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id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 38 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-38" 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">38 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Bensielpenisillien" title="Bensielpenisillien – Afrikaans" lang="af" hreflang="af" data-title="Bensielpenisillien" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A8%D9%86%D8%B2%D9%8A%D9%84_%D8%A8%D9%86%D8%B3%D9%8A%D9%84%D9%8A%D9%86" title="بنزيل بنسيلين – Arabic" lang="ar" hreflang="ar" data-title="بنزيل بنسيلين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A8%D9%86%D8%B2%DB%8C%D9%84_%D9%BE%D9%86%DB%8C%E2%80%8C%D8%B3%DB%8C%D9%84%DB%8C%D9%86" title="بنزیل پنی‌سیلین – South Azerbaijani" lang="azb" hreflang="azb" data-title="بنزیل پنی‌سیلین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-ba mw-list-item"><a href="https://ba.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%B8%D0%BB%D0%BF%D0%B5%D0%BD%D0%B8%D1%86%D0%B8%D0%BB%D0%BB%D0%B8%D0%BD" title="Бензилпенициллин – Bashkir" lang="ba" hreflang="ba" data-title="Бензилпенициллин" data-language-autonym="Башҡортса" data-language-local-name="Bashkir" class="interlanguage-link-target"><span>Башҡортса</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Benzilpenicilin" title="Benzilpenicilin – Bosnian" lang="bs" hreflang="bs" data-title="Benzilpenicilin" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Benzilpenicil%C2%B7lina" title="Benzilpenicil·lina – Catalan" lang="ca" hreflang="ca" data-title="Benzilpenicil·lina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cv mw-list-item"><a href="https://cv.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%B8%D0%BB%D0%BF%D0%B5%D0%BD%D0%B8%D1%86%D0%B8%D0%BB%D0%BB%D0%B8%D0%BD" title="Бензилпенициллин – Chuvash" lang="cv" hreflang="cv" data-title="Бензилпенициллин" data-language-autonym="Чӑвашла" data-language-local-name="Chuvash" class="interlanguage-link-target"><span>Чӑвашла</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Bensylpenisilin" title="Bensylpenisilin – Welsh" lang="cy" hreflang="cy" data-title="Bensylpenisilin" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Benzylpenicillin" title="Benzylpenicillin – Danish" lang="da" hreflang="da" data-title="Benzylpenicillin" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Benzylpenicillin" title="Benzylpenicillin – German" lang="de" hreflang="de" data-title="Benzylpenicillin" 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/Bencilpenicilina" title="Bencilpenicilina – Spanish" lang="es" hreflang="es" data-title="Bencilpenicilina" 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/%D8%A8%D9%86%D8%B2%DB%8C%D9%84_%D9%BE%D9%86%DB%8C%E2%80%8C%D8%B3%DB%8C%D9%84%DB%8C%D9%86" title="بنزیل پنی‌سیلین – Persian" lang="fa" hreflang="fa" data-title="بنزیل پنی‌سیلین" 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/Benzylp%C3%A9nicilline" title="Benzylpénicilline – French" lang="fr" hreflang="fr" data-title="Benzylpénicilline" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%B2%A4%EC%A7%88%ED%8E%98%EB%8B%88%EC%8B%A4%EB%A6%B0" title="벤질페니실린 – Korean" lang="ko" hreflang="ko" data-title="벤질페니실린" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B2%D5%A5%D5%B6%D5%A6%D5%AB%D5%AC%D5%BA%D5%A5%D5%B6%D5%AB%D6%81%D5%AB%D5%AC%D5%AB%D5%B6" title="Բենզիլպենիցիլին – Armenian" lang="hy" hreflang="hy" data-title="Բենզիլպենիցիլին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Benzilpenicilin" title="Benzilpenicilin – Croatian" lang="hr" hreflang="hr" data-title="Benzilpenicilin" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Penisilin_G" title="Penisilin G – Indonesian" lang="id" hreflang="id" data-title="Penisilin G" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Benzilpenicillina" title="Benzilpenicillina – Italian" lang="it" hreflang="it" data-title="Benzilpenicillina" 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%91%D7%A0%D7%96%D7%99%D7%9C%D7%A4%D7%A0%D7%99%D7%A6%D7%99%D7%9C%D7%99%D7%9F" title="בנזילפניצילין – Hebrew" lang="he" hreflang="he" data-title="בנזילפניצילין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Benzilpenicillin" title="Benzilpenicillin – Hungarian" lang="hu" hreflang="hu" data-title="Benzilpenicillin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Benzylpenicilline" title="Benzylpenicilline – Dutch" lang="nl" hreflang="nl" data-title="Benzylpenicilline" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%99%E3%83%B3%E3%82%B8%E3%83%AB%E3%83%9A%E3%83%8B%E3%82%B7%E3%83%AA%E3%83%B3" title="ベンジルペニシリン – Japanese" lang="ja" hreflang="ja" data-title="ベンジルペニシリン" 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-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%AC%E0%AD%87%E0%AC%9E%E0%AD%8D%E0%AC%9C%E0%AC%BE%E0%AC%87%E0%AC%B2%E0%AC%AA%E0%AD%87%E0%AC%A8%E0%AC%BF%E0%AC%B8%E0%AC%BF%E0%AC%B2%E0%AC%BF%E0%AC%A8" title="ବେଞ୍ଜାଇଲପେନିସିଲିନ – Odia" lang="or" hreflang="or" data-title="ବେଞ୍ଜାଇଲପେନିସିଲିନ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target"><span>ଓଡ଼ିଆ</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Benzilpenitsillin" title="Benzilpenitsillin – Uzbek" lang="uz" hreflang="uz" data-title="Benzilpenitsillin" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-ps mw-list-item"><a href="https://ps.wikipedia.org/wiki/%D8%A8%DB%90%D9%86%D8%B2%D9%8A%D9%84_%D9%BE%DB%90%D9%86%D9%8A%D8%B3%D9%8A%D9%84%D9%8A%D9%86" title="بېنزيل پېنيسيلين – Pashto" lang="ps" hreflang="ps" data-title="بېنزيل پېنيسيلين" data-language-autonym="پښتو" data-language-local-name="Pashto" class="interlanguage-link-target"><span>پښتو</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Benzylopenicylina" title="Benzylopenicylina – Polish" lang="pl" hreflang="pl" data-title="Benzylopenicylina" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Benzilpenicilina" title="Benzilpenicilina – Portuguese" lang="pt" hreflang="pt" data-title="Benzilpenicilina" 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/Benzilpenicilin%C4%83" title="Benzilpenicilină – Romanian" lang="ro" hreflang="ro" data-title="Benzilpenicilină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%B8%D0%BB%D0%BF%D0%B5%D0%BD%D0%B8%D1%86%D0%B8%D0%BB%D0%BB%D0%B8%D0%BD" title="Бензилпенициллин – Russian" lang="ru" hreflang="ru" data-title="Бензилпенициллин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sah mw-list-item"><a href="https://sah.wikipedia.org/wiki/%D0%91%D0%B5%D0%BD%D0%B7%D0%B8%D0%BB%D0%BF%D0%B5%D0%BD%D0%B8%D1%86%D0%B8%D0%BB%D0%BB%D0%B8%D0%BD" title="Бензилпенициллин – Yakut" lang="sah" hreflang="sah" data-title="Бензилпенициллин" data-language-autonym="Саха тыла" data-language-local-name="Yakut" class="interlanguage-link-target"><span>Саха тыла</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Penicilin_G" title="Penicilin G – Slovenian" lang="sl" hreflang="sl" data-title="Penicilin G" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Benzilpenicilin" title="Benzilpenicilin – Serbian" lang="sr" hreflang="sr" data-title="Benzilpenicilin" 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/Benzilpenicilin" title="Benzilpenicilin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Benzilpenicilin" 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-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Bensylpenicillin" title="Bensylpenicillin – Swedish" lang="sv" hreflang="sv" data-title="Bensylpenicillin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%80%E0%B8%9A%E0%B8%99%E0%B8%8B%E0%B8%B4%E0%B8%A5%E0%B9%80%E0%B8%9E%E0%B8%99%E0%B8%B4%E0%B8%8B%E0%B8%B4%E0%B8%A5%E0%B8%A5%E0%B8%B4%E0%B8%99" title="เบนซิลเพนิซิลลิน – Thai" lang="th" hreflang="th" data-title="เบนซิลเพนิซิลลิน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9F%D0%B5%D0%BD%D1%96%D1%86%D0%B8%D0%BB%D1%96%D0%BD" title="Пеніцилін – Ukrainian" lang="uk" hreflang="uk" data-title="Пеніцилін" 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/Penicillin_G" title="Penicillin G – Vietnamese" lang="vi" hreflang="vi" data-title="Penicillin G" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%8B%84%E9%9D%92%E9%9C%89%E7%B4%A0" title="苄青霉素 – Chinese" lang="zh" hreflang="zh" data-title="苄青霉素" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</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/Q258450#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> 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id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Antibiotic medication</div> <p class="mw-empty-elt"> </p> <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): Benzylpenicillin">Benzylpenicillin</span></caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span typeof="mw:File"><a href="/wiki/File:Benzylpenicillin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/Benzylpenicillin.svg/250px-Benzylpenicillin.svg.png" decoding="async" width="250" height="132" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/Benzylpenicillin.svg/375px-Benzylpenicillin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/67/Benzylpenicillin.svg/500px-Benzylpenicillin.svg.png 2x" data-file-width="512" data-file-height="271" /></a></span></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span typeof="mw:File"><a href="/wiki/File:Benzylpenicillin-anion-from-xtal-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Benzylpenicillin-anion-from-xtal-3D-bs-17.png/250px-Benzylpenicillin-anion-from-xtal-3D-bs-17.png" decoding="async" width="250" height="200" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Benzylpenicillin-anion-from-xtal-3D-bs-17.png/375px-Benzylpenicillin-anion-from-xtal-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Benzylpenicillin-anion-from-xtal-3D-bs-17.png/500px-Benzylpenicillin-anion-from-xtal-3D-bs-17.png 2x" data-file-width="2972" data-file-height="2372" /></a></span><div class="infobox-caption">Ball and stick model.