retosiban   Click here for help

GtoPdb Ligand ID: 8403

Synonyms: GSK-221,149-A | GSK-221149A | GSK221149A
PDB Ligand
Compound class: Synthetic organic
Comment: Retosiban is a investigational non-peptide oxytocin antagonist [3-4].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 104.98
Molecular weight 494.25
XLogP 1.59
No. Lipinski's rules broken 0
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Canonical SMILES CCC(C1C(=O)NC(C(=O)N1C(C(=O)N1CCOCC1)c1coc(n1)C)C1Cc2c(C1)cccc2)C
Isomeric SMILES CC[C@@H]([C@@H]1C(=O)N[C@@H](C(=O)N1[C@@H](C(=O)N1CCOCC1)c1coc(n1)C)C1Cc2c(C1)cccc2)C
InChI 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
1. Borthwick AD, Liddle J. (2011)
The design of orally bioavailable 2, 5-diketopiperazine oxytocin antagonists: from concept to clinical candidate for premature labor.
Med Res Rev, 31 (4): 576-604. [PMID:20027670]
2. Gimpl G, Fahrenholz F. (2001)
The oxytocin receptor system: structure, function, and regulation.
Physiol Rev, 81 (2): 629-83. [PMID:11274341]
3. Liddle J, Allen MJ, Borthwick AD, Brooks DP, Davies DE, Edwards RM, Exall AM, Hamlett C, Irving WR, Mason AM et al.. (2008)
The discovery of GSK221149A: a potent and selective oxytocin antagonist.
Bioorg Med Chem Lett, 18 (1): 90-4. [PMID:18032036]
4. McCafferty GP, Pullen MA, Wu C, Edwards RM, Allen MJ, Woollard PM, Borthwick AD, Liddle J, Hickey DM, Brooks DP et al.. (2007)
Use of a novel and highly selective oxytocin receptor antagonist to characterize uterine contractions in the rat.
Am J Physiol Regul Integr Comp Physiol, 293 (1): R299-305. [PMID:17395790]
5. Thornton S, Miller H, Valenzuela G, Snidow J, Stier B, Fossler MJ, Montague TH, Powell M, Beach KJ. (2015)
Treatment of spontaneous preterm labour with retosiban: a phase 2 proof-of-concept study.
Br J Clin Pharmacol, 80 (4): 740-9. [PMID:25819462]
6. Thornton S, Valenzuela G, Baidoo C, Fossler MJ, Montague TH, Clayton L, Powell M, Snidow J, Stier B, Soergel D. (2017)
Treatment of spontaneous preterm labour with retosiban: a phase II pilot dose-ranging study.
Br J Clin Pharmacol, 83 (10): 2283-2291. [PMID:28556962]