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Systematic (IUPAC) name
CAS number 27262-47-1
ATC code N01BB10
PubChem 92253
DrugBank APRD00110
Chemical data
Formula C18H28N2O 
Mol. mass 288.43 g/mol
Pharmacokinetic data
Bioavailability n/a
Metabolism Hepatic
Half life 2–2.6 hours
Excretion Renal 70%, faecal 24%
Therapeutic considerations
Pregnancy cat.


Legal status

Prescription Only (S4)(AU)

Routes Parenteral

Levobupivacaine (rINN) (pronounced /liːvoʊbjuːˈpɪvəkeɪn/) is a local anaesthetic drug belonging to the amino amide group. It is the S-enantiomer of bupivacaine. Levobupivacaine hydrochloride is commonly marketed by AstraZeneca under the trade name Chirocaine.


Clinical use

Compared to bupivacaine, levobupivacaine is associated with less vasodilation and has a longer duration of action. It is approximately 13 per cent less potent (by molarity) than racemic bupivacaine.


Levobupivacaine is indicated for local anaesthesia including infiltration, nerve block, ophthalmic, epidural and intrathecal anaesthesia in adults; and infiltration analgesia in children.


Levobupivacaine is contraindicated for IV regional anaesthesia (IVRA).

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. (Rossi, 2006)


This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Levobupivacaine". A list of authors is available in Wikipedia.
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