CINXE.COM

<!DOCTYPE html> <html class="client-nojs vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-sticky-header-disabled vector-feature-page-tools-pinned-disabled vector-feature-toc-pinned-clientpref-1 vector-feature-main-menu-pinned-disabled vector-feature-limited-width-clientpref-1 vector-feature-limited-width-content-enabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-feature-night-mode-enabled skin-theme-clientpref-day vector-toc-available" lang="en" dir="ltr"> <head> <meta charset="UTF-8"> <title>Avermectin - Wikipedia</title> <script>(function(){var className="client-js vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-sticky-header-disabled vector-feature-page-tools-pinned-disabled vector-feature-toc-pinned-clientpref-1 vector-feature-main-menu-pinned-disabled vector-feature-limited-width-clientpref-1 vector-feature-limited-width-content-enabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-feature-night-mode-enabled skin-theme-clientpref-day vector-toc-available";var cookie=document.cookie.match(/(?:^|; )enwikimwclientpreferences=([^;]+)/);if(cookie){cookie[1].split('%2C').forEach(function(pref){className=className.replace(new RegExp('(^| )'+pref.replace(/-clientpref-\w+$|[^\w-]+/g,'')+'-clientpref-\\w+( |$)'),'$1'+pref+'$2');});}document.documentElement.className=className;}());RLCONF={"wgBreakFrames":false,"wgSeparatorTransformTable":["",""],"wgDigitTransformTable":["",""],"wgDefaultDateFormat":"dmy", "wgMonthNames":["","January","February","March","April","May","June","July","August","September","October","November","December"],"wgRequestId":"86e15bb6-28b4-42c5-be90-84085733e343","wgCanonicalNamespace":"","wgCanonicalSpecialPageName":false,"wgNamespaceNumber":0,"wgPageName":"Avermectin","wgTitle":"Avermectin","wgCurRevisionId":1233977336,"wgRevisionId":1233977336,"wgArticleId":5804791,"wgIsArticle":true,"wgIsRedirect":false,"wgAction":"view","wgUserName":null,"wgUserGroups":["*"],"wgCategories":["Articles with short description","Short description matches Wikidata","Articles to be expanded from September 2023","All articles with unsourced statements","Articles with unsourced statements from November 2020","All accuracy disputes","Articles with disputed statements from November 2023","Antiparasitic agents","Polyketides"],"wgPageViewLanguage":"en","wgPageContentLanguage":"en","wgPageContentModel":"wikitext","wgRelevantPageName":"Avermectin","wgRelevantArticleId":5804791, "wgIsProbablyEditable":true,"wgRelevantPageIsProbablyEditable":true,"wgRestrictionEdit":[],"wgRestrictionMove":[],"wgNoticeProject":"wikipedia","wgCiteReferencePreviewsActive":false,"wgFlaggedRevsParams":{"tags":{"status":{"levels":1}}},"wgMediaViewerOnClick":true,"wgMediaViewerEnabledByDefault":true,"wgPopupsFlags":0,"wgVisualEditor":{"pageLanguageCode":"en","pageLanguageDir":"ltr","pageVariantFallbacks":"en"},"wgMFDisplayWikibaseDescriptions":{"search":true,"watchlist":true,"tagline":false,"nearby":true},"wgWMESchemaEditAttemptStepOversample":false,"wgWMEPageLength":20000,"wgRelatedArticlesCompat":[],"wgCentralAuthMobileDomain":false,"wgEditSubmitButtonLabelPublish":true,"wgULSPosition":"interlanguage","wgULSisCompactLinksEnabled":false,"wgVector2022LanguageInHeader":true,"wgULSisLanguageSelectorEmpty":false,"wgWikibaseItemId":"Q416170","wgCheckUserClientHintsHeadersJsApi":["brands","architecture","bitness","fullVersionList","mobile","model","platform","platformVersion"], "GEHomepageSuggestedEditsEnableTopics":true,"wgGETopicsMatchModeEnabled":false,"wgGEStructuredTaskRejectionReasonTextInputEnabled":false,"wgGELevelingUpEnabledForUser":false};RLSTATE={"ext.globalCssJs.user.styles":"ready","site.styles":"ready","user.styles":"ready","ext.globalCssJs.user":"ready","user":"ready","user.options":"loading","ext.cite.styles":"ready","skins.vector.search.codex.styles":"ready","skins.vector.styles":"ready","skins.vector.icons":"ready","jquery.makeCollapsible.styles":"ready","ext.wikimediamessages.styles":"ready","ext.visualEditor.desktopArticleTarget.noscript":"ready","ext.uls.interlanguage":"ready","wikibase.client.init":"ready","ext.wikimediaBadges":"ready"};RLPAGEMODULES=["ext.cite.ux-enhancements","mediawiki.page.media","site","mediawiki.page.ready","jquery.makeCollapsible","mediawiki.toc","skins.vector.js","ext.centralNotice.geoIP","ext.centralNotice.startUp","ext.gadget.ReferenceTooltips","ext.gadget.switcher","ext.urlShortener.toolbar", "ext.centralauth.centralautologin","mmv.bootstrap","ext.popups","ext.visualEditor.desktopArticleTarget.init","ext.visualEditor.targetLoader","ext.echo.centralauth","ext.eventLogging","ext.wikimediaEvents","ext.navigationTiming","ext.uls.interface","ext.cx.eventlogging.campaigns","ext.cx.uls.quick.actions","wikibase.client.vector-2022","ext.checkUser.clientHints","ext.growthExperiments.SuggestedEditSession","wikibase.sidebar.tracking"];</script> <script>(RLQ=window.RLQ||[]).push(function(){mw.loader.impl(function(){return["user.options@12s5i",function($,jQuery,require,module){mw.user.tokens.set({"patrolToken":"+\\","watchToken":"+\\","csrfToken":"+\\"}); }];});});</script> <link rel="stylesheet" href="/w/load.php?lang=en&modules=ext.cite.styles%7Cext.uls.interlanguage%7Cext.visualEditor.desktopArticleTarget.noscript%7Cext.wikimediaBadges%7Cext.wikimediamessages.styles%7Cjquery.makeCollapsible.styles%7Cskins.vector.icons%2Cstyles%7Cskins.vector.search.codex.styles%7Cwikibase.client.init&only=styles&skin=vector-2022"> <script async="" src="/w/load.php?lang=en&modules=startup&only=scripts&raw=1&skin=vector-2022"></script> <meta name="ResourceLoaderDynamicStyles" content=""> <link rel="stylesheet" href="/w/load.php?lang=en&modules=site.styles&only=styles&skin=vector-2022"> <meta name="generator" content="MediaWiki 1.44.0-wmf.4"> <meta name="referrer" content="origin"> <meta name="referrer" content="origin-when-cross-origin"> <meta name="robots" content="max-image-preview:standard"> <meta name="format-detection" content="telephone=no"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Avermectins_skeletal.svg/1200px-Avermectins_skeletal.svg.png"> <meta property="og:image:width" content="1200"> <meta property="og:image:height" content="653"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Avermectins_skeletal.svg/800px-Avermectins_skeletal.svg.png"> <meta property="og:image:width" content="800"> <meta property="og:image:height" content="435"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Avermectins_skeletal.svg/640px-Avermectins_skeletal.svg.png"> <meta property="og:image:width" content="640"> <meta property="og:image:height" content="348"> <meta name="viewport" content="width=1120"> <meta property="og:title" content="Avermectin - Wikipedia"> <meta property="og:type" content="website"> <link rel="preconnect" href="//upload.wikimedia.org"> <link rel="alternate" media="only screen and (max-width: 640px)" href="//en.m.wikipedia.org/wiki/Avermectin"> <link rel="alternate" type="application/x-wiki" title="Edit this page" href="/w/index.php?title=Avermectin&action=edit"> <link rel="apple-touch-icon" href="/static/apple-touch/wikipedia.png"> <link rel="icon" href="/static/favicon/wikipedia.ico"> <link rel="search" type="application/opensearchdescription+xml" href="/w/rest.php/v1/search" title="Wikipedia (en)"> <link rel="EditURI" type="application/rsd+xml" href="//en.wikipedia.org/w/api.php?action=rsd"> <link rel="canonical" href="https://en.wikipedia.org/wiki/Avermectin"> <link rel="license" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en"> <link rel="alternate" type="application/atom+xml" title="Wikipedia Atom feed" href="/w/index.php?title=Special:RecentChanges&feed=atom"> <link rel="dns-prefetch" href="//meta.wikimedia.org" /> <link rel="dns-prefetch" href="//login.wikimedia.org"> </head> <body class="skin--responsive skin-vector skin-vector-search-vue mediawiki ltr sitedir-ltr mw-hide-empty-elt ns-0 ns-subject mw-editable page-Avermectin rootpage-Avermectin skin-vector-2022 action-view"><a class="mw-jump-link" href="#bodyContent">Jump to content</a> <div class="vector-header-container"> <header class="vector-header mw-header"> <div class="vector-header-start"> <nav class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-dropdown" class="vector-dropdown vector-main-menu-dropdown vector-button-flush-left vector-button-flush-right" > <input type="checkbox" id="vector-main-menu-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-main-menu-dropdown" class="vector-dropdown-checkbox " aria-label="Main menu" > <label id="vector-main-menu-dropdown-label" for="vector-main-menu-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-menu mw-ui-icon-wikimedia-menu"></span> <span class="vector-dropdown-label-text">Main menu</span> </label> <div class="vector-dropdown-content"> <div id="vector-main-menu-unpinned-container" class="vector-unpinned-container"> <div id="vector-main-menu" class="vector-main-menu vector-pinnable-element"> <div class="vector-pinnable-header vector-main-menu-pinnable-header vector-pinnable-header-unpinned" data-feature-name="main-menu-pinned" data-pinnable-element-id="vector-main-menu" data-pinned-container-id="vector-main-menu-pinned-container" data-unpinned-container-id="vector-main-menu-unpinned-container" > <div class="vector-pinnable-header-label">Main menu</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-main-menu.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-main-menu.unpin">hide</button> </div> <div id="p-navigation" class="vector-menu mw-portlet mw-portlet-navigation" > <div class="vector-menu-heading"> Navigation </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-mainpage-description" class="mw-list-item"><a href="/wiki/Main_Page" title="Visit the main page [z]" accesskey="z"><span>Main page</span></a></li><li id="n-contents" class="mw-list-item"><a href="/wiki/Wikipedia:Contents" title="Guides to browsing Wikipedia"><span>Contents</span></a></li><li id="n-currentevents" class="mw-list-item"><a href="/wiki/Portal:Current_events" title="Articles related to current events"><span>Current events</span></a></li><li id="n-randompage" class="mw-list-item"><a href="/wiki/Special:Random" title="Visit a randomly selected article [x]" accesskey="x"><span>Random article</span></a></li><li id="n-aboutsite" class="mw-list-item"><a href="/wiki/Wikipedia:About" title="Learn about Wikipedia and how it works"><span>About Wikipedia</span></a></li><li id="n-contactpage" class="mw-list-item"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us" title="How to contact Wikipedia"><span>Contact us</span></a></li> </ul> </div> </div> <div id="p-interaction" class="vector-menu mw-portlet mw-portlet-interaction" > <div class="vector-menu-heading"> Contribute </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-help" class="mw-list-item"><a href="/wiki/Help:Contents" title="Guidance on how to use and edit Wikipedia"><span>Help</span></a></li><li id="n-introduction" class="mw-list-item"><a href="/wiki/Help:Introduction" title="Learn how to edit Wikipedia"><span>Learn to edit</span></a></li><li id="n-portal" class="mw-list-item"><a href="/wiki/Wikipedia:Community_portal" title="The hub for editors"><span>Community portal</span></a></li><li id="n-recentchanges" class="mw-list-item"><a href="/wiki/Special:RecentChanges" title="A list of recent changes to Wikipedia [r]" accesskey="r"><span>Recent changes</span></a></li><li id="n-upload" class="mw-list-item"><a href="/wiki/Wikipedia:File_upload_wizard" title="Add images or other media for use on Wikipedia"><span>Upload file</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> <a