Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Lidocaine: Difference between pages

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{{Short description|Local anesthetic}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid [{{fullurl:Lidocaine|oldid=464290800}} 464290800] of page [[Lidocaine]] with values updated to verified values.}}
{{Use dmy dates|date=January 2024}}
{{Drugbox| Verifiedfields = changed
{{cs1 config |name-list-style=vanc |display-authors=6}}
| verifiedrevid = 417820511
{{Infobox drug
| IUPAC_name = 2-(diethylamino)-<br />''N''-(2,6-dimethylphenyl)acetamide
| verifiedrevid = 464370713
| image = Lidocaine.svg
| Watchedfields = changed
| width = 200px
| image2 = Lidocaine-from-xtal-3D-balls.png
| image = Lidocaine.svg
| width = 200
| width2 = 200px
| alt =
| caption =
| image2 = Lidocaine-from-xtal-3D-balls.png
| width2 = 200
| alt2 =


<!--Clinical data-->
<!-- Clinical data -->
| pronounce = Lidocaine {{IPAc-en|ˈ|l|aɪ|d|ə|ˌ|k|eɪ|n}}<ref>{{MerriamWebsterDictionary|Lidocaine}}</ref><ref>{{Dictionary.com|Lidocaine}}</ref><br />Lignocaine {{IPAc-en|ˈ|l|ɪ|ɡ|n|ə|ˌ|k|eɪ|n}}
| tradename = Xylocaine
| tradename = Xylocaine, Ztlido, others
| Drugs.com = {{drugs.com|CONS|lidocaine}}
| Drugs.com = Local {{drugs.com|monograph|lidocaine-hydrochloride-local-anesthetic}}
| pregnancy_AU = A
Systemic {{drugs.com|monograph|lidocaine-systemic}}
| pregnancy_US = B
Ophthalmic {{drugs.com|ppa|lidocaine-ophthalmic}}
| legal_AU = S4
| MedlinePlus = a682701
| legal_US = Rx Only (U.S.) (excluding 1%)
| DailyMedID = Lidocaine
| routes_of_administration = [[Intravenous therapy|IV]], [[subcutaneous]], [[topical]]
| pregnancy_AU = A
| pregnancy_AU_comment =
| pregnancy_category =
| routes_of_administration = [[Intravenous therapy|Intravenous]], [[Subcutaneous injection|subcutaneous]], [[Topical medication|topical]], [[oral administration|by mouth]]
| class =
| ATCvet =
| ATC_prefix = C01
| ATC_suffix = BB01
| ATC_supplemental = {{ATC|C05|AD01}} {{ATC|D04|AB01}} {{ATC|N01|BB02}} {{ATC|N01|BB52}} {{ATC|R02|AD02}} {{ATC|S01|HA07}} {{ATC|S02|DA01}} {{ATCvet|C01|BB01}} {{ATCvet|C05|AD01}} {{ATCvet|D04|AB01}} {{ATCvet|N01|BB02}} {{ATCvet|N01|BB52}} {{ATCvet|R02|AD02}} {{ATCvet|S01|HA07}} {{ATCvet|S02|DA01}} {{ATCvet|D04|AB51}}


<!--Pharmacokinetic data-->
<!-- Legal status -->
| legal_AU = S5, S4, and S2
| bioavailability = 35% (oral) <br /> 3% (topical)
| legal_AU_comment = <ref>{{cite web | title=Poisons Standard February 2021 | website=Federal Register of Legislation | date=1 January 2021 | url=https://www.legislation.gov.au/Details/F2021C00098 | access-date=11 April 2021}}</ref>
| metabolism = [[Liver|Hepatic]], 90% [[CYP1A2]]-mediated
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| elimination_half-life = 1.5–2 hours
| legal_BR_comment =
| excretion = [[renal]]
| 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, and POM
| legal_UK_comment = <ref>{{cite web | title=Lidocaine Hydrochloride Injection BP 1% w/v - Summary of Product Characteristics (SmPC) | website=(emc) | date=29 June 2020 | url=https://www.medicines.org.uk/emc/product/6277/smpc | access-date=11 April 2021}}</ref>
| legal_US = Rx-only
| legal_US_comment = <ref>{{cite web | title=Xylocaine MPF- lidocaine hydrochloride injection, solution Xylocaine- lidocaine hydrochloride injection, solution Xylocaine- lidocaine hydrochloride,epinephrine bitartrate injection, solution | website=DailyMed | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4dd52202-8eef-4136-92dd-ada573b7cf74 | access-date=11 April 2021}}</ref><ref>{{cite web | title=Ztlido- lidocaine patch | website=DailyMed | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a1b17507-4560-490d-a388-74e7fd7eaa5e | access-date=11 April 2021}}</ref>
| legal_EU =
| 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 -->


<!--Identifiers-->
<!-- Pharmacokinetic data -->
| bioavailability = 35% (by mouth)<br />3% (topical)
| CASNo_Ref = {{cascite|correct|CAS}}
| protein_bound =
| CAS_number_Ref = {{cascite|correct|??}}
| metabolism = [[Liver]],<ref name=AHFS2015A/> 90% [[CYP3A4]]-mediated
| CAS_number = 137-58-6
| metabolites =
| CAS_supplemental = <br/>{{CAS|73-78-9}} (hydrochloride)
| onset = Within 1.5 min (IV)<ref name=AHFS2015A/>
| ATC_prefix = N01
| elimination_half-life = 1.5&nbsp;h to 2&nbsp;h
| ATC_suffix = BB02
| duration_of_action = 10&nbsp;min to 20&nbsp;min (IV),<ref name=AHFS2015A/> 0.5&nbsp;h to 3&nbsp;h (local)<ref name=AHFS2015L/><ref name=Wh1997/>
| ATC_supplemental = {{ATC|C01|BB01}} {{ATC|D04|AB01}} {{ATC|S02|DA01}} {{ATC|C05|AD01}}
| excretion = [[Kidney]]<ref name=AHFS2015A/>
| PubChem = 3676
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB00281
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3548
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 98PI200987
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00358
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 6456
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 79


