Title: Dofetilide
CAS Registry Number: 115256-11-6
CAS Name: N-[4-[2-[Methyl[2-[4-[(methylsulfonyl)amino]phenoxy]ethyl]amino]ethyl]phenyl]methanesulfonamide
Additional Names: 1-(4-methanesulfonamidophenoxy)-2-[N-(4-methanesulfonamidophenethyl)-N-methylamino]ethane
Manufacturers' Codes: UK-68798
Trademarks: Tikosyn (Pfizer)
Molecular Formula: C19H27N3O5S2
Molecular Weight: 441.56
Percent Composition: C 51.68%, H 6.16%, N 9.52%, O 18.12%, S 14.52%
Literature References: Potassium channel blocker. Prepn: J. E. Arrowsmith et al., EP 245997; P. E. Cross et al., US 4959366 (1987, 1990 both to Pfizer); idem et al., J. Med. Chem. 33, 1151 (1990). HPLC determn in urine: D. K. Walker et al., J. Chromatogr. 568, 475 (1991). Mechanism of action study: D. Carmeliet, J. Pharmacol. Exp. Ther. 262, 809 (1992). Review of pharmacology and pharmacokinetics: H. S. Rasmussen et al., ibid. 20, Suppl. 2, S96-S105 (1992). Clinical trial in atrial fibrillation and flutter: B. L. Norgaard et al., Am. Heart J. 137, 1062 (1999); in congestive heart failure: C. Torp-Pedersen et al., N. Engl. J. Med. 341, 857 (1999).
Properties: Crystals from ethyl acetate/methanol (10:1), mp 147-149° (Cross); from hexane/ethyl acetate, mp 151-152° (Arrowsmith). Also reported as white crystalline solid, mp 161° (Rasmussen). pKa 7.0, 9.0, 9.6. Distribution coefficient (pH 7.4): 0.96. Sol in 0.1M NaOH, acetone, 0.1M HCl; very slightly sol in water, propan-2-ol.
Melting point: mp 147-149° (Cross); mp 151-152° (Arrowsmith); mp 161° (Rasmussen)
pKa: pKa 7.0, 9.0, 9.6
Therap-Cat: Antiarrhythmic (class III).
Keywords: Antiarrhythmic; Potassium Channel Blocker. |