Chirality in anaesthesia--ropivacaine, ketamine and thiopentone

Drug chirality (molecular handedness) is a source of pharmacological differences between otherwise chemically identical molecules. Specific applications to the pharmacology of ropivacaine (single enantiomer), ketamine and thiopentone (both racemates) are discussed. Ropivacaine is produced as a single S-enantiomer homologue of the more toxic bupivacaine to preclude the higher central nervous system and heart toxicity found in the R-enantiomer. S-ketamine is presently undergoing trials as a potential replacement for the racemate, on the grounds that it optimizes anaesthesia and minimizes psychotomimetic phenomena. Thiopentone, previously known to have quantitative differences in the pharmacology of its enantiomers, has recently also been shown to have pharmacokinetic differences. The evidence for these claims is discussed in this review.