<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> Legend:<br />Blue=<a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a>; red=<a href="/wiki/Oxygen" title="Oxygen">oxygen</a>; yellow=<a href="/wiki/Sulfur" title="Sulfur">sulfur</a><br />grey=<a href="/wiki/Carbon" title="Carbon">carbon</a> and carbon bonds; white=<a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>.</div></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/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Pfizerpen, other</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">Penicillin G potassium,<sup id="cite_ref-Pro2016_2-0" class="reference"><a href="#cite_note-Pro2016-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> penicillin G sodium</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/international/Benzylpenicillin.html">International Drug Names</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/a685013.html">a685013</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><small><abbr class="country-name" title="Australia">AU</abbr>:</small> A</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/Intravenous_therapy" title="Intravenous therapy">Intravenous therapy</a>, <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</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_J01" title="ATC code J01">J01CE01</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=J01CE01">WHO</a></span>) <a href="/wiki/ATC_code_S01" title="ATC code S01">S01AA14</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=S01AA14">WHO</a></span>) <a href="/wiki/ATC_code_J51" class="mw-redirect" title="ATC code J51">QJ51CE01</a> (<span title="www.whocc.no/atcvet"><a rel="nofollow" class="external text" href="https://www.whocc.no/atcvet/atcvet_index/?code=QJ51CE01">WHO</a></span>)</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">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>In general: ℞ (Prescription only)</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><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">30% oral <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></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">60%</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Liver</a></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">30 min</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">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%;">(2<i>S</i>,5<i>R</i>,6<i>R</i>)-3,3-Dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid</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=61-33-6">61-33-6</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> (free acid)<br /><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=69-57-8&title=">69-57-8</a> (sodium salt)</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/5904">5904</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=4796">4796</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/DB01053">DB01053</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.5693.html">5693</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/Q42T66VG0C">Q42T66VG0C</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/D02336">D02336</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/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:18208">CHEBI:18208</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/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/chembldb/index.php/compound/inspect/ChEMBL29">ChEMBL29</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/E_number" title="E number"><span title="E number (food additive code)">E number</span></a></th><td class="infobox-data">E705 <a href="/wiki/E_number#E700–E799" title="E number">(antibiotics)</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q258450#P628" 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 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/DTXSID5046934">DTXSID5046934</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q258450#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/100.000.461">100.000.461</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q258450#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>16</sub><span title="Hydrogen">H</span><sub>18</sub><span title="Nitrogen">N</span><sub>2</sub><span title="Oxygen">O</span><sub>4</sub><span title="Sulfur">S</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="7002334390000000000♠"></span>334.39</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=CC1%28%5BC%40%40H%5D%28N2%5BC%40H%5D%28S1%29%5BC%40%40H%5D%28C2%3DO%29NC%28%3DO%29Cc3ccccc3%29C%28%3DO%29O%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%;">CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)Cc3ccccc3)C(=O)O)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/C16H18N2O4S/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/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:JGSARLDLIJGVTE-MBNYWOFBSA-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=396298574&page2=Benzylpenicillin">(verify)</a></span></span></td></tr></tbody></table> <p><b>Benzylpenicillin</b>, also known as <b>penicillin G</b> (<b>PenG</b><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>) or <b>BENPEN</b>,<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> is an <a href="/wiki/Antibiotic" title="Antibiotic">antibiotic</a> used to treat a number of <a href="/wiki/Pathogenic_bacteria" title="Pathogenic bacteria">bacterial</a> <a href="/wiki/Infection" title="Infection">infections</a>.<sup id="cite_ref-WHO2008_6-0" class="reference"><a href="#cite_note-WHO2008-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> This includes <a href="/wiki/Pneumonia" title="Pneumonia">pneumonia</a>, <a href="/wiki/Streptococcal_pharyngitis" title="Streptococcal pharyngitis">strep throat</a>, <a href="/wiki/Syphilis" title="Syphilis">syphilis</a>, <a href="/wiki/Necrotizing_enterocolitis" title="Necrotizing enterocolitis">necrotizing enterocolitis</a>, <a href="/wiki/Diphtheria" title="Diphtheria">diphtheria</a>, <a href="/wiki/Gas_gangrene" title="Gas gangrene">gas gangrene</a>, <a href="/wiki/Leptospirosis" title="Leptospirosis">leptospirosis</a>, <a href="/wiki/Cellulitis" title="Cellulitis">cellulitis</a>, and <a href="/wiki/Tetanus" title="Tetanus">tetanus</a>.<sup id="cite_ref-WHO2008_6-1" class="reference"><a href="#cite_note-WHO2008-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> It is not a first-line agent for <a href="/wiki/Pneumococcal_infection" title="Pneumococcal infection">pneumococcal</a> <a href="/wiki/Meningitis" title="Meningitis">meningitis</a>.<sup id="cite_ref-WHO2008_6-2" class="reference"><a href="#cite_note-WHO2008-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Due to benzylpenicillin's limited <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> for oral medications, it is generally taken as an injection in the form of a sodium, potassium, benzathine, or procaine salt.<sup id="cite_ref-Castle_2007_7-0" class="reference"><a href="#cite_note-Castle_2007-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Benzylpenicillin is given by <a href="/wiki/Intravenously" class="mw-redirect" title="Intravenously">injection into a vein</a> or <a href="/wiki/Intramuscular" class="mw-redirect" title="Intramuscular">muscle</a>.<sup id="cite_ref-Pro2016_2-1" class="reference"><a href="#cite_note-Pro2016-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Two long-acting forms <a href="/wiki/Benzathine_benzylpenicillin" title="Benzathine benzylpenicillin">benzathine benzylpenicillin</a> and <a href="/wiki/Procaine_benzylpenicillin" title="Procaine benzylpenicillin">procaine benzylpenicillin</a> are available for use by <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">injection into a muscle</a> only.<sup id="cite_ref-WHO2008_6-3" class="reference"><a href="#cite_note-WHO2008-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Side effects include <a href="/wiki/Diarrhea" title="Diarrhea">diarrhea</a>, <a href="/wiki/Seizures" class="mw-redirect" title="Seizures">seizures</a>, and <a href="/wiki/Allergy" title="Allergy">allergic reactions</a> including <a href="/wiki/Anaphylaxis" title="Anaphylaxis">anaphylaxis</a>.<sup id="cite_ref-WHO2008_6-4" class="reference"><a href="#cite_note-WHO2008-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> When used to treat syphilis or Lyme disease a reaction known as <a href="/wiki/Jarisch%E2%80%93Herxheimer_reaction" title="Jarisch–Herxheimer reaction">Jarisch–Herxheimer</a> may occur.