6926. Oxazepam

Nomenclature

CAS number: 604-75-1
7-Chloro-1,3-dihydro-3-hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-one; 7-chloro-3-hydroxy-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one; Wy-3498; Adumbran (Boehringer, Ing.); Azutranquil (Azupharma); Durazepam (Merck KGaA); Hilong (Wyeth); Limbial (Chiesi); Noctazepam (Hexal); Praxiten (Teofarma); Serax (Wyeth); Serenid (Wyeth); Serepax (Wyeth); Séresta (Biodim); Serpax (Wyeth); Sobril (Pharmacia); Uskan (Desitin).
C15H11ClN2O2; mol wt 286.71.
C 62.84%, H 3.87%, Cl 12.37%, N 9.77%, O 11.16%.

Description and references

Benzodiazepine anxiolytic; metabolite of several other benzodiazepines including diazepam and chlordiazepoxide, q.q.v. Prepn: Bell, Childress, J. Org. Chem. 27, 1691 (1962); NL 298071; S. C. Bell, US 3296249 (1965, 1967 both to American Home Prod.). Crystal and molecular structure: G. Gilli et al., Acta Crystallogr. B34, 2826 (1978). Metabolic studies: Sisenwine et al., Arzneim.-Forsch. 22, 682 (1972); Knowles, Ruelius, ibid. 687. Pharmacokinetics: D. J. Greenblatt, Clin. Pharmacokinet. 6, 89 (1981). HPLC determn in urine: L. A. Berrueta et al., J. Chromatogr. 616, 344 (1993); dynamic HPLC determn of enantiomerization barrier: O. Trapp et al., J. Biochem. Biophys. Methods 54, 301 (2002). Toxicity data: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971). Comprehensive description: C. M. Shearer, C. R. Pilla, Anal. Profiles Drug Subs. 3, 441-464 (1974). Review: Acta Psychiatr. Scand. Suppl. 274, R. Chinnery, A. Sundwall, Eds. (1978) 128 pp.

Chemical structure

Properties

Crystals from alcohol, mp 205-206°. Sol in alcohol, chloroform, dioxane. Practically insol in water. LD50 in mice, rats (mg/kg): >5010, >5010 orally (Goldenthal).

Note

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

Therapeutic Category

Anxiolytic.

Therapeutic Category (Veterinary)

Appetite stimulant in cats.

Keywords

Anxiolytic; Benzodiazepine Derivatives