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{{Short description|Local anaesthetic drug}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Use dmy dates|date=March 2024}}
{{Drugbox
{{Infobox drug
| verifiedrevid = 460210699
| Verifiedfields = changed
| IUPAC_name = (''RS'')-1-butyl-''N''-(2,6-dimethylphenyl)<br />piperidine-2-carboxamide
| Watchedfields = changed
| verifiedrevid = 477374547
| image = Bupivacaine skeletal.svg | image = Bupivacaine skeletal.svg
| width =
| imagename = 1 : 1 mixture (racemate)
| alt =
| drug_name = Bupivacaine
| caption =
| image2 = Bupivacaine-from-xtal-3D-bs-17.png
| alt2 =


<!--Clinical data--> <!-- Clinical data -->
| pronounce = {{IPAc-en|b|juː|ˈ|p|ɪ|v|ə|k|eɪ|n}}
| tradename =
| tradename = Marcaine, Sensorcaine, Posimir, others
| Drugs.com = {{drugs.com|monograph|bupivacaine-hydrochloride}} | Drugs.com = {{drugs.com|monograph|bupivacaine-hydrochloride}}
| MedlinePlus =
| DailyMedID = Bupivacaine
| pregnancy_AU = A | pregnancy_AU = A
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Bupivacaine Use During Pregnancy | website=Drugs.com | date=13 April 2020 | url=https://www.drugs.com/pregnancy/bupivacaine.html | access-date=21 September 2020}}</ref>
| pregnancy_category=
| routes_of_administration = ], ], ]
| class =
| ATC_prefix = N01
| ATC_suffix = BB01
| ATC_supplemental =

<!-- Legal status -->
| legal_AU = S4 | legal_AU = S4
| legal_AU_comment =
| routes_of_administration = ], ]
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment =
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA_comment =
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_UK_comment =
| legal_US = Rx-only
| legal_US_comment = <ref>{{cite web | title=Marcaine- bupivacaine hydrochloride injection, solution Marcaine with epinephrine- bupivacaine hydrochloride and epinephrine bitartrate injection, solution | website=DailyMed | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=67578b56-7540-487e-1fba-481255620e78 | access-date=13 February 2021}}</ref><ref>{{cite web | title=Sensorcaine MPF- bupivacaine hydrochloride injection, solution | website=DailyMed | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e700eb7b-8b14-49c9-96b2-331f18776e45 | access-date=13 February 2021}}</ref>
| legal_EU = Rx-only
| legal_EU_comment =
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment =
| legal_status = <!-- For countries not listed above -->


<!--Pharmacokinetic data--> <!-- Pharmacokinetic data -->
| bioavailability = n/a | bioavailability = n/a
| protein_bound = 95%
| metabolism = ]
| metabolism = ]
| elimination_half-life = 3.5 hours (adults) <br />8.1 hours (neonates)
| metabolites =
| excretion = ], 4–10%
| onset = Within 15 min<ref name=AHFS2015/>
| elimination_half-life = 3.1 hours (adults)<ref name=AHFS2015/><br />8.1 hours (neonates)<ref name=AHFS2015/>
| duration_of_action= 2 to 8 hr<ref name=Wh1997/>
| excretion = ], 4–10%


