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Available in 14 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-14" 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">14 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 mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%85%D9%8A%D8%A8%D9%8A%D9%81%D8%A7%D9%83%D8%A7%D9%8A%D9%8A%D9%86" title="ميبيفاكايين – Arabic" lang="ar" hreflang="ar" data-title="ميبيفاكايين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Mepifacain" title="Mepifacain – Welsh" lang="cy" hreflang="cy" data-title="Mepifacain" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Mepivacain" title="Mepivacain – German" lang="de" hreflang="de" data-title="Mepivacain" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Mepivaca%C3%ADna" title="Mepivacaína – Spanish" lang="es" hreflang="es" data-title="Mepivacaína" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%85%D9%BE%DB%8C%E2%80%8C%D9%88%D8%A7%DA%A9%D8%A7%D8%A6%DB%8C%D9%86" title="مپی‌واکائین – Persian" lang="fa" hreflang="fa" data-title="مپی‌واکائین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/M%C3%A9pivaca%C3%AFne" title="Mépivacaïne – French" lang="fr" hreflang="fr" data-title="Mépivacaïne" 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/Mepivacaina" title="Mepivacaina – Italian" lang="it" hreflang="it" data-title="Mepivacaina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%A1%E3%83%94%E3%83%90%E3%82%AB%E3%82%A4%E3%83%B3" title="メピバカイン – Japanese" lang="ja" hreflang="ja" data-title="メピバカイン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Mepivaca%C3%ADna" title="Mepivacaína – Portuguese" lang="pt" hreflang="pt" data-title="Mepivacaína" 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/Mepivacain%C4%83" title="Mepivacaină – Romanian" lang="ro" hreflang="ro" data-title="Mepivacaină" 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/Mepivakain" title="Mepivakain – Serbian" lang="sr" hreflang="sr" data-title="Mepivakain" 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/Mepivakain" title="Mepivakain – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Mepivakain" 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-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9C%D0%B5%D0%BF%D1%96%D0%B2%D0%B0%D0%BA%D0%B0%D1%97%D0%BD" title="Мепівакаїн – Ukrainian" lang="uk" hreflang="uk" data-title="Мепівакаїн" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Mepivacaine" title="Mepivacaine – Vietnamese" lang="vi" hreflang="vi" data-title="Mepivacaine" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q416760#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul 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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): Mepivacaine">Mepivacaine</span></caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Mepivacaine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a8/Mepivacaine.svg/220px-Mepivacaine.svg.png" decoding="async" width="220" height="131" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a8/Mepivacaine.svg/330px-Mepivacaine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a8/Mepivacaine.svg/440px-Mepivacaine.svg.png 2x" data-file-width="445" data-file-height="265" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></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/cdi/mepivacaine.html">Consumer Drug Information</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/a603026.html">a603026</a></span></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"><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>C, use w/ caution, may cause fetal <a href="/wiki/Bradycardia" title="Bradycardia">bradycardia</a></li></ul> </div></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_N01" title="ATC code N01">N01BB03</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=N01BB03">WHO</a></span>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">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>RS</i>)-<i>N</i>-(2,6-dimethylphenyl)- 