<!--Chemical data-->
<!-- Identifiers -->
| C=14 | H=22 | N=2 | O=1
| index2_label = as HCl
| CAS_number = 137-58-6
| molecular_weight = 234.34 g/mol
| CAS_number_Ref = {{cascite|correct|??}}
| smiles = O=C(Nc1c(cccc1C)C)CN(CC)CC
| CAS_number2 = 73-78-9
| InChI = 1/C14H22N2O/c1-5-16(6-2)10-13(17)15-14-11(3)8-7-9-12(14)4/h7-9H,5-6,10H2,1-4H3,(H,15,17)
| CAS_supplemental =
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| PubChem = 3676
| StdInChI = 1S/C14H22N2O/c1-5-16(6-2)10-13(17)15-14-11(3)8-7-9-12(14)4/h7-9H,5-6,10H2,1-4H3,(H,15,17)
| PubChem2 = 6314
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| IUPHAR_ligand = 2623
| StdInChIKey = NNJVILVZKWQKPM-UHFFFAOYSA-N
| DrugBank = DB00281
| synonyms = ''N''-(2,6-dimethylphenyl)-''N''<sup>2</sup>,''N''<sup>2</sup>-diethylglycinamide
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| melting_point = 68
| DrugBank2 = DBSALT001508
| ChemSpiderID = 3548
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID2 = 6075
| UNII = 98PI200987
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII2 = EC2CNF7XFP
| KEGG = D00358
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG2_Ref = {{keggcite|correct|kegg}}
| KEGG2 = D02086
| ChEBI = 6456
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI2 = 50512
| ChEMBL = 79
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL2 = 541521
| NIAID_ChemDB =
| PDB_ligand = LQZ
| synonyms = lignocaine

<!-- Chemical and physical data -->
| IUPAC_name = 2-(diethylamino)-<br />''N''-(2,6-dimethylphenyl)acetamide
| C = 14
| H = 22
| N = 2
| O = 1
| SMILES = Cc1cccc(C)c1NC(=O)CN(CC)CC
| StdInChI = 1S/C14H22N2O/c1-5-16(6-2)10-13(17)15-14-11(3)8-7-9-12(14)4/h7-9H,5-6,10H2,1-4H3,(H,15,17)
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_comment =
| StdInChIKey = NNJVILVZKWQKPM-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| density =
| density_notes =
| melting_point = 68
| melting_high =
| melting_notes =
| boiling_point =
| boiling_notes =
| solubility =
| sol_units =
| specific_rotation =
}}
}}

<!-- Definition and medical uses -->
'''Lidocaine''', also known as '''lignocaine''' and sold under the brand name '''Xylocaine''' among others, is a [[local anesthetic]] of the [[amino]] [[amide]] type. It is also used to treat [[ventricular tachycardia]].<ref name=AHFS2015A>{{cite web|title=Lidocaine Hydrochloride (Antiarrhythmic)|url=https://www.drugs.com/monograph/lidocaine-hydrochloride-antiarrhythmic.html|publisher=The American Society of Health-System Pharmacists|access-date=26 August 2015|url-status=live|archive-url=https://web.archive.org/web/20150810232359/http://www.drugs.com/monograph/lidocaine-hydrochloride-antiarrhythmic.html|archive-date=10 August 2015}}</ref><ref name="AHFS2015L">{{cite web|title=Lidocaine Hydrochloride (Local)|url=https://www.drugs.com/monograph/lidocaine-hydrochloride-local.html|url-status=live|archive-url=https://web.archive.org/web/20150906023837/http://www.drugs.com/monograph/lidocaine-hydrochloride-local.html|archive-date=6 September 2015|access-date=26 August 2015|publisher=The American Society of Health-System Pharmacists}}</ref> When used for local anaesthesia or in nerve blocks, lidocaine typically begins working within several minutes and lasts for half an hour to three hours.<ref name="AHFS2015L" /><ref name="Wh1997">{{cite book | vauthors = Nolan JP, Baskett PJ |year=1997 |chapter=Analgesia and anaesthesia |editor=David Skinner |editor2=Andrew Swain |editor3=Rodney Peyton |editor4=Colin Robertson |others=Project co-ordinator, Fiona Whinster |title=Cambridge Textbook of Accident and Emergency Medicine |publisher=Cambridge University Press |location=Cambridge, UK |isbn=9780521433792 |page=194 |chapter-url=https://books.google.com/books?id=m0bNaDhkaukC&pg=PA194 |url-status=live |archive-url=https://web.archive.org/web/20170908150741/https://books.google.com/books?id=m0bNaDhkaukC&pg=PA194 |archive-date=8 September 2017 }}</ref> Lidocaine mixtures may also be applied directly to the skin or [[mucous membranes]] to numb the area.<ref name="AHFS2015L" /> It is often used mixed with a small amount of [[adrenaline]] (epinephrine) to prolong its local effects and to decrease bleeding.<ref name=AHFS2015L/>

<!-- Side effects and mechanism -->
If injected intravenously, it may cause cerebral effects such as confusion, changes in vision, numbness, tingling, and vomiting.<ref name=AHFS2015A/> It can cause [[hypotension|low blood pressure]] and an irregular heart rate.<ref name=AHFS2015A/> There are concerns that injecting it into a joint can cause problems with the [[cartilage]].<ref name=AHFS2015L/> It appears to be generally safe for use in [[pregnancy]].<ref name=AHFS2015A/> A lower dose may be required in those with liver problems.<ref name=AHFS2015A/> It is generally safe to use in those allergic to [[tetracaine]] or [[benzocaine]].<ref name=AHFS2015L/> Lidocaine is an [[Antiarrhythmic agent|antiarrhythmic medication]] of the class Ib type.<ref name=AHFS2015A/> This means it works by [[Sodium channel blocker|blocking sodium channels]] and thus decreasing the rate of contractions of the heart.<ref name=AHFS2015A/> When injected near nerves, the nerves cannot conduct signals to or from [[Local anesthetic nerve block|the brain]].<ref name=AHFS2015L/>

<!-- History, society and culture -->
Lidocaine was discovered in 1946 and went on sale in 1948.<ref>{{cite book | vauthors = Scriabine A |year=1999 |chapter=Discovery and development of major drugs currently in use |title=Pharmaceutical Innovation: Revolutionizing Human Health |editor=Ralph Landau |editor2=Basil Achilladelis |editor3=Alexander Scriabine |publisher=Chemical Heritage Press |location=Philadelphia |isbn=9780941901215 |page=211 |chapter-url=https://books.google.com/books?id=IH4lPs6S1bMC&pg=PA211 |url-status=live |archive-url=https://web.archive.org/web/20170908150741/https://books.google.com/books?id=IH4lPs6S1bMC&pg=PA211 |archive-date=8 September 2017 }}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<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> It is available as a [[Generic drug|generic medication]].<ref name=AHFS2015L/><ref>{{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> In 2021, it was the 267th most commonly prescribed medication in the United States, with more than 1{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2021 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=14 January 2024 | archive-date=15 January 2024 | archive-url=https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Lidocaine - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Lidocaine | access-date = 14 January 2024}}</ref>

== Medical uses ==

===Local numbing agent===
The efficacy profile of lidocaine as a local anaesthetic is characterized by a rapid onset of action and intermediate duration of efficacy. Therefore, lidocaine is suitable for infiltration, block, and surface anaesthesia. Longer-acting substances such as [[bupivacaine]] are sometimes given preference for spinal and [[Epidural administration|epidural anaesthesia]]s; lidocaine, though, has the advantage of a rapid onset of action. [[Adrenaline]] vasoconstricts arteries, reducing bleeding and also delaying the resorption of lidocaine, almost doubling the duration of anaesthesia.{{cn|date=March 2023}}

