ASOPRISNIL ECAMATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C31H40N2O5
Molecular Weight	520.6597
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@](COC)(OC)[C@@]1(C)C[C@H](C3=CC=C(\C=N\OC(=O)NCC)C=C3)C4=C5CCC(=O)C=C5CC[C@@]24[H]

InChI

InChIKey=XMCOWVOJIVSMEO-RCCUTSCYSA-N

InChI=1S/C31H40N2O5/c1-5-32-29(35)38-33-18-20-6-8-21(9-7-20)26-17-30(2)27(14-15-31(30,37-4)19-36-3)25-12-10-22-16-23(34)11-13-24(22)28(25)26/h6-9,16,18,25-27H,5,10-15,17,19H2,1-4H3,(H,32,35)/b33-18+/t25-,26+,27-,30-,31+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15714390 | https://www.ncbi.nlm.nih.gov/pubmed/14667995

Asoprisnil (J867) is a novel selective steroid receptor modulator that shows unique pharmacodynamic effects in animal models and humans. Asoprisnil, its major metabolite J912, and other structurally related compounds represent a new class of progesterone receptor (PR) ligands that exhibit partial agonist and antagonist activities in vivo. Asoprisnil demonstrates a high degree of receptor and tissue selectivity, with a high-binding affinity for PR, moderate affinity for glucocorticoid receptor (GR), low affinity for androgen receptor (AR), and no binding affinity for estrogen or mineralocorticoid receptors. This compound was recently in clinical trials for the treatment of uterine fibroids and endometriosis, but those studies were discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Progesterone receptor 61 Target ID: CHEMBL208 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14667995	Modulator 828

Conditions

Condition	Modality	Targets	Highest Phase	Product
Uterine leiomyomata 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15714390	Primary		Phase III 656	Unknown Approved Use Unknown
Endometriosis 32 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15714390	Primary		Phase II 1132	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
50 mg 2 times / day multiple, oral (unknown) Highest studied dose Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17339234	healthy n = 8 Health Status: healthy Sex: F Food Status: UNKNOWN Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/17339234	Other AEs: Headache, Dizziness... Other AEs: Headache (38%) Dizziness (13%) Abdominal pain (25%) Nausea (25%) Metrorrhagia (13%) Sources: https://pubmed.ncbi.nlm.nih.gov/17339234

AEs

AE	Significance	Dose	Population
Dizziness	13%	50 mg 2 times / day multiple, oral (unknown) Highest studied dose Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17339234	healthy n = 8 Health Status: healthy Sex: F Food Status: UNKNOWN Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/17339234
Metrorrhagia	13%	50 mg 2 times / day multiple, oral (unknown) Highest studied dose Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17339234	healthy n = 8 Health Status: healthy Sex: F Food Status: UNKNOWN Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/17339234
Abdominal pain	25%	50 mg 2 times / day multiple, oral (unknown) Highest studied dose Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17339234	healthy n = 8 Health Status: healthy Sex: F Food Status: UNKNOWN Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/17339234
Nausea	25%	50 mg 2 times / day multiple, oral (unknown) Highest studied dose Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17339234	healthy n = 8 Health Status: healthy Sex: F Food Status: UNKNOWN Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/17339234
Headache	38%	50 mg 2 times / day multiple, oral (unknown) Highest studied dose Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17339234	healthy n = 8 Health Status: healthy Sex: F Food Status: UNKNOWN Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/17339234

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY537352	https://www.001chemical.com/chem/199396-76-4
Ambinter	Amb23437681	http://www.ambinter.com/reference/23437681
Axon MedChem	1675	https://www.axonmedchem.com/product/1675
BOC Sciences	199396-76-4	https://www.bocsci.com/asoprisnil-cas-199396-76-4-item-244891.html
Chem Scene	CS-0068353	http://www.chemscene.com/199396-76-4.html
Chemspace	CSSS00102522291	https://chem-space.com/CSSS00102522291
MedChem Express	HY-119433	https://www.medchemexpress.com/asoprisnil.html
MolPort	MolPort-042-665-735	https://www.molport.com/shop/molecule-link/MolPort-042-665-735
Molcore	MC537352	https://www.molcore.com/product/199396-76-4
MuseChem	M139365	https://www.musechem.com/product/M139365.html
Smolecule	S519517	http://www.smolecule.com/products/s519517
Smolecule	S680692	https://www.smolecule.com/products/s680692
THE BioTek	bt-260223	https://www.thebiotek.com/product/inhibitors/bt-260223
eNovation Chemicals	D676178	https://www.enovationchem.com/ProductDetails.asp?ProductID=D676178

PubMed

Title	Date	PubMed
		252160354

Patents

Sample Use Guides

In Vivo Use Guide

10mg Tablet, oral Daily for 12 months

Route of Administration: Oral

In Vitro Use Guide

It was represented the crystal structures of progesterone receptor (PR) ligand binding domain complexed with asoprisnil. Asoprisnil demonstrated antagonism, but not agonism, in a progesterone receptor (PR)-B transfection assay and the T47D breast cancer cell alkaline phosphatase activity assay. Asoprisnil, but not RU486, weakly recruited the coactivators SRC-1 and AIB1. However, asoprisnil strongly recruited the corepressor NCoR in a manner similar to RU486. Unlike RU486, NCoR binding to asoprisnil-bound PR could be displaced with equal affinity by NCoR or TIF2 peptides. In rat leiomyoma ELT3 cells, asoprisnil demonstrated partial P4-like inhibition of cyclooxygenase (COX) enzymatic activity and COX-2 gene expression. In the rat uterotrophic assay, asoprisnil demonstrated no P4-like ability to oppose estrogen.

Name

Type

Language

ASOPRISNIL ECAMATE

Official Name

English

CARBAMAT J-956

Code

English

J-956

Code

English

ASOPRISNIL ECAMATE [MART.]

Common Name

English

J 956

Code

English

BENZALDEHYDE, 4-((11.BETA.,17.BETA.)-17-METHOXY-17-(METHOXYMETHYL)-3-OXOESTRA-4,9-DIEN-11-YL)-, 1-(O-((ETHYLAMINO)CARBONYL)OXIME), (C(E))-

Common Name

English

11.BETA.-(4-((E)-(ETHYLCARBAMOYLOXYIMINO)METHYL)PHENYL)-17.BETA.-METHOXY-17.ALPHA.-(METHOXYMETHYL)ESTRA-4,9-DIEN-3-ONE

Common Name

English

asoprisnil ecamate [INN]

Common Name

English

Code System Code Type Description

CAS

222732-94-7