4128. Fludiazepam

Nomenclature

CAS number: 3900-31-0
7-Chloro-5-(2-fluorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one; ID-540; Ro-5-3438; Erispan (Sumitomo).
C16H12ClFN2O; mol wt 302.73.
C 63.48%, H 4.00%, Cl 11.71%, F 6.28%, N 9.25%, O 5.29%.

Description and references

Fluorinated analog of diazepam, q.v. Prepn: E. Reeder et al., DE 1136709; E. Reeder, L. H. Sternbach, US 3371085 (1962, 1968 both to Hoffmann-LaRoche); L. H. Sternbach et al., J. Org. Chem. 27, 3788 (1962). Synthesis and pharmacology: Y. Asami et al., Arzneim.-Forsch. 24, 1563 (1974). Pharmacodynamics: M. Nakamura, H. Fukushima, J. Pharm. Pharmacol. 30, 56, 254 (1978); T. Tsuchiya, H. Fukushima, Eur. J. Pharmacol. 48, 421 (1978). Anxiolytic vs sedative properties: M. Babbini et al., Life Sci. 25, 15 (1979).

Chemical structure

Properties

Colorless prisms from n-hexane/isopropanol, mp 88-92°, (Asami); also reported as mp 69-72° (Sternbach). LD50 in mice (mg/kg): 910 orally; 360 i.p.; 1150 s.c. (Asami).

Note

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

Therapeutic Category

Anxiolytic.

Keywords

Anxiolytic; Benzodiazepine Derivatives