Lidocaine is one of the most commonly used local anaesthetics in dentistry. It can be administered in multiple ways, most often as a [[Local anesthetic nerve block|nerve block]] or [[Infiltration (medical)|infiltration]], depending on the type of treatment carried out and the area of the mouth worked on.<ref>{{cite web|url=https://bnf.nice.org.uk/treatment-summary/local-anaesthesia.html|title=Local anaesthetic drugs|url-access=limited }}</ref>

For surface anaesthesia, several formulations can be used for [[Endoscopy|endoscopies]], before [[intubation]]s, etc. Lidocaine drops can be used on the eyes for short ophthalmic procedures. There is tentative evidence for [[topical]] lidocaine for [[neuropathic pain]] and [[Skin grafting|skin graft]] donor site pain.<ref name=Coch2014Top>{{cite journal | vauthors = Derry S, Wiffen PJ, Moore RA, Quinlan J | veditors = Derry S | title = Topical lidocaine for neuropathic pain in adults | journal = The Cochrane Database of Systematic Reviews | volume = 7 | issue = 7 | pages = CD010958 | date = July 2014 | pmid = 25058164 | doi = 10.1002/14651858.CD010958.pub2 | pmc = 6540846 }}</ref><ref>{{cite journal | vauthors = Sinha S, Schreiner AJ, Biernaskie J, Nickerson D, Gabriel VA | title = Treating pain on skin graft donor sites: Review and clinical recommendations | journal = The Journal of Trauma and Acute Care Surgery | volume = 83 | issue = 5 | pages = 954–964 | date = November 2017 | pmid = 28598907 | doi = 10.1097/TA.0000000000001615 | s2cid = 44520644 }}</ref> As a local numbing agent, it is used for the treatment of [[premature ejaculation]].<ref>{{cite journal | title = Lidocaine/prilocaine spray for premature ejaculation | journal = Drug and Therapeutics Bulletin | volume = 55 | issue = 4 | pages = 45–48 | date = April 2017 | pmid = 28408390 | doi = 10.1136/dtb.2017.4.0469 | s2cid = 19110955 }}</ref>

An adhesive [[transdermal patch]] containing a 5% concentration of lidocaine in a [[Hydrogel dressing|hydrogel bandage]], is approved by the US FDA for reducing [[Postherpetic neuralgia|nerve pain caused by shingles]].<ref>{{cite journal | vauthors = Kumar M, Chawla R, Goyal M | title = Topical anesthesia | journal = Journal of Anaesthesiology Clinical Pharmacology | volume = 31 | issue = 4 | pages = 450–6 | date = 2015 | pmid = 26702198 | pmc = 4676230 | doi = 10.4103/0970-9185.169049 | doi-access = free }}</ref> The transdermal patch is also used for pain from other causes, such as compressed nerves and persistent nerve pain after some surgeries.

===Heart arrhythmia===
Lidocaine is also the most important [[Antiarrhythmic agent#Class I agents|class-1b antiarrhythmic drug]]; it is used intravenously for the treatment of [[ventricular arrhythmia]]s (for acute [[myocardial infarction]], [[digoxin]] poisoning, [[cardioversion]], or [[cardiac catheterization]]) if [[amiodarone]] is not available or contraindicated. Lidocaine should be given for this indication after [[defibrillation]], CPR, and [[vasopressor]]s have been initiated. A routine preventive dose is no longer recommended after a myocardial infarction as the overall benefit is not convincing.<ref>{{cite journal | vauthors = Martí-Carvajal AJ, Simancas-Racines D, Anand V, Bangdiwala S | title = Prophylactic lidocaine for myocardial infarction | journal = The Cochrane Database of Systematic Reviews | volume = 8 | issue = 8 | pages = CD008553 | date = August 2015 | pmid = 26295202 | doi = 10.1002/14651858.CD008553.pub2 | pmc = 8454263 }}</ref>

===Epilepsy===
A 2013 review on treatment for [[neonatal seizure]]s recommended intravenous lidocaine as a second-line treatment, if [[phenobarbital]] fails to stop seizures.<ref name="pmid23318696">{{cite journal | vauthors = Slaughter LA, Patel AD, Slaughter JL | title = Pharmacological treatment of neonatal seizures: a systematic review | journal = Journal of Child Neurology | volume = 28 | issue = 3 | pages = 351–64 | date = March 2013 | pmid = 23318696 | pmc = 3805825 | doi = 10.1177/0883073812470734 }}</ref>

===Other===
Intravenous lidocaine infusions are also used to treat [[chronic pain]] and [[Acute pain|acute surgical pain]] as an [[opiate]] sparing technique. The quality of evidence for this use is poor so it is difficult to compare it to [[placebo]] or an [[epidural]].<ref>{{cite journal | vauthors = Weibel S, Jelting Y, Pace NL, Helf A, Eberhart LH, Hahnenkamp K, Hollmann MW, Poepping DM, Schnabel A, Kranke P | title = Continuous intravenous perioperative lidocaine infusion for postoperative pain and recovery in adults | journal = The Cochrane Database of Systematic Reviews | volume = 2018 | pages = CD009642 | date = June 2018 | issue = 6 | pmid = 29864216 | pmc = 6513586 | doi = 10.1002/14651858.cd009642.pub3 }}</ref>

Inhaled lidocaine can be used as a [[antitussive|cough suppressor]] acting peripherally to reduce the [[cough reflex]]. This application can be implemented as a safety and comfort measure for patients who have to be intubated, as it reduces the incidence of coughing and any tracheal damage it might cause when emerging from anaesthesia.<ref name="isbn0-7817-9595-8">{{cite book |veditors=Berger AM, Shuster JL, Von Roenn JH | title = Principles and practice of palliative care and supportive oncology | publisher = Lippincott Williams & Wilkins | location = Hagerstwon, MD |year=2007 | isbn = 978-0-7817-9595-1 | vauthors = Biller JA | chapter = Airway obstruction, bronchospasm, and cough | chapter-url = https://books.google.com/books?id=LngD6RFXY_AC&pg=PA297 | pages = 297–307 | quote = Inhaled lidocaine is used to suppress cough during bronchoscopy. Animal studies and a few human studies suggest that lidocaine has an antitussive effect…}}</ref>

