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Available in 39 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-39" 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">39 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%D9%88%D9%86%D8%A7%D9%85%D9%8A%D8%AF_(%D8%B5%D9%8A%D8%AF%D9%84%D8%A9)" title="سلفوناميد (صيدلة) – Arabic" lang="ar" hreflang="ar" data-title="سلفوناميد (صيدلة)" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Sulfanilamid_(d%C9%99rman)" title="Sulfanilamid (dərman) – Azerbaijani" lang="az" hreflang="az" data-title="Sulfanilamid (dərman)" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%A1%D1%83%D0%BB%D1%8C%D1%84%D0%B0%D0%BD%D1%96%D0%BB%D0%B0%D0%BC%D1%96%D0%B4%D1%8B" title="Сульфаніламіды – Belarusian" lang="be" hreflang="be" data-title="Сульфаніламіды" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A1%D1%83%D0%BB%D1%84%D0%BE%D0%BD%D0%B0%D0%BC%D0%B8%D0%B4_(%D0%BC%D0%B5%D0%B4%D0%B8%D1%86%D0%B8%D0%BD%D0%B0)" title="Сулфонамид (медицина) – Bulgarian" lang="bg" hreflang="bg" data-title="Сулфонамид (медицина)" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Sulfamida" title="Sulfamida – Catalan" lang="ca" hreflang="ca" data-title="Sulfamida" 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/Sulfonamidov%C3%A1_antibiotika" title="Sulfonamidová antibiotika – Czech" lang="cs" hreflang="cs" data-title="Sulfonamidová antibiotika" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Sulfonamid_(antibiotika)" title="Sulfonamid (antibiotika) – Danish" lang="da" hreflang="da" data-title="Sulfonamid (antibiotika)" 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/Sulfonamide" title="Sulfonamide – German" lang="de" hreflang="de" data-title="Sulfonamide" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A3%CE%BF%CF%85%CE%BB%CF%86%CE%BF%CE%BD%CE%B1%CE%BC%CE%AF%CE%B4%CE%B9%CE%BF_(%CE%B9%CE%B1%CF%84%CF%81%CE%B9%CE%BA%CE%AE)" title="Σουλφοναμίδιο (ιατρική) – Greek" lang="el" hreflang="el" data-title="Σουλφοναμίδιο (ιατρική)" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Sulfamida" title="Sulfamida – Spanish" lang="es" hreflang="es" data-title="Sulfamida" 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/Sulfamida" title="Sulfamida – Basque" lang="eu" hreflang="eu" data-title="Sulfamida" 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%B3%D9%88%D9%84%D9%81%D9%88%D9%86%D8%A7%D9%85%DB%8C%D8%AF_(%D8%AF%D8%A7%D8%B1%D9%88)" title="سولفونامید (دارو) – Persian" lang="fa" hreflang="fa" data-title="سولفونامید (دارو)" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fo mw-list-item"><a href="https://fo.wikipedia.org/wiki/Sulfonamid" title="Sulfonamid – Faroese" lang="fo" hreflang="fo" data-title="Sulfonamid" data-language-autonym="Føroyskt" data-language-local-name="Faroese" class="interlanguage-link-target"><span>Føroyskt</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Antibiotique_sulfamid%C3%A9" title="Antibiotique sulfamidé – French" lang="fr" hreflang="fr" data-title="Antibiotique sulfamidé" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Sulf%C3%B3naim%C3%ADd%C3%AD" title="Sulfónaimídí – Irish" lang="ga" hreflang="ga" data-title="Sulfónaimídí" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%84%A4%ED%8C%8C%EC%A0%9C" title="설파제 – Korean" lang="ko" hreflang="ko" data-title="설파제" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%8D%D5%B8%D6%82%D5%AC%D6%86%D5%A1%D5%B6%D5%AB%D5%AC%D5%A1%D5%B4%D5%AB%D5%A4%D5%B6%D5%A5%D6%80" title="Սուլֆանիլամիդներ – Armenian" lang="hy" hreflang="hy" data-title="Սուլֆանիլամիդներ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Sulfonamida_(obat)" title="Sulfonamida (obat) – Indonesian" lang="id" hreflang="id" data-title="Sulfonamida (obat)" 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/Sulfamidici" title="Sulfamidici – Italian" lang="it" hreflang="it" data-title="Sulfamidici" 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%A1%D7%95%D7%9C%D7%A4%D7%95%D7%A0%D7%90%D7%9E%D7%99%D7%93" title="סולפונאמיד – Hebrew" lang="he" hreflang="he" data-title="סולפונאמיד" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-lmo mw-list-item"><a href="https://lmo.wikipedia.org/wiki/Sulfamideg" title="Sulfamideg – Lombard" lang="lmo" hreflang="lmo" data-title="Sulfamideg" data-language-autonym="Lombard" data-language-local-name="Lombard" class="interlanguage-link-target"><span>Lombard</span></a></li><li class="interlanguage-link interwiki-my mw-list-item"><a href="https://my.wikipedia.org/wiki/%E1%80%86%E1%80%AC%E1%80%9C%E1%80%96%E1%80%AC%E1%80%86%E1%80%B1%E1%80%B8%E1%80%99%E1%80%BB%E1%80%AC%E1%80%B8" title="ဆာလဖာဆေးများ – Burmese" lang="my" hreflang="my" data-title="ဆာလဖာဆေးများ" data-language-autonym="မြန်မာဘာသာ" data-language-local-name="Burmese" class="interlanguage-link-target"><span>မြန်မာဘာသာ</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B5%E3%83%AB%E3%83%95%E3%82%A1%E8%96%AC" title="サルファ薬 – Japanese" lang="ja" hreflang="ja" data-title="サルファ薬" 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-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Sulfonamider" title="Sulfonamider – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Sulfonamider" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Sulfonamida" title="Sulfonamida – Portuguese" lang="pt" hreflang="pt" data-title="Sulfonamida" 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/Sulfamid%C4%83" title="Sulfamidă – Romanian" lang="ro" hreflang="ro" data-title="Sulfamidă" 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%A1%D1%83%D0%BB%D1%8C%D1%84%D0%B0%D0%BD%D0%B8%D0%BB%D0%B0%D0%BC%D0%B8%D0%B4%D1%8B" title="Сульфаниламиды – Russian" lang="ru" hreflang="ru" data-title="Сульфаниламиды" 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/Sulfonamide_(medicine)" title="Sulfonamide (medicine) – Simple English" lang="en-simple" hreflang="en-simple" data-title="Sulfonamide (medicine)" 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-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Sulfonamidi" title="Sulfonamidi – Slovenian" lang="sl" hreflang="sl" data-title="Sulfonamidi" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Sulfonamid_(medicina)" title="Sulfonamid (medicina) – Serbian" lang="sr" hreflang="sr" data-title="Sulfonamid (medicina)" 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/Sulfonamid_(medicina)" title="Sulfonamid (medicina) – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Sulfonamid (medicina)" 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/Sulfonamidit" title="Sulfonamidit – Finnish" lang="fi" hreflang="fi" data-title="Sulfonamidit" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Sulfonamid" title="Sulfonamid – Swedish" lang="sv" hreflang="sv" data-title="Sulfonamid" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%8B%E0%B8%B1%E0%B8%A5%E0%B9%82%E0%B8%9F%E0%B8%99%E0%B8%B2%E0%B9%84%E0%B8%A1%E0%B8%94%E0%B9%8C" title="ซัลโฟนาไมด์ – Thai" lang="th" hreflang="th" data-title="ซัลโฟนาไมด์" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A1%D1%83%D0%BB%D1%8C%D1%84%D0%B0%D0%BD%D1%96%D0%BB%D0%B0%D0%BC%D1%96%D0%B4%D0%BD%D1%96_%D0%BF%D1%80%D0%B5%D0%BF%D0%B0%D1%80%D0%B0%D1%82%D0%B8" title="Сульфаніламідні препарати – Ukrainian" lang="uk" hreflang="uk" data-title="Сульфаніламідні препарати" 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/Sulfonamide_(thu%E1%BB%91c)" title="Sulfonamide (thuốc) – Vietnamese" lang="vi" hreflang="vi" data-title="Sulfonamide (thuốc)" 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-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E7%A3%BA%E8%83%BA" title="磺胺 – Wu" lang="wuu" 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2024</a> <span class="mw-diff-edit"><a href="/w/index.php?title=Sulfonamide_(medicine)&action=edit" title="Sulfonamide (medicine)">edit</a></span><span class="mw-diff-timestamp" data-timestamp="2024-11-28T21:09:50Z"></span> <span class="mw-diff-undo"><a href="/w/index.php?title=Sulfonamide_(medicine)&action=edit&undoafter=1248047770&undo=1260100987" title=""Undo" reverts this edit and opens the edit form in preview mode. It allows adding a reason in the summary.">undo</a></span></strong></div><div id="mw-diff-ntitle2"><a href="/wiki/Special:Contributions/82.4.194.146" class="mw-userlink mw-anonuserlink" title="Special:Contributions/82.4.194.146" data-mw-revid="1260100987"><bdi>82.4.194.146</bdi></a> <span class="mw-usertoollinks">(<a href="/w/index.php?title=User_talk:82.4.194.146&action=edit&redlink=1" class="new mw-usertoollinks-talk" title="User