href="/wiki/Main_Page" class="mw-logo"> <img class="mw-logo-icon" src="/static/images/icons/wikipedia.png" alt="" aria-hidden="true" height="50" width="50"> <span class="mw-logo-container skin-invert"> <img class="mw-logo-wordmark" alt="Wikipedia" src="/static/images/mobile/copyright/wikipedia-wordmark-en.svg" style="width: 7.5em; height: 1.125em;"> <img class="mw-logo-tagline" alt="The Free Encyclopedia" src="/static/images/mobile/copyright/wikipedia-tagline-en.svg" width="117" height="13" style="width: 7.3125em; height: 0.8125em;"> </span> </a> </div> <div class="vector-header-end"> <div id="p-search" role="search" class="vector-search-box-vue vector-search-box-collapses vector-search-box-show-thumbnail vector-search-box-auto-expand-width vector-search-box"> <a href="/wiki/Special:Search" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only search-toggle" title="Search Wikipedia [f]" accesskey="f"><span class="vector-icon mw-ui-icon-search mw-ui-icon-wikimedia-search"></span> <span>Search</span> </a> <div class="vector-typeahead-search-container"> <div class="cdx-typeahead-search cdx-typeahead-search--show-thumbnail cdx-typeahead-search--auto-expand-width"> <form action="/w/index.php" id="searchform" class="cdx-search-input cdx-search-input--has-end-button"> <div id="simpleSearch" class="cdx-search-input__input-wrapper" data-search-loc="header-moved"> <div class="cdx-text-input cdx-text-input--has-start-icon"> <input class="cdx-text-input__input" type="search" name="search" placeholder="Search Wikipedia" aria-label="Search Wikipedia" autocapitalize="sentences" title="Search Wikipedia [f]" accesskey="f" id="searchInput" > <span class="cdx-text-input__icon cdx-text-input__start-icon"></span> </div> <input type="hidden" name="title" value="Special:Search"> </div> <button class="cdx-button cdx-search-input__end-button">Search</button> </form> </div> </div> </div> <nav class="vector-user-links vector-user-links-wide" aria-label="Personal tools"> <div class="vector-user-links-main"> <div id="p-vector-user-menu-preferences" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-userpage" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-dropdown" class="vector-dropdown " title="Change the appearance of the page's font size, width, and color" > <input type="checkbox" id="vector-appearance-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-appearance-dropdown" class="vector-dropdown-checkbox " aria-label="Appearance" > <label id="vector-appearance-dropdown-label" for="vector-appearance-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-appearance mw-ui-icon-wikimedia-appearance"></span> <span class="vector-dropdown-label-text">Appearance</span> </label> <div class="vector-dropdown-content"> <div id="vector-appearance-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <div id="p-vector-user-menu-notifications" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-overflow" class="vector-menu mw-portlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="https://donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_en.wikipedia.org&uselang=en" class=""><span>Donate</span></a> </li> <li id="pt-createaccount-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:CreateAccount&returnto=Avermectin" title="You are encouraged to create an account and log in; however, it is not mandatory" class=""><span>Create account</span></a> </li> <li id="pt-login-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:UserLogin&returnto=Avermectin" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o" class=""><span>Log in</span></a> </li> </ul> </div> </div> </div> <div id="vector-user-links-dropdown" class="vector-dropdown vector-user-menu vector-button-flush-right vector-user-menu-logged-out" title="Log in and more options" > <input type="checkbox" id="vector-user-links-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-user-links-dropdown" class="vector-dropdown-checkbox " aria-label="Personal tools" > <label id="vector-user-links-dropdown-label" for="vector-user-links-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-ellipsis mw-ui-icon-wikimedia-ellipsis"></span> <span class="vector-dropdown-label-text">Personal tools</span> </label> <div class="vector-dropdown-content"> <div id="p-personal" class="vector-menu mw-portlet mw-portlet-personal user-links-collapsible-item" title="User menu" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport" class="user-links-collapsible-item mw-list-item"><a href="https://donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_en.wikipedia.org&uselang=en"><span>Donate</span></a></li><li id="pt-createaccount" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:CreateAccount&returnto=Avermectin" title="You are encouraged to create an account and log in; however, it is not mandatory"><span class="vector-icon mw-ui-icon-userAdd mw-ui-icon-wikimedia-userAdd"></span> <span>Create account</span></a></li><li id="pt-login" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:UserLogin&returnto=Avermectin" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o"><span class="vector-icon mw-ui-icon-logIn mw-ui-icon-wikimedia-logIn"></span> <span>Log in</span></a></li> </ul> </div> </div> <div id="p-user-menu-anon-editor" class="vector-menu mw-portlet mw-portlet-user-menu-anon-editor" > <div class="vector-menu-heading"> Pages for logged out editors <a href="/wiki/Help:Introduction" aria-label="Learn more about editing"><span>learn more</span></a> </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-anoncontribs" class="mw-list-item"><a href="/wiki/Special:MyContributions" title="A list of edits made from this IP address [y]" accesskey="y"><span>Contributions</span></a></li><li id="pt-anontalk" class="mw-list-item"><a href="/wiki/Special:MyTalk" title="Discussion about edits from this IP address [n]" accesskey="n"><span>Talk</span></a></li> </ul> </div> </div> </div> </div> </nav> </div> </header> </div> <div class="mw-page-container"> <div class="mw-page-container-inner"> <div class="vector-sitenotice-container"> <div id="siteNotice"></div> </div> <div class="vector-column-start"> <div class="vector-main-menu-container"> <div id="mw-navigation"> <nav id="mw-panel" class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-pinned-container" class="vector-pinned-container"> </div> </nav> </div> </div> <div class="vector-sticky-pinned-container"> <nav id="mw-panel-toc" aria-label="Contents" data-event-name="ui.sidebar-toc" class="mw-table-of-contents-container vector-toc-landmark"> <div id="vector-toc-pinned-container" class="vector-pinned-container"> <div id="vector-toc" class="vector-toc vector-pinnable-element"> <div class="vector-pinnable-header vector-toc-pinnable-header vector-pinnable-header-pinned" data-feature-name="toc-pinned" data-pinnable-element-id="vector-toc" > <h2 class="vector-pinnable-header-label">Contents</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">hide</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">(Top)</div> </a> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dosing" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Dosing"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Dosing</span> </div> </a> <ul id="toc-Dosing-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mechanism_of_action" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Mechanism_of_action"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Mechanism of action</span> </div> </a> <ul id="toc-Mechanism_of_action-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toxicity_and_side_effects" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Toxicity_and_side_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Toxicity and side effects</span> </div> </a> <ul id="toc-Toxicity_and_side_effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Avermectin_biosynthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Avermectin_biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Avermectin biosynthesis</span> </div> </a> <ul id="toc-Avermectin_biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Other_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Other uses</span> </div> </a> <ul id="toc-Other_uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Avermectin</span></h1> <div 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 18 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-18" 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">18 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A3%D9%81%D9%8A%D8%B1%D9%85%D9%8A%D9%83%D8%AA%D9%86" title="أفيرميكتن – Arabic" lang="ar" hreflang="ar" data-title="أفيرميكتن" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Avermectina" title="Avermectina – Catalan" lang="ca" hreflang="ca" data-title="Avermectina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Avermectin" title="Avermectin – Danish" lang="da" hreflang="da" data-title="Avermectin" 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/Avermectine" title="Avermectine – German" lang="de" hreflang="de" data-title="Avermectine" 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/Avermectina" title="Avermectina – Spanish" lang="es" hreflang="es" data-title="Avermectina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Avermectina" title="Avermectina – Basque" lang="eu" hreflang="eu" data-title="Avermectina" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D9%88%D8%B1%D9%85%DA%A9%D8%AA%DB%8C%D9%86" title="اورمکتین – Persian" lang="fa" hreflang="fa" data-title="اورمکتین" 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/Avermectine" title="Avermectine – French" lang="fr" hreflang="fr" data-title="Avermectine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Avermectina" title="Avermectina – Galician" lang="gl" hreflang="gl" data-title="Avermectina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%95%84%EB%B2%84%EB%A9%95%ED%8B%B4" title="아버멕틴 – Korean" lang="ko" hreflang="ko" data-title="아버멕틴" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A2%E3%83%99%E3%83%AB%E3%83%A1%E3%82%AF%E3%83%81%E3%83%B3" title="アベルメクチン – Japanese" lang="ja" hreflang="ja" data-title="アベルメクチン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Avermectina" title="Avermectina – Portuguese" lang="pt" hreflang="pt" data-title="Avermectina" 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/Avermectin%C4%83" title="Avermectină – Romanian" lang="ro" hreflang="ro" data-title="Avermectină" 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%90%D0%B2%D0%B5%D1%80%D0%BC%D0%B5%D0%BA%D1%82%D0%B8%D0%BD%D1%8B" title="Авермектины – Russian" lang="ru" hreflang="ru" data-title="Авермектины" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Avermectin" title="Avermectin – Swedish" lang="sv" hreflang="sv" data-title="Avermectin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%90%D0%B2%D0%B5%D1%80%D0%BC%D0%B5%D0%BA%D1%82%D0%B8%D0%BD" title="Авермектин – Ukrainian" lang="uk" hreflang="uk" data-title="Авермектин" 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/Avermectin" title="Avermectin – Vietnamese" lang="vi" hreflang="vi" data-title="Avermectin" 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/%E9%98%BF%E7%BB%B4%E8%8F%8C%E7%B4%A0" title="阿维菌素 – Chinese" lang="zh" hreflang="zh" data-title="阿维菌素" 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/Q416170#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Avermectin" title="View the content page [c]" accesskey="c"><span>Article</span></a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Talk:Avermectin" rel="discussion" title="Discuss