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]]