8101. Ramelteon

Nomenclature

CAS number: 196597-26-9
N-[2-[(8S)-1,6,7,8-Tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl]propanamide; TAK-375; Rozerem (Takeda).
C16H21NO2; mol wt 259.34.
C 74.10%, H 8.16%, N 5.40%, O 12.34%.

Description and references

Melatonin MT1/MT2 receptor agonist. Prepn: S. Ohkawa et al., WO 9732871; eidem US 6034239 (1997, 2000 both to Takeda); O. Uchikawa et al., J. Med. Chem. 45, 4222 (2002). Pharmacology: N. Yukuhiro et al., Brain Res. 1027, 59 (2004). Receptor binding study: K. Kato et al., Neuropharmacology 48, 301 (2005). Reviews of development and therapeutic potential: C. Cajochen, Curr. Opin. Investig. Drugs 6, 114-121 (2005); N. N. Nguyen et al., Formulary 40, 146-155 (2005).

Chemical structure

Properties

Crystals from ethyl acetate, mp 113-115°. [α]D20 -57.8° (c = 1.004 in chloroform).

Therapeutic Category

Sedative, hypnotic.

Keywords

Sedative/Hypnotic; Melatonin Receptor Agonist