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id="toc-Manufacture-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Legal_status" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Legal_status"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Legal status</span> </div> </a> <ul id="toc-Legal_status-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Veterinary_use" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Veterinary_use"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Veterinary use</span> </div> </a> <ul id="toc-Veterinary_use-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">8</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">9</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>External links</span> </div> </a> <ul id="toc-External_links-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">Chondroitin sulfate</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 26 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-26" 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">26 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%B3%D9%84%D9%81%D8%A7%D8%AA_%D8%A7%D9%84%D9%83%D9%88%D9%86%D8%AF%D8%B1%D9%88%D9%8A%D8%AA%D9%8A%D9%86" title="سلفات الكوندرويتين – Arabic" lang="ar" hreflang="ar" data-title="سلفات الكوندرويتين" 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/Sulfat_de_condro%C3%AFtina" title="Sulfat de condroïtina – Catalan" lang="ca" hreflang="ca" data-title="Sulfat de condroïtina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Chondroitin_sulf%C3%A1t" title="Chondroitin sulfát – Czech" lang="cs" hreflang="cs" data-title="Chondroitin sulfát" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Chondroitinsulfat" title="Chondroitinsulfat – German" lang="de" hreflang="de" data-title="Chondroitinsulfat" 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/Condroit%C3%ADn_sulfato" title="Condroitín sulfato – Spanish" lang="es" hreflang="es" data-title="Condroitín sulfato" 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/Kondroitin_sulfato" title="Kondroitin sulfato – Basque" lang="eu" hreflang="eu" data-title="Kondroitin sulfato" 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/%DA%A9%D9%86%D8%AF%D8%B1%D9%88%D8%A7%DB%8C%D8%AA%DB%8C%D9%86_%D8%B3%D9%88%D9%84%D9%81%D8%A7%D8%AA" title="کندروایتین سولفات – Persian" lang="fa" hreflang="fa" data-title="کندروایتین سولفات" 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/Sulfate_de_chondro%C3%AFtine" title="Sulfate de chondroïtine – French" lang="fr" hreflang="fr" data-title="Sulfate de chondroïtine" 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/Condroit%C3%ADn_sulfato" title="Condroitín sulfato – Galician" lang="gl" hreflang="gl" data-title="Condroitín sulfato" 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%BD%98%EB%93%9C%EB%A1%9C%EC%9D%B4%ED%8B%B4_%ED%99%A9%ED%99%94%EC%97%BC" title="콘드로이틴 황화염 – Korean" lang="ko" hreflang="ko" data-title="콘드로이틴 황화염" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Hondroitin-sulfat" title="Hondroitin-sulfat – Croatian" lang="hr" hreflang="hr" data-title="Hondroitin-sulfat" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Kondroitin" title="Kondroitin – Indonesian" lang="id" hreflang="id" data-title="Kondroitin" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Condroitina_solfato" title="Condroitina solfato – Italian" lang="it" hreflang="it" data-title="Condroitina solfato" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%9B%D7%95%D7%A0%D7%93%D7%A8%D7%95%D7%99%D7%98%D7%99%D7%9F_%D7%A1%D7%95%D7%9C%D7%A4%D7%98" title="כונדרויטין סולפט – Hebrew" lang="he" hreflang="he" data-title="כונדרויטין סולפט" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Kondroitin-szulf%C3%A1t" title="Kondroitin-szulfát – Hungarian" lang="hu" hreflang="hu" data-title="Kondroitin-szulfát" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Chondro%C3%AFtine" title="Chondroïtine – Dutch" lang="nl" hreflang="nl" data-title="Chondroïtine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B3%E3%83%B3%E3%83%89%E3%83%AD%E3%82%A4%E3%83%81%E3%83%B3%E7%A1%AB%E9%85%B8" title="コンドロイチン硫酸 – Japanese" lang="ja" hreflang="ja" data-title="コンドロイチン硫酸" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Siarczan_chondroityny" title="Siarczan chondroityny – Polish" lang="pl" hreflang="pl" data-title="Siarczan chondroityny" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/%C3%81cido_condroitinossulf%C3%BArico" title="Ácido condroitinossulfúrico – Portuguese" lang="pt" hreflang="pt" data-title="Ácido condroitinossulfúrico" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A5%D0%BE%D0%BD%D0%B4%D1%80%D0%BE%D0%B8%D1%82%D0%B8%D0%BD%D1%81%D1%83%D0%BB%D1%8C%D1%84%D0%B0%D1%82%D1%8B" title="Хондроитинсульфаты – Russian" lang="ru" hreflang="ru" data-title="Хондроитинсульфаты" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Chondroitin_sulfate" title="Chondroitin sulfate – Simple English" lang="en-simple" hreflang="en-simple" data-title="Chondroitin sulfate" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Hondroitin_sulfat" title="Hondroitin sulfat – Serbian" lang="sr" hreflang="sr" data-title="Hondroitin sulfat" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Hondroitin_sulfat" title="Hondroitin sulfat – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Hondroitin sulfat" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Kondroitiinisulfaatti" title="Kondroitiinisulfaatti – Finnish" lang="fi" hreflang="fi" data-title="Kondroitiinisulfaatti" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A5%D0%BE%D0%BD%D0%B4%D1%80%D0%BE%D1%97%D1%82%D0%B8%D0%BD" title="Хондроїтин – Ukrainian" lang="uk" hreflang="uk" data-title="Хондроїтин" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a 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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">Sulfated glycosaminoglycan (GAG) compound</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Chondroitin_Sulfate_Structure_NTP.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Chondroitin_Sulfate_Structure_NTP.png/240px-Chondroitin_Sulfate_Structure_NTP.png" decoding="async" width="240" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Chondroitin_Sulfate_Structure_NTP.png/360px-Chondroitin_Sulfate_Structure_NTP.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Chondroitin_Sulfate_Structure_NTP.png/480px-Chondroitin_Sulfate_Structure_NTP.png 2x" data-file-width="977" data-file-height="422" /></a><figcaption>Chemical structure of one unit in a chondroitin sulfate chain. Chondroitin-4-sulfate: R<sub>1</sub> = H; R<sub>2</sub> = SO<sub>3</sub>H; R<sub>3</sub> = H. Chondroitin-6-sulfate: R<sub>1</sub> = SO<sub>3</sub>H; R<sub>2</sub>, R<sub>3</sub> = H.</figcaption></figure> <p><b>Chondroitin sulfate</b> is a sulfated <a href="/wiki/Glycosaminoglycan" title="Glycosaminoglycan">glycosaminoglycan</a> (GAG)<sup id="cite_ref-:0_1-0" class="reference"><a href="#cite_note-:0-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> composed of a chain of alternating sugars (<a href="/wiki/N-Acetylgalactosamine" title="N-Acetylgalactosamine">N-acetylgalactosamine</a> and <a href="/wiki/Glucuronic_acid" title="Glucuronic acid">glucuronic acid</a>). It is usually found attached to proteins as part of a <a href="/wiki/Proteoglycan" title="Proteoglycan">proteoglycan</a>.