A 2019 systematic review of the literature found that intraurethral lidocaine reduces pain in men who undergo cystoscopic procedures.<ref>{{cite journal | vauthors = Raskolnikov D, Brown B, Holt SK, Ball AL, Lotan Y, Strope S, Schroeck F, Ullman R, Lipman R, Smith AB, Gore JL | title = Reduction of Pain during Flexible Cystoscopy: A Systematic Review and Meta-Analysis | journal = The Journal of Urology | volume = 202 | issue = 6 | pages = 1136–1142 | date = December 2019 | pmid = 31219763 | doi = 10.1097/JU.0000000000000399 | s2cid = 195192577 }}</ref>

Lidocaine, along with [[ethanol]], [[ammonia]], and [[acetic acid]], may also help in treating [[jellyfish]] stings, both numbing the affected area and preventing further [[nematocyst]] discharge.<ref name="pmid20116454">{{cite journal |vauthors=Birsa LM, Verity PG, Lee RF | title = Evaluation of the effects of various chemicals on discharge of and pain caused by jellyfish nematocysts | journal = Comp. Biochem. Physiol. C | volume = 151 | issue = 4 | pages = 426–30 | date = May 2010 | pmid = 20116454 | doi = 10.1016/j.cbpc.2010.01.007 }}</ref><ref>{{cite journal |vauthors=Morabito R, Marino A, Dossena S, La Spada G | title = Nematocyst discharge in Pelagia noctiluca (Cnidaria, Scyphozoa) oral arms can be affected by lidocaine, ethanol, ammonia and acetic acid | journal = Toxicon | volume = 83 | pages = 52–8 | date = Jun 2014 | pmid = 24637105 | doi=10.1016/j.toxicon.2014.03.002}}</ref>

For [[gastritis]], drinking a viscous lidocaine formulation may help with the pain.<ref>{{cite book| vauthors = Adams JG |title=Emergency Medicine: Clinical Essentials|date=2012|publisher=Elsevier Health Sciences|isbn=9781455733941|chapter-url=https://books.google.com/books?id=rpoH-KYE93IC&pg=PP1314|chapter=32|url-status=live|archive-url= https://web.archive.org/web/20170908150741/https://books.google.com/books?id=rpoH-KYE93IC&pg=PP1314 |archive-date=8 September 2017}}</ref>

== Adverse effects ==
[[Adverse drug reaction]]s (ADRs) are rare when lidocaine is used as a local anesthetic and is administered correctly. Most ADRs associated with lidocaine for anesthesia relate to administration technique (resulting in systemic exposure) or pharmacological effects of anesthesia, and [[allergy|allergic]] reactions only rarely occur.<ref name="pmid7844301">{{cite journal |vauthors=Jackson D, Chen AH, Bennett CR |title = Identifying true lidocaine allergy |journal = J Am Dent Assoc |volume = 125 |issue = 10 |pages = 1362–6 |date = October 1994 |pmid = 7844301 |doi = 10.14219/jada.archive.1994.0180}}</ref> Systemic exposure to excessive quantities of lidocaine 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. ADRs by system are:
* CNS excitation: nervousness, agitation, anxiety, apprehension, tingling around the mouth (circumoral paraesthesia), headache, [[hyperesthesia]], tremor, dizziness, pupillary changes, psychosis, euphoria, hallucinations, and seizures
* CNS depression with increasingly heavier exposure: drowsiness, lethargy, slurred speech, [[hypoesthesia]], confusion, disorientation, loss of consciousness, [[respiratory depression]] and [[apnoea]].
* Cardiovascular: [[hypotension]], [[bradycardia]], [[Heart arrhythmia|arrhythmia]]s, flushing, venous insufficiency, increased defibrillator threshold, [[edema]], and/or [[cardiac arrest]] – some of which may be due to [[Hypoxia (medical)|hypoxemia]] secondary to respiratory depression.<ref name="rossi">{{cite book |title = Australian Medicines Handbook |publisher = Australian Medicines Handbook Pty Ltd |location = Adelaide, S. Aust |year = 2006 | isbn = 978-0-9757919-2-9 | title-link = Australian Medicines Handbook }}{{page needed|date=May 2013}}</ref>
* Respiratory: bronchospasm, dyspnea, respiratory depression or arrest
* Gastrointestinal: metallic taste, nausea, vomiting, agita, and diarrhea
* Ears: [[tinnitus]]
* Eyes: local burning, conjunctival hyperemia, corneal epithelial changes/ulceration, diplopia, visual changes (opacification)
* Skin: itching, depigmentation, rash, [[urticaria]], edema, angioedema, bruising, [[thrombophlebitis|inflammation of the vein]] at the injection site, irritation of the skin when applied topically
* Blood: [[methemoglobinemia]]
* Allergy

ADRs associated with the use of intravenous lidocaine are similar to toxic effects from systemic exposure above. These are dose-related and more frequent at high infusion rates (≥3&nbsp;mg/min). Common ADRs include: headache, dizziness, drowsiness, confusion, visual disturbances, tinnitus, tremor, and/or [[paraesthesia]]. Infrequent ADRs associated with the use of lidocaine include: [[hypotension]], [[bradycardia]], [[Heart arrhythmia|arrhythmia]]s, [[cardiac arrest]], muscle twitching, [[seizure]]s, [[coma]], and/or respiratory depression.<ref name = rossi/>

It is generally safe to use lidocaine with vasoconstrictor such as adrenaline, including in regions such as the [[nose]], ears, [[finger]]s, and [[toes]].<ref name=Nie2014>{{cite journal |vauthors = Nielsen LJ, Lumholt P, Hölmich LR |title = [Local anaesthesia with vasoconstrictor is safe to use in areas with end-arteries in fingers, toes, noses and ears] |journal = Ugeskrift for Laeger |volume = 176 |issue = 44 |date = October 2014 |pmid = 25354008 }}</ref> While concerns of tissue death if used in these areas have been raised, evidence does not support these concerns.<ref name=Nie2014/>

The use of lidocaine for spinal anesthesia may lead to an increased risk of transient neurological symptoms, a painful condition that is sometimes experienced immediately after surgery.<ref name="Forget_2019">{{cite journal | vauthors = Forget P, Borovac JA, Thackeray EM, Pace NL | title = Transient neurological symptoms (TNS) following spinal anaesthesia with lidocaine versus other local anaesthetics in adult surgical patients: a network meta-analysis | journal = The Cochrane Database of Systematic Reviews | volume = 2019 | pages = CD003006 | date = December 2019 | issue = 12 | pmid = 31786810 | pmc = 6885375 | doi = 10.1002/14651858.CD003006.pub4 }}</ref> There is some weak evidence to suggest that the use of alternative anesthetic medications such as [[prilocaine]], [[procaine]], [[bupivacaine]], [[ropivacaine]], or [[levobupivacaine]] may decrease the risk of a person developing transient neurological symptoms.<ref name="Forget_2019" /> Low quality evidence suggests that 2‐[[chloroprocaine]] and [[mepivacaine]] when used for spinal anesthetic have a similar risk of the person developing transient neurological symptoms as lidocaine.<ref name="Forget_2019" />

