EPELSIBAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H38N4O4
Molecular Weight	518.6471
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]1([C@@H](C)CC)N([C@@H](C(=O)N2CCOCC2)C3=CC=C(C)N=C3C)C(=O)[C@H](NC1=O)C4CC5=C(C4)C=CC=C5

InChI

InChIKey=UWHCWRQFNKUYCG-QUZACWSFSA-N

InChI=1S/C30H38N4O4/c1-5-18(2)26-28(35)32-25(23-16-21-8-6-7-9-22(21)17-23)29(36)34(26)27(24-11-10-19(3)31-20(24)4)30(37)33-12-14-38-15-13-33/h6-11,18,23,25-27H,5,12-17H2,1-4H3,(H,32,35)/t18-,25+,26+,27+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22239250 | https://adisinsight.springer.com/drugs/800033691

Epelsiban (GSK557296), a pyridyl-2,5-diketopiperazine, is a potent, highly selective, and orally bioavailable non-peptide oxytocin receptor antagonist. GlaxoSmithKline was developing epelsiban for the treatment of women infertility due to adenomyosis and premature ejaculation.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Oxytocin receptor 19 Target ID: P30559 Gene ID: 5021.0 Gene Symbol: OXTR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22239250	Antagonist 2778		9.9 null [pKi]

PubMed

Title	Date	PubMed
Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency.	2012 Jan 26	22239250
Inhibition of ejaculation by the non-peptide oxytocin receptor antagonist GSK557296: a multi-level site of action.	2013 Aug	23530818
Safety and efficacy of epelsiban in the treatment of men with premature ejaculation: a randomized, double-blind, placebo-controlled, fixed-dose study.	2013 Oct	23937679
A single- and multiple-dose study to investigate the pharmacokinetics of epelsiban and its metabolite, GSK2395448, in healthy female volunteers.	2015 Nov	27137713
Single- and Multiple-Day Dosing Studies to Investigate High-Dose Pharmacokinetics of Epelsiban and Its Metabolite, GSK2395448, in Healthy Female Volunteers.	2018 Jan	28556598

Patents

Sample Use Guides

In Vivo Use Guide

phase I studies: at total daily doses of 600 and 900 mg, epelsiban was generally well tolerated, and there were no significant safety concerns identified.

Route of Administration: Oral

Name

Type

Language

EPELSIBAN

Official Name

English

2,5-PIPERAZINEDIONE, 3-(2,3-DIHYDRO-1H-INDEN-2-YL)-1-((1R)-1-(2,6-DIMETHYL-3-PYRIDINYL)- 2-(4-MORPHOLINYL)-2-OXOETHYL)-6-((1S)-1-METHYLPROPYL)-, (3R,6R)-

Common Name

English

GSK557296

Code

English

epelsiban [INN]

Common Name

English

3R,6R)-3-(2,3-DIHYDRO-1H-INDEN-2-YL)-1-((1R)-1-(2,6-DIMETHYLPYRIDIN-3-YL)-2-(MORPHOLIN-4-YL)-2-OXOETHYL)-6-((1S)-1-METHYLPROPYL)PIPERAZINE-2,5-DIONE

Common Name

English

2,5-PIPERAZINEDIONE, 3-(2,3-DIHYDRO-1H-INDEN-2-YL)-1-((1R)-1-(2,6-DIMETHYL-3-PYRIDINYL)-2-(4-MORPHOLINYL)-2-OXOETHYL)-6-((1S)-1-METHYLPROPYL)-, (3R,6R)-

Systematic Name

English

(3R,6R)-3-(2,3-DIHYDRO-1H-INDEN-2-YL)-1-((1R)-1-(2,6-DIMETHYLPYRIDIN-3-YL)-2-(MORPHOLIN-4-YL)-2-OXOETHYL)-6-((2S)-BUTAN-2-YL)PIPERAZINE-2,5-DIONE

Systematic Name

English

EPELSIBAN [USAN]

Common Name

English

GSK-557296

Code

English

MORPHOLINE, 4-((2R)-((3R,6R)-3-(2,3-DIHYDRO-1H-INDEN-2-YL)-6-((1S)-1-METHYLPROPYL)-2,5-DIOXO-1-PIPERAZINYL)(2,6-DIMETHYL-3-PYRIDINYL)ACETYL)-

Systematic Name

English

Epelsiban [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C98292