<!--Identifiers--> <!-- Identifiers -->
| ATC_prefix = N01 | index2_label = HCl
| CAS_number = 38396-39-3
| ATC_suffix = BB01
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 2180-92-9
| CAS_number2_Ref = {{cascite|correct|CAS}}
| PubChem = 5282419
| CAS_number2 = 73360-54-0
| CAS_supplemental =
| PubChem = 2474
| PubChem2 = 5282419
| IUPHAR_ligand = 2397 | IUPHAR_ligand = 2397
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00297 | DrugBank = DB00297
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2380
| ChemSpiderID2 = 58277
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Y8335394RO | UNII = Y8335394RO
| UNII2 = 7TQO7W3VT8
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07552 | KEGG = D07552
| KEGG2 = D01450
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 3215
| ChEBI = 60789
| ChEBI2 = 31322
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1098 | ChEMBL = 1098
| CASNo = 38396-39-3 | ChEMBL2 = 1200396
| NIAID_ChemDB =
| CAS_number = 2180-92-9
| PubChem = 2474 | PDB_ligand =
| synonyms =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2380
<!-- Chemical and physical data -->
| SMILES = O=C(Nc1c(cccc1C)C)C2N(CCCC)CCCC2
| IUPAC_name = (''RS'')-1-Butyl-''N''-(2,6-dimethylphenyl)piperidine-2-carboxamide
| InChI = 1/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)
| C=18 | H=28 | N=2 | O=1
| InChIKey = LEBVLXFERQHONN-UHFFFAOYAJ
| SMILES = O=C(C1N(CCCC1)CCCC)NC2=C(C)C=CC=C2C
| StdInChI = 1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)
| StdInChIKey = LEBVLXFERQHONN-UHFFFAOYSA-N
| C=18 | H=28 | N=2 | O=1
| molecular_weight = 288.43 g/mol
| smiles = Cl.O=C(Nc1c(cccc1C)C)C2N(CCCC)CCCC2.O
| InChI = 1/C18H28N2O.ClH.H2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3;;/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21);1H;1H2
| InChIKey = HUCIWBPMHXGLFM-UHFFFAOYAK
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21) | StdInChI = 1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)
| StdInChI_comment =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LEBVLXFERQHONN-UHFFFAOYSA-N | StdInChIKey = LEBVLXFERQHONN-UHFFFAOYSA-N
| density =
| density_notes =
| melting_point = 107
| melting_high = 108
| melting_notes =
| boiling_point =
| boiling_notes =
| solubility =
| sol_units =
| specific_rotation =
}} }}

<!-- Definition and medical uses -->
'''Bupivacaine''', marketed under the brand name '''Marcaine''' among others, is a medication used to ].<ref name=AHFS2015>{{cite web|title=Bupivacaine Hydrochloride|url=https://www.drugs.com/monograph/bupivacaine-hydrochloride.html|publisher=The American Society of Health-System Pharmacists|access-date=1 August 2015|url-status=live|archive-url=https://web.archive.org/web/20150630101203/http://www.drugs.com/monograph/bupivacaine-hydrochloride.html|archive-date=30 June 2015}}</ref> In ]s, it is injected around a nerve that supplies the area, or into the ].<ref name=AHFS2015/> It is available mixed with a small amount of ] to increase the duration of its action.<ref name=AHFS2015/> It typically begins working within 15 minutes and lasts for 2 to 8 hours.<ref name=AHFS2015/><ref name=Wh1997>{{cite book| vauthors = Whimster DS |title=Cambridge textbook of accident and emergency medicine|date=1997|publisher=Cambridge University Press |location=Cambridge |isbn=9780521433792 |page=194 |url=https://books.google.com/books?id=m0bNaDhkaukC&pg=PA194 |url-status=live|archive-url= https://web.archive.org/web/20151005030600/https://books.google.ca/books?id=m0bNaDhkaukC&pg=PA194 |archive-date=5 October 2015}}</ref>

<!-- Side effects and mechanism -->
Possible side effects include sleepiness, muscle twitching, ], changes in vision, ], and an irregular heart rate.<ref name=AHFS2015/> Concerns exist that injecting it into a joint can cause problems with the ].<ref name=AHFS2015/> Concentrated bupivacaine is not recommended for epidural freezing.<ref name=AHFS2015/> Epidural freezing may also increase the length of ].<ref name=AHFS2015/> It is a ] of the ].<ref name=AHFS2015/>

