Levobupivacaine
4757087
183812672
2008-01-12T09:49:58Z
76.238.131.101
/* Clinical use */
{{Drugbox|
| image=Levobupivacaine.png
| IUPAC_name = (''S'')-1-butyl-''N''-(2,6-dimethylphenyl)<br />piperidine-2-carboxamide
| ATC_prefix=N01
| ATC_suffix=BB10
| PubChem=92253
| DrugBank=APRD00110
| CAS_number = 27262-47-1
| C = 18 | H = 28 | N = 2 | O = 1
| molecular_weight = 288.43 g/mol
| bioavailability = n/a
| metabolism = [[Liver|Hepatic]]
| elimination_half-life = 2–2.6 hours
| excretion = [[Kidney|Renal]] 70%, [[feces|faecal]] 24%
| pregnancy_AU = B3
| legal_AU = S4
| routes_of_administration = [[Parenteral]]
}}
'''Levobupivacaine''' ([[International Nonproprietary Name|rINN]]) ({{pronEng|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 percent less potent (by molarity) than racemic bupivacaine.
===Indications===
Levobupivacaine is indicated for local anaesthesia including infiltration, [[nerve block]], [[ophthalmic]], [[epidural]] and [[intrathecal]] anaesthesia in adults; and infiltration analgesia in children.
===Contraindications===
Levobupivacaine is contraindicated for IV regional anaesthesia (IVRA).
===Adverse effects===
[[Adverse drug reaction]]s (ADRs) are rare when it is administered correctly. Most ADRs relate to administration technique (resulting in systemic exposure) or pharmacological effects of anesthesia, however [[allergy|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, [[seizure]]s) followed by depression (drowsiness, loss of consciousness, [[respiratory depression]] and [[apnea]]). Cardiovascular effects include [[hypotension]], [[bradycardia]], [[arrhythmia]]s, and/or [[cardiac arrest]] – some of which may be due to [[Hypoxia (medical)|hypoxemia]] secondary to respiratory depression. (Rossi, 2006)
==References==
*Rossi S, editor. [[Australian Medicines Handbook]] 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3
{{Local anesthetics}}
[[Category:Local anesthetics]]
[[fr:Lévobupivacaïne]]