talk:82.4.194.146 (page does not exist)">talk</a>)</span><div class="mw-diff-usermetadata"></div></div><div id="mw-diff-ntitle3"> <span class="comment comment--without-parentheses"><span class="autocomment"><a href="#Preparation">→<bdi dir="ltr">Preparation</bdi></a>: </span>Tag dated statement</span></div><div id="mw-diff-ntitle5"><span class="mw-tag-markers"><a href="/wiki/Special:Tags" title="Special:Tags">Tags</a>: <span class="mw-tag-marker mw-tag-marker-mobile_edit">Mobile edit</span> <span class="mw-tag-marker mw-tag-marker-mobile_web_edit">Mobile web edit</span></span></div><div id="mw-diff-ntitle4"> </div></td> </tr><tr> <td colspan="2" class="diff-lineno">Line 34:</td> <td colspan="2" class="diff-lineno">Line 34:</td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><br /></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><br /></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>== Preparation ==</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>== Preparation ==</div></td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><div>Sulfonamides are prepared by the reaction of a [[sulfonyl chloride]] with ammonia or an amine. Certain sulfonamides (sulfadiazine or [[sulfamethoxazole]]) are sometimes mixed with the drug [[trimethoprim]], which acts against [[dihydrofolate reductase]]. As of<del class="diffchange diffchange-inline"> </del>2013, the [[Republic of Ireland]] is the largest exporter worldwide of sulfonamides, accounting for approximately 32% of total exports.<ref>{{cite web | url=http://atlas.media.mit.edu/hs4/2935/ | title=Trade of Sulfonamides | publisher=Massachusetts Institute of Technology | access-date=26 October 2013}}</ref></div></td> <td class="diff-marker" data-marker="+"></td> <td class="diff-addedline diff-side-added"><div>Sulfonamides are prepared by the reaction of a [[sulfonyl chloride]] with ammonia or an amine. Certain sulfonamides (sulfadiazine or [[sulfamethoxazole]]) are sometimes mixed with the drug [[trimethoprim]], which acts against [[dihydrofolate reductase]]. <ins class="diffchange diffchange-inline">{{</ins>As of<ins class="diffchange diffchange-inline">|</ins>2013<ins class="diffchange diffchange-inline">}}</ins>, the [[Republic of Ireland]] is the largest exporter worldwide of sulfonamides, accounting for approximately 32% of total exports.<ref>{{cite web | url=http://atlas.media.mit.edu/hs4/2935/ | title=Trade of Sulfonamides | publisher=Massachusetts Institute of Technology | access-date=26 October 2013}}</ref></div></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><br /></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><br /></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>== Varieties ==</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>== Varieties ==</div></td> </tr>  </table><hr class='diff-hr' id='mw-oldid' /> <h2 class='diff-currentversion-title'>Latest revision as of 21:09, 28 November 2024</h2> <div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Molecular moiety or the drug class that uses it</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">For chemistry of the functional group, see <a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamide</a>.</div> <p class="mw-empty-elt"> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Sulfonamide.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/59/Sulfonamide.png/220px-Sulfonamide.png" decoding="async" width="220" height="170" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/59/Sulfonamide.png/330px-Sulfonamide.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/59/Sulfonamide.png/440px-Sulfonamide.png 2x" data-file-width="539" data-file-height="416" /></a><figcaption><a href="/wiki/Sulfonamide_(chemistry)" class="mw-redirect" title="Sulfonamide (chemistry)">Sulfonamide functional group</a></figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Hydrochlorothiazide-2D-skeletal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/28/Hydrochlorothiazide-2D-skeletal.png/220px-Hydrochlorothiazide-2D-skeletal.png" decoding="async" width="220" height="135" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/28/Hydrochlorothiazide-2D-skeletal.png/330px-Hydrochlorothiazide-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/28/Hydrochlorothiazide-2D-skeletal.png/440px-Hydrochlorothiazide-2D-skeletal.png 2x" data-file-width="1100" data-file-height="673" /></a><figcaption><a href="/wiki/Hydrochlorothiazide" title="Hydrochlorothiazide">Hydrochlorothiazide</a> is a sulfonamide and a <a href="/wiki/Thiazide" title="Thiazide">thiazide</a>.</figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Furosemide.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/Furosemide.svg/220px-Furosemide.svg.png" decoding="async" width="220" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/Furosemide.svg/330px-Furosemide.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/45/Furosemide.svg/440px-Furosemide.svg.png 2x" data-file-width="512" data-file-height="262" /></a><figcaption><a href="/wiki/Furosemide" title="Furosemide">Furosemide</a> is a sulfonamide, but not a thiazide.</figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Sulfamethoxazole-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1d/Sulfamethoxazole-skeletal.svg/220px-Sulfamethoxazole-skeletal.svg.png" decoding="async" width="220" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1d/Sulfamethoxazole-skeletal.svg/330px-Sulfamethoxazole-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1d/Sulfamethoxazole-skeletal.svg/440px-Sulfamethoxazole-skeletal.svg.png 2x" data-file-width="1000" data-file-height="454" /></a><figcaption><a href="/wiki/Sulfamethoxazole" title="Sulfamethoxazole">Sulfamethoxazole</a> is an antibacterial sulfonamide.</figcaption></figure> <p><b>Sulfonamide</b> is a <a href="/wiki/Functional_group" title="Functional group">functional group</a> (a part of a <a href="/wiki/Molecule" title="Molecule">molecule</a>) that is the basis of several groups of <a href="/wiki/Medication" title="Medication">drugs</a>, which are called <b>sulphonamides</b>, <b>sulfa drugs</b> or <b>sulpha drugs</b>. The original antibacterial sulfonamides are synthetic (nonantibiotic) <a href="/wiki/Antimicrobial" title="Antimicrobial">antimicrobial</a> agents that contain the <a href="/wiki/Sulfonamide_(chemistry)" class="mw-redirect" title="Sulfonamide (chemistry)">sulfonamide</a> group. Some sulfonamides are also devoid of antibacterial activity, e.g., the <a href="/wiki/Anticonvulsant" title="Anticonvulsant">anticonvulsant</a> <a href="/wiki/Sultiame" title="Sultiame">sultiame</a>. The <a href="/wiki/Sulfonylurea" title="Sulfonylurea">sulfonylureas</a> and <a href="/wiki/Thiazide_diuretics" class="mw-redirect" title="Thiazide diuretics">thiazide diuretics</a> are newer drug groups based upon the antibacterial sulfonamides.<sup id="cite_ref-modeofaction_1-0" class="reference"><a href="#cite_note-modeofaction-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-chemicalland21_2-0" class="reference"><a href="#cite_note-chemicalland21-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Drug_allergy" title="Drug allergy">Allergies</a> to sulfonamides are common. The overall incidence of <a href="/wiki/Adverse_drug_reactions" class="mw-redirect" title="Adverse drug reactions">adverse drug reactions</a> to sulfa antibiotics is approximately 3%, close to <a href="/wiki/Penicillin" title="Penicillin">penicillin</a>;<sup id="cite_ref-allergies.about.com_3-0" class="reference"><a href="#cite_note-allergies.about.com-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> hence medications containing sulfonamides are prescribed carefully. </p><p>Sulfonamide drugs were the first broadly effective antibacterials to be used systemically, and paved the way for the antibiotic revolution in medicine. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Function">Function</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sulfonamide_(medicine)&action=edit&section=1" title="Edit section: Function"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Dihydropteroate_synthase_inhibitor" title="Dihydropteroate synthase inhibitor">Dihydropteroate synthase inhibitor</a></div> <p>In bacteria, antibacterial sulfonamides act as <a href="/wiki/Competitive_inhibitor" class="mw-redirect" title="Competitive inhibitor">competitive inhibitors</a> of the enzyme <a href="/wiki/Dihydropteroate_synthase" title="Dihydropteroate synthase">dihydropteroate synthase</a> (DHPS), an enzyme involved in <a href="/wiki/Folate_synthesis" class="mw-redirect" title="Folate synthesis">folate synthesis</a>. Sulfonamides are therefore bacteriostatic and inhibit growth and multiplication of bacteria, but do not kill them. Humans, in contrast to bacteria, acquire <a href="/wiki/Folate" title="Folate">folate</a> (vitamin B<sub>9</sub>) through the diet.