improvements to the content page [t]" accesskey="t"><span>Talk</span></a></li> </ul> </div> </div> <div id="vector-variants-dropdown" class="vector-dropdown emptyPortlet" > <input type="checkbox" id="vector-variants-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-variants-dropdown" class="vector-dropdown-checkbox " aria-label="Change language variant" > <label id="vector-variants-dropdown-label" for="vector-variants-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" ><span class="vector-dropdown-label-text">English</span> </label> <div class="vector-dropdown-content"> <div id="p-variants" class="vector-menu mw-portlet mw-portlet-variants emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> </div> </div> </nav> </div> <div id="right-navigation" class="vector-collapsible"> <nav aria-label="Views"> <div id="p-views" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-views" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-view" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Avermectin"><span>Read</span></a></li><li id="ca-edit" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Avermectin&action=edit" title="Edit this page [e]" accesskey="e"><span>Edit</span></a></li><li id="ca-history" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Avermectin&action=history" title="Past revisions of this page [h]" accesskey="h"><span>View history</span></a></li> </ul> </div> </div> </nav> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-dropdown" class="vector-dropdown vector-page-tools-dropdown" > <input type="checkbox" id="vector-page-tools-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-tools-dropdown" class="vector-dropdown-checkbox " aria-label="Tools" > <label id="vector-page-tools-dropdown-label" for="vector-page-tools-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" ><span class="vector-dropdown-label-text">Tools</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-tools-unpinned-container" class="vector-unpinned-container"> <div id="vector-page-tools" class="vector-page-tools vector-pinnable-element"> <div class="vector-pinnable-header vector-page-tools-pinnable-header vector-pinnable-header-unpinned" data-feature-name="page-tools-pinned" data-pinnable-element-id="vector-page-tools" data-pinned-container-id="vector-page-tools-pinned-container" data-unpinned-container-id="vector-page-tools-unpinned-container" > <div class="vector-pinnable-header-label">Tools</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-page-tools.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-page-tools.unpin">hide</button> </div> <div id="p-cactions" class="vector-menu mw-portlet mw-portlet-cactions emptyPortlet vector-has-collapsible-items" title="More options" > <div class="vector-menu-heading"> Actions </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-more-view" class="selected vector-more-collapsible-item mw-list-item"><a href="/wiki/Avermectin"><span>Read</span></a></li><li id="ca-more-edit" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Avermectin&action=edit" title="Edit this page [e]" accesskey="e"><span>Edit</span></a></li><li id="ca-more-history" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Avermectin&action=history"><span>View history</span></a></li> </ul> </div> </div> <div id="p-tb" class="vector-menu mw-portlet mw-portlet-tb" > <div class="vector-menu-heading"> General </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="t-whatlinkshere" class="mw-list-item"><a href="/wiki/Special:WhatLinksHere/Avermectin" title="List of all English Wikipedia pages containing links to this page [j]" accesskey="j"><span>What links here</span></a></li><li id="t-recentchangeslinked" class="mw-list-item"><a href="/wiki/Special:RecentChangesLinked/Avermectin" rel="nofollow" title="Recent changes in pages linked from this page [k]" accesskey="k"><span>Related changes</span></a></li><li id="t-upload" class="mw-list-item"><a href="/wiki/Wikipedia:File_Upload_Wizard" title="Upload files [u]" accesskey="u"><span>Upload file</span></a></li><li id="t-specialpages" class="mw-list-item"><a href="/wiki/Special:SpecialPages" title="A list of all special pages [q]" accesskey="q"><span>Special pages</span></a></li><li id="t-permalink" class="mw-list-item"><a href="/w/index.php?title=Avermectin&oldid=1233977336" title="Permanent link to this revision of this page"><span>Permanent link</span></a></li><li id="t-info" class="mw-list-item"><a href="/w/index.php?title=Avermectin&action=info" title="More information about this page"><span>Page information</span></a></li><li id="t-cite" class="mw-list-item"><a href="/w/index.php?title=Special:CiteThisPage&page=Avermectin&id=1233977336&wpFormIdentifier=titleform" title="Information on how to cite this page"><span>Cite this page</span></a></li><li id="t-urlshortener" class="mw-list-item"><a href="/w/index.php?title=Special:UrlShortener&url=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FAvermectin"><span>Get shortened URL</span></a></li><li id="t-urlshortener-qrcode" class="mw-list-item"><a href="/w/index.php?title=Special:QrCode&url=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FAvermectin"><span>Download QR code</span></a></li> </ul> </div> </div> <div id="p-coll-print_export" class="vector-menu mw-portlet mw-portlet-coll-print_export" > <div class="vector-menu-heading"> Print/export </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="coll-download-as-rl" class="mw-list-item"><a href="/w/index.php?title=Special:DownloadAsPdf&page=Avermectin&action=show-download-screen" title="Download this page as a PDF file"><span>Download as PDF</span></a></li><li id="t-print" class="mw-list-item"><a href="/w/index.php?title=Avermectin&printable=yes" title="Printable version of this page [p]" accesskey="p"><span>Printable version</span></a></li> </ul> </div> </div> <div id="p-wikibase-otherprojects" class="vector-menu mw-portlet mw-portlet-wikibase-otherprojects" > <div class="vector-menu-heading"> In other projects </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="wb-otherproject-link wb-otherproject-commons mw-list-item"><a href="https://commons.wikimedia.org/wiki/Category:Avermectins" hreflang="en"><span>Wikimedia Commons</span></a></li><li id="t-wikibase" class="wb-otherproject-link wb-otherproject-wikibase-dataitem mw-list-item"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q416170" title="Structured data on this page hosted by Wikidata [g]" accesskey="g"><span>Wikidata item</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div 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">Drugs to treat parasitic worms and insect pests</div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Missing_information plainlinks metadata ambox ambox-content" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Wiki_letter_w.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/en/thumb/6/6c/Wiki_letter_w.svg/44px-Wiki_letter_w.svg.png" decoding="async" width="44" height="44" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/6/6c/Wiki_letter_w.svg/66px-Wiki_letter_w.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/6/6c/Wiki_letter_w.svg/88px-Wiki_letter_w.svg.png 2x" data-file-width="44" data-file-height="44" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This article <b>is missing information</b> about what the chemical structures of A1, A2, B1, B2 each are. The Abamectin pic can be reused, just need one more R group according to YoongKim04.<span class="hide-when-compact"> Please expand the article to include this information. Further details may exist on the <a href="/wiki/Talk:Avermectin" title="Talk:Avermectin">talk page</a>.</span> <span class="date-container"><i>(<span class="date">September 2023</span>)</i></span></div></td></tr></tbody></table> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Avermectins_skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Avermectins_skeletal.svg/300px-Avermectins_skeletal.svg.png" decoding="async" width="300" height="163" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Avermectins_skeletal.svg/450px-Avermectins_skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Avermectins_skeletal.svg/600px-Avermectins_skeletal.svg.png 2x" data-file-width="1360" data-file-height="740" /></a><figcaption>Skeletal structure of the 8 different natural avermectins<sup id="cite_ref-YoonKim2004_1-0" class="reference"><a href="#cite_note-YoonKim2004-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>The <b>avermectins</b> are a series of <a href="/wiki/Drug" title="Drug">drugs</a> and <a href="/wiki/Pesticide" title="Pesticide">pesticides</a> used to treat parasitic worm infestations and to reduce insect <a href="/wiki/Pest_(organism)" title="Pest (organism)">pests</a>. They are a group of 16-membered macrocyclic <a href="/wiki/Lactone" title="Lactone">lactone</a> derivatives with potent <a href="/wiki/Anthelmintic" title="Anthelmintic">anthelmintic</a> and <a href="/wiki/Insecticide" title="Insecticide">insecticidal</a> properties.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Pitterna_3-0" class="reference"><a href="#cite_note-Pitterna-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> These naturally occurring compounds are generated as fermentation products by <i><a href="/wiki/Streptomyces_avermitilis" title="Streptomyces avermitilis">Streptomyces avermitilis</a></i>, a soil <a href="/wiki/Actinomycete" class="mw-redirect" title="Actinomycete">actinomycete</a>. Eight different avermectins were isolated in four pairs of homologue compounds (A1, A2, B1, B2), with a major (a-component) and minor (b-component) component usually in ratios of 80:20 to 90:10.<sup id="cite_ref-Pitterna_3-1" class="reference"><a href="#cite_note-Pitterna-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Avermectin B1, a mixture of B1a and B1b, is the drug and pesticide <a href="/wiki/Abamectin" title="Abamectin">abamectin</a>. Other anthelmintics derived from the avermectins include <a href="/wiki/Ivermectin" title="Ivermectin">ivermectin</a>, <a href="/wiki/Selamectin" title="Selamectin">selamectin</a>, <a href="/wiki/Doramectin" title="Doramectin">doramectin</a>, <a href="/wiki/Eprinomectin" title="Eprinomectin">eprinomectin</a>. </p><p>Half of the 2015 <a href="/wiki/Nobel_Prize_in_Physiology_or_Medicine" title="Nobel Prize in Physiology or Medicine">Nobel Prize in Physiology or Medicine</a> was awarded to <a href="/wiki/William_C._Campbell_(scientist)" title="William C. Campbell (scientist)">William C. Campbell</a> and <a href="/wiki/Satoshi_%C5%8Cmura" title="Satoshi Ōmura">Satoshi Ōmura</a> for discovering avermectin,<sup id="cite_ref-Nobel_4-0" class="reference"><a href="#cite_note-Nobel-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> "the derivatives of which have radically lowered the incidence of <a href="/wiki/Onchocerciasis" title="Onchocerciasis">river blindness</a> and <a href="/wiki/Lymphatic_filariasis" title="Lymphatic filariasis">lymphatic filariasis</a>, as well as showing efficacy against an expanding number of other parasitic diseases." </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Avermectin&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 1978, an actinomycete was isolated at the <a href="/wiki/Kitasato_Institute" class="mw-redirect" title="Kitasato Institute">Kitasato Institute</a> from a soil sample collected at Kawana, <a href="/wiki/It%C5%8D,_Shizuoka" title="Itō, Shizuoka">Ito City</a>, Shizuoka Prefecture, Japan. Later that year, the isolated actinomycete was sent to <a href="/wiki/Merck_Sharp_and_Dohme" class="mw-redirect" title="Merck Sharp and Dohme">Merck Sharp and Dohme</a> Research Laboratories for testing. Various carefully controlled broths were fermented using the isolated actinomycete. Early tests indicated that some of the whole, fermented broths were active against <i><a href="/wiki/Nematospiroides_dubius" class="mw-redirect" title="Nematospiroides dubius">Nematospiroides dubius</a></i> in mice over at least an eight-fold range without notable toxicity. Subsequent to this, the anthelmintic activity was isolated and identified as a family of closely related compounds. The compounds were finally characterized and the novel species that produced them were described by a team at Merck in 1978, and named <i>Streptomyces avermitilis</i> (with the adjective probably intended to mean that it kills worms).<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> </p><p>In 2002, Yoko Takahashi and others at the Kitasato Institute for Life Sciences, Kitasato University, and at the Kitasato Institute, proposed that <i>Streptomyces avermitilis</i> be renamed <i>Streptomyces avermectinius</i>.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Dosing">Dosing</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Avermectin&action=edit&section=2" title="Edit section: Dosing"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A commonly used therapy in recent times has been based on oral, <a href="/wiki/Parenteral" class="mw-redirect" title="Parenteral">parenteral</a>, topical, or spot topical (as in veterinary flea repellant "drops") administration of avermectins. They show activity against a broad range of <a href="/wiki/Nematode" title="Nematode">nematodes</a> and <a href="/wiki/Arthropod" title="Arthropod">arthropod</a> parasites of domestic animals at dose rates of 300 μg/kg or less (200 μg/kg ivermectin appearing to be the common interspecies standard, from humans to horses to house pets, unless otherwise indicated).<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2020)">citation needed</span></a></i>]</sup> Unlike the <a href="/wiki/Macrolide" title="Macrolide">macrolide</a> or <a href="/wiki/Polyene" title="Polyene">polyene</a> antibiotics, they lack significant antibacterial or antifungal activities.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Mechanism_of_action">Mechanism of action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Avermectin&action=edit&section=3" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The avermectins block the transmission of electrical activity in invertebrate nerve and muscle cells mostly by enhancing the effects of <a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a> at the <a href="/wiki/Glutamate-gated_chloride_channel" class="mw-redirect" title="Glutamate-gated chloride channel">glutamate-gated chloride channel</a> that is specific to <a href="/wiki/Protostome" title="Protostome">protostome</a> invertebrates,<sup id="cite_ref-Wolstenholme-2012_8-0" class="reference"><a href="#cite_note-Wolstenholme-2012-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> with minor effects on <a href="/wiki/Gamma-aminobutyric_acid" class="mw-redirect" title="Gamma-aminobutyric acid">gamma-aminobutyric acid</a> receptors.<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><sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> This causes an influx of chloride ions into the cells, leading to hyperpolarisation and subsequent paralysis of invertebrate neuromuscular systems; comparable doses are not toxic for mammals because they do not possess <a href="/wiki/Protostome" title="Protostome">protostome-specific</a> glutamate-gated chloride channels.<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><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Accuracy_dispute#Disputed_statement" title="Wikipedia:Accuracy dispute"><span title="Turtles are also not protostomes, but they appear affected (see the ivermectin article ref). So are border collies with the MDR1 mutation. The role of the blood-brain barrier in selectivity should be mentioned. (November 2023)">dubious</span></a> – <a href="/wiki/Talk:Avermectin#Dubious" title="Talk:Avermectin">discuss</a></i>]</sup><sup id="cite_ref-Wolstenholme-2012_8-1" class="reference"><a href="#cite_note-Wolstenholme-2012-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Toxicity_and_side_effects">Toxicity and side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Avermectin&action=edit&section=4" title="Edit section: Toxicity and side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Anthelmintic_resistance" class="mw-redirect" title="Anthelmintic resistance">Resistance to avermectins</a> has been reported, which suggests moderation in use.<sup id="cite_ref-Clark-et-al-1995_13-0" class="reference"><a href="#cite_note-Clark-et-al-1995-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Resistance in <i><a href="/wiki/Caenorhabditis_elegans" title="Caenorhabditis elegans">Caenorhabditis elegans</a></i> has been observed by the most obvious route – variation of the <a href="/wiki/Glutamate-gated_chloride_channel" class="mw-redirect" title="Glutamate-gated chloride channel">glutamate-gated chloride channel</a>.<sup id="cite_ref-Ghosh-et-al-2012_14-0" class="reference"><a href="#cite_note-Ghosh-et-al-2012-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Horoszok-et-al-2001_15-0" class="reference"><a href="#cite_note-Horoszok-et-al-2001-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Research on <a href="/wiki/Ivermectin" title="Ivermectin">ivermectin</a>, <a href="/wiki/Piperazine" title="Piperazine">piperazine</a>, and <a href="/wiki/Dichlorvos" title="Dichlorvos">dichlorvos</a> in combinations also shows potential for toxicity.<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> Avermectin has been reported to block LPS-induced secretion of <a href="/wiki/Tumor_necrosis_factors" class="mw-redirect" title="Tumor necrosis factors">tumor necrosis factor</a>, <a href="/wiki/Nitric_oxide" title="Nitric oxide">nitric oxide</a>, <a href="/wiki/Prostaglandin" title="Prostaglandin">prostaglandin</a> E2, and increase of intracellular concentration of Ca<sup>2+</sup>.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Adverse effects are usually transient; severe effects are rare and probably occur only with substantial overdose, but include <a href="/wiki/Coma" title="Coma">coma</a>, <a href="/wiki/Hypotension" title="Hypotension">hypotension</a>, and <a href="/wiki/Respiratory_failure" title="Respiratory failure">respiratory failure</a>, which can lead to death. No specific therapy exists, but symptomatic management usually leads to a favorable prognosis.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Avermectin_biosynthesis">Avermectin biosynthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Avermectin&action=edit&section=5" title="Edit section: Avermectin biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Avermectin_Biosynthesis_Pathway.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Avermectin_Biosynthesis_Pathway.png/220px-Avermectin_Biosynthesis_Pathway.png" decoding="async" width="220" height="136" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Avermectin_Biosynthesis_Pathway.png/330px-Avermectin_Biosynthesis_Pathway.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/96/Avermectin_Biosynthesis_Pathway.png/440px-Avermectin_Biosynthesis_Pathway.png 2x" data-file-width="11042" data-file-height="6840" /></a><figcaption>Diagram showing the schematic synthesis of avermectins</figcaption></figure> <p>The gene cluster for biosynthesis of avermectin from <i><a href="/wiki/Streptomyces_avermitilis" title="Streptomyces avermitilis">S. avermitilis</a></i> has been sequenced.<sup id="cite_ref-PMID10449723_20-0" class="reference"><a href="#cite_note-PMID10449723-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> The avermectin <a href="/wiki/Biosynthesis_gene_cluster" class="mw-redirect" title="Biosynthesis gene cluster">biosynthesis gene cluster</a> encodes enzymes responsible for four steps of avermectin production: 1) production of the avermectin <a href="/wiki/Aglycon" class="mw-redirect" title="Aglycon">aglycon</a> by <a href="/wiki/Polyketide_synthases" class="mw-redirect" title="Polyketide synthases">polyketide synthases</a>, 2) modification of the aglycon, 3) synthesis of modified sugars, and 4) glycosylation of the modified avermectin aglycon. This gene cluster can produce eight avermectins which have minor structural differences.<sup id="cite_ref-YoonKim2004_1-1" class="reference"><a href="#cite_note-YoonKim2004-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Avermectin_PKS.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Avermectin_PKS.png/220px-Avermectin_PKS.png" decoding="async" width="220" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Avermectin_PKS.png/330px-Avermectin_PKS.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Avermectin_PKS.png/440px-Avermectin_PKS.png 2x" data-file-width="22374" data-file-height="6359" /></a><figcaption>Organization of the avermectin polyketide synthase</figcaption></figure> <p>The avermectin initial aglycon is synthesized by the <a href="/wiki/Polyketide_synthase" title="Polyketide synthase">polyketide synthase</a> activity of four proteins (AVES 1, AVES 2, AVES 3, and AVES 4). The activity of this enzyme complex is similar to type I polyketide synthases.<sup id="cite_ref-YoonKim2004_1-2" class="reference"><a href="#cite_note-YoonKim2004-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Either 2-methylbutyryl CoA or isobutyryl CoA can be used as starting units and are extended by seven acetate units and five propionate units to produce avermectin “a” series or “b” series, respectively.<sup id="cite_ref-YoonKim2004_1-3" class="reference"><a href="#cite_note-YoonKim2004-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> The initial aglycon is subsequently released from the thioesterase domain of AVES 4 by formation of an intramolecular <a href="/wiki/Lactone" title="Lactone">cyclic ester</a>.<sup id="cite_ref-YoonKim2004_1-4" class="reference"><a href="#cite_note-YoonKim2004-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>The avermectin initial aglycon is further modified by other enzymes in the avermectin biosynthetic gene cluster. AveE has cytochrome P450 monooxygenase activity and facilitates the furan ring formation between C6 and C8.<sup id="cite_ref-YoonKim2004_1-5" class="reference"><a href="#cite_note-YoonKim2004-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> AveF has NAD(P)H-dependent ketoreductase activity which reduces the C5 keto group to a hydroxyl.<sup id="cite_ref-YoonKim2004_1-6" class="reference"><a href="#cite_note-YoonKim2004-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> AveC influences the dehydratase activity in module two (affecting C22-C23), although the mechanism by which it does this is not clear.<sup id="cite_ref-PMID10449723_20-1" class="reference"><a href="#cite_note-PMID10449723-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-YoonKim2004_1-7" class="reference"><a href="#cite_note-YoonKim2004-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> AveD has SAM-dependent C5 O-methyltransferase activity.<sup id="cite_ref-YoonKim2004_1-8" class="reference"><a href="#cite_note-YoonKim2004-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Whether AveC or AveD acts on the aglycon determines whether the resulting avermectin aglycon will produce avermectin, series “A” or “B” and series 1 or 2 (see synthesis schematic diagram table), respectively.