Compound Detail
CHEMBL110691
CHLORMADINONE ACETATE 💊 Approved Drug
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💊 Approved Drug
CC(=O)O[C@]1(C(C)=O)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C
Basic Information
| ChEMBL ID | CHEMBL110691 |
| Name | CHLORMADINONE ACETATE |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | QMBJSIBWORFWQT-DFXBJWIESA-N |
5
Targets
8
Activities
2
Assay Types
0
PK Parameters
20
Publications
7
Known Names
1
Mechanisms
Molecular Properties
404.9
MW (Da)
4.75
ALogP
4
HBA
0
HBD
60.4
PSA (Ų)
0.62
QED
0
Ro5 Violations
2
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| Availability | Withdrawn |
| Chirality | Single Enantiomer |
Mechanism of Action
| Mechanism | Action Type | Target | Direct | Efficacy |
|---|---|---|---|---|
| Progesterone receptor modulator | MODULATOR | Progesterone receptor | ✓ | ✓ |
ATC Classification
G03DB06
chlormadinone
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
Drug Warnings
Withdrawn
carcinogenicity
Animal carcinogenicity (dogs)
Withdrawn
carcinogenicity
Increased incidence of breast tumours in beagle dogs during the course of long-term toxicity tests
Activity Summary
IC50 5 meas. best 8.28
Ki 3 meas. best 9.16
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Progesterone receptor CHEMBL1909044 | Ki | 9.16 | 9.16 | 0.7 | 1 |
| Progesterone receptor CHEMBL1909044 | IC50 | 8.28 | 8.28 | 5.3 | 1 |
| Glucocorticoid receptor CHEMBL2034 | Ki | 7.76 | 7.76 | 17.2 | 1 |
| Androgen receptor CHEMBL3072 | Ki | 7.68 | 7.68 | 20.9 | 1 |
| Androgen receptor CHEMBL3072 | IC50 | 7.5 | 7.5 | 31.3 | 1 |
| Glucocorticoid receptor CHEMBL2034 | IC50 | 7.42 | 7.42 | 37.7 | 1 |
| Cytochrome P450 2C19 CHEMBL3622 | IC50 | 5.52 | 5.52 | 3000.0 | 1 |
| Unchecked CHEMBL612545 | IC50 | 5.34 | 5.34 | 4569.6 | 1 |
Activity Data Samples
Top measurements by pChEMBL value
| Target | Type | Rel. | Value | Units | pChEMBL | Assay | PubMed |
|---|---|---|---|---|---|---|---|
| Progesterone receptor | Ki | = | 0.687 | nM | 9.16 | DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) | - |
| Progesterone receptor | IC50 | = | 5.265 | nM | 8.28 | DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) | - |
| Glucocorticoid receptor | Ki | = | 17.2 | nM | 7.76 | DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) | - |
| Androgen receptor | Ki | = | 20.9 | nM | 7.68 | DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Miboler... | - |
| Androgen receptor | IC50 | = | 31.3 | nM | 7.5 | DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Miboler... | - |
| Glucocorticoid receptor | IC50 | = | 37.7 | nM | 7.42 | DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) | - |
| Cytochrome P450 2C19 | IC50 | = | 3000.0 | nM | 5.52 | DRUGMATRIX: CYP450, 2C19 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) | - |
| Unchecked | IC50 | = | 4569.6 | nM | 5.34 | DRUGMATRIX: ATPase, Na+/K+ enzyme inhibition (substrate: ATP) | - |
Literature References
| PubMed | DOI | Target Context | # Activities |
|---|---|---|---|
| - | 10.6019/CHEMBL3885881 | Rattus norvegicus | 320 |
| - | 10.6019/CHEMBL4495565 | SARS-CoV-2 | 4 |
| 20014752 | 10.1021/tx900326k | Hepatotoxicity | 3 |
| 926114 | 10.1021/jm00219a006 | Progesterone receptor | 3 |
| 37468498 | 10.1038/s41467-023-40064-9 | Thromboxane A2 receptor | 2 |
| 12109909 | 10.1021/jm0102811 | Monoclonal antibody (mAb) | 2 |
| 37468498 | 10.1038/s41467-023-40064-9 | Prostaglandin G/H synthase 1 | 2 |
| 37468498 | 10.1038/s41467-023-40064-9 | Alpha-1A adrenergic receptor | 2 |
| - | 10.6019/CHEMBL4808148 | Histone deacetylase 6 | 2 |
| - | 10.6019/CHEMBL4651402 | SARS-CoV-2 | 2 |
| - | 10.6019/CHEMBL4495564 | Replicase polyprotein 1ab | 2 |
| 37468498 | 10.1038/s41467-023-40064-9 | Muscarinic acetylcholine receptor M1 | 2 |
| - | 10.1101/2020.04.21.054387 | SARS-CoV-2 | 1 |
| - | 10.1101/2020.04.03.023846 | SARS-CoV-2 | 1 |
| 926114 | 10.1021/jm00219a006 | Unchecked | 1 |
| 37468498 | 10.1038/s41467-023-40064-9 | D(1A) dopamine receptor | 1 |
| 23571415 | 10.1124/mol.112.084152 | Solute carrier organic anion transporter family member 1B1 | 1 |
| 37468498 | 10.1038/s41467-023-40064-9 | Sodium-dependent dopamine transporter | 1 |
| 37468498 | 10.1038/s41467-023-40064-9 | Estrogen receptor | 1 |
| 38318365 | 10.1016/j.isci.2024.108907 | Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 | 1 |
Data from ChEMBL 36 via Core Engine