9579. Trazodone

Nomenclature

CAS number: 19794-93-5
2-[3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl]-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one.
C19H22ClN5O; mol wt 371.86.
C 61.37%, H 5.96%, Cl 9.53%, N 18.83%, O 4.30%.

Description and references

Prepn: Palazzo, Silvestrini, US 3381009 (1968 to Angelini Francesco). Pharmacology: Catanese, Lisciani, Boll. Chim. Farm. 109, 369 (1970); B. Silvestrini, E. Quadri, Eur. J. Pharmacol. 12, 231 (1970). Analytical data: Baiocchi et al., Arzneim.-Forsch. 23, 400 (1973). Crystal structure: J. P. Fillers, S. W. Hawkinson, Acta Crystallogr. B35, 498 (1979). Review of pharmacological properties and therapeutic use: R. N. Brogden et al., Drugs 21, 401-429 (1981); B. Silvestrini et al., in Pharmacological and Biochemical Properties of Drug Substances vol. 3, M. E. Goldberg, Ed. (Am. Pharm. Assoc., Washington, DC, 1981) pp 94-119. Comprehensive description: D. Gorecki, R. Verbeeck, Anal. Profiles Drug Subs. 16, 693-729 (1986). Symposium on clinical efficacy: Psychopharmacology 95, Suppl., 1-56 (1988).

Chemical structure

Properties

Crystals, mp 86-87°. Also reported as mp 96° (Baiocchi). pKa (50% ethanol): 6.14.

Derivative

Hydrochloride.

Nomenclature

CAS number: 25332-39-2
AF-1161; Bimaran (Roux-Ocefa); Desyrel (Apothecon); Molipaxin (HMR); Pragmazone (UPSA); Thombran (Thomae); Tombran (Boehringer, Ing.); Trazolan (Continental Pharma); Trittico (Angelini).
C19H22ClN5O.HCl; mol wt 408.32.
C 55.89%, H 5.68%, Cl 17.37%, N 17.15%, O 3.92%.

Properties

White, odorless plates from ethanol, mp 223°. Soluble in chloroform; sparingly sol in water, ethanol, methanol. Practically insol in common organic solvents. uv max (water): 211, 246, 274, 312 nm (ε 50100, 11730, 3840, 3840). LD50 i.v. in mice: 96 mg/kg (Silvestrini, Quadri).

Therapeutic Category

Antidepressant.

Keywords

Antidepressant; Bicyclics