=== Interactions ===
Any drugs that are also [[ligand]]s of [[CYP3A4]] and [[CYP1A2]] can potentially increase serum levels and potential for toxicity or decrease serum levels and the efficacy, depending on whether they induce or inhibit the enzymes, respectively. Drugs that may increase the chance of [[methemoglobinemia]] should also be considered carefully. [[Dronedarone]] and [[liposomal]] [[morphine]] are both absolutely a [[contraindication]], as they may increase the serum levels, but hundreds of other drugs require monitoring for interaction.<ref name=epocrates>{{cite web |url=https://online.epocrates.com/u/104316/lidocaine/Drug+Interactions |title=Lidocaine|publisher=Epocrates |url-status=live |archive-url=https://web.archive.org/web/20140422232823/https://online.epocrates.com/u/104316/lidocaine/Drug+Interactions |archive-date=22 April 2014}}</ref>

=== Contraindications ===
Absolute contraindications for the use of lidocaine include:
* [[Heart block]], second or third degree (without pacemaker)
* Severe [[sinoatrial block]] (without pacemaker)
* Serious [[adverse drug reaction]] to lidocaine or amide local anesthetics
* Hypersensitivity to corn and corn-related products (corn-derived dextrose is used in the mixed injections)
* Concurrent treatment with [[quinidine]], [[flecainide]], [[disopyramide]], [[procainamide]] (class I antiarrhythmic agents)
* Prior use of [[amiodarone hydrochloride]]
* [[Adams–Stokes syndrome]]<ref name="MedWatch_Lidocaine_HCl">{{cite web |url = https://www.fda.gov/Safety/MedWatch/SafetyInformation/ucm342035.htm |title = Lidocaine Hydrochloride and 5% Dextrose Injection |work = Safety Labeling Changes |publisher = FDA Center for Drug Evaluation and Research (CDER) |date = January 2014 |url-status = live |archive-url = https://web.archive.org/web/20130403105258/https://www.fda.gov/Safety/MedWatch/SafetyInformation/ucm342035.htm |archive-date = 3 April 2013 }}</ref>
* [[Wolff–Parkinson–White syndrome]]<ref name="MedWatch_Lidocaine_HCl"/>
* Lidocaine viscous is not recommended by the FDA to treat teething pain in children and infants.<ref name="MedWatch_Lidocaine_Viscous">{{cite web |url = https://www.fda.gov/drugs/drug-safety-and-availability/fda-drug-safety-communication-fda-recommends-not-using-lidocaine-treat-teething-pain-and-requires |title = FDA Drug Safety Communication: FDA recommends not using lidocaine to treat teething pain and requires new Boxed Warning |publisher = FDA Center for Drug Evaluation and Research (CDER) |date = June 2014 | url-status = live |archive-url = https://web.archive.org/web/20140714220256/https://www.fda.gov/Safety/MedWatch/SafetyInformation/SafetyAlertsforHumanMedicalProducts/ucm402790.htm |archive-date = 14 July 2014 }}</ref>

Exercise caution in patients with any of these:
* [[Hypotension]] not due to [[Heart arrhythmia|arrhythmia]]
* [[Bradycardia]]
* [[Accelerated idioventricular rhythm]]
* Elderly
* [[Ehlers–Danlos syndromes]]; efficiency of local anesthetics can be reduced<ref name="Resistance to local anesthesia in people with the Ehlers-Danlos Syndromes presenting for dental surgery - PMC6834718">{{cite journal | vauthors = Schubart JR, Schaefer E, Janicki P, Adhikary SD, Schilling A, Hakim AJ, Bascom R, Francomano CA, Raj SR | title = Resistance to local anesthesia in people with the Ehlers-Danlos Syndromes presenting for dental surgery | journal = Journal of Dental Anesthesia and Pain Medicine | volume = 19 | issue = 5 | pages = 261–270 | date = October 2019 | pmid = 31723666 | pmc = 6834718 | doi = 10.17245/jdapm.2019.19.5.261 | doi-access = free }}</ref>
* [[Pseudocholinesterase deficiency]]
* Intra-articular infusion (this is not an approved indication and can cause [[chondrolysis]])
* [[Porphyria]], especially [[acute intermittent porphyria]]; lidocaine has been classified as porphyrogenic because of the hepatic enzymes it induces,<ref name="url_www.merckmanuals.com">{{cite web |url = http://www.merckmanuals.com/media/professional/pdf/Drugs_porphyria.pdf |title = Table 96–4. Drugs and Porphyria |year = 2011 |work = Merck Manual |publisher = Merck & Company, Inc. |url-status = live |archive-url = https://web.archive.org/web/20140420104822/http://www.merckmanuals.com/media/professional/pdf/Drugs_porphyria.pdf/ |archive-date = 20 April 2014 }}</ref> although clinical evidence suggests it is not.<ref name="urlLidocaine - N01BB02 - Drug porphyrinogenicity monograph">{{cite web |url = http://www.drugs-porphyria.org/monograph.php?id=3448 |title = Lidocaine - N01BB02 |work = Drug porphyrinogenicity monograph |publisher = The Norwegian Porphyria Centre and the Swedish Porphyria Centre |quote = strong clinical evidence points to lidocaine as probably not porphyrinogenic |url-status = live |archive-url = https://web.archive.org/web/20140420040511/http://www.drugs-porphyria.org/monograph.php?id=3448 |archive-date = 20 April 2014 }}</ref> [[Bupivacaine]] is a safe alternative in this case.
* Impaired liver function – people with lowered hepatic function may have an adverse reaction with repeated administration of lidocaine because the drug is metabolized by the liver. Adverse reactions may include neurological symptoms (e.g. dizziness, nausea, muscle twitches, vomiting, or seizures).<ref name=Khan>{{cite book | vauthors = Khan MG |title=Cardiac Drug Therapy |date=2007 |publisher=Humana Press |location=Totowa, NJ |isbn=9781597452380 |edition=7th}}</ref>

===Overdosage===
Overdoses of lidocaine may result from excessive administration by topical or [[parenteral]] routes, accidental oral ingestion of topical preparations by children (who are more susceptible to overdose), accidental intravenous (rather than subcutaneous, [[intrathecal]], or paracervical) injection, or from prolonged use of subcutaneous infiltration anesthesia during cosmetic surgery.{{cn|date=March 2023}}

