312. Alprazolam

Nomenclature

CAS number: 28981-97-7
8-Chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine; 8-chloro-1-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine; D-65MT; U-31889; Alplax (Gador); Cassadan (Temmler); Esparon (Orion); Tafil (Pharmacia); Tranquinal (Bago); Trankimazin (Pharmacia); Xanax (Pharmacia & Upjohn).
C17H13ClN4; mol wt 308.76.
C 66.13%, H 4.24%, Cl 11.48%, N 18.15%.

Description and references

Benzodiazepine anxiolytic. Prepn: J. B. Hester, DE 2012190; idem, US 3987052 (1970, 1976 both to Upjohn); J. B. Hester et al., Tetrahedron Lett. 1971, 1609; A. Walser, G. Zenchoff, J. Med. Chem. 20, 1694 (1977). Central depressant activity: R. Nakajima et al., Jpn. J. Pharmacol. 21, 497 (1971). Pharmacology: V. H. Sethy, Arch. Pharmacol. 301, 157 (1978). Clinical studies: L. F. Fabre, Curr. Ther. Res. 19, 661 (1976); J. B. Cohn, J. Clin. Psychiatry 42, 347 (1981). Pharmacokinetics: D. R. Abernethy et al., ibid. 44, 45 (1983). HPLC determn in tablets: P. Pérez-Lozano et al., J. Pharm. Biomed. Anal. 34, 979 (2004); in plasma: A. Allqvist et al., J. Chromatogr. B 814, 127 (2005). Review of pharmacokinetics, clinical efficacy, and mechanism of action: J. A. Fawcett, H. M. Kravitz, Pharmacotherapy 2, 242-254 (1982); of pharmacology and efficacy in anxiety and depression: G. W. Dawson et al., Drugs 27, 132-147 (1984); of extended release formulation in panic disorder: K. Rickels, Expert Opin. Pharmacother. 5, 1599-1611 (2004).

Chemical structure

Properties

Crystals from ethyl acetate, mp 228-228.5°. Freely sol in chloroform; sol in alc; sparingly sol in acetone; slightly sol in ethyl acetate. Insol in water. uv max (ethanol): 222 nm (ε 40250). LD50 in mice, rats (mg/kg): 1020, >2000 orally; 540, 610 i.p. (Nakajima).

Note

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

Therapeutic Category

Anxiolytic.

Therapeutic Category (Veterinary)

In treatment of behavioral disorders.

Keywords

Anxiolytic; Benzodiazepine Derivatives