Retosiban

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 319898

CAS#: 820957-38-8

Description: Retosiban, also known as GSK-221,149-A; is an oral active, potent and selective, sub-nanomolar (Ki = 0.65 nM) oxytocin receptor antagonist with >1400-fold selectivity over the related vasopressin receptors. Retosiban inhibits the procontractile effect of stretch on human myometrium. retosiban prevented stretch-induced stimulation of human myometrial contractility. Retosiban treatment is a potential approach for preventing preterm birth in multiple pregnancy. Retosiban is being developed by GlaxoSmithKline for the treatment of preterm labour.

Chemical Structure

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Retosiban
CAS# 820957-38-8
Instruction

Theoretical Analysis

MedKoo Cat#: 319898
Name: Retosiban
CAS#: 820957-38-8
Chemical Formula: C27H34N4O5
Exact Mass: 494.25
Molecular Weight: 494.592
Elemental Analysis: C, 65.57; H, 6.93; N, 11.33; O, 16.17

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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

Appearance: Solid powder

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

More Info:

Biological target:
In vitro activity:
In vivo activity:

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.

Recalculate based on batch purity %
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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.