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class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Psychiatric"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Psychiatric</span> </div> </a> <ul id="toc-Psychiatric-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cardiovascular" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cardiovascular"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Cardiovascular</span> </div> </a> <ul id="toc-Cardiovascular-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Allergies" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Allergies"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>Allergies</span> </div> </a> <ul id="toc-Allergies-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Warnings" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Warnings"> <div 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class="vector-toc-numb">5</span> <span>Pharmacology</span> </div> </a> <button aria-controls="toc-Pharmacology-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Pharmacology subsection</span> </button> <ul id="toc-Pharmacology-sublist" class="vector-toc-list"> <li id="toc-Pharmacodynamics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacodynamics"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Pharmacodynamics</span> </div> </a> <ul id="toc-Pharmacodynamics-sublist" class="vector-toc-list"> <li id="toc-Preclinical_research" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Preclinical_research"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1.1</span> <span>Preclinical research</span> </div> </a> <ul id="toc-Preclinical_research-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Pharmacokinetics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacokinetics"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Pharmacokinetics</span> </div> </a> <ul id="toc-Pharmacokinetics-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Chemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Chemistry</span> </div> </a> <button aria-controls="toc-Chemistry-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Chemistry subsection</span> </button> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> <li id="toc-Synthesis" class="vector-toc-list-item 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class="vector-toc-numb">7.1</span> <span>Partial-onset seizures</span> </div> </a> <ul id="toc-Partial-onset_seizures-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Peripheral_neuropathy" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Peripheral_neuropathy"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Peripheral neuropathy</span> </div> </a> <ul id="toc-Peripheral_neuropathy-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Society_and_culture" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Society_and_culture"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Society and culture</span> </div> </a> <button aria-controls="toc-Society_and_culture-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Society and culture subsection</span> </button> <ul id="toc-Society_and_culture-sublist" class="vector-toc-list"> <li id="toc-Names" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Names"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1</span> <span>Names</span> </div> </a> <ul id="toc-Names-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Research" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Research"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Research</span> </div> </a> <ul id="toc-Research-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > 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Available in 16 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-16" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">16 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://ar.wikipedia.org/wiki/%D9%84%D8%A7%D9%83%D9%88%D8%B3%D8%A7%D9%85%D9%8A%D8%AF" title="لاكوساميد – Arabic" lang="ar" hreflang="ar" data-title="لاكوساميد" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Lacosamid" title="Lacosamid – German" lang="de" hreflang="de" data-title="Lacosamid" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9B%CE%B1%CE%BA%CE%BF%CF%83%CE%B1%CE%BC%CE%AF%CE%B4%CE%B7" title="Λακοσαμίδη – Greek" lang="el" hreflang="el" data-title="Λακοσαμίδη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Lacosamida" title="Lacosamida – Spanish" lang="es" hreflang="es" data-title="Lacosamida" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Lacosamide" title="Lacosamide – French" lang="fr" hreflang="fr" data-title="Lacosamide" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Lacosamide" title="Lacosamide – Italian" lang="it" hreflang="it" data-title="Lacosamide" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%9C%D7%A7%D7%95%D7%A1%D7%90%D7%9E%D7%99%D7%93" title="לקוסאמיד – Hebrew" lang="he" hreflang="he" data-title="לקוסאמיד" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Lacosamidum" title="Lacosamidum – Latin" lang="la" hreflang="la" data-title="Lacosamidum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Lacosamide" title="Lacosamide – Dutch" lang="nl" hreflang="nl" data-title="Lacosamide" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%B2%E0%AC%BE%E0%AC%95%E0%AD%8B%E0%AC%B8%E0%AC%BE%E0%AC%AE%E0%AC%BE%E0%AC%87%E0%AC%A1" title="ଲାକୋସାମାଇଡ – Odia" lang="or" hreflang="or" data-title="ଲାକୋସାମାଇଡ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target"><span>ଓଡ଼ିଆ</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Lacosamida" title="Lacosamida – Portuguese" lang="pt" hreflang="pt" data-title="Lacosamida" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Lacosamid%C4%83" title="Lacosamidă – Romanian" lang="ro" hreflang="ro" data-title="Lacosamidă" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Lakosamid" title="Lakosamid – Serbian" lang="sr" hreflang="sr" data-title="Lakosamid" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Lakosamid" title="Lakosamid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Lakosamid" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Lakozamid" title="Lakozamid – Turkish" lang="tr" hreflang="tr" data-title="Lakozamid" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9B%D0%B0%D0%BA%D0%BE%D1%81%D0%B0%D0%BC%D1%96%D0%B4" title="Лакосамід – Ukrainian" lang="uk" hreflang="uk" data-title="Лакосамід" data-language-autonym="Українська" data-language-local-name="Ukrainian" 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class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Anticonvulsant and analgesic medication</div> <p class="mw-empty-elt"> </p> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Lacosamide">Lacosamide</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Lacosamide.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Lacosamide.svg/250px-Lacosamide.svg.png" decoding="async" width="250" height="143" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Lacosamide.svg/375px-Lacosamide.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Lacosamide.svg/500px-Lacosamide.svg.png 2x" data-file-width="512" data-file-height="293" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Vimpat</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">(2<i>R</i>)-2-(acetylamino)-<i>N</i>-benzyl-3-methoxypropanamide</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><span title="www.drugs.com"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/lacosamide.html">Monograph</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/MedlinePlus" title="MedlinePlus">MedlinePlus</a></th><td class="infobox-data"><span title="medlineplus.gov"><a rel="nofollow" class="external text" href="https://medlineplus.gov/druginfo/meds/a609028.html">a609028</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">License data</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"> <ul><li><small><abbr class="country-name" title="European Union">EU</abbr></small> <a href="/wiki/European_Medicines_Agency" title="European Medicines Agency">EMA</a>: <span title="www.ema.europa.eu: 'Lacosamide'"><a rel="nofollow" class="external text" href="https://www.ema.europa.eu/en/medicines/search_api_aggregation_ema_active_substance_and_inn_common_name/Lacosamide">by INN</a></span></li> <li><small><abbr class="country-name" title="United States">US</abbr></small> <a href="/wiki/DailyMed" title="DailyMed">DailyMed</a>: <span title="dailymed.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=Lacosamide">Lacosamide</a></span></li></ul></div> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy<br />category</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> B3<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/Oral_administration" title="Oral administration">By mouth</a>, <a href="/wiki/Intravenous_therapy" title="Intravenous therapy">intravenous</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a href="/wiki/ATC_code_N03" title="ATC code N03">N03AX18</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=N03AX18">WHO</a></span>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> <a href="/wiki/Standard_for_the_Uniform_Scheduling_of_Medicines_and_Poisons#Schedule_4" title="Standard for the Uniform Scheduling of Medicines and Poisons">S4</a> (Prescription only)<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="Brazil">BR</abbr>:</small> <a href="/wiki/Brazilian_Controlled_Drugs_and_Substances_Act#Class_C1" title="Brazilian Controlled Drugs and Substances Act">Class C1</a> (Other controlled substances)<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="United Kingdom">UK</abbr>:</small> <a href="/wiki/Prescription_drug" title="Prescription drug">POM</a> (Prescription only)</li> <li><small><abbr class="country-name" title="United States">US</abbr>:</small> <a href="/wiki/Controlled_Substances_Act#Schedule_V_drugs" title="Controlled Substances Act">Schedule V</a><sup id="cite_ref-Vimpat_FDA_label_5-0" class="reference"><a href="#cite_note-Vimpat_FDA_label-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="European Union">EU</abbr>:</small> Rx-only<sup id="cite_ref-Vimpat_EPAR_6-0" class="reference"><a href="#cite_note-Vimpat_EPAR-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">High</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination <span class="nowrap">half-life</span></a></th><td class="infobox-data">13 hours</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data"><a href="/wiki/Kidney" title="Kidney">Kidney</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;"><i>N</i><sup>2</sup>-acetyl-<i>N</i>-benzyl-<small>D</small>-homoserinamide</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=175481-36-4">175481-36-4</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/219078">219078</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Guide_to_Pharmacology" title="Guide to Pharmacology">IUPHAR/BPS</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=7472">7472</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB06218">DB06218</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.189902.html">189902</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/563KS2PQY5">563KS2PQY5</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D07299">D07299</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL58323">ChEMBL58323</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID1057666">DTXSID1057666</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q420077#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.112.805">100.112.805</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q420077#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>13</sub><span title="Hydrogen">H</span><sub>18</sub><span title="Nitrogen">N</span><sub>2</sub><span title="Oxygen">O</span><sub>3</sub></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002250298000000000♠"></span>250.298</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28N%5BC%40%40H%5D%28C%28%3DO%29NCc1ccccc1%29COC%29C">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">O=C(N[C@@H](C(=O)NCc1ccccc1)COC)C</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C13H18N2O3/c1-10(16)15-12(9-18-2)13(17)14-8-11-6-4-3-5-7-11/h3-7,12H,8-9H2,1-2H3,(H,14,17)(H,15,16)/t12-/m1/s1<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:VPPJLAIAVCUEMN-GFCCVEGCSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><span class="nobold"> <sup><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup> <a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">(what is this?)</a></span><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488" /><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477496955&page2=Lacosamide">(verify)</a></span></span></td></tr></tbody></table> <p><b>Lacosamide</b>, sold under the brand name <b>Vimpat</b> among others, is a <a href="/wiki/Medication" title="Medication">medication</a> used for the treatment of <a href="/wiki/Focal_seizures" class="mw-redirect" title="Focal seizures">partial-onset seizures</a> and primary generalized tonic-clonic seizures.<sup id="cite_ref-Vimpat_FDA_label_5-1" class="reference"><a href="#cite_note-Vimpat_FDA_label-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> It is used <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a> or <a href="/wiki/Intravenous" class="mw-redirect" title="Intravenous">intravenously</a>.<sup id="cite_ref-Vimpat_FDA_label_5-2" class="reference"><a href="#cite_note-Vimpat_FDA_label-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>It is available as a <a href="/wiki/Generic_medication" class="mw-redirect" title="Generic medication">generic medication</a>.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Lacosamide is <a href="/wiki/Indicated" class="mw-redirect" title="Indicated">indicated</a> for the treatment of partial-onset seizures and adjunctive therapy in the treatment of primary generalized tonic-clonic seizures.<sup id="cite_ref-Vimpat_FDA_label_5-3" class="reference"><a href="#cite_note-Vimpat_FDA_label-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Off-label_use">Off-label use</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=2" title="Edit section: Off-label use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As with other <a href="/wiki/Anti-epileptic_drugs" class="mw-redirect" title="Anti-epileptic drugs">anti-epileptic drugs</a> (AEDs), lacosamide may have a variety of off-label uses, including for <a href="/wiki/Pain_management" title="Pain management">pain management</a> and treatment of <a href="/wiki/Mental_health_disorders" class="mw-redirect" title="Mental health disorders">mental health disorders</a>. Lacosamide and other AEDs have been used off-label in the management of <a href="/wiki/Bipolar_disorder" title="Bipolar disorder">bipolar disorder</a>, cocaine addiction, <a href="/wiki/Dementia" title="Dementia">dementia</a>, <a href="/wiki/Depression_(mood)" title="Depression (mood)">depression</a>, <a href="/wiki/Diabetic_neuropathy" title="Diabetic neuropathy">diabetic peripheral neuropathy</a>, <a href="/wiki/Fibromyalgia" title="Fibromyalgia">fibromyalgia</a>, <a href="/wiki/Headache" title="Headache">headache</a>, <a href="/wiki/Hiccups" class="mw-redirect" title="Hiccups">hiccups</a>, <a href="/wiki/Huntington%27s_disease" title="Huntington's disease">Huntington's disease</a>, <a href="/wiki/Mania" title="Mania">mania</a>, <a href="/wiki/Migraine" title="Migraine">migraine</a>, <a href="/wiki/Obsessive-compulsive_disorder" class="mw-redirect" title="Obsessive-compulsive disorder">obsessive-compulsive disorder</a>, <a href="/wiki/Panic_disorder" title="Panic disorder">panic disorder</a>, <a href="/wiki/Restless_leg_syndrome" class="mw-redirect" title="Restless leg syndrome">restless leg syndrome</a>, and <a href="/wiki/Tinnitus" title="Tinnitus">tinnitus</a>. Combinations of AEDs are often employed for seizure reduction. Studies are underway for the use of lacosamide as a monotherapy for partial onset seizures, diabetic neuropathy, and fibromyalgia.