U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of EPELSIBAN

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

Molecular Formula C30H38N4O4
Molecular Weight 518.6471
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P30559
Gene ID: 5021.0
Gene Symbol: OXTR
Target Organism: Homo sapiens (Human)
9.9 null [pKi]
PubMed

PubMed

TitleDatePubMed
Single- and Multiple-Day Dosing Studies to Investigate High-Dose Pharmacokinetics of Epelsiban and Its Metabolite, GSK2395448, in Healthy Female Volunteers.
2018 Jan
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
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:50:05 UTC 2023
Edited
by admin
on Sat Dec 16 17:50:05 UTC 2023
Record UNII
T2EZ19HX73
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPELSIBAN
INN   USAN   WHO-DD  
USAN   INN  
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
Created by admin on Sat Dec 16 17:50:05 UTC 2023 , Edited by admin on Sat Dec 16 17:50:05 UTC 2023
Code System Code Type Description
FDA UNII
T2EZ19HX73
Created by admin on Sat Dec 16 17:50:05 UTC 2023 , Edited by admin on Sat Dec 16 17:50:05 UTC 2023
PRIMARY
USAN
XX-152
Created by admin on Sat Dec 16 17:50:05 UTC 2023 , Edited by admin on Sat Dec 16 17:50:05 UTC 2023
PRIMARY
PUBCHEM
11634973
Created by admin on Sat Dec 16 17:50:05 UTC 2023 , Edited by admin on Sat Dec 16 17:50:05 UTC 2023
PRIMARY
MESH
C571185
Created by admin on Sat Dec 16 17:50:05 UTC 2023 , Edited by admin on Sat Dec 16 17:50:05 UTC 2023
PRIMARY
ChEMBL
CHEMBL2037511
Created by admin on Sat Dec 16 17:50:05 UTC 2023 , Edited by admin on Sat Dec 16 17:50:05 UTC 2023
PRIMARY
CAS
872599-83-2
Created by admin on Sat Dec 16 17:50:05 UTC 2023 , Edited by admin on Sat Dec 16 17:50:05 UTC 2023
PRIMARY
INN
9453
Created by admin on Sat Dec 16 17:50:05 UTC 2023 , Edited by admin on Sat Dec 16 17:50:05 UTC 2023
PRIMARY
EPA CompTox
DTXSID701029864
Created by admin on Sat Dec 16 17:50:05 UTC 2023 , Edited by admin on Sat Dec 16 17:50:05 UTC 2023
PRIMARY
DRUG BANK
DB11934
Created by admin on Sat Dec 16 17:50:05 UTC 2023 , Edited by admin on Sat Dec 16 17:50:05 UTC 2023
PRIMARY
NCI_THESAURUS
C99151
Created by admin on Sat Dec 16 17:50:05 UTC 2023 , Edited by admin on Sat Dec 16 17:50:05 UTC 2023
PRIMARY
SMS_ID
300000034151
Created by admin on Sat Dec 16 17:50:05 UTC 2023 , Edited by admin on Sat Dec 16 17:50:05 UTC 2023
PRIMARY
WIKIPEDIA
Epelsiban
Created by admin on Sat Dec 16 17:50:05 UTC 2023 , Edited by admin on Sat Dec 16 17:50:05 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
>31000-fold selectivity over all three human vasopressin receptors hV1aR, hV2R, and hV1bR,
Ki
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY