Bupivacaine has a chiral centre and is currently available as a racemic mixture of its two enantiomers: R(+)-bupivacaine and S(-)-bupivacaine. Preclinical studies have demonstrated that there is enantiomer selectivity of action with the bulk of central nervous system and cardiovascular toxicity residing with the R(+) isomer. The aim of this study was to compare the clinical efficacy and safety of S(-)-bupivacaine with racemic RS-bupivacaine for extradural anaesthesia. We studied 88 patients undergoing elective lower limb surgery under lumbar extradural anaesthesia who received 15 ml of 0.5% or 0.75% S(-)-bupivacaine, or 0.5% RS-bupivacaine in a randomized, double-blind study. There was no difference in onset time, maximum spread of sensory block or intensity of 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-bupivacaine when used for extradural anaesthesia.
We have compared the efficacy of 0.25% S(-)-bupivacaine with 0.25% RS-bupivacaine in providing epidural analgesia for labour in a randomized, multicentre, double-blind study. Analgesia was initiated with 10 ml of the study solution and maintained with 10-ml top-ups. We studied 137 women and treatments were found to be equivalent for onset, duration and quality of block. Median onset of pain relief was 12 min for both drugs and median duration was 49 (range 3-129) min and 51 (7-157) min for S(-)-bupivacaine and RS bupivacaine, respectively. The estimated treatment difference for duration of pain relief was -4 (90% CI -13, 6) min. Thirty patients failed to achieve pain relief after the first injection (20 patients after S(-)-bupivacaine and 10 after RS-bupivacaine; P = 0.039). However, median duration of pain relief from the first top-up was 82 (range 3-164) min for S(-)-bupivacaine and 76 (22-221) min for RS-bupivacaine. There were no significant differences in the quality of analgesia, as assessed by the investigators. There were no significant differences in the extent of sensory block, percentage of patients with motor block or incidence of adverse events.
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