<sup id="cite_ref-ncbi.nlm.nih.gov_9-0" class="reference"><a href="#cite_note-ncbi.nlm.nih.gov-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Contraindications">Contraindications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=3" title="Edit section: Contraindications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/FDA" class="mw-redirect" title="FDA">FDA</a> has assigned lacosamide to pregnancy category C. Animal studies have reported incidences of fetal mortality and growth deficit. Lacosamide has not been tested during human pregnancy, and should be administered with caution. In addition, it has not been determined whether the excretion of lacosamide occurs in breast milk.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=4" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Lacosamide was generally well tolerated in adult patients with partial-onset seizures.<sup id="cite_ref-lacosa_11-0" class="reference"><a href="#cite_note-lacosa-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> The side-effects most commonly leading to discontinuation were <a href="/wiki/Dizziness" title="Dizziness">dizziness</a>, <a href="/wiki/Ataxia" title="Ataxia">ataxia</a>, <a href="/wiki/Diplopia" title="Diplopia">diplopia</a> (double vision), <a href="/wiki/Nystagmus" title="Nystagmus">nystagmus</a>, <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Vertigo" title="Vertigo">vertigo</a> and <a href="/wiki/Drowsiness" class="mw-redirect" title="Drowsiness">drowsiness</a>. These adverse reactions were observed in at least 10% of patients.<sup id="cite_ref-Vimpat_FDA_label_5-4" class="reference"><a href="#cite_note-Vimpat_FDA_label-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Less common side-effects include <a href="/wiki/Tremor" title="Tremor">tremors</a>, <a href="/wiki/Blurred_vision" title="Blurred vision">blurred vision</a>, <a href="/wiki/Vomiting" title="Vomiting">vomiting</a> and <a href="/wiki/Headache" title="Headache">headache</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (March 2022)">medical citation needed</span></a></i>]</sup><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Gastrointestinal">Gastrointestinal</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=5" title="Edit section: Gastrointestinal"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A generally <a href="/wiki/Tolerability" title="Tolerability">well-tolerated</a> drug, the most commonly reported gastrointestinal side effects of lacosamide are <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>, and <a href="/wiki/Diarrhea" title="Diarrhea">diarrhea</a>.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Central_nervous_system">Central nervous system</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=6" title="Edit section: Central nervous system"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Dizziness" title="Dizziness">Dizziness</a> was the most common treatment-related adverse event. Other CNS effects are <a href="/wiki/Headache" title="Headache">headache</a>, <a href="/wiki/Drowsiness" class="mw-redirect" title="Drowsiness">drowsiness</a>, blurred vision, involuntary movements, memory problems, <a href="/wiki/Diplopia" title="Diplopia">diplopia</a> (double vision), trembling or shaking of the hands, unsteadiness, <a href="/wiki/Ataxia" title="Ataxia">ataxia</a>.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Psychiatric">Psychiatric</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=7" title="Edit section: Psychiatric"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Panic_attacks" class="mw-redirect" title="Panic attacks">Panic attacks</a>; agitation or <a href="/wiki/Psychomotor_agitation" title="Psychomotor agitation">restlessness</a>; <a href="/wiki/Irritability" title="Irritability">irritability</a> and <a href="/wiki/Aggression" title="Aggression">aggression</a>, <a href="/wiki/Anxiety" title="Anxiety">anxiety</a>, or <a href="/wiki/Depression_(mood)" title="Depression (mood)">depression</a>; <a href="/wiki/Suicidality" class="mw-redirect" title="Suicidality">suicidality</a>; <a href="/wiki/Insomnia" title="Insomnia">insomnia</a> and <a href="/wiki/Mania" title="Mania">mania</a>; altered mood; false and unusual sense of well-being. Lacosamide appears to have a low incidence of psychiatric side effects with psychosis reported in only 0.3% of patients.<sup id="cite_ref-ncbi.nlm.nih.gov_9-1" class="reference"><a href="#cite_note-ncbi.nlm.nih.gov-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cardiovascular">Cardiovascular</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=8" title="Edit section: Cardiovascular"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There is the risk of <a href="/wiki/Postural_hypotension" class="mw-redirect" title="Postural hypotension">postural hypotension</a> as well as <a href="/wiki/Arrythmia" class="mw-redirect" title="Arrythmia">arrhythmias</a>. In addition, there is the possibility of <a href="/wiki/Atrioventricular_block" title="Atrioventricular block">atrioventricular block</a>. There have also been post-marketing reports of lacosamide causing <a href="/wiki/Atrial_fibrillation" title="Atrial fibrillation">atrial fibrillation</a> and <a href="/wiki/Atrial_flutter" title="Atrial flutter">atrial flutter</a> in some populations, namely those with <a href="/wiki/Diabetic_neuropathy" title="Diabetic neuropathy">diabetic neuropathy</a>.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Allergies">Allergies</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=9" title="Edit section: Allergies"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There have been reports of <a href="/wiki/Rash" title="Rash">rash</a><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Pruritus" class="mw-redirect" title="Pruritus">pruritus</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Warnings">Warnings</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=10" title="Edit section: Warnings"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Suicidal behavior and ideation have been observed as early as one week after starting treatment with lacosamide, and is an <a href="/wiki/Adverse_reaction" class="mw-redirect" title="Adverse reaction">adverse reaction</a> to the use of most AEDs. In clinical trials with a medial treatment duration of 12 weeks, the incidence of suicidal ideation was 0.43% among 27,863 patients as opposed to 0.24% among 16,029 placebo-treated patients. Suicidal behavior was observed in 1 of every 530 patients treated.<sup id="cite_ref-ncbi.nlm.nih.gov_9-2" class="reference"><a href="#cite_note-ncbi.nlm.nih.gov-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="In_pregnancy">In pregnancy</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=11" title="Edit section: In pregnancy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In a study conducted to assess the <a href="/wiki/Teratogen" class="mw-redirect" title="Teratogen">teratogenic potential</a> of AEDs in the zebrafish embryo, the teratogenicity index of lacosamide was found to be higher than that of <a href="/wiki/Lamotrigine" title="Lamotrigine">lamotrigine</a>, <a href="/wiki/Levetiracetam" title="Levetiracetam">levetiracetam</a>, and <a href="/wiki/Ethosuximide" title="Ethosuximide">ethosuximide</a>. Lacosamide administration resulted in different malformations in the neonatal zebrafish depending on dosage.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Overdose">Overdose</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=12" title="Edit section: Overdose"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There is no known <a href="/wiki/Antidote" title="Antidote">antidote</a> in the event of an overdose.