<sup id="cite_ref-:0_1-1" class="reference"><a href="#cite_note-:0-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> A chondroitin chain can have over 100 individual sugars, each of which can be sulfated in variable positions and quantities. Chondroitin sulfate is an important structural component of <a href="/wiki/Cartilage" title="Cartilage">cartilage</a>,<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> and provides much of its resistance to <a href="/wiki/Compressive_stress" title="Compressive stress">compression</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Along with <a href="/wiki/Glucosamine" title="Glucosamine">glucosamine</a>, chondroitin sulfate has become a widely used <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplement</a> for treatment of <a href="/wiki/Osteoarthritis" title="Osteoarthritis">osteoarthritis</a>, although large <a href="/wiki/Clinical_trial" title="Clinical trial">clinical trials</a> failed to demonstrate any symptomatic benefit of chondroitin. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Medical_use">Medical use</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chondroitin_sulfate&action=edit&section=1" title="Edit section: Medical use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chondroitin is used in <a href="/wiki/Dietary_supplements" class="mw-redirect" title="Dietary supplements">dietary supplements</a> as an <a href="/wiki/Alternative_medicine" title="Alternative medicine">alternative medicine</a> to treat <a href="/wiki/Osteoarthritis" title="Osteoarthritis">osteoarthritis</a>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> It is also approved and regulated as a symptomatic slow-acting <a href="/wiki/Medication" title="Medication">drug</a> for this disease (SYSADOA) in <a href="/wiki/Europe" title="Europe">Europe</a> and some other countries. It is commonly sold together with <a href="/wiki/Glucosamine" title="Glucosamine">glucosamine</a>.<sup id="cite_ref-Cochrane2015_5-0" class="reference"><a href="#cite_note-Cochrane2015-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> A 2015 <a href="/wiki/Cochrane_(organisation)" title="Cochrane (organisation)">Cochrane</a> review of clinical trials found that most were of low quality, but that there was some evidence of short-term improvement in pain and few side effects; it does not appear to <a href="/wiki/Disease-modifying_antirheumatic_drug" title="Disease-modifying antirheumatic drug">improve or maintain the health of affected joints</a>.<sup id="cite_ref-Cochrane2015_5-1" class="reference"><a href="#cite_note-Cochrane2015-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Chondroitin, along with commonly used glucosamine, should not be used to treat people who have symptomatic osteoarthritis of the knee as evidence shows that these treatments fail to provide relief for that condition.<sup id="cite_ref-AAOSfive_6-0" class="reference"><a href="#cite_note-AAOSfive-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Chondroitin has shown to be promising in the treatment of <a href="/wiki/Coronary_artery_disease" title="Coronary artery disease">coronary artery disease</a>. In a 6-year double-blind placebo-controlled study involving 60 test subjects published in 1973, the chondroitin sulfate group showed a 350% reduction in fatal heart attacks compared to the control group. When analyzing the data for non-fatal cardiovascular events, the control group experienced non-fatal heart attacks at a rate of 16%, while those in the chondroitin sulfate-treated group came in at 0%.<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><p>Chondroitin sulfate is used as a dietary supplement for diabetes management.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> It exhibits anti-inflammatory properties, making it a potential alternative to cortisol for treating enteritis.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Adverse_effects">Adverse effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chondroitin_sulfate&action=edit&section=2" title="Edit section: Adverse effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Clinical studies have not identified any significant side effects or overdoses of chondroitin sulfate, which suggest its long-term safety.<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> In 2003 the Task Force of the European League Against Rheumatism (EULAR) committee ranked the level of toxicity of chondroitin sulfate 6 in a 0–100 scale.<sup id="cite_ref-Jordan2003_12-0" class="reference"><a href="#cite_note-Jordan2003-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>Chondroitin sulfate is not metabolized by <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a>.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chondroitin_sulfate&action=edit&section=3" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Mechanisms_of_action">Mechanisms of action</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chondroitin_sulfate&action=edit&section=4" title="Edit section: Mechanisms of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The effect of chondroitin sulfate in people with osteoarthritis is likely the result of a number of reactions including its anti-inflammatory activity, the stimulation of the synthesis of proteoglycans and <a href="/wiki/Hyaluronic_acid" title="Hyaluronic acid">hyaluronic acid</a>, and the decrease in catabolic activity of chondrocytes, inhibiting the synthesis of <a href="/wiki/Protease" title="Protease">proteolytic enzymes</a>, nitric oxide, and other substances that contribute to damage the cartilage matrix and cause death of articular chondrocytes. A recent review summarizes data from relevant reports describing the biochemical basis of the effect of chondroitin sulfate on osteoarthritis articular tissues.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Bioavailability_and_pharmacokinetics">Bioavailability and pharmacokinetics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chondroitin_sulfate&action=edit&section=5" title="Edit section: Bioavailability and pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Pharmacokinetic studies performed on humans and experimental animals after oral administration of chondroitin sulfate revealed that it can be absorbed orally. Chondroitin sulfate shows first-order kinetics up to single doses of 3,000 mg.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><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><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><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> Multiple doses of 800 mg in people with osteoarthritis do not alter the kinetics of chondroitin sulfate. The <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> of chondroitin sulfate ranges from 15% to 24% of the orally administered dose. More particularly, on the articular tissue, Ronca et al.