3360. Disopyramide

Nomenclature

CAS number: 3737-09-5
α-[2-[Bis(1-methylethyl)amino]ethyl]-α-phenyl-2-pyridineacetamide; α-[2-(diisopropylamino)ethyl]-α-phenyl-2-pyridineacetamide; 4-(diisopropylamino)-2-phenyl-2-(2-pyridyl)butyramide; H-3292; SC-7031; Dicorantil (Aventis); Isorythm (Merck KGaA); Lispine (Nippon Chemiphar); Ritmodan (Aventis); Rythmodan (Aventis).
C21H29N3O; mol wt 339.47.
C 74.30%, H 8.61%, N 12.38%, O 4.71%.

Description and references

Prepn: Cusic, Sause, BE 617730 C.A. 58, 12522e (1963) and US 3225054 (1962 and 1965, both to Searle). Synthesis and biological activity: Adelstein, J. Med. Chem. 16, 309 (1973). Pharmacology: J. Am. Med. Assoc. 213, 697 (1970); Mathur, Am. Heart J. 84, 764 (1972); B. Befeler, R. Lazzara, Heart Lung 9, 475 (1980). Conformation-activity study: J. L. Czeisler, R. M. El-Rashidy, J. Pharm. Sci. 74, 750 (1985). Toxicity: P. C. Ruenitz, C. M. Mokler, J. Med. Chem. 22, 1142 (1979). Reviews: R. R. Dean et al., in Pharmacological and Biochemical Properties of Drug Substances vol. 2, M. E. Goldberg, Ed. (Am. Pharm. Assoc., Washington, DC, 1979) pp 165-185; E. H. Taylor, A. A. Pappas, Ann. Clin. Lab. Sci. 16, 289-295 (1986).

Chemical structure

Properties

Crystals from hexane, mp 94.5-95.0°. pKa 10.2; also reported as 10.45. Soly in water: 1 mg/ml. Partition coefficient (chloroform/water): 3.1 (pH 7.2). LD50 i.p. in mice: 517 μmol/kg (Ruenitz, Mokler).

Derivative

Phosphate.

Nomenclature

CAS number: 22059-60-5
SC-13957; Dirythmin SA (AstraZeneca); Diso-Duriles (AstraZeneca); Norpace (Pfizer); Rythmodul (Aventis).
C21H29N3O.H3PO4; mol wt 437.47.
C 57.66%, H 7.37%, N 9.61%, O 18.29%, P 7.08%.

Properties

Freely sol in water.

Therapeutic Category

Antiarrhythmic (class IA).

Keywords

Antiarrhythmic