<sup id="cite_ref-WHO2008_6-5" class="reference"><a href="#cite_note-WHO2008-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> It is not recommended in those with a history of <a href="/wiki/Penicillin#Side_effects" title="Penicillin">penicillin allergy</a>.<sup id="cite_ref-WHO2008_6-6" class="reference"><a href="#cite_note-WHO2008-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Use during pregnancy is generally safe in the <a href="/wiki/Penicillin" title="Penicillin">penicillin</a> and <a href="/wiki/Beta-lactam" class="mw-redirect" title="Beta-lactam">β-lactam</a> class of medications.<sup id="cite_ref-WHO2008_6-7" class="reference"><a href="#cite_note-WHO2008-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Benzylpenicillin is on the <a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">World Health Organization's List of Essential Medicines</a>.<sup id="cite_ref-WHO21st_8-0" class="reference"><a href="#cite_note-WHO21st-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=Benzylpenicillin&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Antimicrobial_potency">Antimicrobial potency</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzylpenicillin&action=edit&section=2" title="Edit section: Antimicrobial potency"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As an antibiotic, benzylpenicillin is noted to possess effectiveness mainly against <a href="/wiki/Gram-positive_bacteria" title="Gram-positive bacteria">gram-positive</a> organisms. Some <a href="/wiki/Gram-negative_bacteria" title="Gram-negative bacteria">gram-negative</a> organisms such as <i><a href="/wiki/Neisseria_gonorrhoeae" title="Neisseria gonorrhoeae">Neisseria gonorrhoeae</a></i> and <i><a href="/wiki/Leptospira_weilii" title="Leptospira weilii">Leptospira weilii</a></i> are also reported to be susceptible to benzylpenicillin.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Adverse_effects">Adverse effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzylpenicillin&action=edit&section=3" title="Edit section: Adverse effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Adverse effects can include hypersensitivity reactions including urticaria, fever, joint pains, rashes, angioedema, anaphylaxis, serum sickness-like reaction. Rarely central nervous system toxicity including convulsions (especially with high doses or in severe renal impairment), interstitial nephritis, haemolytic anaemia, leucopenia, thrombocytopenia, and coagulation disorders. Also reported diarrhoea (including antibiotic-associated colitis). Benzylpenicillin has relatively low toxicity, except for in the nervous system, in which it is one of the most active drugs among β-lactam agents.<sup id="cite_ref-Castle_2007_7-1" class="reference"><a href="#cite_note-Castle_2007-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> In addition, benzylpenicillin is an irritant, a health hazard, and an environmental hazard.<sup id="cite_ref-ACS_MW_10-0" class="reference"><a href="#cite_note-ACS_MW-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>Benzylpenicillin serum concentrations can be monitored either by traditional microbiological assay or by more modern chromatographic techniques. Such measurements can be useful to avoid central nervous system toxicity in any person receiving large doses of the drug on a chronic basis, but they are especially relevant to patients with <a href="/wiki/Kidney_failure" title="Kidney failure">kidney failure</a>, who may accumulate the drug due to reduced urinary excretion rates.<sup id="cite_ref-Fossieck_1974_11-0" class="reference"><a href="#cite_note-Fossieck_1974-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></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-heading2"><h2 id="Manufacture">Manufacture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzylpenicillin&action=edit&section=4" title="Edit section: Manufacture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Benzylpenicillin is produced by fermentation of <i><a href="/wiki/Penicillium_chrysogenum" title="Penicillium chrysogenum">Penicillium chrysogenum</a></i>.<sup id="cite_ref-ACS_MW_10-1" class="reference"><a href="#cite_note-ACS_MW-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> The production of benzylpenicillin involves fermentation, recovery and purification of the penicillin.<sup id="cite_ref-Liu_2016_13-0" class="reference"><a href="#cite_note-Liu_2016-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>The fermentation process of the production of benzylpenicillin creates the product. The presence of the product in solution inhibits the reaction and reduces the product rate and yield. Thus, in order to obtain the most product and increase the rate of reaction, it is continuously extracted.<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> This is done by mixing the mold with either glucose, sucrose, lactose, starch, or dextrin, nitrate, ammonium salt, corn steep liquor, peptone, meat or yeast extract, and small amounts of inorganic salts.<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><p>The recovery of the benzylpenicillin is the most important part of the production process because it affects the later purification steps if done incorrectly.<sup id="cite_ref-Liu_2016_13-1" class="reference"><a href="#cite_note-Liu_2016-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> There are several techniques used to recover benzylpenicillin: aqueous two-phase extraction, liquid membrane extraction, microfiltration, and solvent extraction.<sup id="cite_ref-Liu_2016_13-2" class="reference"><a href="#cite_note-Liu_2016-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>In the purification step, the benzylpenicillin is separated from the extraction solution. This is normally done by using a separation column.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Synonyms">Synonyms</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Benzylpenicillin&action=edit&section=5" title="Edit section: Synonyms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Penicillin II (old UK nomenclature for naming penicillins)<sup id="cite_ref-Science1945_17-0" class="reference"><a href="#cite_note-Science1945-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PenG_18-0" class="reference"><a href="#cite_note-PenG-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup></li> <li>Wonder drug<sup id="cite_ref-ACS_MW_10-2" class="reference"><a href="#cite_note-ACS_MW-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup></li></ul> <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=Benzylpenicillin&action=edit&section=6" 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"><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="CITEREFDextervan_der_Veen1978" class="citation journal cs1">Dexter DD, van der Veen JM (1978). "Conformations of penicillin G: crystal structure of procaine penicillin G monohydrate and a refinement of the structure of potassium penicillin G". <i>Journal of the Chemical Society, Perkin Transactions 1</i>. <b>3</b> (3): 185–190. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fp19780000185">10.1039/p19780000185</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/565366">565366</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+Chemical+Society%2C+Perkin+Transactions+1&rft.atitle=Conformations+of+penicillin+G%3A+crystal+structure+of+procaine+penicillin+G+monohydrate+and+a+refinement+of+the+structure+of+potassium+penicillin+G&rft.volume=3&rft.issue=3&rft.pages=185-190&rft.date=1978&rft_id=info%3Adoi%2F10.1039%2Fp19780000185&rft_id=info%3Apmid%2F565366&rft.aulast=Dexter&rft.aufirst=DD&rft.au=van+der+Veen%2C+JM&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzylpenicillin" class="Z3988"></span></span> </li> <li id="cite_note-Pro2016-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Pro2016_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Pro2016_2-1"><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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.drugs.com/pro/penicillin-g-injection.html">"Penicillin G Injection - FDA prescribing information, side effects and uses"</a>. <i>www.drugs.com</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161220230501/https://www.drugs.com/pro/penicillin-g-injection.html">Archived</a> from the original on 20 December 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">10 December</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.drugs.com&rft.atitle=Penicillin+G+Injection+-+FDA+prescribing+information%2C+side+effects+and+uses&rft_id=https%3A%2F%2Fwww.drugs.com%2Fpro%2Fpenicillin-g-injection.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzylpenicillin" 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 id="CITEREFYipGerriets2023" class="citation book cs1">Yip DW, Gerriets V (2023). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/books/NBK554560">"Penicillin"</a>. <i>StatPearls</i>. StatPearls Publishing. <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/32119447">32119447</a><span class="reference-accessdate">. Retrieved <span class="nowrap">7 December</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Penicillin&rft.btitle=StatPearls&rft.pub=StatPearls+Publishing&rft.date=2023&rft_id=info%3Apmid%2F32119447&rft.aulast=Yip&rft.aufirst=DW&rft.au=Gerriets%2C+V&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fbooks%2FNBK554560&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzylpenicillin" class="Z3988"></span></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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFlaherty2012" class="citation book cs1">Flaherty DK (2012). "Immunogenicity and Antigenicity". <a rel="nofollow" class="external text" href="https://www.sciencedirect.com/book/9780323069472/immunology-for-pharmacy"><i>Immunology for Pharmacy</i></a>. Mosby. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-06947-2" title="Special:BookSources/978-0-323-06947-2"><bdi>978-0-323-06947-2</bdi></a>. <q>Natural penicillin (PenG), penicillinase-resistant penicillin (methicillin), extended-spectrum penicillin (amoxicillin), and broad-spectrum penicillin (carbenicillin) all have the same core β-lactam ring, which is essential for antimicrobial activity.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Immunogenicity+and+Antigenicity&rft.btitle=Immunology+for+Pharmacy&rft.pub=Mosby&rft.date=2012&rft.isbn=978-0-323-06947-2&rft.aulast=Flaherty&rft.aufirst=DK&rft_id=https%3A%2F%2Fwww.sciencedirect.com%2Fbook%2F9780323069472%2Fimmunology-for-pharmacy&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzylpenicillin" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</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://labeling.seqirus.com/PI/AU/Benpen/EN/Benpen-Product-Information.pdf">"Australian Product Information – BENPEN"</a> <span class="cs1-format">(PDF)</span>. <i>Seqirus Pty Ltd</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Seqirus+Pty+Ltd&rft.atitle=Australian+Product+Information+%E2%80%93+BENPEN&rft_id=https%3A%2F%2Flabeling.seqirus.com%2FPI%2FAU%2FBenpen%2FEN%2FBenpen-Product-Information.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzylpenicillin" class="Z3988"></span></span> </li> <li id="cite_note-WHO2008-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-WHO2008_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-WHO2008_6-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-WHO2008_6-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-WHO2008_6-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-WHO2008_6-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-WHO2008_6-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-WHO2008_6-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-WHO2008_6-7"><sup><i><b>h</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStuartKouimtziHill2009" class="citation book cs1">Stuart MC, Kouimtzi M, Hill SR, eds. (2009). <i>WHO Model Formulary 2008</i>. World Health Organization. pp. 98, 105. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/10665%2F44053">10665/44053</a></span>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9789241547659" title="Special:BookSources/9789241547659"><bdi>9789241547659</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=WHO+Model+Formulary+2008&rft.pages=98%2C+105&rft.pub=World+Health+Organization&rft.date=2009&rft_id=info%3Ahdl%2F10665%2F44053&rft.isbn=9789241547659&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzylpenicillin" class="Z3988"></span></span> </li> <li id="cite_note-Castle_2007-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-Castle_2007_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Castle_2007_7-1"><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="CITEREFCastle2007" class="citation book cs1">Castle SS (2007). "Penicillin G". In Enna SJ, Bylund DB (eds.). <i>xPharm: The Comprehensive Pharmacology Reference</i>. New York: Elsevier. pp. 1–6.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Penicillin+G&rft.btitle=xPharm%3A+The+Comprehensive+Pharmacology+Reference&rft.place=New+York&rft.pages=1-6&rft.pub=Elsevier&rft.date=2007&rft.aulast=Castle&rft.aufirst=SS&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzylpenicillin" class="Z3988"></span></span> </li> <li id="cite_note-WHO21st-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-WHO21st_8-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWorld_Health_Organization2019" class="citation book cs1"><a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a> (2019). <i>World Health Organization model list of essential medicines: 21st list 2019</i>. Geneva: World Health Organization. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/10665%2F325771">10665/325771</a></span>. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=World+Health+Organization+model+list+of+essential+medicines%3A+21st+list+2019&rft.place=Geneva&rft.pub=World+Health+Organization&rft.date=2019&rft_id=info%3Ahdl%2F10665%2F325771&rft.au=World+Health+Organization&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABenzylpenicillin" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</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://web.archive.org/web/20160303205812/http://www.toku-e.com/Upload/Products/PDS/20120521008049.pdf">"Penicillin G"</a> <span class="cs1-format">(PDF)</span>. Toku-E. 10 October 2010. 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antibiotics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cell_wall_disruptive_antibiotics" title="Template talk:Cell wall disruptive antibiotics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cell_wall_disruptive_antibiotics" title="Special:EditPage/Template:Cell wall disruptive antibiotics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Antibacterials_active_on_the_cell_wall_and_envelope_(J01C-J01D)" style="font-size:114%;margin:0 4em"><a href="/wiki/Antibiotics" class="mw-redirect" title="Antibiotics">Antibacterials</a> active on the <a href="/wiki/Cell_wall" title="Cell wall">cell wall</a> and <a href="/wiki/Cell_envelope_antibiotic" title="Cell envelope antibiotic">envelope</a> (<a href="/wiki/ATC_code_J01#J01C" title="ATC code J01">J01C</a>-<a href="/wiki/ATC_code_J01#J01D" title="ATC code J01">J01D</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Beta-lactam_antibiotics" class="mw-redirect" title="Beta-lactam antibiotics">β-lactams</a><br /><small><span class="nobold">(inhibit synthesis<br />of peptidoglycan<br />layer of bacterial<br />cell wall by binding<br />to and inhibiting<br /><a href="/wiki/Penicillin-binding_proteins" title="Penicillin-binding proteins">PBPs</a>, a group of<br /><a href="/wiki/DD-Transpeptidase" title="DD-Transpeptidase"><small>D</small>-alanyl-<small>D</small>-alanine<br />transpeptidases</a>)</span></small></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/Penicillin" title="Penicillin">Penicillins</a> (<a href="/wiki/Penam" title="Penam">Penams</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" 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/List_of_%CE%B2-lactam_antibiotics#Narrow-spectrum" title="List of β-lactam antibiotics">Narrow<br />spectrum</a></th><td class="navbox-list-with-group navbox-list navbox-odd" 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/List_of_%CE%B2-lactam_antibiotics#Narrow-spectrum" title="List of β-lactam antibiotics">β-lactamase sensitive</a><br />(1st generation)</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 class="mw-selflink selflink">Benzylpenicillin (G)</a><sup>#</sup></li> <li><a href="/wiki/Benzathine_benzylpenicillin" title="Benzathine benzylpenicillin">Benzathine benzylpenicillin</a><sup>#</sup></li> <li><a href="/wiki/Procaine_benzylpenicillin" title="Procaine benzylpenicillin">Procaine benzylpenicillin</a><sup>#</sup></li> <li><a href="/wiki/Phenoxymethylpenicillin" title="Phenoxymethylpenicillin">Phenoxymethylpenicillin (V)</a><sup>#</sup></li> <li><a href="/wiki/Propicillin" title="Propicillin">Propicillin</a><sup>‡</sup></li> <li><a href="/wiki/Pheneticillin" title="Pheneticillin">Pheneticillin</a><sup>‡</sup></li> <li><a href="/wiki/Azidocillin" title="Azidocillin">Azidocillin</a><sup>‡</sup></li> <li><a href="/wiki/Clometocillin" title="Clometocillin">Clometocillin</a><sup>‡</sup></li> <li><a href="/wiki/Penamecillin" title="Penamecillin">Penamecillin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_%CE%B2-lactam_antibiotics#β-lactamase-resistant" title="List of β-lactam antibiotics">β-lactamase resistant</a><br />(2nd generation)</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/Cloxacillin" title="Cloxacillin">Cloxacillin</a><sup>#</sup> (<a href="/wiki/Dicloxacillin" title="Dicloxacillin">Dicloxacillin</a></li> <li><a href="/wiki/Flucloxacillin" title="Flucloxacillin">Flucloxacillin</a>)</li> <li><a href="/wiki/Oxacillin" title="Oxacillin">Oxacillin</a></li> <li><a href="/wiki/Nafcillin" title="Nafcillin">Nafcillin</a></li> <li><a href="/wiki/Methicillin" title="Methicillin">Methicillin</a><sup>‡</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Extended-spectrum_penicillin" title="Extended-spectrum penicillin">Extended<br />spectrum</a></th><td class="navbox-list-with-group navbox-list navbox-odd" 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/Aminopenicillin" title="Aminopenicillin">Aminopenicillins</a> (3rd