<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> reported that chondroitin sulfate is not rapidly absorbed in the gastro-intestinal tract and a high content of labeled chondroitin sulfate is found in the <a href="/wiki/Synovial_fluid" title="Synovial fluid">synovial fluid</a> and cartilage. </p> <div class="mw-heading mw-heading2"><h2 id="Physical_and_chemical_properties">Physical and chemical properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chondroitin_sulfate&action=edit&section=6" title="Edit section: Physical and chemical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chondroitin sulfate chains are unbranched <a href="/wiki/Polysaccharide" title="Polysaccharide">polysaccharides</a> of variable length containing two alternating monosaccharides: <a href="/wiki/Glucuronic_acid" title="Glucuronic acid"><small>D</small>-glucuronic acid</a> (GlcA) and <a href="/wiki/N-Acetylgalactosamine" title="N-Acetylgalactosamine"><i>N</i>-acetyl-<small>D</small>-galactosamine</a> (GalNAc). Some of these GlcA residues may be <a href="/wiki/Epimer" title="Epimer">epimerized</a> into <a href="/wiki/Iduronic_acid" title="Iduronic acid"><small>L</small>-iduronic acid</a> (IdoA) at which point the resulting glycosaminoglycan is then referred to as <a href="/wiki/Dermatan_sulfate" title="Dermatan sulfate">dermatan sulfate</a>, previously referred to as chondroitin sulfate B. </p><p>Chondroitin sulfate is sourced from natural products, with high variability in terms of chain length and sulfation pattern. The variability in chondroitin sulfate composition extends to its origin, making it possible to differentiate between chondroitin sulfate from terrestrial and marine sources. One way to look at this difference is in terms of the proportion of disaccharide units: chondroitin sulfate from terrestrial animals is almost exclusively composed of non-sulfated (O) and monosulfated (A and C) units, while in marine species the proportion of disulfated (D, E and B) units is higher. Furthermore, marine chondroitin sulfate chains tend to be longer, with molecular weight of up to 70 kDa in chondroitin sulfate from shark, while in terrestrial animals molecular weight is typically below 45 kDa.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><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><p>Chondroitin sulfate chains are linked to hydroxyl groups on <a href="/wiki/Serine" title="Serine">serine</a> residues of certain proteins. Exactly how proteins are selected for attachment of glycosaminoglycans is not understood. Glycosylated serines are often followed by a glycine and have neighboring acidic residues, but this motif does not always predict glycosylation. </p><p>Attachment of the GAG chain begins with four monosaccharides in a fixed pattern: <a href="/wiki/Xylose" title="Xylose">Xyl</a> – <a href="/wiki/Galactose" title="Galactose">Gal</a> – Gal – GlcA. Each sugar is attached by a specific enzyme, allowing for multiple levels of control over GAG synthesis. Xylose begins to be attached to proteins in the <a href="/wiki/Endoplasmic_reticulum" title="Endoplasmic reticulum">endoplasmic reticulum</a>, while the rest of the sugars are attached in the <a href="/wiki/Golgi_apparatus" title="Golgi apparatus">Golgi apparatus</a>.<sup id="cite_ref-Silbert_2002_22-0" class="reference"><a href="#cite_note-Silbert_2002-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p>Chondroitin sulfate is highly <a href="/wiki/Solubility" title="Solubility">soluble</a> in <a href="/wiki/Water" title="Water">water</a>.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <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=Chondroitin_sulfate&action=edit&section=7" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chondroitin sulfate was originally isolated well before the structure was characterised, leading to changes in terminology with time.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Early researchers identified different fractions of the substance with letters. </p> <table class="wikitable"> <tbody><tr> <th>Letter identification</th> <th>Site of sulfation</th> <th>Systematic name </th></tr> <tr> <td><i>Chondroitin sulfate A</i></td> <td>carbon 4 of the N-acetylgalactosamine (GalNAc) sugar</td> <td>chondroitin-4-sulfate </td></tr> <tr> <td><i>Chondroitin sulfate C</i></td> <td>carbon 6 of the GalNAc sugar</td> <td>chondroitin-6-sulfate </td></tr> <tr> <td><i>Chondroitin sulfate D</i></td> <td>carbon 2 of the glucuronic acid and 6 of the GalNAc sugar</td> <td>chondroitin-2,6-sulfate </td></tr> <tr> <td><i>Chondroitin sulfate E</i></td> <td>carbons 4 and 6 of the GalNAc sugar</td> <td>chondroitin-4,6-sulfate </td></tr></tbody></table> <p>"Chondroitin sulfate B" is an old name for <a href="/wiki/Dermatan_sulfate" title="Dermatan sulfate">dermatan sulfate</a>, and it is no longer classified as a form of chondroitin sulfate.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p><i>Chondroitin</i>, without the "sulfate", has been used to describe a fraction with little or no sulfation.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> However, this distinction is not used by all. </p><p>Although the name "chondroitin sulfate" suggests a <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a> with a sulfate <a href="/wiki/Anion" class="mw-redirect" title="Anion">counter-anion</a>, this is not the case, as sulfate is covalently bonded to the sugar. Rather, since the molecule has multiple negative charges at physiological pH, a <a href="/wiki/Cation" class="mw-redirect" title="Cation">cation</a> is present in salts of chondroitin sulfate. Commercial preparations of chondroitin sulfate typically are the sodium salt. Barnhill et al. have suggested that all such preparations of chondroitin sulfate be referred to as "sodium chondroitin" regardless of their sulfation status.<sup id="cite_ref-Barnhill_27-0" class="reference"><a href="#cite_note-Barnhill-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>In 2008 the <a href="/wiki/Food_and_Drug_Administration_(United_States)" class="mw-redirect" title="Food and Drug Administration (United States)">U.S. Food and Drug Administration</a> (FDA) identified "oversulfated chondroitin sulfate" as a contaminant in <a href="/wiki/Heparin" title="Heparin">heparin</a> originating from <a href="/wiki/China" title="China">China</a>.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Clinical_trials_for_osteoarthritis">Clinical trials for osteoarthritis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chondroitin_sulfate&action=edit&section=8" title="Edit section: Clinical trials for osteoarthritis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Clinical_trials_on_glucosamine_and_chondroitin" title="Clinical trials on glucosamine and chondroitin">Clinical trials on glucosamine and chondroitin</a></div> <p>In 2004, a petition was submitted to the FDA that a dietary supplement of chondroitin sulfate be labeled as reducing the risk of osteoarthritis, cartilage deterioration, and osteoarthritis-related joint pain, tenderness, and swelling. The FDA denied the request, stating that experiments conducted by the company did not sufficiently demonstrate the effectiveness of the claim. Among other comments, the FDA noted the poor experimental design of some trials.<sup id="cite_ref-FDACS_31-0" class="reference"><a href="#cite_note-FDACS-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p><p>In 2007, Reichenbach et al. used explicit methods to conduct and report a systematic review of 20 trials and concluded "large-scale, methodologically sound trials indicate that the symptomatic benefit of chondroitin is minimal or nonexistent. Use of chondroitin in routine clinical practice should therefore be discouraged." In contrast, and also in 2007, Bruyere et al. concluded that "there is compelling evidence that glucosamine sulfate and chondroitin sulfate may interfere with progression of OA." </p><p>As of 2015 the largest trial conducted with the product was the Glucosamine and Chondroitin Arthritis Intervention Trial (GAIT), a double-blind, randomized, multicenter clinical trial sponsored by the US National Institutes of Health in 1583 people with knee osteoarthritis, which was published in the New England Journal of Medicine in 2006.