4098. Flecainide

Nomenclature

CAS number: 54143-55-4
N-(2-Piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide.
C17H20F6N2O3; mol wt 414.34.
C 49.28%, H 4.87%, F 27.51%, N 6.76%, O 11.58%.

Description and references

Prepn: E. H. Banitt, W. R. Brown, US 3900481 (1975 to Riker); of the acetate: eidem, US 4005209 (1977 to Riker); E. H. Banitt et al., J. Med. Chem. 20, 821 (1977). Preliminary pharmacological study: J. R. Schmid et al., Fed. Proc. 34, 775 (1975). In vitro electrophysiological study: A. B. Hodess et al., J. Cardiovasc. Pharmacol. 1, 427 (1979). Antiarrhythmic effects: P. Somani, Clin. Pharmacol. Ther. 27, 464 (1980). Use in acute exptl myocardial infarction: H. Gülker et al., Z. Cardiol. 70, 124 (1981). Clinical study in ventricular arrhythmias: J. L. Anderson et al., N. Engl. J. Med. 305, 473 (1981). Determn of acetate in human plasma by spectrophotofluorometry: S. F. Chang et al., Arzneim.-Forsch. 33, 251 (1983). Review of pharmacology and clinical efficacy: D. M. Roden, R. L. Woosley, N. Engl. J. Med. 315, 36-41 (1986). Symposium on clinical experience: Am. J. Cardiol. 62, Suppl., 1D-67D (1988). Comprehensive description: S. Alessi-Severini et al., Anal. Profiles Drug Subs. Excip. 21, 169-195 (1992).

Chemical structure

Properties

uv max (ethanol): 205, 230, 300 nm (E1%1cm 521, 219, 59).

Derivative

Monoacetate.

Nomenclature

CAS number: 54143-56-5
R-818; Almarytm (Synthelabo); Apocard (Esteve); Ecrinal (Pharma Investi); Flécaine (3M Pharma); Tambocor (3M Pharma).
C17H20F6N2O3.C2H4O2; mol wt 474.39.
C 48.10%, H 5.10%, F 24.03%, N 5.91%, O 16.86%.

Properties

White granular solid from isopropyl alcohol/isopropyl ether, mp 145-147°. Soly at 37° (mg/ml): water 48.4, alcohol 300.

Therapeutic Category

Antiarrhythmic (class IC).

Keywords

Antiarrhythmic