<sup id="cite_ref-YoonKim2004_1-9" class="reference"><a href="#cite_note-YoonKim2004-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>Nine open reading frames (orf1 and aveBI-BVIII) are downstream of aveA4, which are known involved with glycosylation and sugar synthesis.<sup id="cite_ref-YoonKim2004_1-10" class="reference"><a href="#cite_note-YoonKim2004-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> AveBII-BVIII are responsible for synthesis of dTDP-L-<a href="/wiki/Oleandrose" title="Oleandrose">oleandrose</a> and AveBI is responsible for glycosylation of the avermectin aglycon with the dTDP-sugar.<sup id="cite_ref-YoonKim2004_1-11" class="reference"><a href="#cite_note-YoonKim2004-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> The sequence of orf1 suggests that its product will have reductase activity, but this functionality does not appear to be necessary for avermectin synthesis.<sup id="cite_ref-YoonKim2004_1-12" class="reference"><a href="#cite_note-YoonKim2004-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Other_uses">Other uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Avermectin&action=edit&section=6" title="Edit section: Other uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Abamectin" title="Abamectin">Abamectin</a> is the active ingredient in some commercial ant bait traps. Ivermectin, formulated from Avermectin, has a wide variety of uses in human beings. According to a paper (Ivermectin: “Wonder Drug” from Japan: the human use perspective) written by the drugs co-creator Satoshi Ōmura and Andy Crump for The Japan Academy, Ivermectin has improved the lives of billions of people worldwide and not solely for uses as an anti parasitic.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Avermectin&action=edit&section=7" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Milbemycin" title="Milbemycin">Milbemycins</a> are a chemically closely related group of parasiticides.</li> <li>Avermectin/ivermectin <a href="/wiki/Glycorandomization" title="Glycorandomization">glycorandomization</a></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=Avermectin&action=edit&section=8" 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 reflist-columns references-column-width reflist-columns-2"> <ol class="references"> <li id="cite_note-YoonKim2004-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-YoonKim2004_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-YoonKim2004_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-YoonKim2004_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-YoonKim2004_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-YoonKim2004_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-YoonKim2004_1-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-YoonKim2004_1-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-YoonKim2004_1-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-YoonKim2004_1-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-YoonKim2004_1-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-YoonKim2004_1-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-YoonKim2004_1-11"><sup><i><b>l</b></i></sup></a> <a href="#cite_ref-YoonKim2004_1-12"><sup><i><b>m</b></i></sup></a></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="CITEREFYoonKimHwangChoi2004" class="citation journal cs1">Yoon, Y. J.; Kim, E.-S.; Hwang, Y.-S.; Choi, C.-Y. (2004). "Avermectin: Biochemical and molecular basis of its biosynthesis and regulation". <i>Applied Microbiology and Biotechnology</i>. <b>63</b> (6): 626–34. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs00253-003-1491-4">10.1007/s00253-003-1491-4</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/14689246">14689246</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:2578270">2578270</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Applied+Microbiology+and+Biotechnology&rft.atitle=Avermectin%3A+Biochemical+and+molecular+basis+of+its+biosynthesis+and+regulation&rft.volume=63&rft.issue=6&rft.pages=626-34&rft.date=2004&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A2578270%23id-name%3DS2CID&rft_id=info%3Apmid%2F14689246&rft_id=info%3Adoi%2F10.1007%2Fs00253-003-1491-4&rft.aulast=Yoon&rft.aufirst=Y.+J.&rft.au=Kim%2C+E.-S.&rft.au=Hwang%2C+Y.-S.&rft.au=Choi%2C+C.-Y.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAvermectin" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFŌmuraShiomi2007" class="citation journal cs1">Ōmura, Satoshi; Shiomi, Kazuro (2007). <a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fpac200779040581">"Discovery, chemistry, and chemical biology of microbial products"</a>. <i>Pure and Applied Chemistry</i>. <b>79</b> (4): 581–591. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fpac200779040581">10.1351/pac200779040581</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pure+and+Applied+Chemistry&rft.atitle=Discovery%2C+chemistry%2C+and+chemical+biology+of+microbial+products&rft.volume=79&rft.issue=4&rft.pages=581-591&rft.date=2007&rft_id=info%3Adoi%2F10.1351%2Fpac200779040581&rft.aulast=%C5%8Cmura&rft.aufirst=Satoshi&rft.au=Shiomi%2C+Kazuro&rft_id=https%3A%2F%2Fdoi.org%2F10.1351%252Fpac200779040581&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAvermectin" class="Z3988"></span></span> </li> <li id="cite_note-Pitterna-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Pitterna_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Pitterna_3-1"><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="CITEREFPitternaCassayreHüterJung2009" class="citation journal cs1">Pitterna, Thomas; Cassayre, Jérôme; Hüter, Ottmar Franz; Jung, Pierre M.J.; Maienfisch, Peter; Kessabi, Fiona Murphy; Quaranta, Laura; Tobler, Hans (2009). "New ventures in the chemistry of avermectins". <i>Bioorganic & Medicinal Chemistry</i>. <b>17</b> (12): 4085–4095. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.bmc.2008.12.069">10.1016/j.bmc.2008.12.069</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/19168364">19168364</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bioorganic+%26+Medicinal+Chemistry&rft.atitle=New+ventures+in+the+chemistry+of+avermectins&rft.volume=17&rft.issue=12&rft.pages=4085-4095&rft.date=2009&rft_id=info%3Adoi%2F10.1016%2Fj.bmc.2008.12.069&rft_id=info%3Apmid%2F19168364&rft.aulast=Pitterna&rft.aufirst=Thomas&rft.au=Cassayre%2C+J%C3%A9r%C3%B4me&rft.au=H%C3%BCter%2C+Ottmar+Franz&rft.au=Jung%2C+Pierre+M.J.&rft.au=Maienfisch%2C+Peter&rft.au=Kessabi%2C+Fiona+Murphy&rft.au=Quaranta%2C+Laura&rft.au=Tobler%2C+Hans&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAvermectin" class="Z3988"></span></span> </li> <li id="cite_note-Nobel-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-Nobel_4-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.nobelprize.org/prizes/medicine/2015/summary/">"The Nobel Prize in Physiology or Medicine 2015"</a>. <i><a href="/wiki/Nobel_Prize" title="Nobel Prize">Nobel Prize</a></i>. 2020-12-03<span class="reference-accessdate">. Retrieved <span class="nowrap">2020-12-03</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Nobel+Prize&rft.atitle=The+Nobel+Prize+in+Physiology+or+Medicine+2015&rft.date=2020-12-03&rft_id=http%3A%2F%2Fwww.nobelprize.org%2Fprizes%2Fmedicine%2F2015%2Fsummary%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAvermectin" 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 id="CITEREFBurgMillerBakerBirnbaum1979" class="citation journal cs1">Burg, R. W.; Miller, B. M.; Baker, E. E.; Birnbaum, J.; Currie, S. A.; Hartman, R.; Kong, Y.-L.; Monaghan, R. L.; Olson, G.; Putter, I.; Tunac, J. B.; Wallick, H.; Stapley, E. O.; Oiwa, R.; Omura, S. (1979). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC352666">"Avermectins, New Family of Potent Anthelmintic Agents: Producing Organism and Fermentation"</a>. <i>Antimicrobial Agents and Chemotherapy</i>. <b>15</b> (3): 361–7. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1128%2FAAC.15.3.361">10.1128/AAC.15.3.361</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC352666">352666</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/464561">464561</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Antimicrobial+Agents+and+Chemotherapy&rft.atitle=Avermectins%2C+New+Family+of+Potent+Anthelmintic+Agents%3A+Producing+Organism+and+Fermentation&rft.volume=15&rft.issue=3&rft.pages=361-7&rft.date=1979&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC352666%23id-name%3DPMC&rft_id=info%3Apmid%2F464561&rft_id=info%3Adoi%2F10.1128%2FAAC.15.3.361&rft.aulast=Burg&rft.aufirst=R.+W.&rft.au=Miller%2C+B.+M.&rft.au=Baker%2C+E.+E.&rft.au=Birnbaum%2C+J.&rft.au=Currie%2C+S.+A.&rft.au=Hartman%2C+R.&rft.au=Kong%2C+Y.-L.&rft.au=Monaghan%2C+R.+L.&rft.au=Olson%2C+G.&rft.au=Putter%2C+I.&rft.au=Tunac%2C+J.+B.&rft.au=Wallick%2C+H.&rft.au=Stapley%2C+E.+O.&rft.au=Oiwa%2C+R.&rft.au=Omura%2C+S.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC352666&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAvermectin" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTakahashi2002" class="citation journal cs1">Takahashi, Y. (2002). "<i>Streptomyces avermectinius</i> sp. nov., an avermectin-producing strain". <i>International Journal of Systematic and Evolutionary Microbiology</i>. <b>52</b> (6): 2163–8. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1099%2F00207713-52-6-2163">10.1099/00207713-52-6-2163</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/12508884">12508884</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=International+Journal+of+Systematic+and+Evolutionary+Microbiology&rft.atitle=Streptomyces+avermectinius+sp.+nov.%2C+an+avermectin-producing+strain&rft.volume=52&rft.issue=6&rft.pages=2163-8&rft.date=2002&rft_id=info%3Adoi%2F10.1099%2F00207713-52-6-2163&rft_id=info%3Apmid%2F12508884&rft.aulast=Takahashi&rft.aufirst=Y.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAvermectin" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHotson1982" class="citation journal cs1">Hotson, I. K. (1982). "The avermectins: A new family of antiparasitic agents". <i>Journal of the South African Veterinary Association</i>. <b>53</b> (2): 87–90. <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/6750121">6750121</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+South+African+Veterinary+Association&rft.atitle=The+avermectins%3A+A+new+family+of+antiparasitic+agents&rft.volume=53&rft.issue=2&rft.pages=87-90&rft.date=1982&rft_id=info%3Apmid%2F6750121&rft.aulast=Hotson&rft.aufirst=I.+K.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAvermectin" class="Z3988"></span></span> </li> <li id="cite_note-Wolstenholme-2012-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-Wolstenholme-2012_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Wolstenholme-2012_8-1"><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="CITEREFWolstenholme2012" class="citation journal cs1">Wolstenholme, Adrian J. (2012-10-04). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3504739">"Glutamate-gated Chloride Channels"</a>. <i><a href="/wiki/Journal_of_Biological_Chemistry" title="Journal of Biological Chemistry">Journal of Biological Chemistry</a></i>. <b>287</b> (48). <a href="/wiki/American_Society_for_Biochemistry_and_Molecular_Biology" title="American Society for Biochemistry and Molecular Biology">American Society for Biochemistry & Molecular Biology</a> (ASBMB): 40232–40238. