RETOSIBAN

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H34N4O5
Molecular Weight	494.5827
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@H](C)[C@H]1N([C@@H](C(=O)N2CCOCC2)C3=COC(C)=N3)C(=O)[C@H](NC1=O)C4CC5=C(C4)C=CC=C5

InChI

InChIKey=PLVGDGRBPMVYPB-FDUHJNRSSA-N

InChI=1S/C27H34N4O5/c1-4-16(2)23-25(32)29-22(20-13-18-7-5-6-8-19(18)14-20)26(33)31(23)24(21-15-36-17(3)28-21)27(34)30-9-11-35-12-10-30/h5-8,15-16,20,22-24H,4,9-14H2,1-3H3,(H,29,32)/t16-,22+,23+,24+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C27H34N4O5
Molecular Weight	494.5827
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26138866 | https://www.ncbi.nlm.nih.gov/pubmed/28556962 | https://clinicaltrials.gov/ct2/show/NCT02377466 | https://clinicaltrials.gov/ct2/show/NCT02292771 | https://www.drugbank.ca/drugs/DB11818

Retosiban is a small molecule oxytocin receptor antagonist that is under evaluation for treatment of premature labor. Retosiban was found to be safe in healthy non-pregnant volunteers in phase I studies. Intravenous retosiban also had good safety and tolerability in phase II studies and was suggested to prolong pregnancies in women with preterm labor. Phase III studies have been conducted to demonstrate the efficacy of retosiban to prolong pregnancy and improve neonatal outcomes, and compare effects with a similar drug atosiban, but these studies were terminated in 2018 (not due to adverse events).

Approval Year

PubMed

Title	Date	PubMed
The design of orally bioavailable 2, 5-diketopiperazine oxytocin antagonists: from concept to clinical candidate for premature labor.	2011-07	20027670
The discovery of GSK221149A: a potent and selective oxytocin antagonist.	2008-01-01	18032036
Use of a novel and highly selective oxytocin receptor antagonist to characterize uterine contractions in the rat.	2007-07	17395790
The oxytocin receptor system: structure, function, and regulation.	2001-04	11274341

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:57:26 GMT 2025` Edited by `admin` on `Mon Mar 31 17:57:26 GMT 2025`
Record UNII	GIE06H28OX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GSK-221149

Preferred Name

English

RETOSIBAN

Official Name

English

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

Systematic Name

English

GSK221149

Code

English

retosiban [INN]

Common Name

English

(3R,6R)-6-[(2S)-Butan-2-yl]-3-(2,3-dihydro-1H-inden-2-yl)-1-[(1R)-1-(2-methyl-1,3-oxazol-4-yl)-2-(morpholin-4-yl)-2-oxoethyl]piperazine-2,5-dione

Systematic Name

English

GSK221149A

Code

English

RETOSIBAN [USAN]

Common Name

English

GSK-221149A

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C98292