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=13" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=14" title="Edit section: Pharmacodynamics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Lacosamide is a functionalized amino acid that produces activity in the maximal electroshock seizure (MES) test, that, like some other <a href="/wiki/Antiepileptic_drugs" class="mw-redirect" title="Antiepileptic drugs">antiepileptic drugs</a> (AEDs), are believed to act through <a href="/wiki/Sodium_channel" title="Sodium channel">voltage-gated sodium channels</a>.<sup id="cite_ref-works.bepress.com_19-0" class="reference"><a href="#cite_note-works.bepress.com-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Lacosamide enhances the slow inactivation of voltage-gated sodium channels without affecting the fast inactivation of <a href="/wiki/Sodium_channel" title="Sodium channel">voltage-gated sodium channels</a>. This inactivation prevents the channel from opening, helping end the action potential. Many antiepileptic drugs, like <a href="/wiki/Carbamazepine" title="Carbamazepine">carbamazepine</a> or <a href="/wiki/Lamotrigine" title="Lamotrigine">lamotrigine</a>, slow the recovery from inactivation and hence reduce the ability of neurons to fire <a href="/wiki/Action_potentials" class="mw-redirect" title="Action potentials">action potentials</a>. Inactivation only occurs in neurons firing action potentials; this means that drugs that modulate fast inactivation selectively reduce the firing in active cells. Slow inactivation is similar but does not produce complete blockade of voltage gated sodium channels, with both activation and inactivation occurring over hundreds of milliseconds or more. Lacosamide makes this inactivation happen at less depolarized <a href="/wiki/Membrane_potential" title="Membrane potential">membrane potentials</a>. This means that lacosamide only affects neurons which are depolarized or active for long periods of time, typical of neurons at the focus of <a href="/wiki/Epilepsy" title="Epilepsy">epilepsy</a>.<sup id="cite_ref-pmid17940193_20-0" class="reference"><a href="#cite_note-pmid17940193-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Lacosamide administration results in the inhibition of repetitive neuronal firing, the stabilization of hyperexcitable neuronal membranes, and the reduction of long-term channel availability, but does not affect physiological function.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> Lacosamide has a dual mechanism of action. It also modulates <a href="/wiki/Collapsin_response_mediator_protein_family" title="Collapsin response mediator protein family">collapsin response mediator protein 2</a> (CRMP-2), preventing the formation of abnormal neuronal connections in the brain.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p>Lacosamide does not affect <a href="/wiki/AMPA_receptor" title="AMPA receptor">AMPA</a>, <a href="/wiki/Kainate_receptor" title="Kainate receptor">kainate</a>, <a href="/wiki/NMDA_receptor" title="NMDA receptor">NMDA</a>, <a href="/wiki/GABAA_receptor" title="GABAA receptor">GABA<sub>A</sub></a>, <a href="/wiki/GABA_B_receptor" class="mw-redirect" title="GABA B receptor">GABA<sub>B</sub></a> or a variety of <a href="/wiki/Dopaminergic" title="Dopaminergic">dopaminergic</a>, <a href="/wiki/Serotonin" title="Serotonin">serotonergic</a>, <a href="/wiki/Adrenergic" title="Adrenergic">adrenergic</a>, muscarinic or <a href="/wiki/Cannabinoid" title="Cannabinoid">cannabinoid</a> receptors and does not block potassium or calcium currents.<sup id="cite_ref-pmid16620882_23-0" class="reference"><a href="#cite_note-pmid16620882-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Lacosamide does not modulate the <a href="/wiki/Reuptake" title="Reuptake">reuptake</a> of <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitters</a> including <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a>, <a href="/wiki/Dopamine" title="Dopamine">dopamine</a>, and <a href="/wiki/Serotonin" title="Serotonin">serotonin</a>.<sup id="cite_ref-Beyreuther_21–42_24-0" class="reference"><a href="#cite_note-Beyreuther_21–42-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> In addition, it does not inhibit <a href="/wiki/4-aminobutyrate_transaminase" title="4-aminobutyrate transaminase">GABA transaminase</a>.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Preclinical_research">Preclinical research</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=15" title="Edit section: Preclinical research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In preclinical trials, the effect of lacosamide administration on animal models of <a href="/wiki/Epilepsy" title="Epilepsy">epilepsy</a> was tested using the Frings audiogenic seizures (AGS)-susceptible mouse model of seizure activity with an <a href="/wiki/Effective_dose_(pharmacology)" title="Effective dose (pharmacology)">effective dose</a> (ED<sub>50</sub>) of 0.63 mg/kg, <a href="/wiki/Intraperitoneal_injection" title="Intraperitoneal injection">i.p.</a>.<sup id="cite_ref-Beyreuther_2007_21–42_26-0" class="reference"><a href="#cite_note-Beyreuther_2007_21–42-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> The effect of lacosamide was also assessed using the MES test to detect inhibition of seizure spread.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> Lacosamide administration was successful in preventing the spread of seizures induced by MES in mice (ED<sub>50</sub> = 4.5 mg/kg, i.p.) and rats (ED<sub>50</sub> = 3.9 mg/kg, <a href="/wiki/Oral_administration" title="Oral administration">p.o.</a>).<sup id="cite_ref-Beyreuther_2007_21–42_26-1" class="reference"><a href="#cite_note-Beyreuther_2007_21–42-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> In preclinical trials, administration of lacosamide in combination with other AEDs resulted in synergistic anticonvulsant effects. Lacosamide produced effects in animal models of <a href="/wiki/Essential_tremor" title="Essential tremor">essential tremor</a>, <a href="/wiki/Tardive_dyskinesia" title="Tardive dyskinesia">tardive dyskinesia</a>, <a href="/wiki/Schizophrenia" title="Schizophrenia">schizophrenia</a>, and <a href="/wiki/Anxiety" title="Anxiety">anxiety</a>.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> Preclinical trials found the S-stereoisomer to be less potent than the R-stereoisomer in the treatment of seizures.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=16" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>When administered orally in healthy individuals, lacosamide is rapidly absorbed from the <a href="/wiki/Human_gastrointestinal_tract" class="mw-redirect" title="Human gastrointestinal tract">gastrointestinal tract</a>. Little of the drug is lost via the <a href="/wiki/First_pass_effect" title="First pass effect">first pass effect</a>, and thus has an oral <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> of nearly 100%.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> In adults, lacosamide demonstrates a low plasma protein binding of <15%, which reduces the potential for interaction with other drugs. Lacosamide is at its highest concentration in blood plasma approximately 1 to 4 hours after oral administration. Lacosamide has a half life of about 12–16 hours, which remains unchanged if the patients is also taking enzyme inducers. Consequently, the drug is administered twice per day at 12-hour intervals. Lacosamide is excreted renally, with 95% of the drug eliminated in the urine.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> 40% of the compound remains unchanged from its original structure, while the rest of the elimination product consists of metabolites of lacosamide. Just 0.5% of the drug is eliminated in the feces.<sup id="cite_ref-Lacosamide_33-0" class="reference"><a href="#cite_note-Lacosamide-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> The major metabolic pathway of lacosamide is CYP2C9, CY2C19, and CYP3A4-mediated <a href="/wiki/Demethylation" title="Demethylation">demethylation</a>.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Dose-response_relationship" class="mw-redirect" title="Dose-response relationship">dose-response curve</a> for lacosamide is linear and proportional for oral doses of up to 800 mg and intravenous doses of up to 300 mg.