<!-- History, society, and culture -->
Bupivacaine was discovered in 1957.<ref>{{cite book| vauthors = Egan TD |title=Pharmacology and physiology for anesthesia : foundations and clinical application|date=2013|publisher=Elsevier/Saunders|location=Philadelphia, PA|isbn=9781437716795|page=291|url=https://books.google.com/books?id=s8CXrbimviMC&pg=PT306|url-status=live|archive-url=https://web.archive.org/web/20160512191237/https://books.google.ca/books?id=s8CXrbimviMC&pg=PT306|archive-date=12 May 2016}}</ref> It is on the ].<ref name="WHO22nd">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}</ref> Bupivacaine is available as a ].<ref name=AHFS2015/><ref name=Ric2015>{{cite book| vauthors = Hamilton R |title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=9781284057560|page=22}}</ref> An ] of bupivacaine (Xaracoll) was approved for medical use in the United States in August 2020.<ref>{{cite web | title=Xaracoll: FDA-Approved Drugs | website=U.S. ] (FDA) | url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=209511 | access-date=2 September 2020}}</ref><ref name="FDA Xaracoll approval letter" /><ref name="Innocoll PR" />

==Medical uses==
Bupivacaine is ] for local infiltration, ], sympathetic nerve block, and ] and caudal blocks. It is sometimes used in combination with ] to prevent systemic absorption and extend the duration of action. The 0.75% (most concentrated) formulation is used in ].<ref>{{cite web|last=Lexicomp|title=Bupivacaine (Lexi-Drugs)|url=http://www.online.lexi.com|access-date=20 April 2014|url-status=dead|archive-url=https://web.archive.org/web/20140410053005/http://online.lexi.com/|archive-date=10 April 2014}}</ref> It is the most commonly used local anesthetic in epidural anesthesia during labor, as well as in postoperative pain management.<ref name="Miller">{{cite book| vauthors = Miller RD |title=Basics of Anesthesia|date=2 November 2006|publisher=Churchill Livingstone}}</ref> Liposomal formulations of bupivacaine (brand name EXPAREL) have not shown clinical benefit compared to plain bupivacaine when used in traditional perineural injections,<ref>{{cite journal | vauthors = Hussain N, Brull R, Sheehy B | title = Perineural Liposomal Bupivacaine Is Not Superior to Nonliposomal Bupivacaine for Peripheral Nerve Block Analgesia: A Systematic Review and Meta-analysis | journal = Anesthesiology | volume = 134 | issue = 2 | pages = 147–164 | date = February 2021 | pmid = 33372953 | doi = 10.1097/ALN.0000000000003651 | doi-access = free }}</ref> although some industry-funded studies have suggested benefits when used in local infiltration.<ref>{{cite journal | vauthors = Ma TT, Wang YH, Jiang YF, Peng CB, Yan C, Liu ZG, Xu WX | title = Liposomal bupivacaine versus traditional bupivacaine for pain control after total hip arthroplasty: A meta-analysis | journal = Medicine | volume = 96 | issue = 25 | pages = e7190 | date = June 2017 | pmid = 28640101 | pmc = 5484209 | doi = 10.1097/MD.0000000000007190 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Mont MA, Beaver WB, Dysart SH, Barrington JW, Del Gaizo DJ | title = Local Infiltration Analgesia With Liposomal Bupivacaine Improves Pain Scores and Reduces Opioid Use After Total Knee Arthroplasty: Results of a Randomized Controlled Trial | journal = The Journal of Arthroplasty | volume = 33 | issue = 1 | pages = 90–96 | date = January 2018 | pmid = 28802777 | pmc = | doi = 10.1016/j.arth.2017.07.024 | doi-access = free }}</ref>