generation)</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="/wiki/Amoxicillin" title="Amoxicillin">Amoxicillin</a><sup>#</sup></li> <li><a href="/wiki/Ampicillin" title="Ampicillin">Ampicillin</a><sup>#</sup> (<a href="/wiki/Pivampicillin" title="Pivampicillin">Pivampicillin</a></li> <li><a href="/wiki/Hetacillin" title="Hetacillin">Hetacillin</a><sup>‡</sup></li> <li><a href="/wiki/Bacampicillin" title="Bacampicillin">Bacampicillin</a><sup>‡</sup></li> <li><a href="/wiki/Lenampicillin" title="Lenampicillin">Lenampicillin</a></li> <li><a href="/wiki/Metampicillin" title="Metampicillin">Metampicillin</a><sup>‡</sup></li> <li><a href="/wiki/Talampicillin" title="Talampicillin">Talampicillin</a><sup>‡</sup>)</li> <li><a href="/wiki/Epicillin" title="Epicillin">Epicillin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carboxypenicillin" title="Carboxypenicillin">Carboxypenicillins</a> (4th generation)</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/Ticarcillin" title="Ticarcillin">Ticarcillin</a></li> <li><a href="/wiki/Carbenicillin" title="Carbenicillin">Carbenicillin</a><sup>‡</sup> / <a href="/wiki/Carindacillin" title="Carindacillin">Carindacillin</a><sup>‡</sup></li> <li><a href="/wiki/Temocillin" title="Temocillin">Temocillin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ureidopenicillin" title="Ureidopenicillin">Ureidopenicillins</a> (4th generation)</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="/wiki/Piperacillin" title="Piperacillin">Piperacillin</a></li> <li><a href="/wiki/Azlocillin" title="Azlocillin">Azlocillin</a><sup>‡</sup></li> <li><a href="/wiki/Mezlocillin" title="Mezlocillin">Mezlocillin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</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/Mecillinam" title="Mecillinam">Mecillinam</a> (<a href="/wiki/Pivmecillinam" title="Pivmecillinam">Pivmecillinam</a>)</li> <li><a href="/wiki/Sulbenicillin" title="Sulbenicillin">Sulbenicillin</a><sup>‡</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbapenem" title="Carbapenem">Carbapenems</a> / <a href="/wiki/Penem" title="Penem">Penems</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>Carbapenems (<a href="/wiki/Ertapenem" title="Ertapenem">Ertapenem</a></li> <li><a href="/wiki/Antipseudomonal" class="mw-redirect" title="Antipseudomonal">Antipseudomonal</a> (<a href="/wiki/Doripenem" title="Doripenem">Doripenem</a></li> <li><a href="/wiki/Imipenem" title="Imipenem">Imipenem</a></li> <li><a href="/wiki/Meropenem" title="Meropenem">Meropenem</a>)</li> <li><a href="/wiki/Biapenem" title="Biapenem">Biapenem</a><sup>‡</sup></li> <li><a href="/wiki/Panipenem" title="Panipenem">Panipenem</a>)</li> <li>Penems (<a href="/wiki/Faropenem" title="Faropenem">Faropenem</a></li> <li><a href="/wiki/Ritipenem" title="Ritipenem">Ritipenem</a><sup>§</sup></li> <li><a href="/wiki/Sulopenem" title="Sulopenem">Sulopenem</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephem" title="Cephem">Cephems</a><br /><a href="/wiki/Cephalosporin" title="Cephalosporin">Cephalosporins</a><br /><a href="/wiki/Cephamycin" title="Cephamycin">Cephamycins</a><br /><a href="/wiki/Carbacephem" title="Carbacephem">Carbacephems</a></th><td class="navbox-list-with-group navbox-list navbox-odd" 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/Cephalosporin#First_generation" title="Cephalosporin">1st generation</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/Cefazolin" title="Cefazolin">Cefazolin</a><sup>#</sup></li> <li><a href="/wiki/Cefalexin" title="Cefalexin">Cefalexin</a> <sup>#</sup></li> <li><a href="/wiki/Cefadroxil" title="Cefadroxil">Cefadroxil</a></li> <li><a href="/wiki/Cefapirin" title="Cefapirin">Cefapirin</a></li> <li><a href="/wiki/Cefazedone" title="Cefazedone">Cefazedone</a><sup>‡</sup></li> <li><a href="/wiki/Cefazaflur" title="Cefazaflur">Cefazaflur</a><sup>‡</sup></li> <li><a href="/wiki/Cefradine" title="Cefradine">Cefradine</a><sup>‡</sup></li> <li><a href="/wiki/Cefroxadine" title="Cefroxadine">Cefroxadine</a><sup>‡</sup></li> <li><a href="/wiki/Ceftezole" title="Ceftezole">Ceftezole</a><sup>‡</sup></li> <li><a href="/wiki/Cefaloglycin" title="Cefaloglycin">Cefaloglycin</a><sup>‡</sup></li> <li><a href="/wiki/Cefacetrile" title="Cefacetrile">Cefacetrile</a><sup>‡</sup></li> <li><a href="/wiki/Cefalonium" title="Cefalonium">Cefalonium</a><sup>‡</sup></li> <li><a href="/wiki/Cefaloridine" class="mw-redirect" title="Cefaloridine">Cefaloridine</a><sup>‡</sup></li> <li><a href="/wiki/Cefalotin" title="Cefalotin">Cefalotin</a></li> <li><a href="/wiki/Cefatrizine" title="Cefatrizine">Cefatrizine</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#Second_generation" title="Cephalosporin">2nd generation</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><a href="/wiki/Cefaclor" title="Cefaclor">Cefaclor</a></li> <li><a href="/wiki/Cefprozil" title="Cefprozil">Cefprozil</a></li> <li><a href="/wiki/Cefuroxime" title="Cefuroxime">Cefuroxime</a></li> <li><a href="/wiki/Cefuroxime_axetil" title="Cefuroxime axetil">Cefuroxime axetil</a></li> <li><a href="/wiki/Cefamandole" title="Cefamandole">Cefamandole</a><sup>‡</sup></li> <li><a href="/wiki/Cefonicid" title="Cefonicid">Cefonicid</a><sup>‡</sup></li> <li><a href="/wiki/Ceforanide" title="Ceforanide">Ceforanide</a><sup>‡</sup></li> <li><a href="/wiki/Cefuzonam" title="Cefuzonam">Cefuzonam</a><sup>‡</sup></li> <li><a href="/wiki/Cephamycin" title="Cephamycin">Cephamycin</a> (<a href="/wiki/Cefoxitin" title="Cefoxitin">Cefoxitin</a></li> <li><a href="/wiki/Cefotetan" title="Cefotetan">Cefotetan</a></li> <li><a href="/wiki/Cefminox" title="Cefminox">Cefminox</a><sup>‡</sup></li> <li><a href="/wiki/Cefbuperazone" title="Cefbuperazone">Cefbuperazone</a><sup>‡</sup></li> <li><a href="/wiki/Cefmetazole" title="Cefmetazole">Cefmetazole</a><sup>‡</sup>)</li> <li><a href="/wiki/Carbacephem" title="Carbacephem">Carbacephem</a> (<a href="/wiki/Loracarbef" title="Loracarbef">Loracarbef</a><sup>‡</sup>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#Third_generation" title="Cephalosporin">3rd generation</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/Cefixime" title="Cefixime">Cefixime</a><sup>#</sup></li> <li><a href="/wiki/Ceftriaxone" title="Ceftriaxone">Ceftriaxone</a><sup>#</sup></li> <li><a href="/wiki/Cefotaxime" title="Cefotaxime">Cefotaxime</a><sup>#</sup></li> <li>Antipseudomonal (<a href="/wiki/Ceftazidime" title="Ceftazidime">Ceftazidime</a><sup>#</sup></li> <li><a href="/wiki/Cefoperazone" title="Cefoperazone">Cefoperazone</a>)</li> <li><a href="/wiki/Cefdinir" title="Cefdinir">Cefdinir</a></li> <li><a href="/wiki/Cefcapene" title="Cefcapene">Cefcapene</a></li> <li><a href="/wiki/Cefdaloxime" title="Cefdaloxime">Cefdaloxime</a></li> <li><a href="/wiki/Ceftizoxime" title="Ceftizoxime">Ceftizoxime</a></li> <li><a href="/wiki/Cefmenoxime" title="Cefmenoxime">Cefmenoxime</a></li> <li><a href="/wiki/Cefpiramide" title="Cefpiramide">Cefpiramide</a></li> <li><a href="/wiki/Cefpodoxime" title="Cefpodoxime">Cefpodoxime</a></li> <li><a href="/wiki/Ceftibuten" title="Ceftibuten">Ceftibuten</a></li> <li><a href="/wiki/Cefditoren" title="Cefditoren">Cefditoren</a></li> <li><a href="/wiki/Cefotiam" title="Cefotiam">Cefotiam</a><sup>‡</sup></li> <li><a href="/wiki/Cefetamet" title="Cefetamet">Cefetamet</a><sup>‡</sup></li> <li><a href="/wiki/Cefodizime" title="Cefodizime">Cefodizime</a><sup>‡</sup></li> <li><a href="/wiki/Cefpimizole" title="Cefpimizole">Cefpimizole</a><sup>‡</sup></li> <li><a href="/wiki/Cefsulodin" title="Cefsulodin">Cefsulodin</a><sup>‡</sup></li> <li><a href="/wiki/Cefteram" title="Cefteram">Cefteram</a><sup>‡</sup></li> <li><a href="/wiki/Ceftiolene" title="Ceftiolene">Ceftiolene</a><sup>‡</sup></li> <li><a href="/wiki/Oxacephem" title="Oxacephem">Oxacephem</a> (<a href="/wiki/Flomoxef" title="Flomoxef">Flomoxef</a></li> <li><a href="/wiki/Latamoxef" title="Latamoxef">Latamoxef</a><sup>‡</sup>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#Fourth_generation" title="Cephalosporin">4th generation</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><a href="/wiki/Cefepime" title="Cefepime">Cefepime</a></li> <li><a href="/wiki/Cefozopran" title="Cefozopran">Cefozopran</a><sup>‡</sup></li> <li><a href="/wiki/Cefpirome" title="Cefpirome">Cefpirome</a></li> <li><a href="/wiki/Cefquinome" title="Cefquinome">Cefquinome</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#Fifth_generation" title="Cephalosporin">5th generation</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/Ceftaroline_fosamil" title="Ceftaroline fosamil">Ceftaroline fosamil</a></li> <li><a href="/wiki/Ceftolozane" class="mw-redirect" title="Ceftolozane">Ceftolozane</a></li> <li><a href="/wiki/Ceftobiprole" title="Ceftobiprole">Ceftobiprole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Siderophore" title="Siderophore">Siderophore</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><a href="/wiki/Cefiderocol" title="Cefiderocol">Cefiderocol</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Veterinary_medicine" title="Veterinary