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Lacosamide has low potential for drug-drug interactions, and no pharmacokinetic interactions have been found to occur with other (AEDs) that act on sodium channels.<sup id="cite_ref-Therapeutic_Class_Review_36-0" class="reference"><a href="#cite_note-Therapeutic_Class_Review-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> A study on the binding of lacosamide to CRMP-2 in <i><a href="/wiki/Xenopus" title="Xenopus">Xenopus</a></i> oocytes showed both competitive and specific binding. Lacosamide has a K<sub>d</sub> value just under 5 μM and a B<sub>max</sub> of about 200 pM/mg.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Volume_of_distribution" title="Volume of distribution">volume of distribution</a> (V<sub>d</sub>) of lacosamide in plasma is 0.6 L/kg, which is close to the total volume of water. Lacosamide is ampiphilic and is thus <a href="/wiki/Hydrophilic" class="mw-redirect" title="Hydrophilic">hydrophilic</a> while also <a href="/wiki/Lipophilic" class="mw-redirect" title="Lipophilic">lipophilic</a> enough to cross the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood-brain barrier</a>.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=17" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Lacosamide is a powdery, white to light yellow crystalline compound. The chemical name of lacosamide is (<i>R</i>)-2-acetamido-<i>N</i>-benzyl-3-methoxypropionamide and the systemic name is <i>N2</i>-Acetyl-<i>N</i>-benzyl-<i>O</i>-methyl-<i>D</i>-serinamide.<sup id="cite_ref-Beyreuther_21–42_24-1" class="reference"><a href="#cite_note-Beyreuther_21–42-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> Lacosamide is a functionalized amino acid molecule that has high solubility in water and DMSO, with a solubility of 20.1 mg/mL in <a href="/wiki/Phosphate-buffered_saline" title="Phosphate-buffered saline">phosphate-buffered saline</a> (PBS, pH 7.5, 25 °C).<sup id="cite_ref-Beyreuther_21–42_24-2" class="reference"><a href="#cite_note-Beyreuther_21–42-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> The molecule has six rotatable bonds and one <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> ring. Lacosamide melts at 143-144 °C and boils at 536.447 °C at a pressure of 760 mmHg.<sup id="cite_ref-Lacosamide_33-1" class="reference"><a href="#cite_note-Lacosamide-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Synthesis">Synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=18" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The following three-step synthesis of lacosamide was proposed in 1996. </p><p><span class="mw-default-size skin-invert-image" typeof="mw:File"><a href="/wiki/File:Synthesis_of_Lacosamide.jpg" class="mw-file-description" title="500pm"><img alt="500pm" src="//upload.wikimedia.org/wikipedia/commons/9/90/Synthesis_of_Lacosamide.jpg" decoding="async" width="496" height="93" class="mw-file-element" data-file-width="496" data-file-height="93" /></a></span> </p><p>(<i>R</i>)-2-amino-3-hydroxypropanoic acid is treated with <a href="/wiki/Acetic_anhydride" title="Acetic anhydride">acetic anhydride</a> and <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>. The product is treated first with <i>N</i>-methylmorpholine, isobutyl chloroformate, and <a href="/wiki/Benzylamine" title="Benzylamine">benzylamine</a>, next with <a href="/wiki/Methyl_iodide" class="mw-redirect" title="Methyl iodide">methyl iodide</a> and <a href="/wiki/Silver_oxide" title="Silver oxide">silver oxide</a>, forming lacosamide.<sup id="cite_ref-pmid_8627614_42-0" class="reference"><a href="#cite_note-pmid_8627614-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p><p>More efficient routes to synthesis have been proposed in recent years, including the following.<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Lacosamide.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/df/Lacosamide.png/500px-Lacosamide.png" decoding="async" width="500" height="164" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/df/Lacosamide.png/750px-Lacosamide.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/df/Lacosamide.png/1000px-Lacosamide.png 2x" data-file-width="1739" data-file-height="570" /></a><figcaption>Lacosamide synthesis<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup></figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=19" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Lacosamide was discovered at the University of Houston in 1996.<sup id="cite_ref-pmid_8627614_42-1" class="reference"><a href="#cite_note-pmid_8627614-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> They hypothesized that modified amino acids may be therapeutically useful in the treatment of epilepsy. A few hundred such molecules were synthesized over several years and these were tested phenotypically in an epilepsy disease model performed in rats. N-benzyl-2-acetamido-3-methoxypropionamide was found to be highly efficacious in this model, with the biological activity traced specifically to its R enantiomer.<sup id="cite_ref-pmid_8627614_42-2" class="reference"><a href="#cite_note-pmid_8627614-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p><p>This compound was to become lacosamide after being licensed by Schwarz Pharma, which completed its pre-clinical and early clinical development. After its purchase of Schwarz Pharma in 2006, <a href="/wiki/UCB_(company)" title="UCB (company)">UCB</a> completed the clinical development program and obtained marketing approval for lacosamide. Its precise mechanism of action was unknown at the time of approval, and the exact amino acid targets involved remain uncertain to this day.<sup id="cite_ref-works.bepress.com_19-1" class="reference"><a href="#cite_note-works.bepress.com-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>The U.S. <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) accepted UCB's <a href="/wiki/New_Drug_Application" title="New Drug Application">New Drug Application</a> for lacosamide as of November 29, 2007, beginning the approval process for the drug.<sup id="cite_ref-press1_46-0" class="reference"><a href="#cite_note-press1-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> UCB also filed for marketing approval in the <a href="/wiki/European_Union" title="European Union">European Union</a> (EU); the <a href="/wiki/European_Medicines_Agency" title="European Medicines Agency">European Medicines Agency</a> accepted the marketing application for review in May 2007.<sup id="cite_ref-press1_46-1" class="reference"><a href="#cite_note-press1-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NeLM_48-0" class="reference"><a href="#cite_note-NeLM-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p><p>The drug was approved in the EU on September 3, 2008.<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> It was approved in the US on October 29, 2008.<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> The release of lacosamide was delayed owing to an objection about its placement into <a href="/wiki/Controlled_Substances_Act#Schedule_V_controlled_substances" title="Controlled Substances Act">schedule V</a> of the <a href="/wiki/Controlled_Substances_Act" title="Controlled Substances Act">Controlled Substances Act</a>. The FDA issued their final rule of placement into Schedule V on June 22, 2009.<sup id="cite_ref-fdarule_51-0" class="reference"><a href="#cite_note-fdarule-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p><p>Lacosamide's US <a href="/wiki/Patent" title="Patent">patent</a> expired on March 17, 2022.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Partial-onset_seizures">Partial-onset seizures</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=20" title="Edit section: Partial-onset seizures"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Lacosamide was tested in three placebo-controlled, <a href="/wiki/Double-blind" class="mw-redirect" title="Double-blind">double-blind</a>, <a href="/wiki/Randomized_controlled_trial" title="Randomized controlled trial">randomized</a> trials of at least 1300 patients.