Zopiclone
Title: Zopiclone
CAS Registry Number: 43200-80-2
CAS Name: 4-Methyl-1-piperazinecarboxylic acid 6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl ester
Additional Names: 6-(5-chloropyrid-2-yl)-5-(4-methylpiperazin-1-yl)carbonyloxy-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine
Manufacturers' Codes: RP-27267
Trademarks: Amoban (Aventis); Imovane (Aventis); Limovan (Aventis); Sopivan (Aventis); Ximovan (Aventis); Zimovane (Aventis)
Molecular Formula: C17H17ClN6O3
Molecular Weight: 388.81
Percent Composition: C 52.51%, H 4.41%, Cl 9.12%, N 21.61%, O 12.34%
Literature References: Cyclopyrrolone member of a family of non-benzodiazepine GABAA receptor agonists. Prepn: C. Cotrel et al., DE 2300491; eidem, US 3862149 (1973, 1975 both to Rhone-Poulenc); C. Jeanmart, C. Cotrel, C.R. Seances Acad. Sci. Ser. C 287, 377 (1978). In vitro and in vivo inhibition of benzodiazepine binding: J. C. Blanchard et al., Life Sci. 24, 2417 (1979); see also P. H. Wu et al., ibid. 28, 1023 (1981). Comparative study with benzodiazepines: E. Wickström, K. E. Giercksky, Eur. J. Clin. Pharmacol. 17, 93 (1980). HPLC determn of enantiomers in plasma: C. Fernandez et al., J. Chromatogr.572, 195 (1991); in urine: eidem, ibid. 617, 271 (1993). Pharmacokinetics of zopiclone and enantiomers: eidem, Drug Metab. Dispos. 21, 1125 (1993). Mechanism of action: A. Doble et al., Eur. Psychiatr. 10, Suppl 3, 117s (1995). Sedative and anxiolytic effects of enantiomers and metabolite in rats: J. N. Carlson et al., Eur. J. Pharmacol. 415, 181 (2001). Series of articles on pharmacokinetics, pharmacology and efficacy in insomnia: Sleep 10, Suppl 1, 1-87 (1987). Clinical overview: B. Musch, F. Maillard, Int. J. Clin. Psychopharmacol. 5, 147-158 (1990). Review of pharmacology, tolerability and therapeutic efficacy: S. Noble et al., Drugs 55, 277-302 (1998).
Properties: Crystals from acetonitrile/diisopropyl ether (1:1), mp 178°.
Melting point: mp 178°
 
Derivative Type: S-Form
CAS Registry Number: 138729-47-2
Additional Names: Eszopiclone
Trademarks: Estorra (Sepracor); Lunesta (Sepracor)
Literature References: Prepn: C. Cotrel, G. Roussel, WO 9212980 (1992 to Rhone-Poulenc Rorer); see also: eidem, US 6319926 (2001 to Sepracor).
Properties: Crystals from acetonitrile, mp 206.5°. [a]D20 +135 ±3° (c = 1.0 in acetone).
Melting point: mp 206.5°
Optical Rotation: [a]D20 +135 ±3° (c = 1.0 in acetone)
 
NOTE: This is a controlled substance (depressant): 21 CFR, 1308.14.
Therap-Cat: Sedative, hypnotic.
Keywords: Sedative/Hypnotic.

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