Such overdoses have often led to severe toxicity or death in both children and adults ([[local anesthetic systemic toxicity]]).<ref>{{cite journal | vauthors = El-Boghdadly K, Pawa A, Chin KJ | title = Local anesthetic systemic toxicity: current perspectives | journal = Local and Regional Anesthesia | volume = 11 | pages = 35–44 | date = 8 August 2018 | pmid = 30122981 | pmc = 6087022 | doi = 10.2147/LRA.S154512 | doi-access = free }}</ref> Symptoms include central nervous system manifestations such as numbness of the tongue, dizziness, tinnitus, visual disturbances, convulsions, reduced consciousness progressing to coma, as well as respiratory arrest and cardiovascular disturbances.<ref>{{cite journal | vauthors = van Donselaar-van der Pant KA, Buwalda M, van Leeuwen HJ | title = [Lidocaine: local anaesthetic with systemic toxicity] | language = nl | journal = Nederlands Tijdschrift voor Geneeskunde | volume = 152 | issue = 2 | pages = 61–65 | date = January 2008 | pmid = 18265791 | url = https://www.ntvg.nl/artikelen/lidocaine-een-lokaal-anestheticum-met-systemische-toxiciteit | trans-title = Lidocaine: local anaesthetic with systemic toxicity }}</ref> Lidocaine and its two major metabolites may be quantified in blood, plasma, or serum to confirm the diagnosis in potential poisoning victims or to assist forensic investigation in a case of fatal overdose. {{cn|date=December 2022}}

Lidocaine is often given intravenously as an antiarrhythmic agent in critical cardiac-care situations.<ref name="isbn0-9626523-7-7">{{cite book | vauthors = Baselt R |title = Disposition of Toxic Drugs and Chemicals in Man |edition = 8th |publisher = Biomedical Publications | location = Foster City, CA | year = 2008 |pages = 840–4 |isbn = 978-0-9626523-7-0 }}</ref> Treatment with intravenous lipid emulsions (used for [[parenteral]] feeding) to reverse the effects of local anaesthetic toxicity is becoming more common.<ref name="pmid19143686">{{cite journal | vauthors = Picard J, Ward SC, Zumpe R, Meek T, Barlow J, Harrop-Griffiths W | title = Guidelines and the adoption of 'lipid rescue' therapy for local anaesthetic toxicity | journal = Anaesthesia | volume = 64 | issue = 2 | pages = 122–125 | date = February 2009 | pmid = 19143686 | doi = 10.1111/j.1365-2044.2008.05816.x | s2cid = 25581037 | doi-access = free }}</ref><ref>{{cite journal | vauthors = El-Boghdadly K, Pawa A, Chin KJ | title = Local anesthetic systemic toxicity: current perspectives | journal = Local and Regional Anesthesia | volume = 11 | pages = 35–44 | year = 2018 | pmid = 30122981 | pmc = 6087022 | doi = 10.2147/LRA.S154512 | doi-access = free }}</ref>

===Postarthroscopic glenohumeral chondrolysis===
Lidocaine in large amounts may be toxic to [[cartilage]] and intra-articular infusions can lead to [[postarthroscopic glenohumeral chondrolysis]].<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 = S200-10 |date = December 2015 |pmid = 27047224 |pmc = 4796530 |doi = 10.1016/j.jor.2015.10.005 }}</ref>

==Pharmacology==

===Mechanism of action===
Lidocaine alters signal conduction in [[neuron]]s by prolonging the inactivation of the fast [[sodium channel|voltage-gated Na<sup>+</sup> channels]] in the neuronal cell membrane responsible for [[action potential]] propagation.<ref name="novartis">{{cite book |doi=10.1002/0470846682.ch14 |chapter=Molecular mechanisms of gating and drug block of sodium channels |title=Sodium Channels and Neuronal Hyperexcitability |series=Novartis Foundation Symposia |year=2001 | vauthors = Carterall WA |isbn=9780470846681 |volume=241 |pages=206–225}}</ref> With sufficient blockage, the voltage-gated sodium channels will not open and an action potential will not be generated. Careful titration allows for a high degree of selectivity in the blockage of sensory neurons, whereas higher concentrations also affect other types of neurons.{{cn|date=March 2023}}

The same principle applies for this drug's actions in the heart. Blocking sodium channels in the conduction system, as well as the muscle cells of the heart, raises the depolarization threshold, making the heart less likely to initiate or conduct early action potentials that may cause an arrhythmia.<ref>{{cite journal |vauthors=Sheu SS, Lederer WJ | title = Lidocaine's negative inotropic and antiarrhythmic actions. Dependence on shortening of action potential duration and reduction of intracellular sodium activity | journal = Circulation Research | volume = 57 | issue = 4 | pages = 578–90 | date = Oct 1985 | pmid = 2412723 | doi=10.1161/01.res.57.4.578| doi-access = free }}</ref>

=== Pharmacokinetics ===
When used as an injectable it typically begins working within four minutes and lasts for half an hour to three hours.<ref name=AHFS2015L/><ref name=Wh1997/> Lidocaine is about 95% metabolized (dealkylated) in the [[liver]] mainly by CYP3A4 to the pharmacologically active [[Metabolomics#Metabolites|metabolites]] [[monoethylglycinexylidide]] (MEGX) and then subsequently to the inactive [[glycine xylidide]]. MEGX has a longer [[Biological half-life|half-life]] than lidocaine, but also is a less potent sodium channel blocker.<ref name="isbn0-07-143763-0">{{cite book |veditors=Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA, Nelson LH | title = Goldfrank's Toxicologic Emergencies | edition = 8th | publisher = McGraw-Hill | location = New York | year = 2006 | pages = 963–4 |vauthors=Lewin NA, Nelson LH | chapter = Chapter 61: Antidysrhythmics | isbn = 978-0-07-143763-9 }}</ref> The [[volume of distribution]] is 1.1&nbsp;L/kg to 2.1&nbsp;L/kg, but congestive heart failure can decrease it. About 60% to 80% circulates bound to the protein [[Orosomucoid|alpha<sub>1</sub> acid glycoprotein]]. The oral [[bioavailability]] is 35% and the topical bioavailability is 3%.

The elimination half-life of lidocaine is biphasic and around 90&nbsp;min to 120&nbsp;min in most patients. This may be prolonged in patients with [[liver failure|hepatic impairment]] (average 343&nbsp;min) or [[heart failure|congestive heart failure]] (average 136&nbsp;min).<ref name="pmid4694036">{{cite journal |vauthors=Thomson PD, Melmon KL, Richardson JA, Cohn K, Steinbrunn W, Cudihee R, Rowland M | title = Lidocaine pharmacokinetics in advanced heart failure, liver disease, and renal failure in humans | journal = Ann. Intern. Med. | volume = 78 | issue = 4 | pages = 499–508 | date = April 1973 | pmid = 4694036 | doi = 10.7326/0003-4819-78-4-499 }}</ref> Lidocaine is excreted in the urine (90% as metabolites and 10% as unchanged drug).<ref name="pmid4609637">{{cite journal |vauthors=Collinsworth KA, Kalman SM, Harrison DC | title = The clinical pharmacology of lidocaine as an antiarrhythymic drug | journal = Circulation | volume = 50 | issue = 6 | pages = 1217–30 | year = 1974 | pmid = 4609637 | doi = 10.1161/01.CIR.50.6.1217 | doi-access = free }}</ref>

== Chemistry ==
=== Molecular structure and conformational flexibility ===
At the heart of lidocaine's molecular structure lies a lipophilic group featuring a 1,5-dimethylbenzene core, contributing to the molecule's hydrophobic characteristics. In addition to this aromatic unit, lidocaine incorporates an aliphatic section comprising amide, carbonyl, and enyl groups. This multifaceted arrangement endows the molecule with unique properties and a capacity to interact with biological systems.

