8728. Sotalol

Nomenclature

CAS number: 3930-20-9
N-[4-[1-Hydroxy-2-[(1-methylethyl)amino]ethyl]phenyl]methanesulfonamide; 4′-[1-hydroxy-2-(isopropylamino)ethyl]methanesulfonanilide.
C12H20N2O3S; mol wt 272.36.
C 52.92%, H 7.40%, N 10.29%, O 17.62%, S 11.77%.

Description and references

β-Adrenergic blocker. Prepn: Uloth et al., J. Med. Chem. 9, 88 (1966). Pharmacology and toxicology: Larsen, Lish, Nature 203, 1283 (1964); Lish et al., J. Pharmacol. Exp. Ther. 149, 161 (1965); Stanton et al., ibid. 175; Kvam et al., ibid. 183. Activity of the d- and l-forms: Somani, Watson, ibid. 164, 317 (1968); Somani, Bachand, Eur. J. Pharmacol. 7, 239 (1969). HPLC determn in body fluids: W. P. Gluth et al., Arzneim.-Forsch. 38, 408 (1988). Enantioselective LC/MS determn in plasma: E. Badaloni et al., J. Chromatogr. B 796, 45 (2003). Review of pharmacology and therapeutic use: B. N. Singh et al., Drugs 34, 311-349 (1987); S. H. Hohnloser, R. L. Woosley, N. Engl. J. Med. 331, 31-38 (1994). Comprehensive description: R. T. Foster, R. A. Carr, Anal. Profiles Drug Subs. Excip. 21, 501-533 (1992). Review of clinical experience: J. L. Anderson, E. N. Prystowsky, Am. Heart J. 137, 388-409 (1999).

Chemical structure

Properties

Crystals. uv max (chloroform): 242.2, 275.2 nm. pK1 8.2, pK2 9.8.

Derivative

Hydrochloride.

Nomenclature

CAS number: 959-24-0
MJ-1999; Beta-Cardone (UCB); Betapace (Schering AG); Darob (Abbott); Rytmobeta (Abbott); Sotacor (BMS); Sotalex (BMS).
C12H20N2O3S.HCl; mol wt 308.82.
C 46.67%, H 6.85%, N 9.07%, O 15.54%, S 10.38%, Cl 11.48%.

Properties

White crystalline solid, mp 206.5-207° (dec), also reported as mp 218-219° (Singh). Freely sol in water; slightly sol in chloroform. Partition coefficient (water/n-octanol): 0.24; (octan-1-ol/pH 7.4 phosphate buffer) at 37°: 0.09. LD50 in male mice, rats (mg/kg): 2600, 3450 orally; 670, 680 i.p.; LD50 orally in rabbits: 1000 mg/kg; LD50 i.p. in dogs: 330 mg/kg (Lish).

Therapeutic Category

Antianginal; antiarrhythmic (class III); antihypertensive.

Therapeutic Category (Veterinary)

Antiarrhythmic (class III).

Keywords

β-Adrenergic Blocker; Antianginal; Antiarrhythmic; Antihypertensive; Arylethanolamine Derivatives