Retosiban

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Retosiban
Retosiban structure.svg
Systematic (IUPAC) name
(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
Clinical data
Legal status
  • Non-regulated
Identifiers
CAS number 820957-38-8
ATC code None
PubChem CID 96025669
ChemSpider 23323798
UNII GIE06H28OX
KEGG D08986
Synonyms GSK-221,149-A
Chemical data
Formula C27H34N4O5 
Mol. mass 494.58 g/mol

Retosiban (GSK-221,149-A)[1][2] is an oral drug which acts as a selective, sub-nanomolar (Ki = 0.65 nM) oxytocin receptor antagonist with >1400-fold selectivity[3] over the related vasopressin receptors and is being developed by GlaxoSmithKline for the treatment of preterm labour.[4][5]

References[edit]

  1. ^ Liddle J, Allen MJ, Borthwick AD, Brooks DP, Davies DE, Edwards RM, Exall AM, Hamlett C, Irving WR, Mason, AM, McCafferty GP, Nerozzi F, Peace S, Philp J, Pollard D, Pullen MA, Shabbir SS, Sollis SL, Westfall TD, Woollard PM, Wu C, Hickey DM (January 2008). "The discovery of GSK221149A: A potent and selective oxytocin antagonist". Bioorganic & Medicinal Chemistry Letters 18 (1): 90–94. doi:10.1016/j.bmcl.2007.11.008. PMID 18032036. 
  2. ^ Borthwick, A. D.; Liddle, J. (January 2013). "Retosiban and Epelsiban: Potent and Selective Orally available Oxytocin Antagonists". In Domling, A. Methods and Principles in Medicinal Chemistry: Protein-Protein Interactions in Drug Discovery. Weinheim: Wiley-VCH. pp. 225–256. ISBN 978-3-527-33107-9. 
  3. ^ McCafferty GP, Pullen MA, Wu C, Edwards RM, Allen M.J, Woollard PM, Borthwick AD, Liddle J, Hickey DM, Brooks DP, Westfall TD (March 2007). "Use of a novel and highly selective oxytocin receptor antagonist to characterize uterine contractions in the rat". American Journal of Physiology - Regulatory, Integrative and Comparative Physiology 293: R299–R305. doi:10.1152/ajpregu.00057.2007. PMID 17395790. 
  4. ^ USAN Council (2007). "Statement on a Nonproprietary Name Adopted by the USAN Council" (PDF). 
  5. ^ Borthwick AD, Liddle J (July 2011). "The Design of Orally Bioavailable 2,5-Diketopiperazine Oxytocin Antagonists: From Concept to Clinical Candidate for Premature Labour". Medicinal Research Reviews 31 (4): 576–604. doi:10.1002/med.20193. PMID 20027670.