1-methyl-piperidine-2-carboxamide</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=96-88-8">96-88-8</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/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/4062">4062</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=7224">7224</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/DB00961">DB00961</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.3922.html">3922</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/B6E06QE59J">B6E06QE59J</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/D08181">D08181</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/ChEBI" title="ChEBI">ChEBI</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/chebi/searchId.do?chebiId=CHEBI:6759">CHEBI:6759</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/ChEMBL1087">ChEMBL1087</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/DTXSID9023259">DTXSID9023259</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q416760#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/100.002.313">100.002.313</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q416760#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">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>15</sub><span title="Hydrogen">H</span><sub>22</sub><span title="Nitrogen">N</span><sub>2</sub><span title="Oxygen">O</span></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="7002246354000000000♠"></span>246.354</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%28Nc1c%28cccc1C%29C%29C2N%28C%29CCCC2">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(Nc1c(cccc1C)C)C2N(C)CCCC2</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/C15H22N2O/c1-11-7-6-8-12(2)14(11)16-15(18)13-9-4-5-10-17(13)3/h6-8,13H,4-5,9-10H2,1-3H3,(H,16,18)<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:INWLQCZOYSRPNW-UHFFFAOYSA-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">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=462248547&page2=Mepivacaine">(verify)</a></span></span></td></tr></tbody></table> <p><b>Mepivacaine</b> <span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="'m' in 'my'">m</span><span title="/ɛ/: 'e' in 'dress'">ɛ</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'p' in 'pie'">p</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'v' in 'vie'">v</span><span title="/ə/: 'a' in 'about'">ə</span><span title="'k' in 'kind'">k</span><span title="/eɪ/: 'a' in 'face'">eɪ</span><span title="'n' in 'nigh'">n</span></span>/</a></span></span> is a <a href="/wiki/Local_anesthetic" title="Local anesthetic">local anesthetic</a><sup id="cite_ref-pmid17195831_1-0" class="reference"><a href="#cite_note-pmid17195831-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> of the amide type. Mepivacaine has a reasonably rapid onset (less rapid than that of <a href="/wiki/Procaine" title="Procaine">procaine</a>) and medium duration of action (longer than that of procaine)<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> and is marketed under various <a href="/wiki/Trade_name" title="Trade name">trade names</a> including <b>Carbocaine</b> and <b>Polocaine</b>. </p><p>Mepivacaine became available in the <a href="/wiki/United_States" title="United States">United States</a> in the 1960s. </p><p>Mepivacaine is used in any infiltration and <a href="/wiki/Local_anesthesia" title="Local anesthesia">local anesthesia</a>. </p><p>It is supplied as the hydrochloride salt of the <a href="/wiki/Racemate" class="mw-redirect" title="Racemate">racemate</a>,<sup id="cite_ref-pmid8989005_4-0" class="reference"><a href="#cite_note-pmid8989005-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> which consists of R(-)-mepivacaine and S(+)-mepivacaine in equal proportions. These two enantiomers have markedly different pharmacokinetic properties.<sup id="cite_ref-pmid8989005_4-1" class="reference"><a href="#cite_note-pmid8989005-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>Mepivacaine was originally synthesized in Sweden at the laboratory of <a href="/wiki/Bofors_Nobelkrut" class="mw-redirect" title="Bofors Nobelkrut">Bofors Nobelkrut</a> in 1956.<sup id="cite_ref-Castrén_1963_5-0" class="reference"><a href="#cite_note-Castrén_1963-5"><span class="cite-bracket">[</span>5<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=Mepivacaine&action=edit&section=1" 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"><ol class="references"> <li id="cite_note-pmid17195831-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid17195831_1-0">^</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="CITEREFPortoVasconcelosGomesAlbert2007" class="citation journal cs1">Porto GG, Vasconcelos BC, Gomes AC, Albert D (January 2007). <a rel="nofollow" class="external text" href="http://www.medicinaoral.com/medoralfree01/v12i1/medoralv12i1p60.pdf">"Evaluation of lidocaine and mepivacaine for inferior third molar surgery"</a> <span class="cs1-format">(PDF)</span>. <i>Medicina oral, patología oral y cirugía bucal</i>. <b>12</b> (1): E60–4. <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/17195831">17195831</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Medicina+oral%2C+patolog%C3%ADa+oral+y+cirug%C3%ADa+bucal&rft.atitle=Evaluation+of+lidocaine+and+mepivacaine+for+inferior+third+molar+surgery&rft.volume=12&rft.issue=1&rft.pages=E60-4&rft.date=2007-01&rft_id=info%3Apmid%2F17195831&rft.aulast=Porto&rft.aufirst=GG&rft.au=Vasconcelos%2C+BC&rft.au=Gomes%2C+AC&rft.au=Albert%2C+D&rft_id=http%3A%2F%2Fwww.medicinaoral.com%2Fmedoralfree01%2Fv12i1%2Fmedoralv12i1p60.