Lidocaine exhibits a remarkable degree of conformational flexibility, resulting in more than 60 probable conformers.<ref name="Khodov_2022">{{cite journal | vauthors = Khodov IA, Belov KV, Dyshin AA, Krestyaninov MA, Kiselev MG |date= December 2022 |title=Pressure effect on lidocaine conformational equilibria in scCO2: A study by 2D NOESY |journal=Journal of Molecular Liquids |language=en |volume=367 |pages=120525 |doi=10.1016/j.molliq.2022.120525|s2cid= 252799787 }}</ref> This adaptability arises from the high lability of the amide and ethyl groups within the molecule. These groups can undergo shifts in their positions, leading to significant variations in the overall molecular configuration.

=== Influence of temperature and pressure on conformational preference ===
The dynamic transformation of lidocaine conformers in supercritical carbon dioxide (scCO<sub>2</sub>) highly depends on external factors such as pressure<ref name="Khodov_2022" /> and temperature.<ref>{{cite journal | vauthors = Khodov IA, Belov KV, Sobornova VV, Dyshin AA, Kiselev MG |date= October 2023 |title=Exploring the temperature-dependent proportions of lidocaine conformers equilibria in supercritical carbon dioxide via NOESY |journal=Journal of Molecular Liquids |language=en |volume=387 |pages=122620 |doi=10.1016/j.molliq.2023.122620|s2cid= 260069284 }}</ref> Alterations in these conditions can lead to distinct conformations, impacting the molecule's physicochemical properties. One notable consequence of these variations is the particle size of lidocaine when produced through micronization using scCO<sub>2</sub>. Changes in the position of the amide group within the molecule can trigger a redistribution of intra- and intermolecular hydrogen bonds, affecting the outcome of the micronization process and the resultant particle size.<ref>{{cite journal | vauthors = Kuznetsova IV, Gilmutdinov II, Gilmutdinov IM, Sabirzyanov AN |date= September 2019 |title=Production of Lidocaine Nanoforms via the Rapid Extension of a Supercritical Solution into Water Medium |journal=High Temperature |language=en |volume=57 |issue=5 |pages=726–730 |doi=10.1134/S0018151X19040138 |s2cid= 213017906 |issn=0018-151X}}</ref>

== History ==
Lidocaine, the first [[amino]] [[amide]]–type local anesthetic (previous were amino esters), was first synthesized under the name 'xylocaine' by Swedish chemist [[Nils Löfgren]] in 1943.<ref name="lofgren_1948">{{cite book | vauthors = Löfgren N |title=Studies on local anesthetics: Xylocaine: a new synthetic drug |type=Inaugural dissertation |publisher=Ivar Heggstroms |location=Stockholm, Sweden |year=1948 |oclc=646046738}}{{page needed|date=May 2013}}</ref><ref>{{cite journal |vauthors=Löfgren N, Lundqvist B | year = 1946 | title = Studies on local anaesthetics II | journal = Svensk Kemisk Tidskrift | volume = 58 | pages = 206–17}}</ref><ref name=Wild2011>{{cite journal | vauthors = Wildsmith JA | year = 2011 | title = Lidocaine: A more complex story than 'simple' chemistry suggests | journal = The Proceedings of the History of Anaesthesia Society | url = http://www.histansoc.org.uk/uploads/9/5/5/2/9552670/vol_43.pdf | volume = 43 | pages = 9–16 | url-status = live | archive-url = https://web.archive.org/web/20140422232909/http://www.histansoc.org.uk/uploads/9/5/5/2/9552670/vol_43.pdf | archive-date = 22 April 2014 }}</ref> His colleague Bengt Lundqvist performed the first injection anesthesia experiments on himself.<ref name="lofgren_1948"/> It was first marketed in 1949.

==Society and culture==

=== Dosage forms ===
Lidocaine, usually in the form of its [[Hydrochloride|hydrochloride salt]], is available in various forms including many [[Topical medication#Classes|topical formulations]] and solutions for injection or infusion.<ref name=brandsforms>{{cite web|title=Lidocaine international forms and names|url=https://www.drugs.com/international/lidocaine.html|publisher=Drugs.com|access-date=29 October 2017}}</ref> It is also available as a [[transdermal patch]], which is applied directly to the skin.{{cn|date=March 2023}}

<gallery mode="packed" widths="360px" heights="220">
File:Lidocaine HCl local anesthetic cartridge.JPG|Lidocaine hydrochloride 2% epinephrine 1:80,000 solution for injection in a cartridge
File:Lidocaine hci.jpg|Lidocaine hydrochloride 1% solution for injection
File:Xylocaina spray.jpg|Topical lidocaine spray
File:Vicouslodi.jpeg|2% viscous lidocaine
</gallery>

===Names===
Lidocaine is the [[International Nonproprietary Name]] (INN), [[British Approved Name]] (BAN), and [[Australian Approved Name]] (AAN),<ref name="Therapeutic Goods Administration">{{cite web |title=Lidocaine Ingredient Summary|url=https://www.ebs.tga.gov.au/ebs/PublicHTML/pdfstore.nsf/TemplateEngineIngredientPDF?OpenAgent&ingredientid=100665&docid=BB294B9EA22D3A2ACA2577DD0000F98B |website=Therapeutic Goods Administration |access-date=20 September 2018 }}</ref> while lignocaine is the former BAN{{citation needed|date=February 2020}} and AAN. Both the old and new names will be displayed on the product label in Australia until at least 2023.<ref>{{cite web |title=Updating medicine ingredient names - list of affected ingredients |url=https://www.tga.gov.au/node/711438 |website=Therapeutic Goods Administration |date=24 June 2019 |access-date=16 February 2020 |archive-date=28 August 2021 |archive-url=https://web.archive.org/web/20210828143930/https://www.tga.gov.au/updating-medicine-ingredient-names-list-affected-ingredients |url-status=dead }}</ref>

