Retosiban

Retosiban (GSK221149A) is a potent, selective, and orally active oxytocin receptor antagonist (Ki (hOT) = 0.65 nM, Ki (rOT) = 4.1 nM) with no detectable agonist activity. Retosiban has nanomolar affinity for the oxytocin receptor with >1400-fold selectivity over the closely related vasopressin receptors. Retosiban inhibits spontaneous and induces uterine contractions. Retosiban can be studied in research for preterm labour[1][2][4].

Product Specifications

CAS Number

[820957-38-8]

Product Name Alternative

GSK 221149; GSK 221149A

UNSPSC

12352005

Target

Oxytocin Receptor

Type

Reference compound

Related Pathways

GPCR/G Protein

Applications

Metabolism-protein/nucleotide metabolism

Field of Research

Neurological Disease; Endocrinology

Assay Protocol

https://www.medchemexpress.com/Retosiban.html

Purity

98.97

Solubility

DMSO : 100 mg/mL (ultrasonic)

Smiles

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

Molecular Formula

C27H34N4O5

Molecular Weight

494.58

References & Citations

[1]Liddle J, et al. The discovery of GSK221149A: a potent and selective oxytocin antagonist. Bioorg Med Chem Lett. 2008 Jan 1;18 (1) :90-4.|[2]Thornton, S., et al., (2015) . Treatment of spontaneous preterm labour with retosiban: a phase 2 proof-of-concept study. British journal of clinical pharmacology, 80 (4), 740-749.|[3]Borthwick, A. D., et al., (2011) . The design of orally bioavailable 2, 5-diketopiperazine oxytocin antagonists: from concept to clinical candidate for premature labor. Medicinal research reviews, 31 (4), 576–604. |[4]McCafferty, G. P., et al., (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 (1), R299–R305.|[5]Moraitis, A. A., et al., (2015) . The Effect of an Oxytocin Receptor Antagonist (Retosiban, GSK221149A) on the Response of Human Myometrial Explants to Prolonged Mechanical Stretch. Endocrinology, 156 (10), 3511–3516.