas. best 7.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cytochrome P450 3A4
CHEMBL340
 IC50 7.57 7.57 26.9 1

Pharmacokinetic Data

Parameter Value Units Species
F 37.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cytochrome P450 3A4 IC50 = 26.9 nM 7.57 Inhibition of CYP3A4M in human liver microsomes using midazolam as substrate in ... 34432448

Literature References

PubMed DOI Target Context # Activities
38071944 10.1016/j.bmc.2023.117543 Candida albicans 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
34432448 10.1021/acs.jmedchem.1c01015 Cytochrome P450 3A4 1
- 10.6019/EOS300108 HepG2 1
37086699 10.1016/j.ejmech.2023.115367 Cytochrome P450 3A4 1
38071944 10.1016/j.bmc.2023.117543 Cryptococcus neoformans 1
38071944 10.1016/j.bmc.2023.117543 Candida parapsilosis 1
38071944 10.1016/j.bmc.2023.117543 Candida tropicalis 1
38071944 10.1016/j.bmc.2023.117543 Trichophyton rubrum 1
38071944 10.1016/j.bmc.2023.117543 Nannizzia gypsea 1
38071944 10.1016/j.bmc.2023.117543 Aspergillus fumigatus 1
38699796 10.1021/acs.jmedchem.4c00652 ADMET 1

Data from ChEMBL 36 via Core Engine