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1074%2Fjbc.r112.406280">10.1074/jbc.r112.406280</a></span>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0021-9258">0021-9258</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3504739">3504739</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23038250">23038250</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+Biological+Chemistry&rft.atitle=Glutamate-gated+Chloride+Channels&rft.volume=287&rft.issue=48&rft.pages=40232-40238&rft.date=2012-10-04&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3504739%23id-name%3DPMC&rft.issn=0021-9258&rft_id=info%3Apmid%2F23038250&rft_id=info%3Adoi%2F10.1074%2Fjbc.r112.406280&rft.aulast=Wolstenholme&rft.aufirst=Adrian+J.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3504739&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAvermectin" 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 id="CITEREFCullyVassilatisLiuParess1994" class="citation journal cs1">Cully, Doris F.; Vassilatis, Demetrios K.; Liu, Ken K.; Paress, Philip S.; Van Der Ploeg, Lex H. T.; Schaeffer, James M.; Arena, Joseph P. (1994). "Cloning of an avermectin-sensitive glutamate-gated chloride channel from Caenorhabditis elegans". <i>Nature</i>. <b>371</b> (6499): 707–11. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1994Natur.371..707C">1994Natur.371..707C</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2F371707a0">10.1038/371707a0</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/7935817">7935817</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:4337014">4337014</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature&rft.atitle=Cloning+of+an+avermectin-sensitive+glutamate-gated+chloride+channel+from+Caenorhabditis+elegans&rft.volume=371&rft.issue=6499&rft.pages=707-11&rft.date=1994&rft_id=info%3Adoi%2F10.1038%2F371707a0&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A4337014%23id-name%3DS2CID&rft_id=info%3Apmid%2F7935817&rft_id=info%3Abibcode%2F1994Natur.371..707C&rft.aulast=Cully&rft.aufirst=Doris+F.&rft.au=Vassilatis%2C+Demetrios+K.&rft.au=Liu%2C+Ken+K.&rft.au=Paress%2C+Philip+S.&rft.au=Van+Der+Ploeg%2C+Lex+H.+T.&rft.au=Schaeffer%2C+James+M.&rft.au=Arena%2C+Joseph+P.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAvermectin" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBloomquist1996" class="citation journal cs1">Bloomquist, Jeffrey R. (1996). "Ion Channels as Targets for Insecticides". <i>Annual Review of Entomology</i>. <b>41</b>: 163–90. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1146%2Fannurev.en.41.010196.001115">10.1146/annurev.en.41.010196.001115</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/8546445">8546445</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annual+Review+of+Entomology&rft.atitle=Ion+Channels+as+Targets+for+Insecticides&rft.volume=41&rft.pages=163-90&rft.date=1996&rft_id=info%3Adoi%2F10.1146%2Fannurev.en.41.010196.001115&rft_id=info%3Apmid%2F8546445&rft.aulast=Bloomquist&rft.aufirst=Jeffrey+R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAvermectin" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBloomquist2003" class="citation journal cs1">Bloomquist, Jeffrey R. (2003). "Chloride channels as tools for developing selective insecticides". <i>Archives of Insect Biochemistry and Physiology</i>. <b>54</b> (4): 145–56. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Farch.10112">10.1002/arch.10112</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/14635176">14635176</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Archives+of+Insect+Biochemistry+and+Physiology&rft.atitle=Chloride+channels+as+tools+for+developing+selective+insecticides&rft.volume=54&rft.issue=4&rft.pages=145-56&rft.date=2003&rft_id=info%3Adoi%2F10.1002%2Farch.10112&rft_id=info%3Apmid%2F14635176&rft.aulast=Bloomquist&rft.aufirst=Jeffrey+R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAvermectin" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBloomquist1993" class="citation journal cs1">Bloomquist, Jeffrey R. (1993). "Toxicology, mode of action and target site-mediated resistance to insecticides acting on chloride channels". <i>Comparative Biochemistry and Physiology C</i>. <b>106</b> (2): 301–314. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0742-8413%2893%2990138-b">10.1016/0742-8413(93)90138-b</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/7904908">7904908</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Comparative+Biochemistry+and+Physiology+C&rft.atitle=Toxicology%2C+mode+of+action+and+target+site-mediated+resistance+to+insecticides+acting+on+chloride+channels&rft.volume=106&rft.issue=2&rft.pages=301-314&rft.date=1993&rft_id=info%3Adoi%2F10.1016%2F0742-8413%2893%2990138-b&rft_id=info%3Apmid%2F7904908&rft.aulast=Bloomquist&rft.aufirst=Jeffrey+R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAvermectin" class="Z3988"></span></span> </li> <li id="cite_note-Clark-et-al-1995-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-Clark-et-al-1995_13-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFClarkScottCamposBloomquist1995" class="citation journal cs1">Clark, J K; Scott, J G; Campos, F; Bloomquist, J R (1995). "Resistance to Avermectins: Extent, Mechanisms, and Management Implications". <i><a href="/wiki/Annual_Review_of_Entomology" title="Annual Review of Entomology">Annual Review of Entomology</a></i>. <b>40</b> (1). <a href="/wiki/Annual_Reviews_(publisher)" title="Annual Reviews (publisher)">Annual Reviews</a>: 1–30. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1146%2Fannurev.en.40.010195.000245">10.1146/annurev.en.40.010195.000245</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0066-4170">0066-4170</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/7810984">7810984</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annual+Review+of+Entomology&rft.atitle=Resistance+to+Avermectins%3A+Extent%2C+Mechanisms%2C+and+Management+Implications&rft.volume=40&rft.issue=1&rft.pages=1-30&rft.date=1995&rft.issn=0066-4170&rft_id=info%3Apmid%2F7810984&rft_id=info%3Adoi%2F10.1146%2Fannurev.en.40.010195.000245&rft.aulast=Clark&rft.aufirst=J+K&rft.au=Scott%2C+J+G&rft.au=Campos%2C+F&rft.au=Bloomquist%2C+J+R&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAvermectin" class="Z3988"></span></span> </li> <li id="cite_note-Ghosh-et-al-2012-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ghosh-et-al-2012_14-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGhoshAndersenShapiroGerke2012" class="citation journal cs1">Ghosh, R.; Andersen, E. C.; Shapiro, J. A.; Gerke, J. P.; Kruglyak, L. (2012-02-02). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3273849">"Natural Variation in a Chloride Channel Subunit Confers Avermectin Resistance in <i>C. elegans</i>"</a>. <i><a href="/wiki/Science_(journal)" title="Science (journal)">Science</a></i>. <b>335</b> (6068). <a href="/wiki/American_Association_for_the_Advancement_of_Science" title="American Association for the Advancement of Science">American Association for the Advancement of Science</a> (AAAS): 574–578. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2012Sci...335..574G">2012Sci...335..574G</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fscience.1214318">10.1126/science.1214318</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0036-8075">0036-8075</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3273849">3273849</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22301316">22301316</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Science&rft.atitle=Natural+Variation+in+a+Chloride+Channel+Subunit+Confers+Avermectin+Resistance+in+C.+elegans&rft.volume=335&rft.issue=6068&rft.pages=574-578&rft.date=2012-02-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3273849%23id-name%3DPMC&rft_id=info%3Abibcode%2F2012Sci...335..574G&rft_id=info%3Apmid%2F22301316&rft_id=info%3Adoi%2F10.1126%2Fscience.1214318&rft.issn=0036-8075&rft.aulast=Ghosh&rft.aufirst=R.&rft.au=Andersen%2C+E.+C.&rft.au=Shapiro%2C+J.+A.&rft.au=Gerke%2C+J.+P.&rft.au=Kruglyak%2C+L.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3273849&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAvermectin" class="Z3988"></span></span> </li> <li id="cite_note-Horoszok-et-al-2001-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-Horoszok-et-al-2001_15-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHoroszokRaymondSattelleWolstenholme2001" class="citation journal cs1">Horoszok, Lucy; Raymond, Valérie; Sattelle, David B; Wolstenholme, Adrian J (2001). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1572670">"GLC-3: a novel fipronil and BIDN-sensitive, but picrotoxinin-insensitive, L-glutamate-gated chloride channel subunit from <i>Caenorhabditis elegans</i>"</a>. <i><a href="/wiki/British_Journal_of_Pharmacology" title="British Journal of Pharmacology">British Journal of Pharmacology</a></i>. <b>132</b> (6). <a href="/wiki/Wiley_(publisher)" title="Wiley (publisher)">Wiley</a>: 1247–1254. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fsj.bjp.0703937">10.1038/sj.bjp.0703937</a></span>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0007-1188">0007-1188</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1572670">1572670</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11250875">11250875</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=British+Journal+of+Pharmacology&rft.atitle=GLC-3%3A+a+novel+fipronil+and+BIDN-sensitive%2C+but+picrotoxinin-insensitive%2C+L-glutamate-gated+chloride+channel+subunit+from+Caenorhabditis+elegans&rft.volume=132&rft.issue=6&rft.pages=1247-1254&rft.date=2001&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1572670%23id-name%3DPMC&rft.issn=0007-1188&rft_id=info%3Apmid%2F11250875&rft_id=info%3Adoi%2F10.1038%2Fsj.bjp.0703937&rft.aulast=Horoszok&rft.aufirst=Lucy&rft.au=Raymond%2C+Val%C3%A9rie&rft.au=Sattelle%2C+David+B&rft.au=Wolstenholme%2C+Adrian+J&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1572670&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAvermectin" class="Z3988"></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTothOberbeckStraignFrazier2000" class="citation journal cs1">Toth, L. A.; Oberbeck, C; Straign, C. M.; Frazier, S; Rehg, J. E. (2000). "Toxicity evaluation of prophylactic treatments for mites and pinworms in mice". <i>Contemporary Topics in Laboratory Animal Science</i>. <b>39</b> (2): 18–21. <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/11487234">11487234</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contemporary+Topics+in+Laboratory+Animal+Science&rft.atitle=Toxicity+evaluation+of+prophylactic+treatments+for+mites+and+pinworms+in+mice&rft.volume=39&rft.issue=2&rft.pages=18-21&rft.date=2000&rft_id=info%3Apmid%2F11487234&rft.aulast=Toth&rft.aufirst=L.+A.&rft.au=Oberbeck%2C+C&rft.au=Straign%2C+C.+M.&rft.au=Frazier%2C+S&rft.au=Rehg%2C+J.+E.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAvermectin" class="Z3988"></span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFViktorovYurkiv2003" class="citation journal cs1">Viktorov, A. V.; Yurkiv, V. A. (2003). "Effect of ivermectin on function of liver macrophages". <i>Bulletin of Experimental Biology and Medicine</i>. <b>136</b> (6): 569–71. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1023%2Fb%3Abebm.0000020206.23474.e9">10.1023/b:bebm.0000020206.23474.e9</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/15500074">15500074</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:851108">851108</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bulletin+of+Experimental+Biology+and+Medicine&rft.atitle=Effect+of+ivermectin+on+function+of+liver+macrophages&rft.volume=136&rft.issue=6&rft.pages=569-71&rft.date=2003&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A851108%23id-name%3DS2CID&rft_id=info%3Apmid%2F15500074&rft_id=info%3Adoi%2F10.1023%2Fb%3Abebm.0000020206.23474.e9&rft.aulast=Viktorov&rft.aufirst=A.