Synonym
GSK557296; GSK 557296; GSK-557296; GSK-557,296-B; Epelsiban
IUPAC/Chemical Name
(3R,6R)-6-((S)-sec-butyl)-3-(2,3-dihydro-1H-inden-2-yl)-1-((R)-1-(2,6-dimethylpyridin-3-yl)-2-morpholino-2-oxoethyl)piperazine-2,5-dione
InChi Key
UWHCWRQFNKUYCG-QUZACWSFSA-N
InChi Code
InChI=1S/C30H38N4O4/c1-5-18(2)26-28(35)32-25(23-16-21-8-6-7-9-22(21)17-23)29(36)34(26)27(24-11-10-19(3)31-20(24)4)30(37)33-12-14-38-15-13-33/h6-11,18,23,25-27H,5,12-17H2,1-4H3,(H,32,35)/t18-,25+,26+,27+/m0/s1
SMILES Code
O=C([C@@H](C1CC2=C(C=CC=C2)C1)N3)N([C@H](C4=CC=C(C)N=C4C)C(N5CCOCC5)=O)[C@H]([C@@H](C)CC)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
518.66
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: Shinghal R, Barnes A, Mahar KM, Stier B, Giancaterino L, Condreay LD, Black L,
McCallum SW. Safety and efficacy of epelsiban in the treatment of men with
premature ejaculation: a randomized, double-blind, placebo-controlled, fixed-dose
study. J Sex Med. 2013 Oct;10(10):2506-17. doi: 10.1111/jsm.12272. Epub 2013 Aug
12. PubMed PMID: 23937679.
2: Clément P, Bernabé J, Compagnie S, Alexandre L, McCallum S, Giuliano F.
Inhibition of ejaculation by the non-peptide oxytocin receptor antagonist
GSK557296: a multi-level site of action. Br J Pharmacol. 2013 Aug;169(7):1477-85.
doi: 10.1111/bph.12198. PubMed PMID: 23530818; PubMed Central PMCID: PMC3724105.
3: Borthwick AD, Liddle J, Davies DE, Exall AM, Hamlett C, Hickey DM, Mason AM,
Smith IE, Nerozzi F, Peace S, Pollard D, Sollis SL, Allen MJ, Woollard PM, Pullen
MA, Westfall TD, Stanislaus DJ. Pyridyl-2,5-diketopiperazines as potent,
selective, and orally bioavailable oxytocin antagonists: synthesis,
pharmacokinetics, and in vivo potency. J Med Chem. 2012 Jan 26;55(2):783-96. doi:
10.1021/jm201287w. Epub 2012 Jan 12. PubMed PMID: 22239250.
