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Compound Detail

CHEMBL267431

ASOPRISNIL
🧪 Phase III
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🧪 Phase III
COC[C@]1(OC)CC[C@H]2[C@@H]3CCC4=CC(=O)CCC4=C3[C@@H](c3ccc(/C=N/O)cc3)C[C@@]21C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL267431
Name ASOPRISNIL
Phase Phase III
Structure Type MOL
InChI Key GJMNAFGEUJBOCE-MEQIQULJSA-N

Known Names

Asoprisnil Asoprisnilo BAY86-5294 J-867 J867
5
Targets
11
Activities
1
Assay Types
0
PK Parameters
12
Publications
5
Known Names
6
Indications
1
Mechanisms

Molecular Properties

449.6
MW (Da)
5.43
ALogP
5
HBA
1
HBD
68.1
PSA (Ų)
0.37
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -pris-; -prisnil
USAN Year 2002

Extended Properties

Molecular Formula C28H35NO4
MW 449.59
Aromatic Rings 1
Heavy Atoms 33
NP-Likeness 1.19

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Progesterone receptor modulator MODULATOR Progesterone receptor ✓ ✓

Indications

Leiomyoma Leiomyoma Menorrhagia Metrorrhagia Endometriosis Menopause

Activity Summary

IC50 11 meas. best 9.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Progesterone receptor
CHEMBL208
 IC50 9.7 9.58 0.2 3
Androgen receptor
CHEMBL1871
 IC50 8.21 8.13 6.1 2
Glucocorticoid receptor
CHEMBL2034
 IC50 7.07 6.995 85.0 2
Mineralocorticoid receptor
CHEMBL1994
 IC50 5.8 5.8 1600.0 2
Estrogen receptor
CHEMBL206
 IC50 5.72 5.71 1900.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Progesterone receptor IC50 = 0.2 nM 9.7 Antagonist activity at human PRB expressed in CHO cells assessed as inhibition o... 18243712
Progesterone receptor IC50 = 0.3 nM 9.52 Antagonist activity at progesterone receptor by cellular reporter gene assay 23079530
Progesterone receptor IC50 = 0.3 nM 9.52 Antagonist activity against progesterone receptor in human T47D cells by alkalin... 23079530
Androgen receptor IC50 = 6.1 nM 8.21 Antagonist activity at human AR ligand binding domain expressed in african green... 18318463
Androgen receptor IC50 = 9.0 nM 8.05 Antagonist activity at androgen receptor by cellular reporter gene assay 23079530
Glucocorticoid receptor IC50 = 85.0 nM 7.07 Antagonist activity at human GR ligand binding domain expressed in african green... 18318463
Glucocorticoid receptor IC50 = 120.0 nM 6.92 Antagonist activity at glucocorticoid receptor by cellular reporter gene assay 23079530
Mineralocorticoid receptor IC50 = 1600.0 nM 5.8 Antagonist activity at human MR ligand binding domain expressed in african green... 18318463
Mineralocorticoid receptor IC50 = 1600.0 nM 5.8 Antagonist activity at mineralocorticoid receptor by cellular reporter gene assa... 23079530
Estrogen receptor IC50 = 1900.0 nM 5.72 Antagonist activity at human ER ligand binding domain expressed in african green... 18318463
Estrogen receptor IC50 = 2000.0 nM 5.7 Antagonist activity at estrogen receptor by cellular reporter gene assay 23079530

Literature References

PubMed DOI Target Context # Activities
18243712 10.1016/j.bmc.2008.01.010 Progesterone receptor 3
23079530 10.1016/j.bmcl.2012.09.077 Progesterone receptor 3
18318463 10.1021/jm701080t Androgen receptor 2
18318463 10.1021/jm701080t Glucocorticoid receptor 2
18318463 10.1021/jm701080t Mineralocorticoid receptor 2
18318463 10.1021/jm701080t Estrogen receptor 2
24900294 10.1021/ml100220b Oryctolagus cuniculus 2
23079530 10.1016/j.bmcl.2012.09.077 Estrogen receptor 2
23079530 10.1016/j.bmcl.2012.09.077 Mineralocorticoid receptor 2
23079530 10.1016/j.bmcl.2012.09.077 Glucocorticoid receptor 2
23079530 10.1016/j.bmcl.2012.09.077 Androgen receptor 2
24900294 10.1021/ml100220b Rattus norvegicus 1

Data from ChEMBL 36 via Core Engine