6529. Nifekalant

Nomenclature

CAS number: 130636-43-0
6-[[2-[(2-Hydroxyethyl)[3-(4-nitrophenyl)propyl]amino]ethyl]amino]-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione.
C19H27N5O5; mol wt 405.45.
C 56.28%, H 6.71%, N 17.27%, O 19.73%.

Description and references

Nonselective potassium channel blocker. Prepn: T. Katakami et al., EP 369627; eidem, US 5008267 (1990, 1991 both to Mitsui Toatsu Chem.); eidem, J. Med. Chem. 35, 3325 (1992). Pharmacology: J. Kamiya et al., Drug Dev. Res. 30, 37 (1993). Clinical experience: M. Igawa et al., J. Cardiovasc. Pharmacol. 40, 735 (2002); T. Minami et al., Pacing Clin. Electrophysiol. 27, 212 (2004). Review of pharmacology: H. Nakaya, H. Uemura, Cardiovasc. Drug Rev. 16, 133-144 (1998); of development and therapeutic potential: A. Zaza, Curr. Opin. Cardiovasc. Pulm. Renal Invest. Drugs 2, 86-94 (2000). Clinical evaluation in ventricular tachyarrhythmias: T. Katoh et al., Circ. J. 69, 1237 (2005); T. Washizuka et al., ibid. 1508; in shock-refractory ventricular fibrillation: Y. Tahara et al., ibid. 70, 442 (2006).

Chemical structure

Properties

Crystals from ethanol, mp 117.5-118.5°. Also reported as mp 125-126° (Katakami, 1992).

Derivative

Hydrochloride.

Nomenclature

CAS number: 130656-51-8
MS-551; Shinbit (Nihon Schering).
C19H27N5O5.HCl; mol wt 441.91.
C 51.64%, H 6.39%, N 15.85%, O 18.10%, Cl 8.02%.

Properties

Light yellow to yellow crystals from methanol, mp 172-174°. Very sol in water, slightly sol in methanol, very slightly sol in ethanol. Practically insol in ether. pH 4.0 - 5.5 (5 mg/ml saline soln). pKa 7.05.

Therapeutic Category

Antiarrhythmic (class III).

Keywords

Antiarrhythmic; Potassium Channel Blocker