<sup id="cite_ref-Doty_56–68_53-0" class="reference"><a href="#cite_note-Doty_56–68-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> In a multi center, multinational, placebo-controlled, double-blind, randomized clinical trial conducted to determine the <a href="/wiki/Efficacy" title="Efficacy">efficacy</a> and safety of different doses of lacosamide on individuals with poorly controlled partial-onset seizures, lacosamide was found <a href="/wiki/Statistical_significance" title="Statistical significance">significantly</a> to reduce seizure frequency when given in addition to other antiepileptics, at doses of 400 and 600 milligrams a day.<sup id="cite_ref-Ben-Menachem_54-0" class="reference"><a href="#cite_note-Ben-Menachem-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Peripheral_neuropathy">Peripheral neuropathy</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=21" title="Edit section: Peripheral neuropathy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In a smaller trial of patients with <a href="/wiki/Diabetic_neuropathy" title="Diabetic neuropathy">diabetic neuropathy</a>, lacosamide also provided significantly better <a href="/wiki/Pain_management" title="Pain management">pain relief</a> when compared to <a href="/wiki/Placebo" title="Placebo">placebo</a>.<sup id="cite_ref-Rauck_55-0" class="reference"><a href="#cite_note-Rauck-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> Lacosamide administration in combination with 1-3 other AEDs was well tolerated in patients. Lacosamide administered at 400 mg/day was found to significantly reduce pain in patients with diabetic neuropathy in a multi center, double-blind, placebo-controlled Phase III trial with a treatment duration of 18 weeks.<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> </p><p>A small (n=24) study for <a href="/wiki/Small_fiber_peripheral_neuropathy" class="mw-redirect" title="Small fiber peripheral neuropathy">small fiber peripheral neuropathy</a> also showed positive results.<sup id="cite_ref-pmid30649227_57-0" class="reference"><a href="#cite_note-pmid30649227-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=22" title="Edit section: Society and culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Names">Names</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=23" title="Edit section: Names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Lacosamide is the international nonproprietary name (INN). It was formerly known as erlosamide, harkoseride, SPM-927, and ADD 234037.<sup id="cite_ref-Beyreuther_21–42_24-3" class="reference"><a href="#cite_note-Beyreuther_21–42-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>Lacosamide is sold under the brand name Vimpat by <a href="/wiki/UCB_(company)" title="UCB (company)">UCB</a>, and under the brand name Motpoly XR by Acute Pharmaceuticals.<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> In <a href="/wiki/Pakistan" title="Pakistan">Pakistan</a>, it is marketed by <a href="/wiki/G.D._Searle,_LLC" title="G.D. Searle, LLC">G.D. Searle</a> as Lacolit.<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=24" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Update plainlinks metadata ambox ambox-content ambox-Update" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Ambox_current_red_Americas.svg/42px-Ambox_current_red_Americas.svg.png" decoding="async" width="42" height="34" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Ambox_current_red_Americas.svg/63px-Ambox_current_red_Americas.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/53/Ambox_current_red_Americas.svg/84px-Ambox_current_red_Americas.svg.png 2x" data-file-width="360" data-file-height="290" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section needs to be <b>updated</b>.<span class="hide-when-compact"> Please help update this article to reflect recent events or newly available information.</span> <span class="date-container"><i>(<span class="date">March 2022</span>)</i></span></div></td></tr></tbody></table> <p>Clinical trials are underway for the use of lacosamide as monotherapy for partial-onset seizures.<sup id="cite_ref-Doty_56–68_53-1" class="reference"><a href="#cite_note-Doty_56–68-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> There is no evidence that lacosamide provides additional value over current antiepileptic drugs (AEDs) for the treatment of partial-onset seizures, but it may offer a safety advantage.<sup id="cite_ref-Therapeutic_Class_Review_36-1" class="reference"><a href="#cite_note-Therapeutic_Class_Review-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> Newer AEDs, including lacosamide, <a href="/wiki/Vigabatrin" title="Vigabatrin">vigabatrin</a>, <a href="/wiki/Felbamate" title="Felbamate">felbamate</a>, <a href="/wiki/Gabapentin" title="Gabapentin">gabapentin</a>, <a href="/wiki/Tiagabine" title="Tiagabine">tiagabine</a>, and <a href="/wiki/Rufinamide" title="Rufinamide">rufinamide</a> have been found to be more tolerable and safer than older drugs such as <a href="/wiki/Carbamazepine" title="Carbamazepine">carbamazepine</a>, <a href="/wiki/Phenytoin" title="Phenytoin">phenytoin</a>, and <a href="/wiki/Valproate" title="Valproate">valproate</a>.<sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=25" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external free" href="https://www.tga.gov.au/resources/auspar/auspar-lacosamide">https://www.tga.gov.au/resources/auspar/auspar-lacosamide</a></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external free" href="https://www.tga.gov.au/resources/prescription-medicines-registrations/lacosamide-interpharma-interpharma-pty-ltd">https://www.tga.gov.au/resources/prescription-medicines-registrations/lacosamide-interpharma-interpharma-pty-ltd</a></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external free" href="https://www.tga.gov.au/resources/artg/446110">https://www.tga.gov.au/resources/artg/446110</a></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFAnvisa2023" class="citation web cs1 cs1-prop-foreign-lang-source"><a href="/wiki/Brazilian_Health_Regulatory_Agency" title="Brazilian Health Regulatory Agency">Anvisa</a> (March 31, 2023). <a rel="nofollow" class="external text" href="https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992">"RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial"</a> [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). <a href="/wiki/Di%C3%A1rio_Oficial_da_Uni%C3%A3o" title="Diário Oficial da União">Diário Oficial da União</a> (published April 4, 2023). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992">Archived</a> from the original on August 3, 2023<span class="reference-accessdate">. Retrieved <span class="nowrap">August 16,</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=RDC+N%C2%BA+784+-+Listas+de+Subst%C3%A2ncias+Entorpecentes%2C+Psicotr%C3%B3picas%2C+Precursoras+e+Outras+sob+Controle+Especial&rft.pub=Di%C3%A1rio+Oficial+da+Uni%C3%A3o&rft.date=2023-03-31&rft.au=Anvisa&rft_id=https%3A%2F%2Fwww.in.gov.br%2Fen%2Fweb%2Fdou%2F-%2Fresolucao-rdc-n-784-de-31-de-marco-de-2023-474904992&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALacosamide" class="Z3988"></span></span> </li> <li id="cite_note-Vimpat_FDA_label-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-Vimpat_FDA_label_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Vimpat_FDA_label_5-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Vimpat_FDA_label_5-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Vimpat_FDA_label_5-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Vimpat_FDA_label_5-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9e79b42c-38a3-4b2c-a196-a5a1948250e2">"Vimpat- lacosamide tablet, film coated VIMPAT- lacosamide kit VIMPAT- lacosamide injection VIMPAT- lacosamide solution"</a>. <i>DailyMed</i>. 