2D- and 3D-QSAR of tocainide and mexiletine analogues acting as Na(v)1.4 channel blockers

Eur J Med Chem. 2009 Apr;44(4):1477-85. doi: 10.1016/j.ejmech.2008.10.005. Epub 2008 Oct 14.

Abstract

Enantiomeric forms of Tocainide, Mexiletine, and structurally related local anaesthetic compounds, were analyzed with respect to their potency in blocking Na(v)1.4 channel. Structure-activity relationships based on in vitro pharmacological assays, suggested that an increase in terms of lipophilicity and/or molecular surface as well as the presence of specific polar spacers might be determinant for receptor interactions. QSAR and pharmacophore models were then used to support at 3D level this hypothesis.

MeSH terms

  • Crystallography, X-Ray
  • Mexiletine / analogs & derivatives
  • Mexiletine / chemistry*
  • Mexiletine / pharmacology*
  • Protein Isoforms / antagonists & inhibitors
  • Quantitative Structure-Activity Relationship*
  • Sodium Channel Blockers / chemistry*
  • Sodium Channel Blockers / pharmacology*
  • Sodium Channels / metabolism
  • Substrate Specificity
  • Tocainide / analogs & derivatives
  • Tocainide / chemistry*
  • Tocainide / pharmacology*

Substances

  • Protein Isoforms
  • Sodium Channel Blockers
  • Sodium Channels
  • Mexiletine
  • Tocainide