<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> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Sulfa_folate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/Sulfa_folate.svg/350px-Sulfa_folate.svg.png" decoding="async" width="350" height="145" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/Sulfa_folate.svg/525px-Sulfa_folate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/09/Sulfa_folate.svg/700px-Sulfa_folate.svg.png 2x" data-file-width="432" data-file-height="179" /></a><figcaption>Structural similarity between sulfanilamide (left) and <a href="/wiki/4-Aminobenzoic_acid" title="4-Aminobenzoic acid">PABA</a> (center) is the basis for the inhibitory activity of sulfa drugs on tetrahydrofolate (right) biosynthesis.</figcaption></figure> <p>Sulfonamides are used to treat allergies and coughs, as well as having antifungal and antimalarial functions. The moiety is also present in other medications that are not antimicrobials, including <a href="/wiki/Thiazide" title="Thiazide">thiazide</a> <a href="/wiki/Diuretic" title="Diuretic">diuretics</a> (including <a href="/wiki/Hydrochlorothiazide" title="Hydrochlorothiazide">hydrochlorothiazide</a>, <a href="/wiki/Metolazone" title="Metolazone">metolazone</a>, and <a href="/wiki/Indapamide" title="Indapamide">indapamide</a>, among others), loop diuretics (including <a href="/wiki/Furosemide" title="Furosemide">furosemide</a>, <a href="/wiki/Bumetanide" title="Bumetanide">bumetanide</a>, and <a href="/wiki/Torsemide" class="mw-redirect" title="Torsemide">torsemide</a>), <a href="/wiki/Acetazolamide" title="Acetazolamide">acetazolamide</a>, <a href="/wiki/Sulfonylureas" class="mw-redirect" title="Sulfonylureas">sulfonylureas</a> (including <a href="/wiki/Glipizide" title="Glipizide">glipizide</a>, <a href="/wiki/Glyburide" class="mw-redirect" title="Glyburide">glyburide</a>, among others), and some <a href="/wiki/COX-2_inhibitor" class="mw-redirect" title="COX-2 inhibitor">COX-2 inhibitors</a> (e.g., <a href="/wiki/Celecoxib" title="Celecoxib">celecoxib</a>). </p><p><a href="/wiki/Sulfasalazine" title="Sulfasalazine">Sulfasalazine</a>, in addition to its use as an antibiotic, is also used in the treatment of <a href="/wiki/Inflammatory_bowel_disease" title="Inflammatory bowel disease">inflammatory bowel disease</a>.<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> <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=Sulfonamide_(medicine)&action=edit&section=2" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sulfonamide drugs were the first broadly effective antibacterials to be used systemically, and paved the way for the antibiotic revolution in medicine. The first sulfonamide, trade-named <a href="/wiki/Prontosil" title="Prontosil">Prontosil</a>, was a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a>. Experiments with Prontosil began in 1932 in the laboratories of <a href="/wiki/Bayer" title="Bayer">Bayer</a> AG, at that time a component of the huge German chemical trust <a href="/wiki/IG_Farben" title="IG Farben">IG Farben</a>. The Bayer team believed that <a href="/wiki/Aniline#History" title="Aniline">coal-tar dyes</a> which are able to bind preferentially to bacteria and parasites might be used to attack harmful organisms in the body. After years of fruitless trial-and-error work on hundreds of dyes, a team led by physician/researcher <a href="/wiki/Gerhard_Domagk" title="Gerhard Domagk">Gerhard Domagk</a><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> (working under the general direction of IG Farben executive <a href="/wiki/Heinrich_H%C3%B6rlein" title="Heinrich Hörlein">Heinrich Hörlein</a>) finally found one that worked: a red dye synthesized by Bayer chemist <a href="/w/index.php?title=Josef_Klarer&action=edit&redlink=1" class="new" title="Josef Klarer (page does not exist)">Josef Klarer</a> that had remarkable effects on stopping some bacterial infections in mice.