(Biphenyl-4-yl)methylammonium chlorides: potent anticonvulsants that modulate Na+ currents

J Med Chem. 2013 Jul 25;56(14):5931-9. doi: 10.1021/jm4007092. Epub 2013 Jul 3.

Abstract

We have reported that compounds containing a biaryl linked unit (Ar-X-Ar') modulated Na(+) currents by promoting slow inactivation and fast inactivation processes and by inducing frequency (use)-dependent inhibition of Na(+) currents. These electrophysiological properties have been associated with the mode of action of several antiepileptic drugs. In this study, we demonstrate that the readily accessible (biphenyl-4-yl)methylammonium chlorides (compound class B) exhibited a broad range of anticonvulsant activities in animal models, and in the maximal electroshock seizure test the activity of (3'-trifluoromethoxybiphenyl-4-yl)methylammonium chloride (8) exceeded that of phenobarbital and phenytoin upon oral administration to rats. Electrophysiological studies of 8 using mouse catecholamine A-differentiated cells and rat embryonic cortical neurons confirmed that 8 promoted slow and fast inactivation in both cell types but did not affect the frequency (use)-dependent block of Na(+) currents.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Ammonium Compounds / chemical synthesis*
  • Ammonium Compounds / pharmacology
  • Animals
  • Anticonvulsants / chemical synthesis*
  • Anticonvulsants / pharmacology
  • Biphenyl Compounds / chemical synthesis*
  • Biphenyl Compounds / pharmacology
  • Male
  • Methylamines
  • Mice
  • Rats
  • Rats, Sprague-Dawley
  • Sodium Channels / drug effects*
  • Sodium Channels / physiology

Substances

  • Ammonium Compounds
  • Anticonvulsants
  • Biphenyl Compounds
  • Methylamines
  • Sodium Channels
  • methylamine