4883. Ibutilide

Nomenclature

CAS number: 122647-31-8
N-[4-[4-(Ethylheptylamino)-1-hydroxybutyl]phenyl]methanesulfonamide.
C20H36N2O3S; mol wt 384.58.
C 62.46%, H 9.44%, N 7.28%, O 12.48%, S 8.34%.

Description and references

Methanesulfonanilide antiarrhythmic agent; prolongs myocardial action potential duration, predominantly by activation of slow inward sodium current. Prepn: J. B. Hester, EP 164865; idem, US 5155268 (1985, 1992 both to Upjohn); idem et al., J. Med. Chem. 34, 308 (1991). HPLC determn of enantiomers: C. L. Hsu, R. R. Walters, J. Chromatogr. B 667, 115 (1995); determn of racemate in plasma: L. Tian et al., J. Chromatogr. B 816, 81 (2005). Review of electrophysiology and pharmacology: G. V. Naccarelli et al., Am. J. Cardiol. 78, Suppl. 8A, 12-16 (1996); of pharmacology and clinical potential: R. H. Foster et al., Drugs 54, 312-330 (1997). Clinical trial in atrial flutter or fibrillation: B. S. Stambler et al., Circulation 94, 1613 (1996); J. T. VanderLugt et al., ibid. 100, 369 (1999); in elderly patients: R. M. Gowda et al., Am. J. Ther. 11, 95 (2004).

Chemical structure

Derivative

Fumarate.

Nomenclature

CAS number: 122647-32-9
U-70226E; Corvert (Pfizer).
(C20H36N2O3S)2.C4H4O4; mol wt 885.23.
C 59.70%, H 8.65%, N 6.33%, O 18.07%, S 7.24%.

Properties

Crystals from acetone, mp 117-119°. uv max (95% ethanol): 228, 267 nm (ε 16670, 894) Soly (mg/ml): aqueous >100 (pH ≤ 7).

Therapeutic Category

Antiarrhythmic (class III).

Keywords

Antiarrhythmic