The ] of bupivacaine with ] (brand name Xaracoll) is indicated for acute postsurgical ] (pain relief) for up to 24 hours in adults following ].<ref name="FDA Xaracoll approval letter">{{cite web | url=https://www.accessdata.fda.gov/drugsatfda_docs/appletter/2020/209511Orig1s000ltr.pdf | title=FDA approval letter | website=U.S. ] (FDA) | date=28 August 2020 | access-date=2 September 2020}} {{PD-notice}}</ref><ref name="Innocoll PR">{{cite press release | title=FDA Approves Xaracoll (bupivacaine HCl) Implant, a Non-opioid, Drug-device Treatment Option for Acute Postsurgical Pain Relief for up to 24 Hours Following Open Inguinal Hernia Repair in Adults | publisher=Innocoll Pharmaceuticals | via=PR Newswire | date=31 August 2020 | url=https://www.prnewswire.com/news-releases/fda-approves-xaracoll-bupivacaine-hcl-implant-a-non-opioid-drug-device-treatment-option-for-acute-postsurgical-pain-relief-for-up-to-24-hours-following-open-inguinal-hernia-repair-in-adults-301120771.html | access-date=2 September 2020}}</ref>

Bupivacaine (Posimir) is indicated in adults for administration into the subacromial space under direct arthroscopic visualization to produce post-surgical analgesia for up to 72 hours following arthroscopic subacromial decompression.<ref name="FDA Xaracoll approval letter" /><ref>{{cite press release | title=Durect Corporation Announces U.S. FDA Approval of Posimir For Post-Surgical Pain Reduction for up to 72 Hours Following Arthroscopic Subacromial Decompression | publisher=Durect Corporation | via=PR Newswire | date=2 February 2021 | url=https://www.prnewswire.com/news-releases/durect-corporation-announces-us-fda-approval-of-posimir-for-post-surgical-pain-reduction-for-up-to-72-hours-following-arthroscopic-subacromial-decompression-301220159.html | access-date=13 February 2021}}</ref>

==Contraindications==
Bupivacaine is contraindicated in patients with known hypersensitivity reactions to bupivacaine or amino-amide anesthetics. It is also contraindicated in obstetrical paracervical blocks and intravenous regional anaesthesia (]) because of potential risk of tourniquet failure and systemic absorption of the drug and subsequent ]. The 0.75% formulation is contraindicated in epidural anesthesia during labor because of the association with refractory cardiac arrest.<ref name="Lexicomp"/>

==Adverse effects==

Compared to other local anaesthetics, bupivacaine is markedly ].<ref>{{cite journal | vauthors = de La Coussaye JE, Eledjam JJ, Brugada J, Sassine A | title = | journal = Cahiers d'Anesthésiologie | volume = 41 | issue = 6 | pages = 589–598 | date = 1993 | pmid = 8287299 }}</ref> However, ]s are rare when it is administered correctly. Most reactions are caused by accelerated absorption from the injection site, unintentional intravascular injection, or slow metabolic degradation. However, ] reactions can rarely occur.<ref name="Lexicomp"/>

Clinically significant adverse events result from systemic absorption of bupivacaine and primarily involve the central nervous and cardiovascular systems. Effects on the central nervous system typically occur at lower ] concentrations. Initially, cortical inhibitory pathways are selectively inhibited, causing symptoms of neuronal excitation. At higher plasma concentrations, both inhibitory and excitatory pathways are inhibited, causing central nervous system depression and potentially coma. Higher plasma concentrations also lead to cardiovascular effects, though cardiovascular collapse may also occur with low concentrations.<ref>{{cite book|title=Australian Medicines Handbook|date=2006|publisher=Adelaide|isbn=978-0-9757919-2-9}}</ref> Adverse effects on the central nervous system may indicate impending cardiotoxicity and should be carefully monitored.<ref name=Lexicomp>{{cite web|title=Bupivacaine (Lexi-Drugs)|url=http://www.online.lexi.com|access-date=20 April 2014|url-status=dead|archive-url=https://web.archive.org/web/20140410053005/http://online.lexi.com/|archive-date=10 April 2014}}</ref>

* Central nervous system: circumoral numbness, facial tingling, ], ], restlessness, anxiety, dizziness, ], ]
* Cardiovascular: ], ], ], ], ]<ref name="Miller"/><ref name="Lexicomp"/>

