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Background: In comparison with bupivacaine, ropivacaine exhibits comparable anaesthetic effects but with less motor impairment and systemic toxicity. However, the analgesic potency may differ. For example, ropivacaine during obstetric epidural analgesia provides an approximately 40% lower analgesic potency than bupivacaine. Equal visual analogue pain scores require significantly higher dosages of ropivacaine, and general statements about a favourable benefit–risk profile relative to that of bupivacaine may therefore have limited clinical impact. We addressed this topic in a male pain model by evaluating the analgesic efficacy of epidural ropivacaine 0.2% vs. bupivacaine 0.125% after retropubic prostatectomy. Methods: Forty patients scheduled for retropubic prostatectomy were randomly assigned to two groups (20 patients per group). In a double-blind prospective design, patient-controlled lumbar epidural analgesia was provided by ropivacaine 0.2% in the ropivacaine group and by bupivacaine 0.125% in the bupivacaine group. The primary endpoint was the total amount of local anaesthetic consumption. The secondary endpoints were the numeric rating scale scores for rest and dynamic pain and the degree of motor impairment. Results: Ropivacaine consumption was 60% higher (mean ± standard deviation, 1372.5 ± 108.3 mg) than that of bupivacaine (852 ± 75.2 mg) (P < 0.001). There were no significant differences in the numeric rating scale scores and motor impairment. Conclusions: In male patients, lumbar epidural administration of ropivacaine 0.2% after retropubic prostatectomy does not appear to provide benefits over bupivacaine 0.125%. Moreover, in view of the significantly higher drug requirements, general statements focusing on the favourable therapeutic index of ropivacaine may require critical analysis, at least during epidural administration.