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Retrieved <span class="nowrap">March 24,</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=DailyMed&rft.atitle=Vimpat-+lacosamide+tablet%2C+film+coated+VIMPAT-+lacosamide+kit+VIMPAT-+lacosamide+injection+VIMPAT-+lacosamide+solution&rft.date=2021-12-13&rft_id=https%3A%2F%2Fdailymed.nlm.nih.gov%2Fdailymed%2FdrugInfo.cfm%3Fsetid%3D9e79b42c-38a3-4b2c-a196-a5a1948250e2&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALacosamide" class="Z3988"></span></span> </li> <li id="cite_note-Vimpat_EPAR-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-Vimpat_EPAR_6-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.ema.europa.eu/en/medicines/human/EPAR/vimpat">"Vimpat EPAR"</a>. <i>European Medicines Agency</i>. 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Retrieved <span class="nowrap">July 5,</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=professionals.optumrx.com&rft.atitle=Motpoly+XR+%28lacosamide%29+%E2%80%93+New+drug+approval&rft_id=https%3A%2F%2Fprofessionals.optumrx.com%2Fpublications%2Flibrary%2Fdrugapproval_motpolyxr_2023-0508.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALacosamide" class="Z3988"></span></span> </li> <li id="cite_note-60"><span class="mw-cite-backlink"><b><a href="#cite_ref-60">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.druginfosys.com//brand.aspx?code=44896">"Alternate brands of LACOLIT"</a>. <i>www.druginfosys.com</i><span class="reference-accessdate">. Retrieved <span class="nowrap">July 5,</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.druginfosys.com&rft.atitle=Alternate+brands+of+LACOLIT&rft_id=https%3A%2F%2Fwww.druginfosys.com%2F%2Fbrand.aspx%3Fcode%3D44896&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALacosamide" class="Z3988"></span></span> </li> <li id="cite_note-61"><span class="mw-cite-backlink"><b><a href="#cite_ref-61">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.medscape.com/viewarticle/747276">"Antiepileptic drugs"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150306042917/http://www.medscape.com/viewarticle/747276">Archived</a> from the original on March 6, 2015<span class="reference-accessdate">. Retrieved <span class="nowrap">April 2,</span> 2014</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Antiepileptic+drugs&rft_id=http%3A%2F%2Fwww.medscape.com%2Fviewarticle%2F747276&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALacosamide" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lacosamide&action=edit&section=26" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDean2018" class="citation book cs1">Dean L (2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/books/NBK493589/">"Lacosamide Therapy and CYP2C19 Genotype"</a>. In Pratt VM, McLeod HL, Rubinstein WS, Scott SA, Dean LC, Kattman BL, et al. (eds.). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/books/NBK61999/"><i>Medical Genetics Summaries</i></a>. <a href="/wiki/National_Center_for_Biotechnology_Information" title="National Center for Biotechnology Information">National Center for Biotechnology Information</a> (NCBI). <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/29671994">29671994</a>. Bookshelf ID: NBK493589.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Lacosamide+Therapy+and+CYP2C19+Genotype&rft.btitle=Medical+Genetics+Summaries&rft.pub=National+Center+for+Biotechnology+Information+%28NCBI%29&rft.date=2018&rft_id=info%3Apmid%2F29671994&rft.aulast=Dean&rft.aufirst=L&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fbooks%2FNBK493589%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALacosamide" class="Z3988"></span></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl 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.navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /></div><div role="navigation" class="navbox" aria-labelledby="Anticonvulsants_(N03)431" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Anticonvulsants" title="Template:Anticonvulsants"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Anticonvulsants" title="Template talk:Anticonvulsants"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Anticonvulsants" title="Special:EditPage/Template:Anticonvulsants"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Anticonvulsants_(N03)431" style="font-size:114%;margin:0 4em"><a href="/wiki/Anticonvulsant" title="Anticonvulsant">Anticonvulsants</a> (<a href="/wiki/ATC_code_N03" title="ATC code N03">N03</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/GABAergic" title="GABAergic">GABAergics</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/GABAA_receptor" title="GABAA receptor">GABA<sub>A</sub>R</a> <a href="/wiki/Allosteric_modulator" title="Allosteric modulator">PAMs</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a>:</b> <a href="/wiki/Barbexaclone" title="Barbexaclone">Barbexaclone</a></li> <li><a href="/wiki/Metharbital" title="Metharbital">Metharbital</a></li> <li><a href="/wiki/Methylphenobarbital" title="Methylphenobarbital">Methylphenobarbital</a></li> <li><a href="/wiki/Pentobarbital" title="Pentobarbital">Pentobarbital</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a><sup>#</sup></li> <li><a href="/wiki/Primidone" title="Primidone">Primidone</a>; <b><a href="/wiki/Carbamate" title="Carbamate">Carbamates</a></b>: <a href="/wiki/Cenobamate" title="Cenobamate">Cenobamate</a></li> <li><a href="/wiki/Felbamate" title="Felbamate">Felbamate</a>; <b><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a></b>: <a href="/wiki/Clobazam" title="Clobazam">Clobazam</a></li> <li><a href="/wiki/Clonazepam" title="Clonazepam">Clonazepam</a></li> <li><a href="/wiki/Clorazepate" title="Clorazepate">Clorazepate</a></li> <li><a href="/wiki/Diazepam" title="Diazepam">Diazepam</a><sup>#</sup></li> <li><a href="/wiki/Lorazepam" title="Lorazepam">Lorazepam</a><sup>#</sup></li> <li><a href="/wiki/Midazolam" title="Midazolam">Midazolam</a></li> <li><a href="/wiki/Nimetazepam" title="Nimetazepam">Nimetazepam</a></li> <li><a href="/wiki/Nitrazepam" title="Nitrazepam">Nitrazepam</a></li> <li><a href="/wiki/Temazepam" title="Temazepam">Temazepam</a>; <b>Others:</b> <a href="/wiki/Bromide" title="Bromide">Bromide</a> (<a href="/wiki/Potassium_bromide" title="Potassium bromide">potassium bromide</a>, <a href="/wiki/Sodium_bromide" title="Sodium bromide">sodium bromide</a>)</li> <li><a href="/wiki/Imepitoin" title="Imepitoin">Imepitoin</a></li> <li><a href="/wiki/Paraldehyde" title="Paraldehyde">Paraldehyde</a></li> <li><a href="/wiki/Stiripentol" title="Stiripentol">Stiripentol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/GABA_transaminase_inhibitor" title="GABA transaminase inhibitor">GABA-T inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/Fatty_acid" title="Fatty acid">Fatty acids</a> (and related):</b> <a href="/wiki/Valproate" title="Valproate">Valproate</a></li> <li><a href="/wiki/Valpromide" title="Valpromide">Valpromide</a></li> <li><a href="/wiki/Valproate_pivoxil" title="Valproate pivoxil">Valproate pivoxil</a></li> <li><a href="/wiki/Vigabatrin" title="Vigabatrin">Vigabatrin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/GABA_receptor_agonist" title="GABA receptor agonist">GABAR agonists</a></b>: <a href="/wiki/Progabide" title="Progabide">Progabide</a>; <b><a href="/wiki/GABA_reuptake_inhibitor" title="GABA reuptake inhibitor">GAT-1 inhibitors</a>:</b> <a href="/wiki/Tiagabine" title="Tiagabine">Tiagabine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Channel_modulator" title="Channel modulator">Channel<br />modulators</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sodium_channel_blocker" title="Sodium channel blocker">Sodium blockers</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/Hydantoin" title="Hydantoin">Hydantoins</a>:</b> <a href="/wiki/Ethotoin" title="Ethotoin">Ethotoin</a></li> <li><a href="/wiki/Fosphenytoin" title="Fosphenytoin">Fosphenytoin</a></li> <li><a