<sup id="cite_ref-Cochrane2015_5-2" class="reference"><a href="#cite_note-Cochrane2015-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Clegg_DO_2006_32-0" class="reference"><a href="#cite_note-Clegg_DO_2006-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> Subjects were randomly assigned to one of five orally administered treatments: two 250 mg capsules of glucosamine hydrochloride three times daily, two 200 mg capsules of chondroitin sulfate three times daily, two capsules of 250 mg of glucosamine hydrochloride plus 200 mg of chondroitin sulfate three times daily, 200 mg of <a href="/wiki/Celecoxib" title="Celecoxib">celecoxib</a> daily, or placebo. Treatment was administered for 24 weeks. It showed no difference from placebo.<sup id="cite_ref-Cochrane2015_5-3" class="reference"><a href="#cite_note-Cochrane2015-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Sawitzke A, et al. 2010 evaluated the efficacy and safety of glucosamine and chondroitin sulfate, alone or in combination, as well as celecoxib and placebo on painful knee osteoarthritis over 2 years as a continuation of the GAIT trial. This was a 24-month, double-blind, placebo-controlled study, enrolling 662 people with knee osteoarthritis who satisfied radiographic criteria (Kellgren/Lawrence grade 2 or 3 changes and baseline joint space width of at least 2 mm). This subset continued to receive their randomized treatment (glucosamine 500 mg three times daily, chondroitin sulfate 400 mg three times daily, the combination of glucosamine and chondroitin sulfate, celecoxib 200 mg daily, or placebo) over 24 months. The primary outcome was a 20% reduction in pain over 24 months as measured by the Western Ontario and McMaster University Osteoarthritis Index (WOMAC). Secondary outcomes included an Outcome Measures in Rheumatology/Osteoarthritis Research Society International response and change from baseline in WOMAC pain and function.<sup id="cite_ref-Cochrane2015_5-4" class="reference"><a href="#cite_note-Cochrane2015-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sawitzke2010_33-0" class="reference"><a href="#cite_note-Sawitzke2010-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> Over 2 years, none of the treatments (not even the positive control celecoxib) achieved a clinically important difference in WOMAC pain or function as compared with placebo. Adverse reactions were similar among treatment groups and serious adverse events were rare for all treatments.<sup id="cite_ref-Sawitzke2010_33-1" class="reference"><a href="#cite_note-Sawitzke2010-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Research">Research</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chondroitin_sulfate&action=edit&section=9" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A 2021 study showed a remarkable (about 40%) reduction of the acute <a href="/wiki/Myocardial_infarction" title="Myocardial infarction">myocardial infarction</a> risk in current chondroitin sulfate users in the high risk cardiovascular subgroups.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chondroitin_sulfate&action=edit&section=10" title="Edit section: Society and culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Manufacture">Manufacture</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chondroitin_sulfate&action=edit&section=11" title="Edit section: Manufacture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Most chondroitin appears to be made from extracts of cartilaginous cow and pig tissues (cow <a href="/wiki/Vertebrate_trachea" class="mw-redirect" title="Vertebrate trachea">trachea</a> and pig ear and nose), but other sources such as <a href="/wiki/Shark_cartilage" title="Shark cartilage">shark</a>, fish, and bird cartilage are also used. Since chondroitin is not a uniform substance, and is naturally present in a wide variety of forms, the precise composition of each supplement will vary.<sup id="cite_ref-Barnhill_27-1" class="reference"><a href="#cite_note-Barnhill-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> In fact, although many <a href="/wiki/Food_supplement" class="mw-redirect" title="Food supplement">food supplement</a> companies produce their products in compliance with human food processing <a href="/wiki/Good_Manufacturing_Practice" class="mw-redirect" title="Good Manufacturing Practice">Good Manufacturing Practice (GMP)</a>, most of them do not produce their products in compliance with the GMP regulations for pharmaceuticals, resulting in products not meeting pharmaceutical requirements.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Legal_status">Legal status</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chondroitin_sulfate&action=edit&section=12" title="Edit section: Legal status"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>While it is a prescription or over-the-counter drug in 22 countries, chondroitin is regulated in the U.S. as a dietary supplement<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> by the <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a>. In Europe, chondroitin sulfate formulations are approved as drugs with evidenced efficacy and safety demonstrated by clinical trials in people with osteoarthritis.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> Adebowale et al. reported in 2000 that of 32 chondroitin supplements they analysed, only 5 were labeled correctly, and more than half contained less than 40% of the labeled amount.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> With the introduction of <a href="/wiki/Good_Manufacturing_Practice" class="mw-redirect" title="Good Manufacturing Practice">GMP</a> regulations for <a href="/wiki/Dietary_supplements" class="mw-redirect" title="Dietary supplements">dietary supplements</a> in 2008, chondroitin sulfate preparations are subject in the US to mandatory labeling standards as well as testing requirements for identity, purity, strength, and composition.<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. (April 2013)">citation needed</span></a></i>]</sup> <a href="/wiki/United_States_Pharmacopoeia" class="mw-redirect" title="United States Pharmacopoeia">United States Pharmacopoeia</a> (USP) testing standards for the identification and quantification of chondroitin are well-established.<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. (April 2013)">citation needed</span></a></i>]</sup> </p><p>There are no FDA regulations on chondroitin sulfate as a food additive, as it is recognized by the FDA as a component of food and is "generally recognized as safe".<sup id="cite_ref-FDACS_31-1" class="reference"><a href="#cite_note-FDACS-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> However, a proposed application of chondroitin sulfate dietary supplement as a means of preventing joint degeneration was highly scrutinized by the FDA, who stated: </p> <style data-mw-deduplicate="TemplateStyles:r1244412712">.mw-parser-output .templatequote{overflow:hidden;margin:1em 0;padding:0 32px}.mw-parser-output .templatequotecite{line-height:1.5em;text-align:left;margin-top:0}@media(min-width:500px){.mw-parser-output .templatequotecite{padding-left:1.6em}}</style><blockquote class="templatequote"><p>" For conventional foods, this evaluation involves considering whether the ingredient that is the source of the substance is generally recognized as safe (GRAS), approved as a food additive, or authorized by a prior sanction issued by FDA (see 21 CFR 101.70(f)). Dietary ingredients in dietary supplements, however, are not subject to the food additive provisions of the act (see section 201(s)(6) of the Act (21 U.S.C. § 321(s)(6)). Rather, they are subject to the adulteration provisions in section 402 of the Act (21 U.S.C. 342) and, if applicable, the new dietary ingredient provisions in section 413 of the Act (21 U.S.C. 350b), which pertain to dietary ingredients that were not marketed in the United States before October 15, 1994."