<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> The first official communication about the breakthrough discovery was not published until 1935, more than two years after the drug was patented by Klarer and his research partner Fritz Mietzsch.<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> </p><p>Prontosil, as Bayer named the new drug, was the first medicine ever discovered that could effectively treat a range of bacterial infections inside the body. It had a strong protective action against infections caused by <a href="/wiki/Streptococcus" title="Streptococcus">streptococci</a>, including blood infections, <a href="/wiki/Childbed_fever" class="mw-redirect" title="Childbed fever">childbed fever</a>, and <a href="/wiki/Erysipelas" title="Erysipelas">erysipelas</a>, and a lesser effect on infections caused by other cocci. However, it had no effect at all in the test tube, exerting its antibacterial action only in live animals. Later, it was discovered by <a href="/wiki/Daniel_Bovet" title="Daniel Bovet">Daniel Bovet</a>,<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> Federico Nitti, and <a href="/wiki/Jacques_Tr%C3%A9fou%C3%ABl_(chemist)" class="mw-redirect" title="Jacques Tréfouël (chemist)">Jacques</a> and <a href="/wiki/Th%C3%A9r%C3%A8se_Tr%C3%A9fou%C3%ABl" title="Thérèse Tréfouël">Thérèse Tréfouël</a>, a French research team led by <a href="/wiki/Ernest_Fourneau" title="Ernest Fourneau">Ernest Fourneau</a> at the <a href="/wiki/Pasteur_Institute" title="Pasteur Institute">Pasteur Institute</a>, that the drug was metabolized into two parts inside the body, releasing from the inactive dye portion a smaller, colorless, active compound called <a href="/wiki/Sulfanilamide" title="Sulfanilamide">sulfanilamide</a>.<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> The discovery helped establish the concept of "bioactivation" and dashed the German corporation's dreams of enormous profit; the active molecule sulfanilamide (or sulfa) had first been synthesized in 1906 and was widely used in the dye-making industry; its patent had since expired and the drug was available to anyone.<sup id="cite_ref-britannica_10-0" class="reference"><a href="#cite_note-britannica-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>The result was a sulfa craze.<sup id="cite_ref-wordpress_11-0" class="reference"><a href="#cite_note-wordpress-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> For several years in the late 1930s, hundreds of manufacturers produced myriad forms of sulfa. This and the lack of testing requirements led to the <a href="/wiki/Elixir_sulfanilamide" title="Elixir sulfanilamide">elixir sulfanilamide</a> disaster in the fall of 1937, during which at least 100 people were poisoned with <a href="/wiki/Diethylene_glycol" title="Diethylene glycol">diethylene glycol</a>. This led to the passage of the <a href="/wiki/Federal_Food,_Drug,_and_Cosmetic_Act" class="mw-redirect" title="Federal Food, Drug, and Cosmetic Act">Federal Food, Drug, and Cosmetic Act</a> in 1938 in the United States. As the first and only effective broad-spectrum antibiotic available in the years before <a href="/wiki/Penicillin" title="Penicillin">penicillin</a>, heavy use of sulfa drugs continued into the early years of <a href="/wiki/World_War_II" title="World War II">World War II</a>.<sup id="cite_ref-att_12-0" class="reference"><a href="#cite_note-att-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> They are credited with saving the lives of tens of thousands of patients, including <a href="/wiki/Franklin_Delano_Roosevelt_Jr." class="mw-redirect" title="Franklin Delano Roosevelt Jr.">Franklin Delano Roosevelt Jr.</a> (son of US President <a href="/wiki/Franklin_Delano_Roosevelt" class="mw-redirect" title="Franklin Delano Roosevelt">Franklin Delano Roosevelt</a>) and <a href="/wiki/Winston_Churchill" title="Winston Churchill">Winston Churchill</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><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> Sulfa had a central role in preventing wound infections during the war. American soldiers were issued a <a href="/wiki/First-aid_kit" class="mw-redirect" title="First-aid kit">first-aid kit</a> containing sulfa pills and powder and were told to sprinkle it on any open wound.