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| {{Drugbox|
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| | image = Bupivacaine.svg
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| | IUPAC_name = 1-butyl-''N''-(2,6-dimethylphenyl)<br />piperidine-2-carboxamide
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| | ATC_prefix=N01
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| | ATC_suffix=BB01
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| | PubChem=2474
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| | DrugBank=APRD00247
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| | CAS_number = 36637-18-0
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| | C = 18 | H = 28 | N = 2 | O = 1
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| | molecular_weight = 288.43 g/mol
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| | bioavailability = n/a
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| | metabolism = [[hepatic]]
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| | elimination_half-life = 3.5 hours (adults) <br /> 8.1 hours (neonates)
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| | excretion = [[Kidney|Renal]], 4–10%
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| | pregnancy_AU = A
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| | legal_AU = S4
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| | routes_of_administration = [[parenteral]], [[topical]]
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| }}
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| '''Bupivacaine''' ([[International Nonproprietary Name|rINN]]) ({{pronEng|bjuːˈpɪvəkeɪn}}) is a [[local anaesthetic]] drug belonging to the [[amino]] [[amide]] group. [[AstraZeneca]] commonly markets it under various [[trade name]]s, including '''Marcain''', '''Marcaine''','''Sensorcaine''' and '''Vivacaine'''.
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| ==Indications==
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| Bupivacaine is indicated for local anaesthesia including infiltration, [[nerve block]], [[epidural]], and [[intrathecal]] anaesthesia. Bupivacaine often is administered by epidural injection before total hip [[arthroplasty]]. It also is commonly injected to surgical wound sites to reduce pain for up to 20 hours after the surgery. Sometimes, bupivacaine is co-administered with [[adrenaline]] to prolong the duration of its action, [[fentanyl]] for epidural [[analgesia]], or [[glucose]].
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| ==Contraindications==
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| Bupivacaine is contraindicated for IV regional anaesthesia (IVRA) because of potential risk of tourniquet failure and systemic absorption of the drug.
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| ==Adverse effects==
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| Compared to other local anaesthetics, bupivacaine is markedly [[cardiotoxic]]. However, [[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.
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| 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.<ref name="AMH2006">Rossi S, editor. [[Australian Medicines Handbook]] 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3</ref>
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| Bupivacaine has caused several deaths when the [[epidural]] anaesthetic has been administered intravenously accidentally.<ref>[http://www.abs-cbnnews.com/storypage.aspx?StoryId=104790 ABS-CBN Interactive: Filipino nurse dies in UK due to wrong use of anaesthetic]</ref>
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| ===Treatment of overdose: lipid rescue===
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| {{further|[[Lipid rescue]]}}
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| There is animal evidence<ref name="Weinberg 1998">Weinberg GL, VadeBoncouer T, Ramaraju GA, Garcia-Amaro MF, Cwik MJ. Pretreatment or resuscitation with a lipid infusion shifts the dose-response to bupivacaine-induced asystole in rats. Anesthesiology 1998; 88: 1071-5.</ref><ref name="Weinberg 2003">Weinberg G, Ripper R, Feinstein DL, Hoffman W. Lipid emulsion infusion rescues dogs from bupivacaine-induced cardiac toxicity. Regional Anesthesia and Pain Medicine 2003; 28: 198-202..</ref> that [[Intralipid]], a commonly available intravenous lipid emulsion, can be effective in treating severe cardiotoxicity secondary to local anaesthetic overdose, and human case reports of successful use in this way.<ref name="Rosenblatt2006">Rosenblatt MA, Abel M, Fischer GW, Itzkovich CJ, Eisenkraft JB. Successful Use of a 20% lipid emulsion to resuscitate a patient after a presumed bupivacaine-related cardiac arrest. Anesthesiology 2006;105:217-8. PMID 16810015</ref><ref name="Litz2006">Litz, RJ, Popp M, Stehr S N, Koch T. Successful resuscitation of a patient with ropivacaine-induced asystole after axillary plexus block using lipid infusion. Anaesthesia 2006;61:800-1.</ref> Schemes to publicise this use more widely have been published.<ref name="Picard2006">Picard J, Meek T. Lipid emulsion to treat overdose of local anaesthetic: the gift of the glob. Anaesthesia 2006;61:107-9. PMID 16430560</ref>
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| ==Mechanism of action==
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| Bupivacaine binds to the intracellular portion of [[sodium channels]] and blocks sodium influx into [[neuron|nerve cells]], which prevents
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| [[depolarization]]. Since [[nociceptor| pain transmitting nerve fibres]] tend to be thinner
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| and either unmyelinated or lightly myelinated, the agent can diffuse more readily into them than into thicker and more heavily [[myelin]]ated nerve fibres like touch, proprioception, etc. (Myelin is [[non-polar]] / [[lipophilic]]).
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| ==Developments==
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| [[Levobupivacaine]] is the ''S''(-)-[[enantiomer]] of bupivacaine, with a longer duration of action and produces less vasodilation. Durect Corporation is developing a biodegradable controlled-release drug delivery system for post surgery. It is currently in Phase II.{{Fact|date=October 2007}}
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| ==References==
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| {{Reflist}}
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| == External links ==
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| *[http://www.rxlist.com/cgi/generic2/bupivacaine.htm RxList.com]
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| *[http://www.drugs.com/pdr/bupivacaine_hydrochloride.html Drugs.com]
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| *[http://www.lipidrescue.org More on lipid rescue]
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| {{Local anesthetics}}
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| [[Category:Local anesthetics]]
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| [[de:Bupivacain]]
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| [[fr:Bupivacaïne]]
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| [[hu:Bupivakain]]
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