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Levobupivacaine hydrochloride

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Levobupivacaine hydrochloride Basic information
Levobupivacaine hydrochloride Chemical Properties
  • Melting point:254 °C (dec.)(lit.)
  • alpha -12.5 º (c=2, water)
  • storage temp. 2-8°C
  • solubility H2O: soluble20mg/mL, clear
  • form powder
  • color white to beige
  • optical activity[α]/D -10 to -14°, c = 1.0 in H2O
  • InChIKeySIEYLFHKZGLBNX-NTISSMGPSA-N
  • CAS DataBase Reference27262-48-2(CAS DataBase Reference)
Safety Information
MSDS
Levobupivacaine hydrochloride Usage And Synthesis
  • DescriptionLevobupivacaine 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.
  • Chemical Propertieswhite crystalline powder
  • OriginatorChiroscience (UK)
  • UsesLocal anesthetic; analgesic.
  • DefinitionChEBI: The monohydrochloride salt of levobupivacaine.
  • brand nameChirocaine (Purdue).
  • Biological FunctionsLevobupivacaine hydrochloride (Chirocaine) is the S-enantiomer of bupivacaine. It too has long action. Animal studies show that it has less CNS and cardiac toxicity than does bupivacaine. It also is slightly more motor sparing than is bupivacaine.
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