</p><div class="templatequotecite">— <cite>Letter Regarding the Relationship Between the Consumption of Glucosamine and/or Chondroitin Sulfate and a Reduced Risk of: Osteoarthritis; Osteoarthritis-related Joint Pain, Joint Tenderness, and Joint Swelling; Joint Degeneration; and Cartilage Deterioration</cite></div></blockquote> <p>In the same letter, the FDA found that studies performed on the dietary supplement form of chondroitin sulfate were insufficient to substantiate claims that it is efficacious in the prevention of joint deterioration, and denied the request to be allowed to label the supplement as such. They further denied the request to market it as safe, given that no human clinical trials were done, citing that animal studies are not sufficient for the approval of a dietary supplement.<sup id="cite_ref-FDACS_31-2" class="reference"><a href="#cite_note-FDACS-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Veterinary_use">Veterinary use</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chondroitin_sulfate&action=edit&section=13" title="Edit section: Veterinary use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chondroitin and glucosamine are also used in veterinary medicine for osteoarthritis.<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chondroitin_sulfate&action=edit&section=14" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Proteoglycan" title="Proteoglycan">Proteoglycan</a></li> <li><a href="/wiki/Heparin" title="Heparin">Hepar<i>in</i> sulfate</a> – a glycosaminoglycan of major pharmaceutical importance for many decades</li> <li><a href="/wiki/Heparan_sulfate" title="Heparan sulfate">Hepar<i>an</i> sulfate</a> – a glycosaminoglycan component of <a href="/wiki/Proteoglycan" title="Proteoglycan">proteoglycans</a> in a wide range of vertebrate & invertebrate life</li> <li><a href="/wiki/Methylsulfonylmethane" title="Methylsulfonylmethane">Methylsulfonylmethane</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=Chondroitin_sulfate&action=edit&section=15" 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-:0-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-:0_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:0_1-1"><sup><i><b>b</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="CITEREFMcAteeBaryckiSimpson2014" class="citation cs2">McAtee, Caitlin O.; Barycki, Joseph J.; Simpson, Melanie A. 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Osteoarthritis-related Joint Pain, Joint Tenderness, and Joint Swelling; Joint Degeneration; and Cartilage Deterioration(Docket No. 2004P-0059). 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"Medical treatment of osteoarthritis in the horse – a review". <i>Veterinary Journal</i>. <b>171</b> (1): 51–69. <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.tvjl.2004.07.008">10.1016/j.tvjl.2004.07.008</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/16427582">16427582</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Veterinary+Journal&rft.atitle=Medical+treatment+of+osteoarthritis+in+the+horse+%E2%80%93+a+review&rft.volume=171&rft.issue=1&rft.pages=51-69&rft.date=2006-01&rft_id=info%3Adoi%2F10.1016%2Fj.tvjl.2004.07.008&rft_id=info%3Apmid%2F16427582&rft.aulast=Goodrich&rft.aufirst=LR&rft.au=Nixon%2C+AJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChondroitin+sulfate" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chondroitin_sulfate&action=edit&section=16" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20061105140135/http://www.arthritis.org/conditions/alttherapies/Glucosamine.asp">General Glucosamine and Chondroitin Sulfate information</a> at <a href="/wiki/Arthritis_Foundation" title="Arthritis Foundation">Arthritis Foundation</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20080820150410/http://www.consumerlabs.com/results/gluco.asp">"Product Review: Joint Supplements (Glucosamine, Chondroitin, and MSM)"</a> Summary of a Consumer Labs test of the actual composition of these supplements at consumerlabs.com</li> <li><a rel="nofollow" class="external text" href="http://www.webmd.com/content/article/22/1728_56163">"Glucosamine/Chondroitin Products Not Measuring Up"</a>, News report of the analysis of commercial supplements by Adebowale et al. at <a href="/wiki/WebMD" title="WebMD">WebMD</a></li> <li><a rel="nofollow" class="external text" href="http://www.stoneclinic.com/chondroitin_extraction.htm">"Chondroitin Sulfate Manufacturing and Risk of Mad Cow Disease"</a> by Winston Wicomb, Ph.D., September 24, 2002. Information on methods for extraction of chondroitin sulfate from cow trachea, at the Stone Clinic of San Francisco, at stoneclinic.com</li> <li><a rel="nofollow" class="external text" href="https://ntp.niehs.nih.gov/go/ts-09029">"Testing Status of Glucosamine Hydrochloride + Chondroitin Sulfate 09029"</a>, A thorough review of available information on the use of chondroitin sulfate in humans from the National Toxicology Program at <a href="/wiki/National_Institute_of_Environmental_Health_Sciences" title="National Institute of Environmental Health Sciences">National Institute of Environmental Health Sciences</a></li> <li><a rel="nofollow" class="external text" href="http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/cho_0071.shtml">Chondroitin Sulfate</a>, summary of information on the use of chondroitin sulfate from the publishers of the <i><a href="/wiki/Physicians%27_Desk_Reference" title="Physicians' Desk Reference">Physicians' Desk Reference</a></i>.</li> <li>"<a rel="nofollow" class="external text" href="https://www.clinicaltrials.gov/show/NCT00032890">Glucosamine/Chondroitin Arthritis Intervention Trial (GAIT)</a>," ClinicalTrials.gov information on the purpose, design, and analysis of the study at clinicaltrials.gov</li> <li><a rel="nofollow" class="external text" href="http://www.nih.gov/news/pr/feb2006/nccih-22.htm">"NIH News: Efficacy of Glucosamine and Chondroitin Sulfate May Depend on Level of Osteoarthritis Pain"</a>, Wednesday, February 22, 2006, at <a href="/wiki/National_Institutes_of_Health" title="National Institutes of Health">National Institutes of Health</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline 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title="Energy drink">Energy drink</a></li> <li><a href="/wiki/Energy_bar" title="Energy bar">Energy bar</a></li> <li><a href="/wiki/Essential_fatty_acid" title="Essential fatty acid">Fatty acids</a></li> <li><a href="/wiki/Herbal_medicine" title="Herbal medicine">Herbal supplements</a></li> <li><a href="/wiki/Mineral_(nutrient)" title="Mineral (nutrient)">Minerals</a></li> <li><a href="/wiki/Prebiotic_(nutrition)" title="Prebiotic (nutrition)">Prebiotics</a></li> <li><a href="/wiki/Probiotic" title="Probiotic">Probiotics</a> (<a href="/wiki/Lactobacillus" title="Lactobacillus">Lactobacillus</a></li> <li><a