medicine">Veterinary</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/Ceftiofur" title="Ceftiofur">Ceftiofur</a></li> <li><a href="/wiki/Cefquinome" title="Cefquinome">Cefquinome</a></li> <li><a href="/wiki/Cefovecin" title="Cefovecin">Cefovecin</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/Monobactam" title="Monobactam">Monobactams</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><a href="/wiki/Aztreonam" title="Aztreonam">Aztreonam</a></li> <li><a href="/wiki/Tigemonam" title="Tigemonam">Tigemonam</a><sup>‡</sup></li> <li><a href="/wiki/Carumonam" title="Carumonam">Carumonam</a><sup>‡</sup></li> <li><a href="/wiki/Nocardicin_A" title="Nocardicin A">Nocardicin A</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/%CE%92-Lactamase_inhibitor" title="Β-Lactamase inhibitor">β-lactamase 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><a href="/wiki/Penam" title="Penam">Penam</a> (<a href="/wiki/Sulbactam" title="Sulbactam">Sulbactam</a></li> <li><a href="/wiki/Tazobactam" title="Tazobactam">Tazobactam</a>)</li> <li><a href="/wiki/Clavam" title="Clavam">Clavam</a> (<a href="/wiki/Clavulanic_acid" title="Clavulanic acid">Clavulanic acid</a>)</li> <li>non-β-lactam (<a href="/wiki/Avibactam" title="Avibactam">Avibactam</a></li> <li><a href="/wiki/Durlobactam" title="Durlobactam">Durlobactam</a></li> <li><a href="/wiki/Relebactam" title="Relebactam">Relebactam</a></li> <li><a href="/wiki/Vaborbactam" title="Vaborbactam">Vaborbactam</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" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amoxicillin/clavulanic_acid" title="Amoxicillin/clavulanic acid">Amoxicillin/clavulanic acid</a><sup>#</sup></li> <li><a href="/wiki/Ampicillin/flucloxacillin" title="Ampicillin/flucloxacillin">Ampicillin/flucloxacillin</a></li> <li><a href="/wiki/Ampicillin/sulbactam" title="Ampicillin/sulbactam">Ampicillin/sulbactam</a> (<a href="/wiki/Sultamicillin" title="Sultamicillin">Sultamicillin</a>)</li> <li><a href="/wiki/Aztreonam/avibactam" title="Aztreonam/avibactam">Aztreonam/avibactam</a></li> <li><a href="/wiki/Benzathine_benzylpenicillin/procaine_benzylpenicillin" title="Benzathine benzylpenicillin/procaine benzylpenicillin">Benzathine benzylpenicillin/procaine benzylpenicillin</a></li> <li><a href="/wiki/Cefepime/enmetazobactam" title="Cefepime/enmetazobactam">Cefepime/enmetazobactam</a></li> <li><a href="/wiki/Cefoperazone/sulbactam" title="Cefoperazone/sulbactam">Cefoperazone/sulbactam</a></li> <li><a href="/wiki/Ceftazidime/avibactam" title="Ceftazidime/avibactam">Ceftazidime/avibactam</a></li> <li><a href="/wiki/Ceftolozane/tazobactam" title="Ceftolozane/tazobactam">Ceftolozane/tazobactam</a></li> <li><a href="/wiki/Imipenem/cilastatin" title="Imipenem/cilastatin">Imipenem/cilastatin</a><sup>#</sup></li> <li><a href="/wiki/Imipenem/cilastatin/relebactam" title="Imipenem/cilastatin/relebactam">Imipenem/cilastatin/relebactam</a></li> <li><a href="/wiki/Meropenem/vaborbactam" title="Meropenem/vaborbactam">Meropenem/vaborbactam</a></li> <li><a href="/wiki/Panipenem/betamipron" title="Panipenem/betamipron">Panipenem/betamipron</a></li> <li><a href="/wiki/Piperacillin/tazobactam" title="Piperacillin/tazobactam">Piperacillin/tazobactam</a></li> <li><a href="/wiki/Sulbactam/durlobactam" title="Sulbactam/durlobactam">Sulbactam/durlobactam</a></li> <li><a href="/wiki/Sulopenem/probenecid" title="Sulopenem/probenecid">Sulopenem/probenecid</a></li> <li><a href="/wiki/Ticarcillin/clavulanic_acid" title="Ticarcillin/clavulanic acid">Ticarcillin/clavulanic acid</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/Polypeptide_antibiotic" title="Polypeptide antibiotic">Polypeptides</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/Lipopeptide" title="Lipopeptide">Lipopeptides</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>Insert into bacterial cell wall causing perforation and depolarization: <a href="/wiki/Daptomycin" title="Daptomycin">Daptomycin</a></li> <li><a href="/wiki/Surfactin" title="Surfactin">Surfactin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Inhibits PG elongation and crosslinking: <a href="/wiki/Ramoplanin" title="Ramoplanin">Ramoplanin</a><sup>§</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Intracellular</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>Inhibit <a href="/wiki/Peptidoglycan" title="Peptidoglycan">PG</a> subunit synthesis and transport: <a href="/wiki/N-Acetylmuramic_acid" title="N-Acetylmuramic acid">NAM</a> synthesis inhibition (<a href="/wiki/Fosfomycin" title="Fosfomycin">Fosfomycin</a>)</li> <li><a href="/wiki/D-alanine%E2%80%94D-alanine_ligase" title="D-alanine—D-alanine ligase">DADAL</a>/<a href="/wiki/Alanine_racemase" title="Alanine racemase">AR</a> inhibitors (<a href="/wiki/Cycloserine" title="Cycloserine">Cycloserine</a>)</li> <li><a href="/wiki/Bactoprenol" title="Bactoprenol">bactoprenol</a> inhibitors (<a href="/wiki/Bacitracin" title="Bacitracin">Bacitracin</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</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>Hydrolyze NAM-NAG <ul><li><a href="/wiki/Lysozyme" title="Lysozyme">lysozyme</a></li></ul></li> <li><a href="/wiki/Tyrothricin" title="Tyrothricin">Tyrothricin</a> <ul><li><a href="/wiki/Gramicidin" title="Gramicidin">Gramicidin</a></li> <li><a href="/wiki/Tyrocidine" title="Tyrocidine">Tyrocidine</a></li></ul></li> <li><a href="/wiki/Isoniazid" title="Isoniazid">Isoniazid</a><sup>#</sup></li> <li><a href="/wiki/Teixobactin" title="Teixobactin">Teixobactin</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: transparent; 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="Glycine_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed 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:Glycine_receptor_modulators" title="Template:Glycine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Glycine_receptor_modulators" title="Template talk:Glycine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Glycine_receptor_modulators" title="Special:EditPage/Template:Glycine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Glycine_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Glycine_receptor" title="Glycine receptor">Glycine receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptor</a><br /><small>(<a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" 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:4em;;text-align:center;"><a href="/wiki/Glycine_receptor" title="Glycine receptor"><abbr title="Glycine receptor">GlyR</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 Glycine receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/%CE%92-Alanine" title="Β-Alanine">β-Alanine</a></li> <li><a href="/wiki/Beta-Aminobutyric_acid" class="mw-redirect" title="Beta-Aminobutyric acid">β-ABA (BABA)</a></li> <li><a href="/w/index.php?title=%CE%92-Aminoisobutyric_acid&action=edit&redlink=1" class="new" title="Β-Aminoisobutyric acid (page does not exist)">β-AIBA</a></li> <li><a href="/wiki/Caesium" title="Caesium">Caesium</a></li> <li><a href="/wiki/Alanine" title="Alanine"><small>D</small>-Alanine</a></li> <li><a href="/wiki/Serine" title="Serine"><small>D</small>-Serine</a></li> <li><a href="/wiki/Gamma-Aminobutyric_acid" class="mw-redirect" title="Gamma-Aminobutyric acid">GABA</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Hypotaurine" title="Hypotaurine">Hypotaurine</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/Alanine" title="Alanine"><small>L</small>-Alanine</a></li> <li><a href="/wiki/Proline" title="Proline"><small>L</small>-Proline</a></li> <li><a href="/wiki/Serine" title="Serine"><small>L</small>-Serine</a></li> <li><a href="/wiki/Threonine" title="Threonine"><small>L</small>-Threonine</a></li> <li><a href="/w/index.php?title=MDL-27531&action=edit&redlink=1" class="new" title="MDL-27531 (page does not exist)">MDL-27531</a></li> <li><a href="/wiki/Milacemide" title="Milacemide">Milacemide</a></li> <li><a href="/wiki/Picolinic_acid" title="Picolinic acid">Picolinic acid</a></li> <li><a href="/wiki/Propofol" title="Propofol">Propofol</a></li> <li><a href="/wiki/Quisqualamine" title="Quisqualamine">Quisqualamine</a></li> <li><a href="/wiki/Sarcosine" title="Sarcosine">Sarcosine</a></li> <li><a href="/wiki/Taurine" title="Taurine">Taurine</a></li></ul> <ul><li><b>Positive modulators:</b> <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a> (e.g., <a href="/w/index.php?title=Brometone&action=edit&redlink=1" class="new" title="Brometone (page does not exist)">brometone</a>, <a href="/wiki/Chlorobutanol" title="Chlorobutanol">chlorobutanol (chloretone)</a>, <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">ethanol (alcohol)</a>, <a href="/wiki/Tert-Butyl_alcohol" title="Tert-Butyl alcohol"><i>tert</i>-butanol (2M2P)</a>, <a href="/wiki/Tribromoethanol" title="Tribromoethanol">tribromoethanol</a>, <a href="/wiki/Trichloroethanol" class="mw-redirect" title="Trichloroethanol">trichloroethanol</a>, <a href="/wiki/Trifluoroethanol" class="mw-redirect" title="Trifluoroethanol">trifluoroethanol</a>)</li> <li><a href="/wiki/Alkylbenzene_sulfonate" title="Alkylbenzene sulfonate">Alkylbenzene sulfonate</a></li> <li><a