ASOPRISNIL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H35NO4
Molecular Weight	449.5818
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\O)C=C3)C4=C5CCC(=O)C=C5CC[C@@]24[H]

InChI

InChIKey=GJMNAFGEUJBOCE-MEQIQULJSA-N

InChI=1S/C28H35NO4/c1-27-15-24(19-6-4-18(5-7-19)16-29-31)26-22-11-9-21(30)14-20(22)8-10-23(26)25(27)12-13-28(27,33-3)17-32-2/h4-7,14,16,23-25,31H,8-13,15,17H2,1-3H3/b29-16+/t23-,24+,25-,27-,28+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C28H35NO4
Molecular Weight	449.5818
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	1
Optical Activity	UNSPECIFIED

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:47:25 GMT 2023` Edited by `admin` on `Fri Dec 15 15:47:25 GMT 2023`
Record UNII	72W09924WP
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ASOPRISNIL

Official Name

English

asoprisnil [INN]

Common Name

English

ASOPRISNIL [MI]

Common Name

English

11β-[4-[(E)-(Hydroxyimino)methyl]phenyl]-17β-methoxy-17-(methoxymethyl)estra-4,9-dien-3-one

Systematic Name

English

J867

Code

English

Asoprisnil [WHO-DD]

Common Name

English

J-867

Code

English

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

Common Name

English

BAY86-5294

Code

English

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

Common Name

English

ASOPRISNIL [MART.]

Common Name

English

ASOPRISNIL [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1891

Created by admin on Fri Dec 15 15:47:26 GMT 2023 , Edited by admin on Fri Dec 15 15:47:26 GMT 2023

Code System Code Type Description

CAS

199396-76-4

Created by admin on Fri Dec 15 15:47:25 GMT 2023 , Edited by admin on Fri Dec 15 15:47:25 GMT 2023

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FDA UNII

72W09924WP

Created by admin on Fri Dec 15 15:47:26 GMT 2023 , Edited by admin on Fri Dec 15 15:47:26 GMT 2023

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DRUG BANK

DB06680

Created by admin on Fri Dec 15 15:47:25 GMT 2023 , Edited by admin on Fri Dec 15 15:47:25 GMT 2023

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EPA CompTox

DTXSID40904033

Created by admin on Fri Dec 15 15:47:26 GMT 2023 , Edited by admin on Fri Dec 15 15:47:26 GMT 2023

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MERCK INDEX

m2094

Created by admin on Fri Dec 15 15:47:26 GMT 2023 , Edited by admin on Fri Dec 15 15:47:26 GMT 2023

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Merck Index

MESH

C488516

Created by admin on Fri Dec 15 15:47:26 GMT 2023 , Edited by admin on Fri Dec 15 15:47:26 GMT 2023

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PUBCHEM

9577221

Created by admin on Fri Dec 15 15:47:26 GMT 2023 , Edited by admin on Fri Dec 15 15:47:26 GMT 2023

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ChEMBL

CHEMBL267431

Created by admin on Fri Dec 15 15:47:25 GMT 2023 , Edited by admin on Fri Dec 15 15:47:25 GMT 2023

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WIKIPEDIA

Asoprisnil

Created by admin on Fri Dec 15 15:47:26 GMT 2023 , Edited by admin on Fri Dec 15 15:47:26 GMT 2023

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EVMPD

SUB21660

Created by admin on Fri Dec 15 15:47:25 GMT 2023 , Edited by admin on Fri Dec 15 15:47:25 GMT 2023

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SMS_ID

100000085027

Created by admin on Fri Dec 15 15:47:26 GMT 2023 , Edited by admin on Fri Dec 15 15:47:26 GMT 2023

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INN

8202

Created by admin on Fri Dec 15 15:47:26 GMT 2023 , Edited by admin on Fri Dec 15 15:47:26 GMT 2023

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USAN

OO-78

Created by admin on Fri Dec 15 15:47:26 GMT 2023 , Edited by admin on Fri Dec 15 15:47:26 GMT 2023

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NCI_THESAURUS

C91054

Created by admin on Fri Dec 15 15:47:26 GMT 2023 , Edited by admin on Fri Dec 15 15:47:26 GMT 2023

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Related Record Type Details


					DXN1OSB4IB

PROGESTERONE RECEPTOR

TARGET->MODULATOR

Amount:

Related Record Type Details


					72W09924WP

ASOPRISNIL

ACTIVE MOIETY

Amount:

Details

SMILES

InChI

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

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

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