Referenced in: none

Automatically associated channels: Kir2.3

Title: Stereospecific synthesis of "para-hydroxymexiletine" and sodium channel blocking activity evaluation.

Authors: Alessia Catalano, Alessia Carocci, Giuseppe Fracchiolla, Carlo Franchini, Giovanni Lentini, Vincenzo Tortorella, Annamaria De Luca, Michela De Bellis, Jean-François Desaphy, Diana Conte Camerino

Journal, date & volume: , 2004 Feb , 16, 72-8

PubMed link: http://www.ncbi.nlm.nih.gov/pubmed/14712469

Abstract
Both enantiomers of "para-hydroxymexiletine" (PHM), one of the main metabolites of mexiletine, were synthesized and fully characterized. Properties of (R)- and (S)-PHM, in terms of blocking potency and stereoselectivity on frog skeletal muscle Na(+) channels, were evaluated. The presence of a hydroxy group on the aryloxy moiety in the 4-position, as in PHM, reduced potency with respect to mexiletine in reducing I(Na max). However, PHM showed clear use-dependent behavior similar to that of mexiletine and, in contrast with what is observed with the parent compound, maintained its stereoselectivity during the use-dependent block. Chirality 16:72-78, 2004.