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMepivacaine" class="Z3988"></span></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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://go.drugbank.com/drugs/DB00721">"Procaine"</a>. <i>go.drugbank.com</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2023-06-27</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=go.drugbank.com&rft.atitle=Procaine&rft_id=https%3A%2F%2Fgo.drugbank.com%2Fdrugs%2FDB00721&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMepivacaine" class="Z3988"></span></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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://go.drugbank.com/drugs/DB00961">"Mepivacaine"</a>. <i>go.drugbank.com</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2023-06-27</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=go.drugbank.com&rft.atitle=Mepivacaine&rft_id=https%3A%2F%2Fgo.drugbank.com%2Fdrugs%2FDB00961&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMepivacaine" class="Z3988"></span></span> </li> <li id="cite_note-pmid8989005-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid8989005_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid8989005_4-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBurmCohenvan_KleefVletter1997" class="citation journal cs1">Burm AG, Cohen IM, van Kleef JW, Vletter AA, Olieman W, Groen K (January 1997). <a rel="nofollow" class="external text" href="https://doi.org/10.1097%2F00000539-199701000-00016">"Pharmacokinetics of the enantiomers of mepivacaine after intravenous administration of the racemate in volunteers"</a>. <i>Anesthesia & Analgesia</i>. <b>84</b> (1): 85–9. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1097%2F00000539-199701000-00016">10.1097/00000539-199701000-00016</a></span>. <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/8989005">8989005</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:22363370">22363370</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Anesthesia+%26+Analgesia&rft.atitle=Pharmacokinetics+of+the+enantiomers+of+mepivacaine+after+intravenous+administration+of+the+racemate+in+volunteers&rft.volume=84&rft.issue=1&rft.pages=85-9&rft.date=1997-01&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A22363370%23id-name%3DS2CID&rft_id=info%3Apmid%2F8989005&rft_id=info%3Adoi%2F10.1097%2F00000539-199701000-00016&rft.aulast=Burm&rft.aufirst=AG&rft.au=Cohen%2C+IM&rft.au=van+Kleef%2C+JW&rft.au=Vletter%2C+AA&rft.au=Olieman%2C+W&rft.au=Groen%2C+K&rft_id=https%3A%2F%2Fdoi.org%2F10.1097%252F00000539-199701000-00016&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMepivacaine" class="Z3988"></span></span> </li> <li id="cite_note-Castrén_1963-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-Castrén_1963_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCastrén1963" class="citation journal cs1">Castrén, J.A. (1963). "A clinical evaluation of mepivacaine (Carbocain) in ocular surgery". <i>Acta Ophthalmologica</i>. <b>41</b> (3): 262–9. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1755-3768.1963.tb02436.x">10.1111/j.1755-3768.1963.tb02436.x</a>. <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/14047466">14047466</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:32119846">32119846</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Ophthalmologica&rft.atitle=A+clinical+evaluation+of+mepivacaine+%28Carbocain%29+in+ocular+surgery&rft.volume=41&rft.issue=3&rft.pages=262-9&rft.date=1963&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A32119846%23id-name%3DS2CID&rft_id=info%3Apmid%2F14047466&rft_id=info%3Adoi%2F10.1111%2Fj.1755-3768.1963.tb02436.x&rft.aulast=Castr%C3%A9n&rft.aufirst=J.A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMepivacaine" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mepivacaine&action=edit&section=2" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" 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<ul><li><a href="/wiki/Benzocaine" title="Benzocaine">Benzocaine</a></li> <li><a href="/wiki/Benzonatate" title="Benzonatate">Benzonatate</a></li> <li><a href="/wiki/Butacaine" title="Butacaine">Butacaine</a></li> <li><a