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Levobupivacaine and ropivacaine are 2 left enantiomeric molecules frequently used for peripheral nerve blocks because of their safe clinical profile. Levobupivacaine is more lipophilic and theoretically more potent than ropivacaine, but clinical studies show conflicting results in terms of anesthetic and analgesic characteristics. We hypothesized that the pure S-enantiomer of bupivacaine provides longer-lasting analgesia than ropivacaine.We compared the analgesic characteristics of 20 mL levobupivacaine versus 20 mL ropivacaine 0.5% in a posterior sciatic nerve block (Labat approach) for foot and ankle surgery. In a double-blind, randomized, prospective design, 80 patients received either substance. We assessed the onset, duration, and success of the block, and the need for rescue analgesia and technical or neurologic complications over 24 hours.The onset of sensory block (minutes) and the success rate were similar in levobupivacaine and ropivacaine groups (onset, 15 minutes [5–40 minutes] vs 15 minutes [5–60 minutes], respectively; success rate, 90% vs 92.5%). The average time for the first request of pain medication provided by 20 mL levobupivacaine 0.5% was significantly longer than with ropivacaine (1605 minutes [575–2400 minutes] vs 1035 minutes [590–1500 minutes], P < 0.001). The need for postoperative rescue analgesia was higher in the ropivacaine group (37 of 40 [92.5%] vs 30 of 40 [75%], P < 0.034). No complications were noted in either group at 24 hours.Twenty milliliters levobupivacaine 0.5% in posterior gluteal (Labat) sciatic nerve block provided longer-lasting analgesia after foot and ankle surgery compared with the same dose of ropivacaine.