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Compound Detail

CHEMBL139835

CYPROTERONE ACETATE
🧪 Phase III
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🧪 Phase III
CC(=O)O[C@]1(C(C)=O)CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3CC[C@@]21C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL139835
Name CYPROTERONE ACETATE
Phase Phase III
Structure Type MOL
InChI Key UWFYSQMTEOIJJG-FDTZYFLXSA-N
Therapeutic ✓ Yes

Known Names

Androcur Androcur 10 Ciproterona Cyprostat Cyproterone Cyproterone 17.alpha.-acetate Cyproterone acetate Diane NSC-81430 SH 714 SH-714 SH714
12
Targets
35
Activities
3
Assay Types
0
PK Parameters
20
Publications
12
Known Names
8
Indications
3
Mechanisms

Molecular Properties

416.9
MW (Da)
4.61
ALogP
4
HBA
0
HBD
60.4
PSA (Ų)
0.62
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -terone
USAN Year 1965

Extended Properties

Molecular Formula C24H29ClO4
MW 416.95
Aromatic Rings 0
Heavy Atoms 29
NP-Likeness 1.83

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Androgen Receptor antagonist ANTAGONIST Androgen receptor ✓ ✓
Glucocorticoid receptor antagonist ANTAGONIST Glucocorticoid receptor ✓ ✓
Progesterone receptor agonist AGONIST Progesterone receptor ✓ ✓

Indications

Acne Vulgaris Endometriosis Hot Flashes Prostatic Neoplasms Prostatic Neoplasms, Castration-Resistant Menopause Polycystic Ovary Syndrome Hyperplasia

ATC Classification

G03HA01
cyproterone
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM

Activity Summary

IC50 24 meas. best 8.3
Ki 9 meas. best 9.12
EC50 2 meas. best 5.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A1
CHEMBL318
 Ki 9.12 9.005 0.8 2
Progesterone receptor
CHEMBL1909044
 Ki 8.31 8.31 4.8 1
Adenosine receptor A1
CHEMBL318
 IC50 8.3 7.6 5.0 2
Androgen receptor
CHEMBL1871
 IC50 8.15 7.46 7.1 3
Androgen receptor
CHEMBL1871
 Ki 7.85 7.85 14.0 1
Androgen receptor
CHEMBL3072
 Ki 7.51 7.51 31.0 1
Progesterone receptor
CHEMBL1909044
 IC50 7.43 7.43 37.0 1
Androgen receptor
CHEMBL3072
 IC50 7.33 6.0933 47.0 3
Glucocorticoid receptor
CHEMBL2034
 Ki 6.99 6.99 102.0 1
Glucocorticoid receptor
CHEMBL2034
 IC50 6.65 6.65 225.0 1
Adenosine A2 receptor
CHEMBL2094117
 Ki 6.47 6.335 336.0 2
Mu-type opioid receptor
CHEMBL233
 Ki 6.05 6.05 886.0 1
Mu-type opioid receptor
CHEMBL233
 IC50 5.66 5.66 2183.0 1
Androgen receptor
CHEMBL1871
 EC50 5.4 5.4 4000.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.1 4.9667 7943.3 6
Trypanosoma cruzi
CHEMBL368
 EC50 4.5 4.5 32000.0 1
PC-3
CHEMBL390
 IC50 4.49 4.41 32300.0 3
LNCaP
CHEMBL612518
 IC50 4.37 4.32 43000.0 3
DU-145
CHEMBL613508
 IC50 4.29 4.29 50700.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A1 Ki = 0.76 nM 9.12 Binding affinity against adenosine A1 receptor from rat brain membranes using [3... 1495019
Adenosine receptor A1 Ki = 1.3 nM 8.89 Adenosine A1 receptor binding was measured in adenosine deaminase (ADA) pretreat... 2362269
Progesterone receptor Ki = 4.842 nM 8.31 DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) -
Adenosine receptor A1 IC50 = 5.0 nM 8.3 Displacement of [3H]DPCPX from adenosine A1 receptor of rat cortical membranes w... 15084123
Androgen receptor IC50 = 7.1 nM 8.15 Inhibition of androgen receptor (unknown origin) by KINOMEscan analysis 37948954
Androgen receptor Ki = 14.0 nM 7.85 Binding affinity for human androgen receptor in transiently-transfected COS-1 ce... 9484511
Androgen receptor IC50 = 23.0 nM 7.64 Antagonistic activity against human androgen receptor (hAR) in co-transfected CV... 9484511
Androgen receptor Ki = 31.0 nM 7.51 DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Miboler... -
Progesterone receptor IC50 = 37.0 nM 7.43 DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) -
Androgen receptor IC50 = 47.0 nM 7.33 DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Miboler... -
Glucocorticoid receptor Ki = 102.0 nM 6.99 DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) -
Adenosine receptor A1 IC50 = 125.0 nM 6.9 Displacement of [3H]DPCPX from adenosine A1 receptor of rat cortical membranes w... 15084123
Glucocorticoid receptor IC50 = 225.0 nM 6.65 DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) -
Androgen receptor IC50 = 258.6 nM 6.59 Antagonist activity at human AR AF2 assessed as inhibition of fluorescent-labell... 35077161
Adenosine A2 receptor Ki = 336.0 nM 6.47 Binding affinity against adenosine A2 receptor from rat striatum using [3H]NECA ... 1495019
Androgen receptor IC50 = 630.96 nM 6.2 Inhibitory concentration against recombinant rat androgen receptor expressed in ... 16134935
Adenosine A2 receptor Ki = 636.0 nM 6.2 Binding to Adenosine A2 receptor was measured in ADA-pretreated rat striatal mem... 2362269
Mu-type opioid receptor Ki = 886.0 nM 6.05 DRUGMATRIX: Opiate mu (OP3, MOP) radioligand binding (ligand: [3H] Diprenorphine... -
Mu-type opioid receptor IC50 = 2183.0 nM 5.66 DRUGMATRIX: Opiate mu (OP3, MOP) radioligand binding (ligand: [3H] Diprenorphine... -
Androgen receptor EC50 = 4000.0 nM 5.4 Antagonist activity at AR (unknown origin) expressed in chemically activated Luc... 37467618

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 523
- 10.5281/zenodo.13943903 ADMET 68
19734910 10.1038/nchembio.215 Plasmodium falciparum 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 4
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 3
20014752 10.1021/tx900326k Hepatotoxicity 3
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 3
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 3
9484511 10.1021/jm970699s Androgen receptor 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
15084123 10.1021/jm031092g Adenosine receptor A1 3
9484511 10.1021/jm970699s Progesterone receptor 2
1495019 10.1021/jm00093a022 Rattus norvegicus 2
2374140 10.1021/jm00170a008 Androgen receptor 2
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Adenosine receptor A1 2
37468498 10.1038/s41467-023-40064-9 Sodium-dependent dopamine transporter 2

Data from ChEMBL 36 via Core Engine