10351. Vernakalant

Nomenclature

CAS number: 794466-70-9
(3R)-1-[(1R,2R)-2-[2-(3,4-Dimethoxyphenyl)ethoxy]cyclohexyl]-3-pyrrolidinol; (1R,2R)-2-[(3R)-hydroxypyrrolidinyl]-1-(3,4-dimethoxyphenethoxy)cyclohexane.
C20H31NO4; mol wt 349.46.
C 68.74%, H 8.94%, N 4.01%, O 18.31%.

Description and references

Atrial selective antifibrillary agent. Mixed ion channel antagonist; blocks frequency- and voltage-dependent sodium channels and Kv1.5 potassium channels. Prepn: G. N. Beatch et al., WO 04099137; eidem, US 7057053 (2002, 2005 to Cardiome). Comparative binding with inner pore of Kv1.5 channel: J. Eldstrom et al., Mol. Pharmacol. 72, 1522 (2007) DOI PubMed. Mechanism of action: D. Fedida et al., J. Cardiovasc. Electrophysiol. 16, 1227 (2005) DOI PubMed. Clinical trial for rapid conversion of atrial fibrillation: D. Roy et al., Circulation 117, 1518 (2008) DOI PubMed. Review of clinical pharmacology and electrophysiology: D. Fedida, Expert Opin. Invest. Drugs 16, 519-532 (2007) DOI PubMed; of pharmacology and clinical experience: J. W. M. Cheng, Ann. Pharmacother. 42, 533-542 (2008) DOI PubMed.

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 748810-28-8
RSD-1235; Kynapid (Astellas).
C20H31NO4.HCl; mol wt 385.93.
C 62.24%, H 8.36%, N 3.63%, O 16.58%, Cl 9.19%.

Properties

Crystals from ethyl acetate, mp 144-150°. [α]D 46.7° (c = 1.52 in CH3OH); [α]D 39.6° (c = 1.00 in CHCl3).

Therapeutic Category

Antiarrhythmic.

Keywords

Antiarrhythmic