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Stereospecific Synthesis of m-Hydroxymexiletine Enantiomers

Stereospecific Synthesis of m-Hydroxymexiletine Enantiomers

Alessia Catalano, Alessia Carocci, Giovanni Lentini, Ivana Defrenza, Claudio Bruno, Carlo Franchini

Drug Metab Lett. 2012 Sep 1;6(3):182-6.

PMID: 23140556

Abstract:

m-Hydroxymexiletine (MHM) is a metabolite of mexiletine, a well known class IB anti-arrhythmic drug, which presents almost twice the activity of the parent compound on cardiac voltage-gated sodium channels. Given the different activity of mexiletine enantiomers on sodium currents (being the R-isomer the eutomer), it is conceivable that (R)- and(S)-MHM could differ in pharmacodynamic and pharmacokinetic properties, too. Herein we report the efficient synthesis of MHM enantiomers that could represent useful tools for further investigations on stereospecific requirements of the voltage-gated sodium channel binding site. MHM enantiomers and all the homochiral intermediates were fully characterized. The ee values for (R)- and (S)-MHM were >99%, as assessed by capillary electrophoresis using β-cyclodextrin sulfated sodium salt as a chiral selector.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP37191698	β-Cyclodextrin, sulfated sodium salt		37191-69-8	Price

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