10111. Zaleplon

Nomenclature

CAS number: 151319-34-5
N-[3-(3-Cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethylacetamide; CL-284846; Sonata (Wyeth).
C17H15N5O; mol wt 305.33.
C 66.87%, H 4.95%, N 22.94%, O 5.24%.

Description and references

Selective non-benzodiazepine GABAA receptor agonist. Prepn: J. P. Dusza et al., US 4626538 (1986 to Am. Cyanamid). Clinical pharmacology: D. Allen et al., Eur. J. Clin. Pharmacol. 45, 313 (1993); B. Beer et al., J. Clin. Pharmacol. 34, 335 (1994). Clinical pharmacokinetics: A. S. Rosen et al., Biopharm. Drug Dispos. 20, 171 (1999). Clinical comparison with zolpidem, q.v.: R. Elie et al., J. Clin. Psychiatry 60, 536 (1999). CE-LIF determn of metabolites in urine: C. Horstktter et al., J. Chromatogr. A 1014, 71 (2003). Review of pharmacology and clinical experience: W. E. Heydorn, Expert Opin. Invest. Drugs 9, 841-858 (2000).

Chemical structure

Properties

White to off-white powder. mp 186-187°. Log P (octanol/water): 1.23 (pH 1-7). Sparingly sol in alcohol, propylene glycol. Practically insol in water.

Note

This is a controlled substance (depressant): 21 CFR, 1308.14.

Therapeutic Category

Sedative, hypnotic.

Keywords

Sedative/Hypnotic; Imidazopyridines