Stereospecific Interaction of Bupivacaine Enantiomers with Lipid Membranes

Bupivacaine stereostructure-specifically interacts with membranes containing cholesterol, which is consistent with the clinical features of S(−)-bupivacaine. Membrane cholesterol appears to increase the chirality of lipid bilayers and enable them to interact with S(−)-, racemic and R(+)-bupivacaine differently.