Levobupivacaine was first launched in the US for the production of local anesthesia for surgery and obstetrics and for post-operative pain management. It is the (S)-enantiomer of the long acting, highly potent local anesthetic bupivacaine (Marcaine) that can be prepared by a three step sequence from (S)-pipecolic acid or from (S)-lysine by oxidative deamination and stereospecific ring closure to (S)-pipecolamide core structure. Levobupivacaine exhibits its long-acting local anesthetic effect by blocking neuronal sodium channel ion flow in nerve axons. Clinical studies demonstrated an efficacy and a general profile closely resembling those of the racemic bupivacaine currently in use; however, it produced an enhanced safety profile, in particular substantially reduced (about one-third) cardiotoxicity (less effect on myocardial contractility and QT, prolongation) and CNS depressive side effects. Onset and duration of blockade were also equivalent or even better.

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