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Bupivacaine (Molecule of the Month for August 2015)

Marcain, Marcaine, Sensorcaine

Bupivacaine is a local anaesthetic drug belonging to the amino amide group. Bupivacaine is used for local anaesthesia including infiltration, nerve block, epidural, and intrathecal anaesthesia. Bupivacaine often is administered by epidural injection before total hip arthroplasty.

Compared to other local anaesthetics, bupivacaine is markedly cardiotoxic. However, adverse drug reactions are rare when it is administered correctly. Most problems relate to administration technique (resulting in systemic exposure) or pharmacological effects of anesthesia, though allergic reactions can sometimes 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.

Formal Chemical Name (IUPAC)



Picture of Bupivacaine 3D model

click on the picture of  Bupivacaine above to interact
with the 3D model of the
Bupivacaine structure
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Picture of Bupivacaine

C18 H28 N2 O

Update by Karl Harrison
(Molecule of the Month for August 2015 )

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