SB-649868

(Redirected from GSK-649868) Chemical compound Pharmaceutical compound

SB-649868
Clinical data

ATC code	None
Legal status
Legal status	Investigational
Identifiers
IUPAC name N-(carbonyl)-2-piperidinyl]methyl)-4-benzofurancarboxamide
CAS Number	380899-24-1
PubChem CID	25195495
ChemSpider	25069706
UNII	1L1V1K2M4V
ChEMBL	ChEMBL1272307
CompTox Dashboard (EPA)	DTXSID90191491
Chemical and physical data
Formula	C₂₆H₂₄FN₃O₃S
Molar mass	477.55 g·mol
3D model (JSmol)	Interactive image
SMILES CC1=NC(=C(S1)C2=CC=C(C=C2)F)C(=O)N3CCCC3CNC(=O)C4=C5C=COC5=CC=C4
InChI InChI=1S/C26H24FN3O3S/c1-16-29-23(24(34-16)17-8-10-18(27)11-9-17)26(32)30-13-3-2-5-19(30)15-28-25(31)21-6-4-7-22-20(21)12-14-33-22/h4,6-12,14,19H,2-3,5,13,15H2,1H3,(H,28,31)/t19-/m0/s1 Key:ZJXIUGNEAIHSBI-IBGZPJMESA-N

SB-649868 is a dual orexin receptor antagonist that was being developed by GlaxoSmithKline as a treatment for insomnia.

A phase I clinical trial evaluated doses up to 80 mg, resulting in significant improvement in sleep latency without adverse effects. In randomized, double-blind, placebo-controlled crossover trials, the 10 and 30 mg doses increased sleep time and reduced sleep latency. The subsequent phase II study added a 60 mg dose and observed dose-dependent sleep promotion.

The compound no longer appears to be under active development, with the last study posted to ClinicalTrials.gov completed in 2010.

References

Renzulli C, Nash M, Wright M, Thomas S, Zamuner S, Pellegatti M, et al. (February 2011). "Disposition and metabolism of SB-649868, an orexin 1 and 2 receptor antagonist, in humans". Drug Metabolism and Disposition. 39 (2): 215–27. doi:10.1124/dmd.110.035386. PMID 21045199. S2CID 1995624.
Bettica P, Nucci G, Pyke C, Squassante L, Zamuner S, Ratti E, et al. (August 2012). "Phase I studies on the safety, tolerability, pharmacokinetics and pharmacodynamics of SB-649868, a novel dual orexin receptor antagonist". Journal of Psychopharmacology. 26 (8): 1058–70. doi:10.1177/0269881111408954. PMID 21730017. S2CID 29578953.
Bettica P, Squassante L, Groeger JA, Gennery B, Winsky-Sommerer R, Dijk DJ (April 2012). "Differential effects of a dual orexin receptor antagonist (SB-649868) and zolpidem on sleep initiation and consolidation, SWS, REM sleep, and EEG power spectra in a model of situational insomnia". Neuropsychopharmacology. 37 (5): 1224–33. doi:10.1038/npp.2011.310. PMC 3306884. PMID 22237311.
Bettica P, Squassante L, Zamuner S, Nucci G, Danker-Hopfe H, Ratti E (August 2012). "The orexin antagonist SB-649868 promotes and maintains sleep in men with primary insomnia". Sleep. 35 (8): 1097–104. doi:10.5665/sleep.1996. PMC 3397789. PMID 22851805.

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