+V.&rft.au=Yurkiv%2C+V.+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAvermectin" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFYang2012" class="citation journal cs1">Yang, Chen-Chang (2012). "Acute Human Toxicity of Macrocyclic Lactones". <i>Current Pharmaceutical Biotechnology</i>. <b>13</b> (6): 999–1003. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2174%2F138920112800399059">10.2174/138920112800399059</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/22039794">22039794</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Pharmaceutical+Biotechnology&rft.atitle=Acute+Human+Toxicity+of+Macrocyclic+Lactones&rft.volume=13&rft.issue=6&rft.pages=999-1003&rft.date=2012&rft_id=info%3Adoi%2F10.2174%2F138920112800399059&rft_id=info%3Apmid%2F22039794&rft.aulast=Yang&rft.aufirst=Chen-Chang&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAvermectin" class="Z3988"></span></span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPeter" class="citation news cs1">Peter, John. <a rel="nofollow" class="external text" href="https://www.firstmedinc.com">"Ivermectin"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Ivermectin&rft.aulast=Peter&rft.aufirst=John&rft_id=https%3A%2F%2Fwww.firstmedinc.com&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAvermectin" class="Z3988"></span></span> </li> <li id="cite_note-PMID10449723-20"><span class="mw-cite-backlink">^ <a href="#cite_ref-PMID10449723_20-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PMID10449723_20-1"><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="CITEREFIkedaNonomiyaUsamiOhta1999" class="citation journal cs1">Ikeda, H.; Nonomiya, T.; Usami, M.; Ohta, T.; Omura, S. (1999). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC22239">"Organization of the biosynthetic gene cluster for the polyketide anthelmintic macrolide avermectin in Streptomyces avermitilis"</a>. <i>Proceedings of the National Academy of Sciences</i>. <b>96</b> (17): 9509–9514. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1999PNAS...96.9509I">1999PNAS...96.9509I</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1073%2Fpnas.96.17.9509">10.1073/pnas.96.17.9509</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC22239">22239</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/10449723">10449723</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+National+Academy+of+Sciences&rft.atitle=Organization+of+the+biosynthetic+gene+cluster+for+the+polyketide+anthelmintic+macrolide+avermectin+in+Streptomyces+avermitilis&rft.volume=96&rft.issue=17&rft.pages=9509-9514&rft.date=1999&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC22239%23id-name%3DPMC&rft_id=info%3Apmid%2F10449723&rft_id=info%3Adoi%2F10.1073%2Fpnas.96.17.9509&rft_id=info%3Abibcode%2F1999PNAS...96.9509I&rft.aulast=Ikeda&rft.aufirst=H.&rft.au=Nonomiya%2C+T.&rft.au=Usami%2C+M.&rft.au=Ohta%2C+T.&rft.au=Omura%2C+S.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC22239&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAvermectin" class="Z3988"></span></span> </li> <li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCrumpŌmura2011" class="citation journal cs1">Crump, Andy; Ōmura, Satoshi (2011). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3043740">"Ivermectin, 'wonder drug' from Japan: the human use perspective"</a>. <i>Proceedings of the Japan Academy. Series B, Physical and Biological Sciences</i>. <b>87</b> (2): 13–28. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2011PJAB...87...13C">2011PJAB...87...13C</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.2183%2Fpjab.87.13">10.2183/pjab.87.13</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3043740">3043740</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21321478">21321478</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+Japan+Academy.+Series+B%2C+Physical+and+Biological+Sciences&rft.atitle=Ivermectin%2C+%27wonder+drug%27+from+Japan%3A+the+human+use+perspective.&rft.volume=87&rft.issue=2&rft.pages=13-28&rft.date=2011&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3043740%23id-name%3DPMC&rft_id=info%3Apmid%2F21321478&rft_id=info%3Adoi%2F10.2183%2Fpjab.87.13&rft_id=info%3Abibcode%2F2011PJAB...87...13C&rft.aulast=Crump&rft.aufirst=Andy&rft.au=%C5%8Cmura%2C+Satoshi&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3043740&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAvermectin" class="Z3988"></span></span> </li> </ol></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · ";font-weight:bold}.mw-parser-output .hlist dd:last-child::after,.mw-parser-output .hlist dt:last-child::after,.mw-parser-output .hlist li:last-child::after{content:none}.mw-parser-output .hlist dd dd:first-child::before,.mw-parser-output .hlist dd dt:first-child::before,.mw-parser-output .hlist dd li:first-child::before,.mw-parser-output .hlist dt dd:first-child::before,.mw-parser-output .hlist dt dt:first-child::before,.mw-parser-output .hlist dt li:first-child::before,.mw-parser-output .hlist li dd:first-child::before,.mw-parser-output .hlist li dt:first-child::before,.mw-parser-output .hlist li li:first-child::before{content:" (";font-weight:normal}.mw-parser-output .hlist dd dd:last-child::after,.mw-parser-output .hlist dd dt:last-child::after,.mw-parser-output .hlist dd li:last-child::after,.mw-parser-output .hlist dt dd:last-child::after,.mw-parser-output .hlist dt dt:last-child::after,.mw-parser-output .hlist dt li:last-child::after,.mw-parser-output .hlist li dd:last-child::after,.mw-parser-output .hlist li dt:last-child::after,.mw-parser-output .hlist li li:last-child::after{content:")";font-weight:normal}.mw-parser-output .hlist ol{counter-reset:listitem}.mw-parser-output .hlist ol>li{counter-increment:listitem}.mw-parser-output .hlist ol>li::before{content:" "counter(listitem)"\a0 "}.mw-parser-output .hlist dd ol>li:first-child::before,.mw-parser-output .hlist dt ol>li:first-child::before,.mw-parser-output .hlist li ol>li:first-child::before{content:" ("counter(listitem)"\a0 "}</style><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output .navbox-subgroup{width:100%}.mw-parser-output .navbox-group,.mw-parser-output .navbox-title,.mw-parser-output .navbox-abovebelow{padding:0.25em 1em;line-height:1.5em;text-align:center}.mw-parser-output .navbox-group{white-space:nowrap;text-align:right}.mw-parser-output .navbox,.mw-parser-output .navbox-subgroup{background-color:#fdfdfd}.mw-parser-output .navbox-list{line-height:1.5em;border-color:#fdfdfd}.mw-parser-output .navbox-list-with-group{text-align:left;border-left-width:2px;border-left-style:solid}.mw-parser-output tr+tr>.navbox-abovebelow,.mw-parser-output tr+tr>.navbox-group,.mw-parser-output tr+tr>.navbox-image,.mw-parser-output tr+tr>.navbox-list{border-top:2px solid #fdfdfd}.mw-parser-output .navbox-title{background-color:#ccf}.mw-parser-output .navbox-abovebelow,.mw-parser-output .navbox-group,.mw-parser-output .navbox-subgroup .navbox-title{background-color:#ddf}.mw-parser-output .navbox-subgroup .navbox-group,.mw-parser-output .navbox-subgroup .navbox-abovebelow{background-color:#e6e6ff}.mw-parser-output .navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Antiparasitics_–_Anthelmintics_(P02)_and_endectocides_(QP54)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Anthelmintics" title="Template:Anthelmintics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Anthelmintics" title="Template talk:Anthelmintics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Anthelmintics" title="Special:EditPage/Template:Anthelmintics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Antiparasitics_–_Anthelmintics_(P02)_and_endectocides_(QP54)" style="font-size:114%;margin:0 4em"><a href="/wiki/Antiparasitic" title="Antiparasitic">Antiparasitics</a> – <a href="/wiki/Anthelmintic" title="Anthelmintic">Anthelmintics</a> (<a href="/wiki/ATC_code_P02" title="ATC code P02">P02</a>) and <a href="/wiki/Endectocides" class="mw-redirect" title="Endectocides">endectocides</a> (<a href="/wiki/ATCvet_code_QP54" title="ATCvet code QP54">QP54</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antiplatyhelmintic_agent" title="Antiplatyhelmintic agent">Antiplatyhelmintic agents</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/Trematoda" title="Trematoda">Antitrematodals</a><br />(<a href="/wiki/Schistosomicide" class="mw-redirect" title="Schistosomicide">schistosomicides</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%">Binds <a href="/wiki/Tubulin" title="Tubulin">tubulin</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><i><a href="/wiki/Benzimidazole" title="Benzimidazole">benzimidazole</a></i> <ul><li><a href="/wiki/Triclabendazole" title="Triclabendazole">Triclabendazole</a><sup>#</sup></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Acetylcholinesterase_inhibitor" title="Acetylcholinesterase inhibitor">AChE inhibitor</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><i><a href="/wiki/Phosphonic_acid" class="mw-redirect" title="Phosphonic acid">phosphonic acid</a></i> <ul><li><a href="/wiki/Metrifonate" title="Metrifonate">Metrifonate</a><sup>‡</sup></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other/unknown</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Quinoline" title="Quinoline">quinoline</a></i> <ul><li><a href="/wiki/Arpraziquantel" title="Arpraziquantel">Arpraziquantel</a></li> <li><a href="/wiki/Praziquantel" title="Praziquantel">Praziquantel</a><sup>#</sup> (<a href="/wiki/Esafoxolaner/eprinomectin/praziquantel" title="Esafoxolaner/eprinomectin/praziquantel">+esafoxolaner/eprinomectin</a>)</li> <li><a href="/wiki/Oxamniquine" title="Oxamniquine">Oxamniquine</a><sup>#</sup></li></ul></li> <li><i><a href="/wiki/Phenol" title="Phenol">phenol</a></i> <ul><li><a href="/wiki/Bithionol" title="Bithionol">Bithionol</a></li></ul></li> <li><i><a href="/wiki/Thiazole" title="Thiazole">thiazole</a></i> <ul><li><a href="/wiki/Niridazole" title="Niridazole">Niridazole</a></li></ul></li> <li><i><a href="/wiki/Thioxanthone" title="Thioxanthone">thioxanthone</a></i> <ul><li><a href="/wiki/Hycanthone" title="Hycanthone">Hycanthone</a></li> <li><a href="/wiki/Lucanthone" title="Lucanthone">Lucanthone</a></li></ul></li> <li><i><a href="/wiki/Antimony" title="Antimony">antimony</a> compounds</i> <ul><li><a href="/wiki/Stibophen" title="Stibophen">Stibophen</a></li> <li><a href="/wiki/Tartar_emetic" class="mw-redirect" title="Tartar emetic">Tartar emetic</a><sup>‡</sup></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anticestodal_agent" title="Anticestodal agent">Anticestodals</a><br />(<a href="/wiki/Taeniacide" title="Taeniacide">taeniacides</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%">Binds <a href="/wiki/Tubulin" title="Tubulin">tubulin</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><i><a href="/wiki/Benzimidazole" title="Benzimidazole">benzimidazole</a></i> <ul><li><a href="/wiki/Albendazole" title="Albendazole">Albendazole</a><sup>#</sup></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other/unknown</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Quinoline" title="Quinoline">quinoline</a></i> <ul><li><a href="/wiki/Praziquantel" title="Praziquantel">Praziquantel</a><sup>#</sup> (<a href="/wiki/Esafoxolaner/eprinomectin/praziquantel" title="Esafoxolaner/eprinomectin/praziquantel">+esafoxolaner/eprinomectin</a>)</li></ul></li> <li><i><a