Levobupivacaine hydrochloride Basic Info.
Synonyms: TIMTEC-BB SBB001337;(S)-(-)-BUPIVACAINE HCL;(S)-(-)-BUPIVACAINE HYDROCHLORIDE;(S)-(-)-1-N-BUTYL-2',6'-DIMETHYL-2-PIPERIDINCARBOXANILID HYDROCHLORIDE;(S)-(-)-1-BUTYL-2-(2,6-XYLYLCARBAMOYL)-PIPERIDINE HYDROCHLORIDE;s-(-)-1-butyl-2',6'-pipecoloxylidide hydrochloride;(s)-1-butyl-2',6'-piperidinecarboxamidemonohydrochloride;(s)-1-butyl-n-(2,6-dimethylphenyl)-2-piperidinecarboxamidemonohydrochloride
CAS: 27262-48-2
MF: C18H29ClN2O
MW: 324.89
Chemical Properties:white crystalline powder
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Levobupivacaine is a local anaesthetic drug belonging to the amino amide group. It is the S-enantiomer of bupivacaine. Levobupivacaine hydrochloride is commonly marketed by Abbott under the trade name Chirocaine. Bupivacaine is an amide-type local anaesthetic. Although it blocks neuro transmission, its membrane stabilising action also affects the myocardium. This can cause fatal cardiotoxicity. As bupivacaine is widely used in surgery and obstetrics, attempts have been made to develop a safer long-acting local anaesthetic.
The hydrochloride salt of levobupivacaine, an amide derivative with anesthetic property. Levobupivacaine reversibly binds voltage-gated sodium channels to modulate ionic flux and prevent the initiation and transmission of nerve impulses (stabilizing neuronal membrane), thereby resulting in analgesia and anesthesia. In comparison with racemic bupivacaine, levobupivacaine is associated with less vasodilation and has a longer duration of action.
Levobupivacaine Hydrochloride use
Compared to bupivacaine, levobupivacaine is associated with less vasodilation and has a longer duration of action. It is approximately 13 percent less potent (by molarity) than racemic bupivacaine and has a longer motor block onset time.
Levobupivacaine Hydrochloride Indications
Levobupivacaine is indicated for local anaesthesia including infiltration, nerve block, ophthalmic, epidural and intrathecal anaesthesia in adults; and infiltration analgesia in children.
Levobupivacaine Hydrochloride Contraindications
Levobupivacaine is contraindicated for IV regional anaesthesia (IVRA).
Levobupivacaine Hydrochloride Adverse effects
Adverse drug reactions (ADRs) are rare when it is administered correctly. Most ADRs relate to administration technique (resulting in systemic exposure) or pharmacological effects of anesthesia, however allergic reactions can rarely occur.
Systemic exposure to excessive quantities of bupivacaine mainly result in central nervous system (CNS) and cardiovascular effects - CNS effects usually occur at lower blood plasma concentrations and additional cardiovascular effects present at higher concentrations, though cardiovascular collapse may also occur with low concentrations. CNS effects may include CNS excitation (nervousness, tingling around the mouth, tinnitus, tremor, dizziness, blurred vision, seizures) followed by depression (drowsiness, loss of consciousness, respiratory depression and apnea). Cardiovascular effects include hypotension, bradycardia, arrhythmias, and/or cardiac arrest - some of which may be due to hypoxemia secondary to respiratory depression.
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