SB-649868

SB-649868 is a dual orexin receptor antagonist that was being developed by GlaxoSmithKline as a treatment for insomnia.^[1]

SB-649868

Clinical data
ATC code	None
Legal status
Legal status	Investigational
Identifiers
IUPAC name N-([(2S)-1-([5-(4-fluorophenyl)-2-methyl-4-thiazolyl]carbonyl)-2-piperidinyl]methyl)-4-benzofurancarboxamide
CAS Number	380899-24-1 Y
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−1
3D model (JSmol)	Interactive image
SMILES CC1=NC(=C(S1)C2=CC=C(C=C2)F)C(=O)N3CCCC[C@H]3CNC(=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

A phase I clinical trial evaluated doses up to 80 mg, resulting in significant improvement in sleep latency without adverse effects.^[2] In randomized, double-blind, placebo-controlled crossover trials, the 10 and 30 mg doses increased sleep time and reduced sleep latency.^[3] The subsequent phase II study added a 60 mg dose and observed dose-dependent sleep promotion.^[4]

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

See also

• Almorexant
• Filorexant
• Lemborexant
• Suvorexant