Bupivacaine has a chiral centre and is currently available as a racemi
c mixture of its two enantiomers: R(+)-bupivacaine and S(-)-bupivacain
e. Preclinical studies have demonstrated that there is enantiomer sele
ctivity of action with the bulk of central nervous system and cardiova
scular toxicity residing with the R(+) isomer. The aim of this study w
as to compare the clinical efficacy and safety of S(-)-bupivacaine wit
h racemic RS-bupivacaine for extradural anaesthesia. We studied 88 pat
ients undergoing elective tower limb surgery under lumbar extradural a
naesthesia who received 15 mi of 0.5% or 0.75% S(-)-bupivacaine, or 0.
5% RS-bupivacaine in a randomized, double-blind study. There was no di
fference in onset time, maximum spread of sensory block or intensity o
f motor block between the three groups. Duration of sensory block was
significantly longer for 0.75% S(-)-bupivacaine. We conclude that S(-)
-bupivacaine has similar local anaesthetic characteristics to RS-bupiv
acaine when used for extradural anaesthesia.