href="/wiki/Salicylanilide" title="Salicylanilide">salicylanilide</a></i> <ul><li><a href="/wiki/Niclosamide" title="Niclosamide">Niclosamide</a><sup>#</sup></li></ul></li> <li><i><a href="/wiki/9-Aminoacridine" title="9-Aminoacridine">aminoacridine</a></i> <ul><li><a href="/wiki/Quinacrine" class="mw-redirect" title="Quinacrine">Quinacrine</a></li></ul></li> <li><i><a href="/wiki/Butyrophenone" title="Butyrophenone">butyrophenone</a></i> <ul><li><a href="/wiki/Desaspidin" title="Desaspidin">Desaspidin</a></li></ul></li> <li><i><a href="/wiki/Chlorophenol" title="Chlorophenol">chlorophenol</a></i> <ul><li><a href="/wiki/Dichlorophen" title="Dichlorophen">Dichlorophen</a></li></ul></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/Antinematodal_agent" class="mw-redirect" title="Antinematodal agent">Antinematodal agents</a><br />(including<br /><a href="/wiki/Macrofilaricide" class="mw-redirect" title="Macrofilaricide">macrofilaricides</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%">Binds <a href="/wiki/Tubulin" title="Tubulin">tubulin</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><i><a href="/wiki/Benzimidazole" title="Benzimidazole">benzimidazole</a></i> <ul><li><a href="/wiki/Mebendazole" title="Mebendazole">Mebendazole</a><sup>#</sup></li> <li><a href="/wiki/Albendazole" title="Albendazole">Albendazole</a><sup>#</sup></li> <li><a href="/wiki/Tiabendazole" title="Tiabendazole">Tiabendazole</a></li> <li><a href="/wiki/Fenbendazole" title="Fenbendazole">Fenbendazole</a></li> <li><a href="/wiki/Ciclobendazole" title="Ciclobendazole">Ciclobendazole</a></li> <li><a href="/wiki/Flubendazole" title="Flubendazole">Flubendazole</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glutamate-gated_chloride_channel" class="mw-redirect" title="Glutamate-gated chloride channel">Glutamate-gated chloride channel</a>, <a href="/wiki/GABA_receptor" title="GABA receptor">GABA receptor</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><i><a class="mw-selflink selflink">avermectins</a></i> <ul><li><a href="/wiki/Abamectin" title="Abamectin">Abamectin</a></li> <li><a href="/wiki/Doramectin" title="Doramectin">Doramectin</a></li> <li><a href="/wiki/Emamectin" title="Emamectin">Emamectin</a></li> <li><a href="/wiki/Eprinomectin" title="Eprinomectin">Eprinomectin</a> (<a href="/wiki/Esafoxolaner/eprinomectin/praziquantel" title="Esafoxolaner/eprinomectin/praziquantel">+esafoxolaner/praziquantel</a>)</li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a><sup>#</sup></li> <li><a href="/wiki/Selamectin" title="Selamectin">Selamectin</a></li></ul></li> <li><i><a href="/wiki/Milbemycin" title="Milbemycin">milbemycins</a></i> <ul><li><a href="/wiki/Moxidectin" title="Moxidectin">Moxidectin</a> (<a href="/wiki/Fluralaner/moxidectin" class="mw-redirect" title="Fluralaner/moxidectin">+fluralaner</a>)</li> <li><a href="/wiki/Milbemycin_oxime" title="Milbemycin oxime">Milbemycin oxime</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Neuromuscular_depolarizing_agent" class="mw-redirect" title="Neuromuscular depolarizing agent">NMDA</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><i><a href="/wiki/Tetrahydropyrimidine" class="mw-redirect" title="Tetrahydropyrimidine">tetrahydropyrimidine</a></i> <ul><li><a href="/wiki/Pyrantel" title="Pyrantel">Pyrantel</a><sup>#</sup> <ul><li><a href="/wiki/Pyrantel_pamoate" class="mw-redirect" title="Pyrantel pamoate">pyrantel pamoate</a></li></ul></li> <li><a href="/wiki/Oxantel" title="Oxantel">Oxantel</a></li> <li><a href="/wiki/Morantel" title="Morantel">Morantel</a></li> <li><a href="/w/index.php?title=Carbantel&action=edit&redlink=1" class="new" title="Carbantel (page does not exist)">Carbantel</a></li> <li><a href="/w/index.php?title=Febantel&action=edit&redlink=1" class="new" title="Febantel (page does not exist)">Febantel</a> (aka <a href="/w/index.php?title=Felsantel&action=edit&redlink=1" class="new" title="Felsantel (page does not exist)">felsantel</a>)</li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other/unknown</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>piperazine</i> <ul><li><a href="/wiki/Piperazine" title="Piperazine">Piperazine</a></li> <li><a href="/wiki/Diethylcarbamazine" title="Diethylcarbamazine">Diethylcarbamazine</a><sup>#</sup></li></ul></li> <li><i><a href="/wiki/Thiazole" title="Thiazole">thiazole</a></i> <ul><li><a href="/wiki/Levamisole" title="Levamisole">Levamisole</a><sup>#</sup></li></ul></li> <li><i><a href="/wiki/Quinolinium" class="mw-redirect" title="Quinolinium">quinolinium</a></i> <ul><li><a href="/wiki/Pyrvinium" title="Pyrvinium">Pyrvinium</a></li></ul></li> <li><i><a href="/wiki/Benzylammonium" class="mw-redirect" title="Benzylammonium">benzylammonium</a></i> <ul><li><a href="/wiki/Bephenium_hydroxynaphthoate" title="Bephenium hydroxynaphthoate">Bephenium</a></li></ul></li> <li><i><a href="/wiki/Naphthalenesulfonate" title="Naphthalenesulfonate">naphthalenesulfonate</a></i> <ul><li><a href="/wiki/Suramin" title="Suramin">Suramin</a><sup>#</sup></li></ul></li> <li><a href="/wiki/Ascaridole" title="Ascaridole">Ascaridole</a><sup>‡</sup></li> <li><a href="/wiki/Hexylresorcinol" class="mw-redirect" title="Hexylresorcinol">Hexylresorcinol</a></li> <li><a href="/wiki/Santonin" title="Santonin">Santonin</a><sup>‡</sup></li> <li><a href="/wiki/Tribendimidine" title="Tribendimidine">Tribendimidine</a></li> <li><a href="/wiki/Tetrachloroethylene" title="Tetrachloroethylene">Tetrachloroethylene</a><sup>‡</sup></li></ul> </div></td></tr></tbody></table><div></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><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Avermectin&oldid=1233977336">https://en.wikipedia.org/w/index.php?title=Avermectin&oldid=1233977336</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Antiparasitic_agents" title="Category:Antiparasitic agents">Antiparasitic agents</a></li><li><a href="/wiki/Category:Polyketides" title="Category:Polyketides">Polyketides</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_matches_Wikidata" title="Category:Short description matches Wikidata">Short description matches Wikidata</a></li><li><a href="/wiki/Category:Articles_to_be_expanded_from_September_2023" title="Category:Articles to be expanded from September 2023">Articles to be expanded from September 2023</a></li><li><a href="/wiki/Category:All_articles_with_unsourced_statements" title="Category:All articles with unsourced statements">All articles with unsourced statements</a></li><li><a href="/wiki/Category:Articles_with_unsourced_statements_from_November_2020" title="Category:Articles with unsourced statements from November 2020">Articles with unsourced statements from November 2020</a></li><li><a href="/wiki/Category:All_accuracy_disputes" title="Category:All accuracy disputes">All accuracy disputes</a></li><li><a href="/wiki/Category:Articles_with_disputed_statements_from_November_2023" title="Category:Articles with disputed statements from November 2023">Articles with disputed statements from November 2023</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 11 July 2024, at 22:49<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. By using this site, you agree to the <a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Terms_of_Use" class="extiw" title="foundation:Special:MyLanguage/Policy:Terms of Use">Terms of Use</a> and <a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy" class="extiw" title="foundation:Special:MyLanguage/Policy:Privacy policy">Privacy Policy</a>. Wikipedia® is a registered trademark of the <a rel="nofollow" class="external text" href="https://wikimediafoundation.org/">Wikimedia Foundation, Inc.</a>, a non-profit organization.</li> </ul> <ul id="footer-places"> <li id="footer-places-privacy"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy">Privacy policy</a></li> <li id="footer-places-about"><a href="/wiki/Wikipedia:About">About Wikipedia</a></li> <li id="footer-places-disclaimers"><a href="/wiki/Wikipedia:General_disclaimer">Disclaimers</a></li> <li id="footer-places-contact"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us">Contact Wikipedia</a></li> <li id="footer-places-wm-codeofconduct"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Universal_Code_of_Conduct">Code of Conduct</a></li> <li id="footer-places-developers"><a href="https://developer.wikimedia.org">Developers</a></li> <li id="footer-places-statslink"><a href="https://stats.wikimedia.org/#/en.wikipedia.org">Statistics</a></li> <li id="footer-places-cookiestatement"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Cookie_statement">Cookie statement</a></li> <li id="footer-places-mobileview"><a href="//en.m.wikipedia.org/w/index.php?title=Avermectin&mobileaction=toggle_view_mobile" class="noprint stopMobileRedirectToggle">Mobile view</a></li> </ul> <ul id="footer-icons" class="noprint"> <li id="footer-copyrightico"><a href="https://wikimediafoundation.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><img src="/static/images/footer/wikimedia-button.svg" width="84" height="29" alt="Wikimedia Foundation" loading="lazy"></a></li> <li id="footer-poweredbyico"><a href="https://www.mediawiki.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><img src="/w/resources/assets/poweredby_mediawiki.svg" alt="Powered by MediaWiki" width="88" height="31" loading="lazy"></a></li> </ul> </footer> </div> </div> </div> <div class="vector-settings" id="p-dock-bottom"> <ul></ul> </div><script>(RLQ=window.RLQ||[]).push(function(){mw.config.set({"wgHostname":"mw-web.codfw.main-f69cdc8f6-6vrgq","wgBackendResponseTime":151,"wgPageParseReport":{"limitreport":{"cputime":"0.559","walltime":"0.687","ppvisitednodes":{"value":2231,"limit":1000000},"postexpandincludesize":{"value":97345,"limit":2097152},"templateargumentsize":{"value":2956,"limit":2097152},"expansiondepth":{"value":12,"limit":100},"expensivefunctioncount":{"value":4,"limit":500},"unstrip-depth":{"value":1,"limit":20},"unstrip-size":{"value":99006,"limit":5000000},"entityaccesscount":{"value":0,"limit":400},"timingprofile":["100.00% 596.811 1 -total"," 44.69% 266.716 1 Template:Reflist"," 37.08% 221.296 19 Template:Cite_journal"," 20.58% 122.812 5 Template:Navbox"," 19.86% 118.514 1 Template:Endectocides"," 15.71% 93.767 1 Template:Short_description"," 9.34% 55.744 2 Template:Pagetype"," 9.07% 54.123 1 Template:Missing_information"," 8.19% 48.899 1 Template:Ambox"," 7.09% 42.318 1 Template:PharmNavFootnote"]},"scribunto":{"limitreport-timeusage":{"value":"0.331","limit":"10.000"},"limitreport-memusage":{"value":6168313,"limit":52428800}},"cachereport":{"origin":"mw-web.codfw.main-f69cdc8f6-44cqd","timestamp":"20241122142120","ttl":2592000,"transientcontent":false}}});});</script> <script type="application/ld+json">{"@context":"https:\/\/schema.org","@type":"Article","name":"Avermectin","url":"https:\/\/en.wikipedia.org\/wiki\/Avermectin","sameAs":"http:\/\/www.wikidata.org\/entity\/Q416170","mainEntity":"http:\/\/www.wikidata.org\/entity\/Q416170","author":{"@type":"Organization","name":"Contributors to Wikimedia projects"},"publisher":{"@type":"Organization","name":"Wikimedia Foundation, Inc.","logo":{"@type":"ImageObject","url":"https:\/\/www.wikimedia.org\/static\/images\/wmf-hor-googpub.png"}},"datePublished":"2006-07-03T01:03:00Z","dateModified":"2024-07-11T22:49:05Z","image":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/3\/3f\/Avermectins_skeletal.svg","headline":"drugs to treat parasitic worms and insect pests"}</script> </body> </html>