href="/wiki/Bifidobacterium" title="Bifidobacterium">Bifidobacterium</a>)</li> <li><a href="/wiki/Protein_supplement" title="Protein supplement">Protein supplements</a></li> <li><a href="/wiki/Vitamin" title="Vitamin">Vitamins</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin" title="Vitamin">Vitamins</a> and<br /><a href="/wiki/Mineral_(nutrient)" title="Mineral (nutrient)">chemical elements<br /> ("minerals")</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Vitamin_A" title="Vitamin A">Retinol (Vitamin A)</a></li> <li><a href="/wiki/B_vitamins" title="B vitamins">B vitamins</a> <ul><li><a href="/wiki/Thiamine" title="Thiamine">Thiamine (B<sub>1</sub>)</a></li> <li><a href="/wiki/Riboflavin" title="Riboflavin">Riboflavin (B<sub>2</sub>)</a></li> <li><a href="/wiki/Niacin_(nutrient)" class="mw-redirect" title="Niacin (nutrient)">Niacin (B<sub>3</sub>)</a></li> <li><a href="/wiki/Pantothenic_acid" title="Pantothenic acid">Pantothenic acid (B<sub>5</sub>)</a></li> <li><a href="/wiki/Vitamin_B6" title="Vitamin B6">Pyridoxine (B<sub>6</sub>)</a></li> <li><a href="/wiki/Biotin" title="Biotin">Biotin (B<sub>7</sub>)</a></li> <li><a href="/wiki/Folate" title="Folate">Folic acid (B<sub>9</sub>)</a></li> <li><a href="/wiki/Cyanocobalamin" title="Cyanocobalamin">Cyanocobalamin (B<sub>12</sub>)</a></li></ul></li> <li><a href="/wiki/Vitamin_C" title="Vitamin C">Ascorbic acid (Vitamin C)</a></li> <li><a href="/wiki/Vitamin_D" title="Vitamin D">Ergocalciferol and Cholecalciferol (Vitamin D)</a></li> <li><a href="/wiki/Vitamin_E" title="Vitamin E">Tocopherol (Vitamin E)</a></li> <li><a href="/wiki/Vitamin_K" title="Vitamin K">Naphthoquinone (Vitamin K)</a></li></ul> <ul><li><a href="/wiki/Calcium_supplement" title="Calcium supplement">Calcium</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a></li> <li><a href="/wiki/Chromium" title="Chromium">Chromium</a></li> <li><a href="/wiki/Cobalt" title="Cobalt">Cobalt</a></li> <li><a href="/wiki/Copper" title="Copper">Copper</a></li> <li><a href="/wiki/Fluorine" title="Fluorine">Fluorine</a></li> <li><a href="/wiki/Iodine" title="Iodine">Iodine</a></li> <li><a href="/wiki/Iron" title="Iron">Iron</a></li> <li><a href="/wiki/Magnesium" title="Magnesium">Magnesium</a></li> <li><a href="/wiki/Manganese" title="Manganese">Manganese</a></li> <li><a href="/wiki/Molybdenum" title="Molybdenum">Molybdenum</a></li> <li><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a></li> <li><a href="/wiki/Potassium" title="Potassium">Potassium</a></li> <li><a href="/wiki/Selenium" title="Selenium">Selenium</a></li> <li><a href="/wiki/Sodium" title="Sodium">Sodium</a></li> <li><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other common <br />ingredients</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Arginine_alpha-ketoglutarate" title="Arginine alpha-ketoglutarate">AAKG</a></li> <li><a href="/wiki/Beta-Hydroxy_beta-methylbutyric_acid" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyric acid">β-hydroxy β-methylbutyrate</a></li> <li><a href="/wiki/Carnitine" title="Carnitine">Carnitine</a></li> <li><a class="mw-selflink selflink">Chondroitin sulfate</a></li> <li><a href="/wiki/Cod_liver_oil" title="Cod liver oil">Cod liver oil</a></li> <li><a href="/wiki/Copper_gluconate" title="Copper gluconate">Copper gluconate</a></li> <li><a href="/wiki/Creatine" title="Creatine">Creatine</a></li> <li><a href="/wiki/Dietary_fiber" title="Dietary fiber">Dietary fiber</a></li> <li><a href="/wiki/Echinacea#Medicinal_effects" title="Echinacea">Echinacea</a></li> <li><a href="/wiki/Ephedra_(medicine)" title="Ephedra (medicine)">Ephedra</a></li> <li><a href="/wiki/Fish_oil" title="Fish oil">Fish oil</a></li> <li><a href="/wiki/Folate" title="Folate">Folic acid</a></li> <li><a href="/wiki/Ginseng" title="Ginseng">Ginseng</a></li> <li><a href="/wiki/Glucosamine" title="Glucosamine">Glucosamine</a></li> <li><a href="/wiki/Glutamine" title="Glutamine">Glutamine</a></li> <li><a href="/wiki/Grape_seed_extract" title="Grape seed extract">Grape seed extract</a></li> <li><a href="/wiki/Guarana" title="Guarana">Guarana</a></li> <li><a href="/wiki/Iron_supplement" title="Iron supplement">Iron supplements</a></li> <li><a href="/wiki/Lonicera_japonica" title="Lonicera japonica">Japanese honeysuckle</a></li> <li><a href="/wiki/Krill_oil" title="Krill oil">Krill oil</a></li> <li><a href="/wiki/Lingzhi_(mushroom)" title="Lingzhi (mushroom)">Lingzhi</a></li> <li><a href="/wiki/Linseed_oil" title="Linseed oil">Linseed oil</a></li> <li><a href="/wiki/Lipoic_acid" title="Lipoic acid">Lipoic acid</a></li> <li><a href="/wiki/Silybum_marianum#Health_benefits" title="Silybum marianum">Milk thistle</a></li> <li><a href="/wiki/Melatonin_(supplement)" class="mw-redirect" title="Melatonin (supplement)">Melatonin</a></li> <li><a href="/wiki/Red_yeast_rice" title="Red yeast rice">Red yeast rice</a></li> <li><a href="/wiki/Royal_jelly" title="Royal jelly">Royal jelly</a></li> <li><a href="/wiki/Saw_palmetto_extract" title="Saw palmetto extract">Saw palmetto</a></li> <li><a href="/wiki/Spirulina_(dietary_supplement)" title="Spirulina (dietary supplement)">Spirulina</a></li> <li><a href="/wiki/Hypericum_perforatum#Medicinal_uses" title="Hypericum perforatum">St John's wort</a></li> <li><a href="/wiki/Taurine" title="Taurine">Taurine</a></li> <li><a href="/wiki/Wheatgrass" title="Wheatgrass">Wheatgrass</a></li> <li><a href="/wiki/Goji" title="Goji">Wolfberry</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li> <li><a href="/wiki/Zinc_gluconate" title="Zinc gluconate">Zinc gluconate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related articles</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Codex_Alimentarius" title="Codex Alimentarius">Codex Alimentarius</a></li> <li><a href="/wiki/Enzyte" title="Enzyte">Enzyte</a></li> <li><a href="/wiki/Hadacol" title="Hadacol">Hadacol</a></li> <li><a href="/wiki/Herbal_tea" title="Herbal tea">Herbal tea</a></li> <li><a href="/wiki/Nutraceutical" title="Nutraceutical">Nutraceutical</a></li> <li><a href="/wiki/Multivitamin" title="Multivitamin">Multivitamin</a></li> <li><a href="/wiki/Nutrition" title="Nutrition">Nutrition</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Polysaccharides:_glycosaminoglycans" 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" style="background:LightGray"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Glycosaminoglycans" title="Template:Glycosaminoglycans"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Glycosaminoglycans" title="Template talk:Glycosaminoglycans"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Glycosaminoglycans" title="Special:EditPage/Template:Glycosaminoglycans"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Polysaccharides:_glycosaminoglycans" style="font-size:114%;margin:0 4em"><a href="/wiki/Polysaccharide" title="Polysaccharide">Polysaccharides</a>: <a href="/wiki/Glycosaminoglycan" title="Glycosaminoglycan">glycosaminoglycans</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: LightGray">Unsulfated, extracellular</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hyaluronan" class="mw-redirect" title="Hyaluronan">Hyaluronan</a></li> <li><a href="/wiki/Sodium_hyaluronate" title="Sodium hyaluronate">Sodium hyaluronate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: LightGray">Sulfated, extracellular</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chondroitin" title="Chondroitin">Chondroitin</a> <ul><li><a