4198. Flurazepam

Nomenclature

CAS number: 17617-23-1
7-Chloro-1-[2-(diethylamino)ethyl]-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one; Felmane; Noctosom; Stauroderm.
C21H23ClFN3O; mol wt 387.88.
C 65.03%, H 5.98%, Cl 9.14%, F 4.90%, N 10.83%, O 4.12%.

Description and references

Prepn: G. A. Archer et al., BE 629005 C.A. 60, 15896f (1964); NL 6401335 C.A. 62, 5289a (1965); G. A. Archer et al., US 3299053 (1963, 1964, 1967 all to Hoffmann-La Roche). Manuf process: R. Fryer, L. H. Sternbach, US 3567710 (1971 to Hoffmann-La Roche). Synthesis: S. Inaba et al., Chem. Pharm. Bull. 19, 263 (1971). Structure-activity studies: L. H. Sternbach et al., J. Med. Chem. 8, 815 (1965); Armagnac et al., Therapie 26, 439 (1971). Metabolism: Schwartz et al., J. Med. Chem. 11, 770 (1968); eidem, J. Pharm. Sci. 59, 1800 (1970). Pharmacology: L. O. Randall et al., Arch. Int. Pharmacodyn. Ther. 178, 216 (1969). Toxicology: H. C. Rosenberg, Pharmacol. Biochem. Behav. 13, 415 (1980). GC determn in plasma: Z. Salama et al., Arzneim.-Forsch. 38, 400 (1988). Comprehensive description: B. C. Rudy, B. Z. Senkowski, Anal. Profiles Drug Subs. 3, 307-331 (1974).

Chemical structure

Properties

White rods from ether-petr ether, mp 77-82°.

Derivative

Dihydrochloride.

Nomenclature

CAS number: 1172-18-5
Flurazepam hydrochloride; Ro-5-6901; Benozil (Kyowa); Dalmadorm (Roche); Dalmane (Roche); Dalmate (Roche); Dormodor (Roche); Felison (Sigurta); Insumin (Kyorin); Lunipax (SKB); Somlan (Sintyal).
C21H23ClFN3O.2HCl; mol wt 460.80.
C 54.74%, H 5.47%, Cl 23.08%, F 4.12%, N 9.12%, O 3.47%.

Properties

Pale yellow crystals from methanol + ether, mp 190-220°. LD50 in mice (mg/kg): 290 i.p.; 870 orally; 84 i.v. (Randall).

Note

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

Therapeutic Category

Sedative, hypnotic.

Keywords

Sedative/Hypnotic; Benzodiazepine Derivatives