href="/wiki/Anandamide" title="Anandamide">Anandamide</a></li> <li><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a> (e.g., <a href="/wiki/Pentobarbital" title="Pentobarbital">pentobarbital</a>, <a href="/wiki/Sodium_thiopental" title="Sodium thiopental">sodium thiopental</a>)</li> <li><a href="/wiki/Chlormethiazole" class="mw-redirect" title="Chlormethiazole">Chlormethiazole</a></li> <li><a href="/w/index.php?title=D12-116&action=edit&redlink=1" class="new" title="D12-116 (page does not exist)">D12-116</a></li> <li><a href="/wiki/Dihydropyridine" class="mw-redirect" title="Dihydropyridine">Dihydropyridines</a> (e.g., <a href="/wiki/Nicardipine" title="Nicardipine">nicardipine</a>)</li> <li><a href="/wiki/Etomidate" title="Etomidate">Etomidate</a></li> <li><a href="/wiki/Ginseng" title="Ginseng">Ginseng</a> constituents (e.g., <a href="/wiki/Ginsenoside" title="Ginsenoside">ginsenosides</a> (e.g., <a href="/w/index.php?title=Ginsenoside-Rf&action=edit&redlink=1" class="new" title="Ginsenoside-Rf (page does not exist)">ginsenoside-Rf</a>))</li> <li><a href="/wiki/Glutamic_acid" title="Glutamic acid">Glutamic acid (glutamate)</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neuroactive steroids</a> (e.g., <a href="/wiki/Alfaxolone" class="mw-redirect" title="Alfaxolone">alfaxolone</a>, <a href="/wiki/Pregnenolone" title="Pregnenolone">pregnenolone (eltanolone)</a>, <a href="/wiki/Pregnenolone_acetate" title="Pregnenolone acetate">pregnenolone acetate</a>, <a href="/wiki/Minaxolone" title="Minaxolone">minaxolone</a>, <a href="/wiki/ORG-20599" title="ORG-20599">ORG-20599</a>)</li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Penicillin_G" class="mw-redirect" title="Penicillin G">Penicillin G</a></li> <li><a href="/wiki/Propofol" title="Propofol">Propofol</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">Tetrahydrocannabinol</a></li> <li><a href="/wiki/Triclofos" title="Triclofos">Triclofos</a></li> <li><a href="/w/index.php?title=Tropeine&action=edit&redlink=1" class="new" title="Tropeine (page does not exist)">Tropeines</a> (e.g., <a href="/wiki/Atropine" title="Atropine">atropine</a>, <a href="/wiki/Bemesetron" title="Bemesetron">bemesetron</a>, <a href="/wiki/Cocaine" title="Cocaine">cocaine</a>, <a href="/w/index.php?title=LY-278584&action=edit&redlink=1" class="new" title="LY-278584 (page does not exist)">LY-278584</a>, <a href="/wiki/Tropisetron" title="Tropisetron">tropisetron</a>, <a href="/wiki/Zatosetron" title="Zatosetron">zatosetron</a>)</li> <li><a href="/wiki/Volatility_(chemistry)" title="Volatility (chemistry)">Volatiles</a>/<a href="/wiki/Gas" title="Gas">gases</a> (e.g., <a href="/wiki/Chloral_hydrate" title="Chloral hydrate">chloral hydrate</a>, <a href="/wiki/Chloroform" title="Chloroform">chloroform</a>, <a href="/wiki/Desflurane" title="Desflurane">desflurane</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether (ether)</a>, <a href="/wiki/Enflurane" title="Enflurane">enflurane</a>, <a href="/wiki/Halothane" title="Halothane">halothane</a>, <a href="/wiki/Isoflurane" title="Isoflurane">isoflurane</a>, <a href="/wiki/Methoxyflurane" title="Methoxyflurane">methoxyflurane</a>, <a href="/wiki/Sevoflurane" title="Sevoflurane">sevoflurane</a>, <a href="/wiki/Toluene" title="Toluene">toluene</a>, <a href="/wiki/1,1,1-trichloroethane" class="mw-redirect" title="1,1,1-trichloroethane">trichloroethane (methyl chloroform)</a>, <a href="/wiki/Trichloroethylene" title="Trichloroethylene">trichloroethylene</a>)</li> <li><a href="/wiki/Xenon" title="Xenon">Xenon</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=2-Aminostrychnine&action=edit&redlink=1" class="new" title="2-Aminostrychnine (page does not exist)">2-Aminostrychnine</a></li> <li><a href="/w/index.php?title=2-Nitrostrychnine&action=edit&redlink=1" class="new" title="2-Nitrostrychnine (page does not exist)">2-Nitrostrychnine</a></li> <li><a href="/w/index.php?title=4-Phenyl-4-formyl-N-methylpiperidine&action=edit&redlink=1" class="new" title="4-Phenyl-4-formyl-N-methylpiperidine (page does not exist)">4-Phenyl-4-formyl-N-methylpiperidine</a></li> <li><a href="/w/index.php?title=%CE%91-Ethyl-%CE%B1-methyl-%CE%B3-thiobutyrolactone&action=edit&redlink=1" class="new" title="Α-Ethyl-α-methyl-γ-thiobutyrolactone (page does not exist)">αEMBTL</a></li> <li><a href="/wiki/Bicuculline" title="Bicuculline">Bicuculline</a></li> <li><a href="/wiki/Brucine" title="Brucine">Brucine</a></li> <li><a href="/wiki/Cacotheline" title="Cacotheline">Cacotheline</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Colchicine" title="Colchicine">Colchicine</a></li> <li><a href="/wiki/Colubrine" class="mw-redirect" title="Colubrine">Colubrine</a></li> <li><a href="/w/index.php?title=Cyanotriphenylborate&action=edit&redlink=1" class="new" title="Cyanotriphenylborate (page does not exist)">Cyanotriphenylborate</a></li> <li><a href="/wiki/Dendrobine" title="Dendrobine">Dendrobine</a></li> <li><a href="/w/index.php?title=Diaboline&action=edit&redlink=1" class="new" title="Diaboline (page does not exist)">Diaboline</a></li> <li><a href="/wiki/Endocannabinoid" class="mw-redirect" title="Endocannabinoid">Endocannabinoids</a> (e.g., <a href="/wiki/2-arachidonylglycerol" class="mw-redirect" title="2-arachidonylglycerol">2-AG</a>, <a href="/wiki/Anandamide" title="Anandamide">anandamide (AEA)</a>)</li> <li><a href="/wiki/Gaboxadol" title="Gaboxadol">Gaboxadol (THIP)</a></li> <li><a href="/wiki/Gelsemine" title="Gelsemine">Gelsemine</a></li> <li><a href="/w/index.php?title=Iso-THAZ&action=edit&redlink=1" class="new" title="Iso-THAZ (page does not exist)">iso-THAZ</a></li> <li><a href="/wiki/Isobutyric_acid" title="Isobutyric acid">Isobutyric acid</a></li> <li><a href="/wiki/Isonipecotic_acid" title="Isonipecotic acid">Isonipecotic acid</a></li> <li><a href="/w/index.php?title=Isostrychnine&action=edit&redlink=1" class="new" title="Isostrychnine (page does not exist)">Isostrychnine</a></li> <li><a href="/wiki/Laudanosine" title="Laudanosine">Laudanosine</a></li> <li><a href="/w/index.php?title=N-Methylbicuculline&action=edit&redlink=1" class="new" title="N-Methylbicuculline (page does not exist)">N-Methylbicuculline</a></li> <li><a href="/w/index.php?title=N-Methylstrychnine&action=edit&redlink=1" class="new" title="N-Methylstrychnine (page does not exist)">N-Methylstrychnine</a></li> <li><a href="/w/index.php?title=N,N-Dimethylmuscimol&action=edit&redlink=1" class="new" title="N,N-Dimethylmuscimol (page does not exist)">N,N-Dimethylmuscimol</a></li> <li><a href="/wiki/Nipecotic_acid" title="Nipecotic acid">Nipecotic acid</a></li> <li><a href="/wiki/Pitrazepin" title="Pitrazepin">Pitrazepin</a></li> <li><a href="/w/index.php?title=Pseudostrychnine&action=edit&redlink=1" class="new" title="Pseudostrychnine (page does not exist)">Pseudostrychnine</a></li> <li><a href="/wiki/Quinoline" title="Quinoline">Quinolines</a> (e.g., <a href="/w/index.php?title=4-hydroxyquinoline&action=edit&redlink=1" class="new" title="4-hydroxyquinoline (page does not exist)">4-hydroxyquinoline</a>, <a href="/w/index.php?title=4-hydroxyquinoline-3-carboxylic_acid&action=edit&redlink=1" class="new" title="4-hydroxyquinoline-3-carboxylic acid (page does not exist)">4-hydroxyquinoline-3-carboxylic acid</a>, <a href="/w/index.php?title=5,7-dichloro-4-hydroxyquinoline-3-carboxylic_acid&action=edit&redlink=1" class="new" title="5,7-dichloro-4-hydroxyquinoline-3-carboxylic acid (page does not exist)">5,7-CIQA</a>, <a href="/w/index.php?title=7-chloro-4-hydroxyquinoline&action=edit&redlink=1" class="new" title="7-chloro-4-hydroxyquinoline (page does not exist)">7-CIQ</a>, <a href="/w/index.php?title=7-trifluoromethyl-4-hydroxyquinoline&action=edit&redlink=1" class="new" title="7-trifluoromethyl-4-hydroxyquinoline (page does not exist)">7-TFQ</a>, <a href="/w/index.php?title=7-trifluoromethyl-4-hydroxyquinoline-3-carboxylic_acid&action=edit&redlink=1" class="new" title="7-trifluoromethyl-4-hydroxyquinoline-3-carboxylic acid (page does not exist)">7-TFQA</a>)</li> <li><a href="/w/index.php?title=RU-5135&action=edit&redlink=1" class="new" title="RU-5135 (page does not exist)">RU-5135</a></li> <li><a href="/wiki/Sinomenine" title="Sinomenine">Sinomenine</a></li> <li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li> <li><a href="/wiki/Thiocolchicoside" title="Thiocolchicoside">Thiocolchicoside</a></li> <li><a href="/wiki/Tutin_(toxin)" title="Tutin (toxin)">Tutin</a></li></ul> <ul><li><b>Negative modulators:</b> <a href="/wiki/Amiloride" title="Amiloride">Amiloride</a></li> <li><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a> (e.g., <a href="/wiki/Bromazepam" title="Bromazepam">bromazepam</a>, <a href="/wiki/Clonazepam" title="Clonazepam">clonazepam</a>, <a href="/wiki/Diazepam" title="Diazepam">diazepam</a>, <a href="/wiki/Flunitrazepam" title="Flunitrazepam">flunitrazepam</a>, <a href="/wiki/Flurazepam" title="Flurazepam">flurazepam</a>)</li> <li><a href="/wiki/Corymine" title="Corymine">Corymine</a></li> <li><a href="/w/index.php?title=Cyanotriphenylborate&action=edit&redlink=1" class="new" title="Cyanotriphenylborate (page does not