class="mw-selflink selflink">Chondroitin sulfate</a></li> <li><a href="/wiki/Dermatan_sulfate" title="Dermatan sulfate">Dermatan sulfate</a></li></ul></li> <li><a href="/wiki/Heparan_sulfate" title="Heparan sulfate">Heparan sulfate</a></li> <li><a href="/wiki/Keratan_sulfate" title="Keratan sulfate">Keratan sulfate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: LightGray">Sulfated, intracellular</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Heparin" title="Heparin">Heparin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: LightGray">Synthetic</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Polysulfated_glycosaminoglycan" title="Polysulfated glycosaminoglycan">Polysulfated glycosaminoglycan</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Non-steroidal_anti-inflammatory_drugs_(NSAIDs)_(primarily_M01A_and_M02A,_also_N02BA)" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Anti-inflammatory_products" title="Template:Anti-inflammatory products"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Anti-inflammatory_products" title="Template talk:Anti-inflammatory products"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Anti-inflammatory_products" title="Special:EditPage/Template:Anti-inflammatory products"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Non-steroidal_anti-inflammatory_drugs_(NSAIDs)_(primarily_M01A_and_M02A,_also_N02BA)" style="font-size:114%;margin:0 4em"><a href="/wiki/Non-steroidal_anti-inflammatory_drug" class="mw-redirect" title="Non-steroidal anti-inflammatory drug">Non-steroidal anti-inflammatory drugs</a> (NSAIDs) (primarily <a href="/wiki/ATC_code_M01#M01A" title="ATC code M01">M01A</a> and <a href="/wiki/ATC_code_M02#M02A" title="ATC code M02">M02A</a>, also <a href="/wiki/ATC_code_N02#N02BA" title="ATC code N02">N02BA</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pyrazolone" title="Pyrazolone">pyrazolones</a> /<br /><a href="/wiki/Pyrazolidine" title="Pyrazolidine">pyrazolidines</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aminophenazone" title="Aminophenazone">Aminophenazone</a></li> <li><a href="/wiki/Ampyrone" title="Ampyrone">Ampyrone</a></li> <li><a href="/wiki/Azapropazone" title="Azapropazone">Azapropazone</a></li> <li><a href="/wiki/Clofezone" title="Clofezone">Clofezone</a></li> <li><a href="/wiki/Difenamizole" title="Difenamizole">Difenamizole</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Feprazone" title="Feprazone">Feprazone</a></li> <li><a href="/wiki/Kebuzone" title="Kebuzone">Kebuzone</a></li> <li><a href="/wiki/Metamizole" title="Metamizole">Metamizole</a></li> <li><a href="/wiki/Mofebutazone" title="Mofebutazone">Mofebutazone</a></li> <li><a href="/wiki/Morazone" title="Morazone">Morazone</a></li> <li><a href="/wiki/Nifenazone" title="Nifenazone">Nifenazone</a></li> <li><a href="/wiki/Oxyphenbutazone" title="Oxyphenbutazone">Oxyphenbutazone</a></li> <li><a href="/wiki/Phenazone" title="Phenazone">Phenazone</a></li> <li><u><a href="/wiki/Phenylbutazone" title="Phenylbutazone">Phenylbutazone</a></u></li> <li><a href="/wiki/Propyphenazone" title="Propyphenazone">Propyphenazone</a></li> <li><a href="/wiki/Sulfinpyrazone" title="Sulfinpyrazone">Sulfinpyrazone</a></li> <li><a href="/wiki/Suxibuzone" title="Suxibuzone">Suxibuzone</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Salicylic_acid" title="Salicylic acid">salicylates</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><u><a href="/wiki/Aspirin" title="Aspirin">Aspirin (acetylsalicylic acid)</a></u><sup>#</sup></li> <li><a href="/wiki/Aloxiprin" title="Aloxiprin">Aloxiprin</a></li> <li><a href="/wiki/Benorilate" title="Benorilate">Benorylate</a></li> <li><a href="/wiki/Carbasalate_calcium" title="Carbasalate calcium">Carbasalate calcium</a></li> <li><a href="/wiki/Diflunisal" title="Diflunisal">Diflunisal</a></li> <li><a href="/wiki/Dipyrocetyl" title="Dipyrocetyl">Dipyrocetyl</a></li> <li><a href="/wiki/Ethenzamide" title="Ethenzamide">Ethenzamide</a></li> <li><a href="/wiki/Guacetisal" title="Guacetisal">Guacetisal</a></li> <li><a href="/wiki/Magnesium_salicylate" title="Magnesium salicylate">Magnesium salicylate</a></li> <li><a href="/wiki/Methyl_salicylate" title="Methyl salicylate">Methyl salicylate</a></li> <li><a href="/wiki/Salsalate" title="Salsalate">Salsalate</a></li> <li><a href="/wiki/Salicin" title="Salicin">Salicin</a></li> <li><a href="/wiki/Salicylamide" title="Salicylamide">Salicylamide</a></li> <li><a href="/wiki/Salicylic_acid" title="Salicylic acid">Salicylic acid (salicylate)</a></li> <li><a href="/wiki/Sodium_salicylate" title="Sodium salicylate">Sodium salicylate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> derivatives<br />and related substances</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aceclofenac" title="Aceclofenac">Aceclofenac</a></li> <li><a href="/wiki/Acemetacin" title="Acemetacin">Acemetacin</a></li> <li><a href="/wiki/Alclofenac" title="Alclofenac">Alclofenac</a></li> <li><a href="/wiki/Amfenac" title="Amfenac">Amfenac</a></li> <li><a href="/wiki/Bendazac" title="Bendazac">Bendazac</a></li> <li><a href="/wiki/Bromfenac" title="Bromfenac">Bromfenac</a></li> <li><a href="/wiki/Bufexamac" title="Bufexamac">Bufexamac</a></li> <li><a href="/wiki/Bumadizone" title="Bumadizone">Bumadizone</a></li> <li><u><a href="/wiki/Diclofenac" title="Diclofenac">Diclofenac</a></u></li> <li><a href="/wiki/Difenpiramide" title="Difenpiramide">Difenpiramide</a></li> <li><a href="/wiki/Etodolac" title="Etodolac">Etodolac</a></li> <li><a href="/wiki/Felbinac" title="Felbinac">Felbinac</a></li> <li><a href="/wiki/Fenclozic_acid" title="Fenclozic acid">Fenclozic acid</a></li> <li><a href="/wiki/Fentiazac" title="Fentiazac">Fentiazac</a></li> <li><a href="/wiki/Indometacin" title="Indometacin">Indometacin</a></li> <li><a href="/wiki/Indometacin_farnesil" title="Indometacin farnesil">Indometacin farnesil</a></li> <li><a href="/w/index.php?title=Isoxepac&action=edit&redlink=1" class="new" title="Isoxepac (page does not exist)">Isoxepac</a></li> <li><a href="/wiki/Ketorolac" title="Ketorolac">Ketorolac</a></li> <li><a href="/wiki/Lonazolac" title="Lonazolac">Lonazolac</a></li> <li><a href="/wiki/Mofezolac" title="Mofezolac">Mofezolac</a></li> <li><a href="/wiki/Oxametacin" title="Oxametacin">Oxametacin</a></li> <li><a href="/w/index.php?title=Prodolic_acid&action=edit&redlink=1" class="new" title="Prodolic acid (page does not exist)">Prodolic acid</a></li> <li><a href="/wiki/Proglumetacin" title="Proglumetacin">Proglumetacin</a></li> <li><a href="/wiki/Sulindac" title="Sulindac">Sulindac</a></li> <li><a href="/w/index.php?title=Tiopinac&action=edit&redlink=1" class="new" title="Tiopinac (page does not exist)">Tiopinac</a></li> <li><a href="/wiki/Tolmetin" title="Tolmetin">Tolmetin</a></li> <li><a href="/wiki/Zomepirac" title="Zomepirac">Zomepirac</a><sup>†</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Oxicam" title="Oxicam">oxicams</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ampiroxicam" title="Ampiroxicam">Ampiroxicam</a></li> <li><a href="/wiki/Droxicam" title="Droxicam">Droxicam</a></li> <li><a href="/wiki/Isoxicam" title="Isoxicam">Isoxicam</a></li> <li><a href="/wiki/Lornoxicam" title="Lornoxicam">Lornoxicam</a></li> <li><a href="/wiki/Meloxicam" title="Meloxicam">Meloxicam</a></li> <li><u><a href="/wiki/Piroxicam" title="Piroxicam">Piroxicam</a></u></li> <li><a