href="/wiki/Mephenytoin" title="Mephenytoin">Mephenytoin</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a><sup>#</sup>; <b><a href="/wiki/Acylurea" title="Acylurea">Ureides</a>:</b> <a href="/w/index.php?title=Acetylpheneturide&action=edit&redlink=1" class="new" title="Acetylpheneturide (page does not exist)">Acetylpheneturide</a></li> <li><a href="/wiki/Chlorphenacemide" title="Chlorphenacemide">Chlorphenacemide</a></li> <li><a href="/wiki/Phenacemide" title="Phenacemide">Phenacemide</a><sup>‡</sup></li> <li><a href="/wiki/Pheneturide" title="Pheneturide">Pheneturide</a>; <b><a href="/wiki/Fatty_acid" title="Fatty acid">Fatty acids</a>:</b> <a href="/wiki/Valproate" title="Valproate">Valproate</a></li> <li><a href="/wiki/Valpromide" title="Valpromide">Valpromide</a></li> <li><a href="/wiki/Valproate_pivoxil" title="Valproate pivoxil">Valproate pivoxil</a>; <b><a href="/wiki/Carboxamide" class="mw-redirect" title="Carboxamide">Carboxamides</a>:</b></li> <li><a href="/wiki/Carbamazepine" title="Carbamazepine">Carbamazepine</a><sup>#</sup></li> <li><a href="/wiki/Eslicarbazepine_acetate" title="Eslicarbazepine acetate">Eslicarbazepine acetate</a></li> <li><a href="/wiki/Oxcarbazepine" title="Oxcarbazepine">Oxcarbazepine</a>; <b>Others:</b> <a class="mw-selflink selflink">Lacosamide</a></li> <li><a href="/wiki/Lamotrigine" title="Lamotrigine">Lamotrigine</a><sup>#</sup></li> <li><a href="/wiki/Rufinamide" title="Rufinamide">Rufinamide</a></li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><a href="/wiki/Zonisamide" title="Zonisamide">Zonisamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Calcium_channel_blocker" title="Calcium channel blocker">Calcium blockers</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/2,4-Oxazolidinedione" title="2,4-Oxazolidinedione">Oxazolidinediones</a>:</b> <a href="/wiki/Ethadione" title="Ethadione">Ethadione</a></li> <li><a href="/wiki/Paramethadione" title="Paramethadione">Paramethadione</a></li> <li><a href="/wiki/Trimethadione" title="Trimethadione">Trimethadione</a>; <b><a href="/wiki/Succinimide" title="Succinimide">Succinimides</a></b>: <a href="/wiki/Ethosuximide" title="Ethosuximide">Ethosuximide</a><sup>#</sup></li> <li><a href="/wiki/Mesuximide" title="Mesuximide">Mesuximide</a></li> <li><a href="/wiki/Phensuximide" title="Phensuximide">Phensuximide</a>; <b><a href="/wiki/Gabapentinoid" title="Gabapentinoid">Gabapentinoids</a>:</b> <a href="/wiki/Gabapentin" title="Gabapentin">Gabapentin</a></li> <li><a href="/wiki/Pregabalin" title="Pregabalin">Pregabalin</a>; <b>Others:</b> <a href="/wiki/Imepitoin" title="Imepitoin">Imepitoin</a></li> <li><a href="/wiki/Lamotrigine" title="Lamotrigine">Lamotrigine</a><sup>#</sup></li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><a href="/wiki/Zonisamide" title="Zonisamide">Zonisamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Potassium_channel_opener" title="Potassium channel opener">Potassium openers</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Retigabine" title="Retigabine">Retigabine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonic_anhydrase_inhibitor" title="Carbonic anhydrase inhibitor">CA inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/Sulfonamide_(medicine)#Anticonvulsant" title="Sulfonamide (medicine)">Sulfonamides</a>:</b> <a href="/wiki/Acetazolamide" title="Acetazolamide">Acetazolamide</a></li> <li><a href="/wiki/Ethoxzolamide" title="Ethoxzolamide">Ethoxzolamide</a></li> <li><a href="/wiki/Sultiame" title="Sultiame">Sultiame</a></li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><a href="/wiki/Zonisamide" title="Zonisamide">Zonisamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Albutoin" title="Albutoin">Albutoin</a></li> <li><a href="/wiki/Beclamide" title="Beclamide">Beclamide</a></li> <li><a href="/wiki/Brivaracetam" title="Brivaracetam">Brivaracetam</a></li> <li><a href="/wiki/Cannabidiol" title="Cannabidiol">Cannabidiol</a></li> <li><a href="/wiki/Carisbamate" title="Carisbamate">Carisbamate</a></li> <li><a href="/wiki/Etiracetam" title="Etiracetam">Etiracetam</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a></li> <li><a href="/wiki/Ganaxolone" title="Ganaxolone">Ganaxolone</a></li> <li><a href="/wiki/Levetiracetam" title="Levetiracetam">Levetiracetam</a></li> <li><a href="/wiki/Perampanel" title="Perampanel">Perampanel</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Neuropathic_pain_and_fibromyalgia_pharmacotherapies131" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Neuropathic_pain_and_fibromyalgia_pharmacotherapies" title="Template:Neuropathic pain and fibromyalgia pharmacotherapies"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Neuropathic_pain_and_fibromyalgia_pharmacotherapies" title="Template talk:Neuropathic pain and fibromyalgia pharmacotherapies"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Neuropathic_pain_and_fibromyalgia_pharmacotherapies" title="Special:EditPage/Template:Neuropathic pain and fibromyalgia pharmacotherapies"><abbr 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height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Serotonin–norepinephrine reuptake inhibitor</span> (e.g., <a href="/wiki/Duloxetine" title="Duloxetine">duloxetine</a>, <a href="/wiki/Milnacipran" title="Milnacipran">milnacipran</a>)</li> <li><a href="/wiki/Tricyclic_antidepressants" class="mw-redirect" title="Tricyclic antidepressants"><abbr title="Tricyclic antidepressants">TCAs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Tricyclic antidepressants</span> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a>, <a href="/wiki/Nortriptyline" title="Nortriptyline">nortriptyline</a>, <a href="/wiki/Dosulepin" title="Dosulepin">dosulepin</a>)</li> <li><a href="/wiki/Opioid" title="Opioid">Opioid</a> <a href="/wiki/Monoamine_reuptake_inhibitors" class="mw-redirect" title="Monoamine reuptake inhibitors"><abbr title="monoamine reuptake inhibitors">MRIs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip monoamine reuptake inhibitors</span> (e.g., <a href="/wiki/Tapentadol" title="Tapentadol">tapentadol</a>, <a href="/wiki/Tramadol" title="Tramadol">tramadol</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ion_channel_blocker" class="mw-redirect" title="Ion channel blocker">Ion channel blockers</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anticonvulsant" title="Anticonvulsant">Anticonvulsants</a> (e.g., <a href="/wiki/Gabapentin" title="Gabapentin">gabapentin</a>, <a href="/wiki/Pregabalin" title="Pregabalin">pregabalin</a>, <a href="/wiki/Mirogabalin" title="Mirogabalin">mirogabalin</a>, <a href="/wiki/Carbamazepine" title="Carbamazepine">carbamazepine</a>, <a href="/wiki/Oxcarbazepine" title="Oxcarbazepine">oxcarbazepine</a>, <a class="mw-selflink selflink">lacosamide</a>, <a href="/wiki/Lamotrigine" title="Lamotrigine">lamotrigine</a>)</li> <li><a href="/wiki/Local_anesthetic" title="Local anesthetic">Local anesthetics</a> (e.g., <a href="/wiki/Lidocaine" title="Lidocaine">lidocaine</a>)</li> <li><a href="/wiki/Mexiletine" title="Mexiletine">Mexiletine</a></li> <li><a href="/wiki/Tricyclic_antidepressants" class="mw-redirect" title="Tricyclic antidepressants"><abbr title="Tricyclic antidepressants">TCAs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Tricyclic antidepressants</span> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a>, <a href="/wiki/Nortriptyline" title="Nortriptyline">nortriptyline</a>, <a href="/wiki/Desipramine" title="Desipramine">desipramine</a>)</li> <li><a href="/wiki/Ziconotide" title="Ziconotide">Ziconotide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alpha_lipoic_acid" class="mw-redirect" title="Alpha lipoic acid">Alpha lipoic acid</a></li> <li><a href="/wiki/Benfotiamine" title="Benfotiamine">Benfotiamine</a></li> <li><a href="/wiki/Botulinum_toxin_A" class="mw-redirect" title="Botulinum toxin A">Botulinum toxin A</a></li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/Cannabinoid" 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