6691. Nordazepam

Nomenclature

CAS number: 1088-11-5
7-Chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one; desmethyldiazepam; nordiazepam; DMDZ; A-101; Ro-5-2180; Calmday (Will-Pharma); Madar (Ravizza); Nordaz (Bouchara); Praxadium (Bottu); Stilny (Will-Pharma).
C15H11ClN2O; mol wt 270.71.
C 66.55%, H 4.10%, Cl 13.10%, N 10.35%, O 5.91%.

Description and references

Desmethyl analog and principal metabolite of diazepam, q.v. Prepn: L. H. Sternbach, E. Reeder, J. Org. Chem. 26, 4936 (1961); E. Reeder et al., DE 1136709; E. Reeder, L. Sternbach, US 3051701 (both 1962 to Hoffmann-La Roche); A. Stempel, BE 620020; idem, US 3202699 (1963, 1965, both to Hoffmann-La Roche); S. C. Bell et al., J. Org. Chem. 27, 562 (1962); A. Stempel, G. W. Landgraf, ibid. 4675. Pharmacology: U. Traversa et al., J. Pharm. Pharmacol. 29, 504 (1977); M. Babbini et al., Pharmacology 17, 121 (1978). Metabolism: U. Klotz et al., Br. J. Clin. Pharmacol. 7, 119 (1979). Pharmacokinetics: M. Konishi, J. Pharm. Sci. 67, 1777 (1978). Clinical study: V. Andreoli et al., Arzneim.-Forsch. 27, 436 (1977). Toxicity study: L. O. Randall et al., Curr. Ther. Res. 7, 590 (1965). Teratogenicity study: R. P. Miller et al., Toxicol. Appl. Pharmacol. 25, 453 (1973).

Chemical structure

Properties

White or pale yellow crystalline powder from acetone, mp 216-217°. uv max (chloroform): 313 nm (E1%1cm 82). Slightly sol in alc, chloroform. Practically insol in water. LD50 in mice (mg/kg): 2750 orally, >400 i.p. (Randall). Also reported as LD50 in mice, rats (mg/kg): 1300, >5200 orally (company communication).

Note

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

Therapeutic Category

Anxiolytic.

Keywords

Anxiolytic; Benzodiazepine Derivatives