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

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 of RETOSIBAN

SMILES

[H][C@]1([C@@H](C)CC)N([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
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

PubMed

TitleDatePubMed
Use of a novel and highly selective oxytocin receptor antagonist to characterize uterine contractions in the rat.
2007 Jul
The design of orally bioavailable 2, 5-diketopiperazine oxytocin antagonists: from concept to clinical candidate for premature labor.
2011 Jul
Patents
Name Type Language
RETOSIBAN
INN   USAN  
INN   USAN  
Official Name English
GSK-221149
Code 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
Created by admin on Fri Dec 15 15:25:47 GMT 2023 , Edited by admin on Fri Dec 15 15:25:47 GMT 2023
Code System Code Type Description
PUBCHEM
11340891
Created by admin on Fri Dec 15 15:25:47 GMT 2023 , Edited by admin on Fri Dec 15 15:25:47 GMT 2023
PRIMARY
EPA CompTox
DTXSID00231559
Created by admin on Fri Dec 15 15:25:47 GMT 2023 , Edited by admin on Fri Dec 15 15:25:47 GMT 2023
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EVMPD
SUB181222
Created by admin on Fri Dec 15 15:25:47 GMT 2023 , Edited by admin on Fri Dec 15 15:25:47 GMT 2023
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FDA UNII
GIE06H28OX
Created by admin on Fri Dec 15 15:25:47 GMT 2023 , Edited by admin on Fri Dec 15 15:25:47 GMT 2023
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WIKIPEDIA
Retosiban
Created by admin on Fri Dec 15 15:25:47 GMT 2023 , Edited by admin on Fri Dec 15 15:25:47 GMT 2023
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USAN
TT-30
Created by admin on Fri Dec 15 15:25:47 GMT 2023 , Edited by admin on Fri Dec 15 15:25:47 GMT 2023
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CAS
820957-38-8
Created by admin on Fri Dec 15 15:25:47 GMT 2023 , Edited by admin on Fri Dec 15 15:25:47 GMT 2023
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ChEMBL
CHEMBL429736
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SMS_ID
100000166887
Created by admin on Fri Dec 15 15:25:47 GMT 2023 , Edited by admin on Fri Dec 15 15:25:47 GMT 2023
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DRUG BANK
DB11818
Created by admin on Fri Dec 15 15:25:47 GMT 2023 , Edited by admin on Fri Dec 15 15:25:47 GMT 2023
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INN
8924
Created by admin on Fri Dec 15 15:25:47 GMT 2023 , Edited by admin on Fri Dec 15 15:25:47 GMT 2023
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NCI_THESAURUS
C76681
Created by admin on Fri Dec 15 15:25:47 GMT 2023 , Edited by admin on Fri Dec 15 15:25:47 GMT 2023
PRIMARY