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Compound Detail

CHEMBL1908373

ONAPRISTONE
🧪 Phase II
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🧪 Phase II
CN(C)c1ccc([C@H]2C[C@]3(C)[C@@H](CC[C@]3(O)CCCO)[C@@H]3CCC4=CC(=O)CCC4=C32)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1908373
Name ONAPRISTONE
Phase Phase II
Structure Type MOL
InChI Key IEXUMDBQLIVNHZ-YOUGDJEHSA-N
Therapeutic ✓ Yes

Known Names

Onapristona Onapristone ZK-299 Zk-98299 ZK299 Zk98299
4
Targets
21
Activities
3
Assay Types
0
PK Parameters
20
Publications
6
Known Names
3
Indications
1
Mechanisms

Molecular Properties

449.6
MW (Da)
5.16
ALogP
4
HBA
2
HBD
60.8
PSA (Ų)
0.65
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -pris-; -pristone

Extended Properties

Molecular Formula C29H39NO3
MW 449.64
Aromatic Rings 1
Heavy Atoms 33
NP-Likeness 1.34

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Progesterone receptor antagonist ANTAGONIST Progesterone receptor ✓ ✓

Indications

Breast Neoplasms Neoplasms Prostatic Neoplasms

Activity Summary

IC50 13 meas. best 8.8
Ki 6 meas. best 7.75
EC50 2 meas. best 8.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Progesterone receptor
CHEMBL208
 EC50 8.8 8.73 1.6 2
Progesterone receptor
CHEMBL208
 IC50 8.8 8.595 1.6 6
Progesterone receptor
CHEMBL208
 Ki 7.75 7.75 18.0 5
Glucocorticoid receptor
CHEMBL2034
 IC50 7.57 7.57 27.0 3
Glucocorticoid receptor
CHEMBL2034
 Ki 7.38 7.38 41.8 1
Androgen receptor
CHEMBL1871
 IC50 6.57 6.57 269.0 3
Mineralocorticoid receptor
CHEMBL1994
 IC50 6.33 6.33 470.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Progesterone receptor IC50 = 1.6 nM 8.8 Concentration required to give half-maximal inhibition against human Progesteron... 8627601
Progesterone receptor EC50 = 1.6 nM 8.8 Antagonist activity against hPR (human progesterone receptor) compared to that o... 9873735
Progesterone receptor EC50 = 2.2 nM 8.66 Antagonistic activity at human progesterone receptor in CV-1 cells. 12781198
Progesterone receptor IC50 = 2.2 nM 8.66 Antagonist activity against human progesterone receptor (hPR) using cotransfecti... 10743938
Progesterone receptor IC50 = 2.2 nM 8.66 In vitro antagonist activity against human progesterone receptor isoform B(hPR-B... 9719599
Progesterone receptor IC50 = 3.2 nM 8.49 Antagonistic potency to the human progesterone receptor measured in the T-47D al... 8627601
Progesterone receptor IC50 = 3.3 nM 8.48 Antagonist activity against human progesterone receptor (hPR) in T47D human brea... 10743938
Progesterone receptor IC50 = 3.3 nM 8.48 Inhibition of human progesterone receptor activation in T47D human breast cancer... 12781198
Progesterone receptor Ki = 18.0 nM 7.75 Binding affinity against Baculovirus-Expressed hPR-A 9719599
Progesterone receptor Ki = 18.0 nM 7.75 Binding affinity at human progesterone receptor. 12781198
Progesterone receptor Ki = 18.0 nM 7.75 Binding affinity was determined against hPR-A (human progesterone receptor) usin... 9873735
Progesterone receptor Ki = 18.0 nM 7.75 Binding affinity determined for human Progesterone receptor A isoform 8627601
Progesterone receptor Ki = 18.0 nM 7.75 Binding affinity against human progesterone receptor (hPR) in a competitive bind... 10743938
Glucocorticoid receptor IC50 = 27.0 nM 7.57 Inhibition of antagonist activity towards glucocorticoid receptor 12781198
Glucocorticoid receptor IC50 = 27.0 nM 7.57 Inhibitory activity against human glucocorticoid receptor (hGR) 8627601
Glucocorticoid receptor IC50 = 27.0 nM 7.57 Cross-reactivity as binding to human glucocorticoid receptor (hGR) 10743938
Glucocorticoid receptor Ki = 41.8 nM 7.38 Binding affinity was determined for human glucocorticoid receptor(hGR). 8627601
Androgen receptor IC50 = 269.0 nM 6.57 Inhibition of antagonist activity towards Androgen receptor 12781198
Androgen receptor IC50 = 269.0 nM 6.57 Inhibitory activity against human Androgen receptor 8627601
Androgen receptor IC50 = 269.0 nM 6.57 Cross-reactivity as binding to human androgen receptor (hAR) 10743938

Literature References

PubMed DOI Target Context # Activities
10743938 10.1016/s0960-894x(00)00011-1 Progesterone receptor 9
12781198 10.1016/s0960-894x(03)00256-7 Progesterone receptor 7
8627601 10.1021/jm950747d Progesterone receptor 6
9873735 10.1016/s0960-894x(98)00608-8 Progesterone receptor 5
8627601 10.1021/jm950747d Androgen receptor 3
8627601 10.1021/jm950747d Estrogen receptor 3
8627601 10.1021/jm950747d Glucocorticoid receptor 3
9719599 10.1021/jm9801915 Progesterone receptor 3
10743938 10.1016/s0960-894x(00)00011-1 Androgen receptor 2
9719599 10.1021/jm9801915 Glucocorticoid receptor 2
9719599 10.1021/jm9801915 Estrogen receptor 2
9719599 10.1021/jm9801915 Androgen receptor 2
12781198 10.1016/s0960-894x(03)00256-7 Mineralocorticoid receptor 2
12781198 10.1016/s0960-894x(03)00256-7 Estrogen receptor 2
12781198 10.1016/s0960-894x(03)00256-7 Glucocorticoid receptor 2
12781198 10.1016/s0960-894x(03)00256-7 Androgen receptor 2
8627601 10.1021/jm950747d Mineralocorticoid receptor 2
10743938 10.1016/s0960-894x(00)00011-1 Mineralocorticoid receptor 2
10743938 10.1016/s0960-894x(00)00011-1 Estrogen receptor 2
10743938 10.1016/s0960-894x(00)00011-1 Glucocorticoid receptor 2

Data from ChEMBL 36 via Core Engine