href="/w/index.php?title=Pivoxicam&action=edit&redlink=1" class="new" title="Pivoxicam (page does not exist)">Pivoxicam</a></li> <li><a href="/wiki/Tenoxicam" title="Tenoxicam">Tenoxicam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Propionic_acid" title="Propionic acid">propionic acid</a><br />derivatives (<a href="/wiki/Profens" class="mw-redirect" title="Profens">profens</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alminoprofen" title="Alminoprofen">Alminoprofen</a></li> <li><a href="/wiki/Benoxaprofen" title="Benoxaprofen">Benoxaprofen</a><sup>†</sup></li> <li><a href="/wiki/Carprofen" title="Carprofen">Carprofen</a><sup>‡</sup></li> <li><a href="/wiki/Dexibuprofen" title="Dexibuprofen">Dexibuprofen</a></li> <li><a href="/wiki/Dexketoprofen" title="Dexketoprofen">Dexketoprofen</a></li> <li><a href="/wiki/Fenbufen" title="Fenbufen">Fenbufen</a></li> <li><a href="/wiki/Fenoprofen" title="Fenoprofen">Fenoprofen</a></li> <li><a href="/wiki/Flunoxaprofen" title="Flunoxaprofen">Flunoxaprofen</a></li> <li><a href="/wiki/Flurbiprofen" title="Flurbiprofen">Flurbiprofen</a></li> <li><u><a href="/wiki/Ibuprofen" title="Ibuprofen">Ibuprofen</a></u><sup>#</sup></li> <li><a href="/wiki/Ibuproxam" title="Ibuproxam">Ibuproxam</a></li> <li><a href="/wiki/Indoprofen" title="Indoprofen">Indoprofen</a><sup>†</sup></li> <li><a href="/wiki/Ketoprofen" title="Ketoprofen">Ketoprofen</a></li> <li><a href="/wiki/Loxoprofen" title="Loxoprofen">Loxoprofen</a></li> <li><a href="/wiki/Miroprofen" title="Miroprofen">Miroprofen</a></li> <li><u><a href="/wiki/Naproxen" title="Naproxen">Naproxen</a></u></li> <li><a href="/wiki/Oxaprozin" title="Oxaprozin">Oxaprozin</a></li> <li><a href="/wiki/Pelubiprofen" title="Pelubiprofen">Pelubiprofen</a></li> <li><a href="/wiki/Piketoprofen" title="Piketoprofen">Piketoprofen</a></li> <li><a href="/wiki/Pirprofen" title="Pirprofen">Pirprofen</a></li> <li><a href="/wiki/Suprofen" title="Suprofen">Suprofen</a></li> <li><a href="/wiki/Tarenflurbil" title="Tarenflurbil">Tarenflurbil</a></li> <li><a href="/wiki/Tepoxalin" title="Tepoxalin">Tepoxalin</a><sup>‡</sup></li> <li><a href="/wiki/Tiaprofenic_acid" title="Tiaprofenic acid">Tiaprofenic acid</a></li> <li><a href="/wiki/Vedaprofen" title="Vedaprofen">Vedaprofen</a><sup>‡</sup></li> <li><a href="/wiki/Zaltoprofen" title="Zaltoprofen">Zaltoprofen</a></li> <li><i><a href="/wiki/COX-inhibiting_nitric_oxide_donator" title="COX-inhibiting nitric oxide donator">COX-inhibiting nitric oxide donator</a></i>: <a href="/wiki/Naproxcinod" title="Naproxcinod">Naproxcinod</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>n</i>-arylanthranilic<br />acids (<a href="/wiki/Fenamate" class="mw-redirect" title="Fenamate">fenamates</a>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Azapropazone" title="Azapropazone">Azapropazone</a></li> <li><a href="/wiki/Clonixin" title="Clonixin">Clonixin</a></li> <li><a href="/wiki/Etofenamate" title="Etofenamate">Etofenamate</a></li> <li><a href="/wiki/Floctafenine" title="Floctafenine">Floctafenine</a></li> <li><a href="/wiki/Flufenamic_acid" title="Flufenamic acid">Flufenamic acid</a></li> <li><a href="/wiki/Flunixin" title="Flunixin">Flunixin</a></li> <li><a href="/w/index.php?title=Flutiazin&action=edit&redlink=1" class="new" title="Flutiazin (page does not exist)">Flutiazin</a></li> <li><a href="/wiki/Glafenine" title="Glafenine">Glafenine</a><sup>†</sup></li> <li><a href="/wiki/Meclofenamic_acid" title="Meclofenamic acid">Meclofenamic acid</a></li> <li><u><a href="/wiki/Mefenamic_acid" title="Mefenamic acid">Mefenamic acid</a></u></li> <li><a href="/wiki/Morniflumate" title="Morniflumate">Morniflumate</a></li> <li><a href="/wiki/Niflumic_acid" title="Niflumic acid">Niflumic acid</a></li> <li><a href="/wiki/Tolfenamic_acid" title="Tolfenamic acid">Tolfenamic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/COX-2_inhibitor" class="mw-redirect" title="COX-2 inhibitor">COX-2 inhibitors</a><br />(coxibs)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Apricoxib" title="Apricoxib">Apricoxib</a></li> <li><u><a href="/wiki/Celecoxib" title="Celecoxib">Celecoxib</a></u> (<a href="/wiki/Celecoxib/tramadol" title="Celecoxib/tramadol">+tramadol</a>)</li> <li><a href="/wiki/Cimicoxib" title="Cimicoxib">Cimicoxib</a><sup>‡</sup></li> <li><a href="/wiki/Deracoxib" title="Deracoxib">Deracoxib</a><sup>‡</sup></li> <li><a href="/wiki/Etoricoxib" title="Etoricoxib">Etoricoxib</a></li> <li><a href="/wiki/Firocoxib" title="Firocoxib">Firocoxib</a><sup>‡</sup></li> <li><a href="/wiki/Lumiracoxib" title="Lumiracoxib">Lumiracoxib</a><sup>†</sup></li> <li><a href="/wiki/Mavacoxib" title="Mavacoxib">Mavacoxib</a><sup>‡</sup></li> <li><a href="/wiki/Parecoxib" title="Parecoxib">Parecoxib</a></li> <li><a href="/wiki/Robenacoxib" title="Robenacoxib">Robenacoxib</a><sup>‡</sup></li> <li><a href="/wiki/Rofecoxib" title="Rofecoxib">Rofecoxib</a><sup>†</sup></li> <li><a href="/wiki/Valdecoxib" title="Valdecoxib">Valdecoxib</a><sup>†</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aminopropionitrile" title="Aminopropionitrile">Aminopropionitrile</a></li> <li><a href="/wiki/Benzydamine" title="Benzydamine">Benzydamine</a></li> <li><a class="mw-selflink selflink">Chondroitin sulfate</a></li> <li><a href="/wiki/Diacerein" title="Diacerein">Diacerein</a></li> <li><a href="/wiki/Fluproquazone" title="Fluproquazone">Fluproquazone</a></li> <li><a href="/wiki/Glucosamine" title="Glucosamine">Glucosamine</a></li> <li><a href="/wiki/Glycosaminoglycan" title="Glycosaminoglycan">Glycosaminoglycan</a></li> <li><a href="/wiki/Hyperforin" title="Hyperforin">Hyperforin</a></li> <li><a href="/wiki/Nabumetone" title="Nabumetone">Nabumetone</a></li> <li><a href="/wiki/Nimesulide" title="Nimesulide">Nimesulide</a></li> <li><a href="/wiki/Oxaceprol" title="Oxaceprol">Oxaceprol</a></li> <li><a href="/wiki/Proquazone" title="Proquazone">Proquazone</a></li> <li><a href="/wiki/Superoxide_dismutase" title="Superoxide dismutase">Superoxide dismutase / orgotein</a></li> <li><a href="/wiki/Tenidap" title="Tenidap">Tenidap</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">NSAID<br />combinations</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ibuprofen/famotidine" title="Ibuprofen/famotidine">Ibuprofen/famotidine</a></li> <li><a href="/wiki/Hydrocodone/ibuprofen" title="Hydrocodone/ibuprofen">Ibuprofen/hydrocodone</a></li> <li><a href="/wiki/Oxycodone/ibuprofen" title="Oxycodone/ibuprofen">Ibuprofen/oxycodone</a></li> <li><a href="/wiki/Ibuprofen/paracetamol" title="Ibuprofen/paracetamol">Ibuprofen/paracetamol</a></li> <li><a href="/wiki/Bupivacaine/meloxicam" title="Bupivacaine/meloxicam">Meloxicam/bupivacaine</a></li> <li><a href="/wiki/Naproxen/diphenhydramine" title="Naproxen/diphenhydramine">Naproxen/diphenhydramine</a></li> <li><a href="/wiki/Naproxen/esomeprazole" title="Naproxen/esomeprazole">Naproxen/esomeprazole</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">Key: <u>underline</u> indicates initially developed first-in-class compound of specific group; <sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-Essential Medicines</a>; <sup>†</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">withdrawn drugs</a>; <sup>‡</sup><a href="/wiki/Veterinary_medicine" title="Veterinary medicine">veterinary use</a>.</div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" 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