Toxicity can also occur in the setting of subarachnoid injection during high spinal anesthesia. These effects include: ], ], ], ], ], and ]. Additionally, bupivacaine can cause ] after continuous infusion into a joint space.<ref name="Lexicomp"/>

Bupivacaine has caused several deaths when the epidural anaesthetic has been administered intravenously accidentally.<ref>{{cite web |url = http://www.abs-cbnnews.com/storypage.aspx?StoryId=104790 |work = ABS-CBN Interactive |title = Filipino nurse dies in UK due to wrong use of anaesthetic |date = 28 January 2014 |archive-url=https://archive.today/20070709212017/http://www.abs-cbnnews.com/storypage.aspx?StoryId=104790 |archive-date=9 July 2007 |url-status=dead}}</ref>

===Treatment of overdose===
{{further|Lipid rescue}}

Animal evidence<ref name="Weinberg 1998">{{cite journal | vauthors = Weinberg GL, VadeBoncouer T, Ramaraju GA, Garcia-Amaro MF, Cwik MJ | title = Pretreatment or resuscitation with a lipid infusion shifts the dose-response to bupivacaine-induced asystole in rats | journal = Anesthesiology | volume = 88 | issue = 4 | pages = 1071–1075 | date = April 1998 | pmid = 9579517 | doi = 10.1097/00000542-199804000-00028 | s2cid = 1661916 | doi-access = free }}</ref><ref name="Weinberg 2003">{{cite journal | vauthors = Weinberg G, Ripper R, Feinstein DL, Hoffman W | title = Lipid emulsion infusion rescues dogs from bupivacaine-induced cardiac toxicity | journal = Regional Anesthesia and Pain Medicine | volume = 28 | issue = 3 | pages = 198–202 | year = 2003 | pmid = 12772136 | doi = 10.1053/rapm.2003.50041 | s2cid = 6247454 }}</ref> indicates ], 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">{{cite journal | vauthors = Rosenblatt MA, Abel M, Fischer GW, Itzkovich CJ, Eisenkraft JB | title = Successful use of a 20% lipid emulsion to resuscitate a patient after a presumed bupivacaine-related cardiac arrest | journal = Anesthesiology | volume = 105 | issue = 1 | pages = 217–218 | date = July 2006 | pmid = 16810015 | doi = 10.1097/00000542-200607000-00033 | s2cid = 40214528 | doi-access = free }}</ref><ref name="Litz2006">{{cite journal | vauthors = Litz RJ, Popp M, Stehr SN, Koch T | title = Successful resuscitation of a patient with ropivacaine-induced asystole after axillary plexus block using lipid infusion | journal = Anaesthesia | volume = 61 | issue = 8 | pages = 800–801 | date = August 2006 | pmid = 16867094 | doi = 10.1111/j.1365-2044.2006.04740.x | s2cid = 43125067 }}</ref> Plans to publicize this treatment more widely have been published.<ref name="Picard2006">{{cite journal | vauthors = Picard J, Meek T | title = Lipid emulsion to treat overdose of local anaesthetic: the gift of the glob | journal = Anaesthesia | volume = 61 | issue = 2 | pages = 107–109 | date = February 2006 | pmid = 16430560 | doi = 10.1111/j.1365-2044.2005.04494.x | s2cid = 29843241 }}</ref>

===Pregnancy and lactation===
Bupivacaine crosses the placenta and is a pregnancy category C drug. However, it is approved for use at term in obstetrical anesthesia. Bupivacaine is excreted in breast milk. Risks of stopping breast feeding versus stopping bupivacaine should be discussed with the patient.<ref name="Lexicomp"/>

===Postarthroscopic glenohumeral chondrolysis===
Bupivacaine is toxic to ] and its ] may lead to ].<ref name="pmid27047224">{{cite journal | vauthors = Gulihar A, Robati S, Twaij H, Salih A, Taylor GJ | title = Articular cartilage and local anaesthetic: A systematic review of the current literature | journal = Journal of Orthopaedics | volume = 12 | issue = Suppl 2 | pages = S200–S210 | date = December 2015 | pmid = 27047224 | pmc = 4796530 | doi = 10.1016/j.jor.2015.10.005 }}</ref>

==Pharmacology==
===Pharmacodynamics===
Bupivacaine binds to the intracellular portion of voltage-gated ] and blocks sodium influx into ], which prevents ]. Without depolarization, no initiation or conduction of a pain signal can occur.