exist)">Cyanotriphenylborate</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/Dihydropyridine" class="mw-redirect" title="Dihydropyridine">Dihydropyridines</a> (e.g., <a href="/wiki/Nicardipine" title="Nicardipine">nicardipine</a>, <a href="/wiki/Nifedipine" title="Nifedipine">nifedipine</a>, <a href="/wiki/Nitrendipine" title="Nitrendipine">nitrendipine</a>)</li> <li><a href="/wiki/Furosemide" title="Furosemide">Furosemide</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/wiki/Ginkgo_biloba" title="Ginkgo biloba">Ginkgo</a> constituents (e.g., <a href="/wiki/Bilobalide" title="Bilobalide">bilobalide</a>, <a href="/wiki/Ginkgolide" title="Ginkgolide">ginkgolides</a> (e.g., <a href="/w/index.php?title=Ginkgolide_A&action=edit&redlink=1" class="new" title="Ginkgolide A (page does not exist)">ginkgolide A</a>, <a href="/wiki/Ginkgolide_B" class="mw-redirect" title="Ginkgolide B">ginkgolide B</a>, <a href="/w/index.php?title=Ginkgolide_C&action=edit&redlink=1" class="new" title="Ginkgolide C (page does not exist)">ginkgolide C</a>, <a href="/w/index.php?title=Ginkgolide_J&action=edit&redlink=1" class="new" title="Ginkgolide J (page does not exist)">ginkgolide J</a>, <a href="/w/index.php?title=Ginkgolide_M&action=edit&redlink=1" class="new" title="Ginkgolide M (page does not exist)">ginkgolide M</a>))</li> <li><a href="/wiki/Imipramine" title="Imipramine">Imipramine</a></li> <li><a href="/wiki/NBQX" title="NBQX">NBQX</a></li> <li><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neuroactive steroids</a> (e.g., <a href="/wiki/3%CE%B1-androsterone_sulfate" class="mw-redirect" title="3α-androsterone sulfate">3α-androsterone sulfate</a>, <a href="/w/index.php?title=3%CE%B2-androsterone_sulfate&action=edit&redlink=1" class="new" title="3β-androsterone sulfate (page does not exist)">3β-androsterone sulfate</a>, <a href="/wiki/11-deoxycorticosterone" class="mw-redirect" title="11-deoxycorticosterone">deoxycorticosterone</a>, <a href="/wiki/DHEA_sulfate" class="mw-redirect" title="DHEA sulfate">DHEA sulfate</a>, <a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">pregnenolone sulfate</a>, <a href="/wiki/Progesterone" title="Progesterone">progesterone</a>)</li> <li><a href="/wiki/Opioid" title="Opioid">Opioids</a> (e.g., <a href="/wiki/Codeine" title="Codeine">codeine</a>, <a href="/wiki/Dextromethorphan" title="Dextromethorphan">dextromethorphan</a>, <a href="/wiki/Dextrorphan" title="Dextrorphan">dextrorphan</a>, <a href="/wiki/Levomethadone" title="Levomethadone">levomethadone</a>, <a href="/wiki/Levorphanol" title="Levorphanol">levorphanol</a>, <a href="/wiki/Morphine" title="Morphine">morphine</a>, <a href="/wiki/Oripavine" title="Oripavine">oripavine</a>, <a href="/wiki/Pethidine" title="Pethidine">pethidine</a>, <a href="/wiki/Thebaine" title="Thebaine">thebaine</a>)</li> <li><a href="/wiki/Picrotoxin" title="Picrotoxin">Picrotoxin</a> (i.e., <a href="/wiki/Picrotin" class="mw-redirect" title="Picrotin">picrotin</a> and <a href="/wiki/Picrotoxinin" class="mw-redirect" title="Picrotoxinin">picrotoxinin</a>)</li> <li><a href="/w/index.php?title=Phenylbenzene_%CF%89-phosphono-%CE%B1-amino_acid&action=edit&redlink=1" class="new" title="Phenylbenzene ω-phosphono-α-amino acid (page does not exist)">PMBA</a></li> <li><a href="/wiki/Riluzole" title="Riluzole">Riluzole</a></li> <li><a href="/w/index.php?title=Tropeine&action=edit&redlink=1" class="new" title="Tropeine (page does not exist)">Tropeines</a> (e.g., <a href="/wiki/Bemesetron" title="Bemesetron">bemesetron</a>, <a href="/w/index.php?title=LY-278584&action=edit&redlink=1" class="new" title="LY-278584 (page does not exist)">LY-278584</a>, <a href="/wiki/Tropisetron" title="Tropisetron">tropisetron</a>, <a href="/wiki/Zatosetron" title="Zatosetron">zatosetron</a>)</li> <li><a href="/wiki/Verapamil" title="Verapamil">Verapamil</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/N-Methyl-D-aspartate_receptor" class="mw-redirect" title="N-Methyl-D-aspartate receptor"><abbr title="N-Methyl-D-aspartate receptor">NMDAR</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 N-Methyl-D-aspartate receptor</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>See <a href="/wiki/Template:Ionotropic_glutamate_receptor_modulators" title="Template:Ionotropic glutamate receptor modulators">here</a> instead.</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/Neurotransmitter_transporter" title="Neurotransmitter transporter">Transporter</a><br /><small>(<a href="/wiki/Reuptake_inhibitor" title="Reuptake inhibitor">blockers</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" 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:4em;;text-align:center;"><a href="/wiki/Glycine_transporter_1" class="mw-redirect" title="Glycine transporter 1"><abbr title="Glycine transporter 1">GlyT1</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 Glycine transporter 1</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=ACPPB&action=edit&redlink=1" class="new" title="ACPPB (page does not exist)">ACPPB</a></li> <li><a href="/w/index.php?title=ALX-5407&action=edit&redlink=1" class="new" title="ALX-5407 (page does not exist)">ALX-5407 (NFPS)</a></li> <li><a href="/wiki/ASP2535" title="ASP2535">ASP2535</a></li> <li><a href="/wiki/Bitopertin" title="Bitopertin">Bitopertin (RG1678/RO4917838)</a></li> <li><a href="/w/index.php?title=CP-802079&action=edit&redlink=1" class="new" title="CP-802079 (page does not exist)">CP-802079</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/w/index.php?title=Glycyldodecylamide&action=edit&redlink=1" class="new" title="Glycyldodecylamide (page does not exist)">Glycyldodecylamide</a></li> <li><a href="/w/index.php?title=GSK1018921&action=edit&redlink=1" class="new" title="GSK1018921 (page does not exist)">GSK1018921</a></li> <li><a href="/wiki/Iclepertin" title="Iclepertin">Iclepertin</a></li> <li><a href="/wiki/LY-2365109" title="LY-2365109">LY-2365109</a></li> <li><a href="/wiki/Mardepodect" title="Mardepodect">Mardepodect</a></li> <li><a href="/wiki/ORG-24598" title="ORG-24598">ORG-24598</a></li> <li><a href="/wiki/ORG-25935" title="ORG-25935">ORG-25935 (SCH-900435)</a></li> <li><a href="/wiki/Pesampator" title="Pesampator">Pesampator (BIIB-104, PF-04958242)</a></li> <li><a href="/w/index.php?title=PF-03463275&action=edit&redlink=1" class="new" title="PF-03463275 (page does not exist)">PF-03463275</a></li> <li><a href="/wiki/Sarcosine" title="Sarcosine">Sarcosine</a></li> <li><a href="/wiki/SNG-12" title="SNG-12">SNG-12 (Synapsinae)</a></li> <li><a href="/w/index.php?title=SSR-103,800&action=edit&redlink=1" class="new" title="SSR-103,800 (page does not exist)">SSR-103,800</a></li> <li><a href="/w/index.php?title=SSR-504,734&action=edit&redlink=1" class="new" title="SSR-504,734 (page does not exist)">SSR-504,734</a></li> <li><a href="/wiki/Tilapertin" title="Tilapertin">Tilapertin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Glycine_transporter_2" class="mw-redirect" title="Glycine transporter 2"><abbr title="Glycine transporter 2">GlyT2</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 Glycine transporter 2</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/ALX-1393" title="ALX-1393">ALX-1393</a></li> <li><a href="/wiki/Amoxapine" title="Amoxapine">Amoxapine</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/wiki/N-Arachidonylglycine" title="N-Arachidonylglycine">NAGly</a></li> <li><a href="/wiki/Opiranserin" title="Opiranserin">Opiranserin (VVZ-149)</a></li> <li><a href="/w/index.php?title=ORG-25543&action=edit&redlink=1" class="new" title="ORG-25543 (page does not exist)">ORG-25543</a></li> <li><a href="/w/index.php?title=VVZ-368&action=edit&redlink=1" class="new" title="VVZ-368 (page does not exist)">VVZ-368</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><i><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></dd> <dd><i><a href="/wiki/Template:GABA_receptor_modulators" title="Template:GABA receptor modulators">GABA receptor modulators</a></i></dd> <dd><i><a href="/wiki/Template:GABAA_receptor_positive_modulators" title="Template:GABAA receptor positive modulators">GABA<sub>A</sub> receptor positive modulators</a></i></dd> <dd><i><a href="/wiki/Template:Ionotropic_glutamate_receptor_modulators" title="Template:Ionotropic glutamate receptor modulators">Ionotropic glutamate receptor modulators</a></i></dd></dl> </div></td></tr></tbody></table></div> <style data-mw-deduplicate="TemplateStyles:r1130092004">.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;justify-content:center;align-items:baseline}.mw-parser-output .portal-bar-bordered{padding:0 2em;background-color:#fdfdfd;border:1px solid #a2a9b1;clear:both;margin:1em auto 0}.mw-parser-output .portal-bar-related{font-size:100%;justify-content:flex-start}.mw-parser-output .portal-bar-unbordered{padding:0 1.7em;margin-left:0}.mw-parser-output .portal-bar-header{margin:0 1em 0 0.5em;flex:0 0 auto;min-height:24px}.mw-parser-output .portal-bar-content{display:flex;flex-flow:row wrap;flex:0 1 auto;padding:0.15em 0;column-gap:1em;align-items:baseline;margin:0;list-style:none}.mw-parser-output .portal-bar-content-related{margin:0;list-style:none}.mw-parser-output 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