Synonym
GSK221149A; GSK 221149A; GSK-221149A; GSK221149; GSK 221149; GSK-221149; GSK221,149; GSK 221,149; GSK-221,149; Retosiban
IUPAC/Chemical 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
InChi Key
PLVGDGRBPMVYPB-FDUHJNRSSA-N
InChi Code
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
SMILES Code
O=C([C@@H](C1CC2=C(C=CC=C2)C1)N3)N([C@H](C4=COC(C)=N4)C(N5CCOCC5)=O)[C@H]([C@H](CC)C)C3=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
494.59
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Moraitis AA, Cordeaux Y, Charnock-Jones DS, Smith GC. The Effect of an Oxytocin Receptor Antagonist (Retosiban, GSK221149A) on the Response of Human Myometrial Explants to Prolonged Mechanical Stretch. Endocrinology. 2015 Oct;156(10):3511-6. doi: 10.1210/en.2015-1378. Epub 2015 Jul 24. PubMed PMID: 26207346.
2: Stier B, Fossler M, Liu F, Caltabiano S. Effect of Retosiban on Cardiac Repolarization in a Randomized, Placebo- and Positive-controlled, Crossover Thorough QT/QTc Study in Healthy Men and Women. Clin Ther. 2015 Jul 1;37(7):1541-54. doi: 10.1016/j.clinthera.2015.05.007. Epub 2015 Jun 29. PubMed PMID: 26138866.
3: Thornton S, Miller H, Valenzuela G, Snidow J, Stier B, Fossler MJ, Montague TH, Powell M, Beach KJ. Treatment of spontaneous preterm labour with retosiban: a phase 2 proof-of-concept study. Br J Clin Pharmacol. 2015 Oct;80(4):740-9. doi: 10.1111/bcp.12646. Epub 2015 Jun 1. Erratum in: Br J Clin Pharmacol. 2015 Sep;80(3):609. PubMed PMID: 25819462; PubMed Central PMCID: PMC4594710.
4: Manning M, Misicka A, Olma A, Bankowski K, Stoev S, Chini B, Durroux T, Mouillac B, Corbani M, Guillon G. Oxytocin and vasopressin agonists and antagonists as research tools and potential therapeutics. J Neuroendocrinol. 2012 Apr;24(4):609-28. doi: 10.1111/j.1365-2826.2012.02303.x. Review. PubMed PMID: 22375852; PubMed Central PMCID: PMC3490377.
5: Vrachnis N, Malamas FM, Sifakis S, Deligeoroglou E, Iliodromiti Z. The oxytocin-oxytocin receptor system and its antagonists as tocolytic agents. Int J Endocrinol. 2011;2011:350546. doi: 10.1155/2011/350546. Epub 2011 Dec 6. PubMed PMID: 22190926; PubMed Central PMCID: PMC3235456.
6: Borthwick AD, Liddle J. The design of orally bioavailable 2, 5-diketopiperazine oxytocin antagonists: from concept to clinical candidate for premature labor. Med Res Rev. 2011 Jul;31(4):576-604. doi: 10.1002/med.20193. Epub 2009 Dec 21. PubMed PMID: 20027670.