===Pharmacokinetics===
The rate of systemic absorption of bupivacaine and other local anesthetics is dependent upon the dose and concentration of drug administered, the route of administration, the vascularity of the administration site, and the presence or absence of epinephrine in the preparation.<ref name="Package Insert">{{cite web|title=bupivacaine hydrochloride (Bupivacaine Hydrochloride) injection, solution|url=http://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=1828|publisher=FDA|access-date=20 April 2014|url-status=live|archive-url=https://web.archive.org/web/20140421052148/http://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=1828|archive-date=21 April 2014}}</ref>
* Onset of action (route and dose-dependent): 1–17 min
* Duration of action (route and dose-dependent): 2–9 hr
* Half life: neonates, 8.1 hr, adults: 2.7 hr
* Time to peak plasma concentration (for peripheral, epidural, or caudal block): 30–45 min
* Protein binding: about 95%
* Metabolism: hepatic
* Excretion: renal (6% unchanged)<ref name="Lexicomp"/>

==Chemical structure==
Like ], bupivacaine is an amino-amide anesthetic; the aromatic head and the hydrocarbon chain are linked by an ] rather than an ester as in earlier local anesthetics. As a result, the amino-amide anesthetics are more stable and less likely to cause allergic reactions. Unlike lidocaine, the terminal amino portion of bupivacaine (as well as ], ropivacaine, and levobupivacaine) is contained within a ] ring; these agents are known as pipecholyl xylidines.<ref name="Miller"/>

== Society and culture ==
=== Legal status ===
On 17 September 2020, the ] (CHMP) of the ] (EMA) adopted a positive opinion, recommending the granting of a marketing authorization for the medicinal product Exparel, intended for the treatment of post-operative pain.<ref name="Exparel: Pending EC decision">{{cite web | title=Exparel: Pending EC decision | website=] (EMA) | date=17 September 2020 | url=https://www.ema.europa.eu/en/medicines/human/summaries-opinion/exparel | access-date=21 September 2020 | archive-date=23 September 2020 | archive-url=https://web.archive.org/web/20200923011055/https://www.ema.europa.eu/en/medicines/human/summaries-opinion/exparel | url-status=dead }} Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.</ref> The applicant for this medicinal product is Pacira Ireland Limited.<ref name="Exparel: Pending EC decision" /> Exparel liposomal was approved for medical use in the European Union in November 2020.<ref name="Exparel liposomal EPAR">{{cite web | title=Exparel liposomal EPAR | website=] (EMA) | date=15 September 2020 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/exparel-liposomal | access-date=11 December 2020}}</ref>

=== Economics ===
Bupivacaine is available as a ].<ref name=AHFS2015/><ref name=Ric2015/>

==Research==
] is the (''S'')-(–)-] of bupivacaine, with a longer duration of action, producing less vasodilation. Durect Corporation is developing a biodegradable, controlled-release drug delivery system for after surgery. As of 2010, it has completed a phase-III clinical trial.<ref>{{cite web | title=Bupivacaine Effectiveness and Safety in SABER Trial (BESST) | website=ClinicalTrials.gov | date=20 January 2010 | url=https://clinicaltrials.gov/ct2/show/NCT01052012 | access-date=1 March 2012 | url-status=live | archive-url=https://web.archive.org/web/20111227221026/http://clinicaltrials.gov/ct2/show/NCT01052012 | archive-date=27 December 2011 }}</ref>

== See also ==
* ]

== References ==
{{Reflist}}

{{Local anesthetics}}
{{Portal bar|Medicine}}

]
]
]
]
]
]
]