Xylocaine is a brand name, referring to the major synthetic building block [[2,6-xylidine]]. The "ligno" prefix is chosen because "xylo" means [[wood]] in Greek while "ligno" means the same in Latin. The "lido" prefix instead refers to the fact that the drug is chemically related to [[acetanilide]].<ref name=Wild2011/>

=== Recreational use ===
{{As of|2021||post=,}} lidocaine is not listed by the [[World Anti-Doping Agency]] as a substance whose use is banned in sport.<ref name="url_www.wada-ama.org">{{cite web|date=1 January 2021|title=The 2021 Prohibited List International Standard|url=https://www.wada-ama.org/sites/default/files/resources/files/2021_wada_code.pdf|archive-url=https://web.archive.org/web/20210513023441/https://www.wada-ama.org/sites/default/files/resources/files/2021_wada_code.pdf|archive-date=13 May 2021|access-date=18 May 2021|work=The World Anti-Doping Code|publisher=World Anti-Doping Agency (WADA)}}</ref> It is used as an [[adjuvant]], adulterant, and diluent to street drugs such as [[cocaine]] and [[heroin]].<ref>{{cite web | url = http://www.justice.gov/archive/ndic/pubs2/2580/heroin.htm | publisher = National Drug Intelligence Center | title = New York Drug Threat Assessment | date = November 2002 | url-status = live | archive-url = https://web.archive.org/web/20120812004029/http://www.justice.gov/archive/ndic///pubs2/2580/heroin.htm | archive-date = 12 August 2012 }}</ref> It is one of the three common ingredients in [[site enhancement oil]] used by [[Bodybuilding|bodybuilders]].<ref>{{cite journal | vauthors = Pupka A, Sikora J, Mauricz J, Cios D, Płonek T | title = [The usage of synthol in the body building] | journal = Polimery W Medycynie | volume = 39 | issue = 1 | pages = 63–5 | date = 2009 | pmid = 19580174 }}</ref>

=== Adulterant in cocaine ===
Lidocaine is often added to [[cocaine]] as a [[diluent]].<ref>{{cite journal | vauthors = Bernardo NP, Siqueira ME, De Paiva MJ, Maia PP | title = Caffeine and other adulterants in seizures of street cocaine in Brazil |year=2003 | journal = International Journal of Drug Policy | volume = 14 | issue = 4 | pages = 331–4 | doi = 10.1016/S0955-3959(03)00083-5 }}</ref><ref name="url599 F.2d 635">{{cite web | url = https://bulk.resource.org/courts.gov/c/F2/599/599.F2d.635.78-5314.html | title = UNITED STATES of America, Plaintiff-Appellee, v. Luis A. CUELLO, Alvaro Bastides-Benitez, John Doe, a/k/a Hugo Hurtado, and Alvaro Carvajal, Defendants-Appellants | date = 25 July 1979 | work = Docket No. 78-5314 | publisher = United States Court of Appeals, Fifth Circuit | url-status = dead | archive-url = https://web.archive.org/web/20120524141840/http://bulk.resource.org/courts.gov/c/F2/599/599.F2d.635.78-5314.html | archive-date = 24 May 2012 }}</ref> Cocaine and lidocaine both numb the [[gums]] when applied. This gives the user the impression of high-quality cocaine, when in actuality the user is receiving a diluted product.<ref>{{cite news| vauthors = Winterman D |title=How cutting drugs became big business|url=https://www.bbc.com/news/magazine-11177126|publisher=BBC News Magazine|access-date=20 January 2017|url-status=live|archive-url=https://web.archive.org/web/20170202020256/http://www.bbc.com/news/magazine-11177126|archive-date=2 February 2017|work=BBC News Online|date=7 September 2010}}</ref>

=== Compendial status ===
* [[Japanese Pharmacopoeia]] 15
* [[United States Pharmacopeia]] 31<ref>{{cite web |url=http://www.usp.org/usp-nf/official-text/accelerated-revision-process/accelerated-revision-history/lidocaine-and-prilocaine-cream-revision-related |title=Revision Bulletin: Lidocaine and Prilocaine Cream–Revision to Related Compounds Test |date=30 November 2007 |publisher=The United States Pharmacopeial Convention |url-status=live |archive-url=https://web.archive.org/web/20130501222459/http://www.usp.org/usp-nf/official-text/accelerated-revision-process/accelerated-revision-history/lidocaine-and-prilocaine-cream-revision-related |archive-date=1 May 2013 }}</ref>

==Veterinary use==
It is a component of the [[Veterinary medicine|veterinary]] drug [[Tributame]] along with [[embutramide]] and [[chloroquine]] used to carry out [[Animal euthanasia|euthanasia]] on horses and dogs.<ref>{{cite book|url=https://books.google.com/books?id=BLkPFlB15v0C|title=Small Animal Toxicology| vauthors = Peterson ME, Talcott PA |date=7 August 2013|publisher=Elsevier Health Sciences|isbn=978-0323241984|language=en|url-status=live|archive-url=https://web.archive.org/web/20170908150741/https://books.google.com/books?id=BLkPFlB15v0C|archive-date=8 September 2017}}</ref><ref>{{cite web|url=https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm051493.pdf|title=FDA Freedom of Information Summary - Tributame|website=[[Food and Drug Administration]]|url-status=dead|archive-url=https://web.archive.org/web/20150518090208/https://www.fda.gov/downloads/animalveterinary/products/approvedanimaldrugproducts/foiadrugsummaries/ucm051493.pdf|archive-date=18 May 2015}}</ref>

== References ==
{{reflist}}

== External links ==
* {{cite web | title=Lidocaine Transdermal Patch | website=MedlinePlus | url=https://medlineplus.gov/druginfo/meds/a603026.html }}
* {{cite patent |country=US |number=2441498 |status=patent |title=Alkyl glycinanilides |pubdate=1948-05-11 |gdate=1948-05-11 |fdate=1944-07-12 |pridate=1943-07-15 |invent1=Nils Magnus Loefgren |invent2=Bengt Josef Lundqvist |assign1=ASTRA APOTEKARNES KEM FAB |url=https://worldwide.espacenet.com/publicationDetails/biblio?II=1&ND=3&adjacent=true&locale=en_EP&FT=D&date=19480511&CC=US&NR=2441498A&KC=A}}

{{Antiarrhythmic agents}}
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{{Antipruritics}}
{{Local anesthetics}}
{{Neuropathic pain and fibromyalgia pharmacotherapies}}
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{{Ion channel modulators}}
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[[Category:Acetamides]]
[[Category:Antiarrhythmic agents]]
[[Category:Chemical substances for emergency medicine]]
[[Category:Drugs developed by AstraZeneca]]
[[Category:Diethylamino compounds]]
[[Category:Local anesthetics]]
[[Category:Sodium channel blockers]]
[[Category:World Health Organization essential medicines]]
[[Category:Wikipedia medicine articles ready to translate]]