href="/wiki/Butamben" title="Butamben">Butamben</a></li> <li><a href="/wiki/Chloroprocaine" title="Chloroprocaine">Chloroprocaine</a></li> <li><a href="/wiki/Dimethocaine" title="Dimethocaine">Dimethocaine</a></li> <li><a href="/wiki/Lucaine" class="mw-redirect" title="Lucaine">Lucaine</a></li> <li><a href="/wiki/Meprylcaine" title="Meprylcaine">Meprylcaine</a></li> <li><a href="/wiki/Metabutethamine" title="Metabutethamine">Metabutethamine</a></li> <li><a href="/wiki/Metabutoxycaine" title="Metabutoxycaine">Metabutoxycaine</a></li> <li><a href="/wiki/Nitracaine" title="Nitracaine">Nitracaine</a></li> <li><a href="/wiki/Orthocaine" title="Orthocaine">Orthocaine</a></li> <li><a href="/wiki/Propoxycaine" title="Propoxycaine">Propoxycaine</a></li> <li><a href="/wiki/Procaine" title="Procaine">Procaine (Novocaine)</a></li> <li><a href="/wiki/Proxymetacaine" title="Proxymetacaine">Proxymetacaine</a></li> <li><a href="/wiki/Risocaine" title="Risocaine">Risocaine</a></li> <li><a href="/wiki/Tetracaine" title="Tetracaine">Tetracaine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Benzoic_acid" title="Benzoic acid">Benzoic</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/Amylocaine" title="Amylocaine">Amylocaine</a></li> <li><a href="/wiki/Cocaine" title="Cocaine">Cocaine</a></li> <li><a href="/wiki/Cyclomethycaine" title="Cyclomethycaine">Cyclomethycaine</a></li> <li><a href="/wiki/Alpha-Eucaine" class="mw-redirect" title="Alpha-Eucaine">α-Eucaine</a></li> <li><a href="/wiki/Eucaine" title="Eucaine">β-Eucaine</a></li> <li><a href="/wiki/Hexylcaine" title="Hexylcaine">Hexylcaine</a></li> <li><a href="/wiki/Isobucaine" title="Isobucaine">Isobucaine</a></li> <li><a href="/wiki/Piperocaine" title="Piperocaine">Piperocaine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">ArCO2- (not para-amino or Ph)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Amoproxan&action=edit&redlink=1" class="new" title="Amoproxan (page does not exist)">Amoproxan</a> (3,4,5-Trimethoxybenzoyl)</li> <li><a href="/wiki/3-(p-Fluorobenzoyloxy)tropane" title="3-(p-Fluorobenzoyloxy)tropane">3-(p-Fluorobenzoyloxy)tropane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Amide" title="Amide">Amides</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/Articaine" title="Articaine">Articaine</a></li> <li><a href="/wiki/Bupivacaine" title="Bupivacaine">Bupivacaine</a><sup>#</sup>/<a href="/wiki/Levobupivacaine" title="Levobupivacaine">Levobupivacaine</a>/<a href="/wiki/Ropivacaine" title="Ropivacaine">Ropivacaine</a></li> <li><a href="/wiki/Butanilicaine" title="Butanilicaine">Butanilicaine</a></li> <li><a href="/wiki/Articaine" title="Articaine">Carticaine</a></li> <li><a href="/wiki/Cinchocaine" title="Cinchocaine"> Cinchocaine (Dibucaine)</a></li> <li><a href="/wiki/Etidocaine" title="Etidocaine">Etidocaine</a></li> <li><a href="/wiki/Lidocaine" title="Lidocaine">Lidocaine</a><sup>#</sup></li> <li><a class="mw-selflink selflink">Mepivacaine</a></li> <li><a href="/wiki/Prilocaine" title="Prilocaine">Prilocaine</a></li> <li><a href="/wiki/Trimecaine" title="Trimecaine">Trimecaine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Combinations</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/Local_anesthetic_with_vasoconstrictor" class="mw-redirect" title="Local anesthetic with vasoconstrictor">Anesthetic/vasoconstrictor</a></li> <li><a href="/wiki/Bupivacaine/meloxicam" title="Bupivacaine/meloxicam">Bupivacaine/meloxicam</a></li> <li><a href="/wiki/Lidocaine/prilocaine" title="Lidocaine/prilocaine">Lidocaine/prilocaine</a></li> <li><a href="/wiki/Topical_tac" title="Topical tac">TAC</a></li> <li><a href="/wiki/Iontocaine" title="Iontocaine">Iontocaine</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background:transparent;padding:0;"><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> <style data-mw-deduplicate="TemplateStyles:r1012311289">.mw-parser-output .asbox{position:relative;overflow:hidden}.mw-parser-output .asbox table{background:transparent}.mw-parser-output .asbox p{margin:0}.mw-parser-output .asbox p+p{margin-top:0.25em}.mw-parser-output .asbox-body{font-style:italic}.mw-parser-output .asbox-note{font-size:smaller}.mw-parser-output .asbox .navbar{position:absolute;top:-0.75em;right:1em;display:none}</style><div role="note" class="metadata plainlinks asbox stub"><table role="presentation"><tbody><tr class="noresize"><td><span typeof="mw:File"><a href="/wiki/File:Diazepam-from-xtal-3D-vdW.png" class="mw-file-description"><img alt="Stub icon" 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