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>The sulfanilamide compound is more active in the <a href="/wiki/Protonated" class="mw-redirect" title="Protonated">protonated</a> form. The drug has very low solubility and sometimes can crystallize in the kidneys, due to its first pK<sub>a</sub> of around 10.<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="(March 2019)">clarification needed</span></a></i>]</sup> This is a very painful experience, so patients are told to take the medication with copious amounts of water. Newer analogous compounds prevent this complication because they have a lower pK<sub>a</sub>, around 5–6,<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. (May 2012)">citation needed</span></a></i>]</sup> making them more likely to remain in a soluble form. </p><p>Many thousands of molecules containing the sulfanilamide structure have been created since its discovery (by one account, over 5,400 permutations by 1945), yielding improved formulations with greater effectiveness and less toxicity. Sulfa drugs are still widely used for conditions such as acne and urinary tract infections, and are receiving renewed interest for the treatment of infections caused by bacteria resistant to other antibiotics.<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. (December 2019)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Preparation">Preparation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sulfonamide_(medicine)&action=edit&section=3" title="Edit section: Preparation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sulfonamides are prepared by the reaction of a <a href="/wiki/Sulfonyl_chloride" class="mw-redirect" title="Sulfonyl chloride">sulfonyl chloride</a> with ammonia or an amine. Certain sulfonamides (sulfadiazine or <a href="/wiki/Sulfamethoxazole" title="Sulfamethoxazole">sulfamethoxazole</a>) are sometimes mixed with the drug <a href="/wiki/Trimethoprim" title="Trimethoprim">trimethoprim</a>, which acts against <a href="/wiki/Dihydrofolate_reductase" title="Dihydrofolate reductase">dihydrofolate reductase</a>. As of 2013<sup class="plainlinks noexcerpt noprint asof-tag update" style="display:none;"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Sulfonamide_(medicine)&action=edit">[update]</a></sup>, the <a href="/wiki/Republic_of_Ireland" title="Republic of Ireland">Republic of Ireland</a> is the largest exporter worldwide of sulfonamides, accounting for approximately 32% of total exports.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Varieties">Varieties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sulfonamide_(medicine)&action=edit&section=4" title="Edit section: Varieties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/List_of_sulfonamides" title="List of sulfonamides">List of sulfonamides</a></div> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sulfonamide_(medicine)&action=edit&section=5" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1237032888/mw-parser-output/.tmulti">.mw-parser-output .tmulti .multiimageinner{display:flex;flex-direction:column}.mw-parser-output .tmulti .trow{display:flex;flex-direction:row;clear:left;flex-wrap:wrap;width:100%;box-sizing:border-box}.mw-parser-output .tmulti .tsingle{margin:1px;float:left}.mw-parser-output .tmulti .theader{clear:both;font-weight:bold;text-align:center;align-self:center;background-color:transparent;width:100%}.mw-parser-output .tmulti .thumbcaption{background-color:transparent}.mw-parser-output .tmulti .text-align-left{text-align:left}.mw-parser-output .tmulti .text-align-right{text-align:right}.mw-parser-output .tmulti .text-align-center{text-align:center}@media all and (max-width:720px){.mw-parser-output .tmulti .thumbinner{width:100%!important;box-sizing:border-box;max-width:none!important;align-items:center}.mw-parser-output .tmulti .trow{justify-content:center}.mw-parser-output .tmulti .tsingle{float:none!important;max-width:100%!important;box-sizing:border-box;text-align:center}.mw-parser-output .tmulti .tsingle .thumbcaption{text-align:left}.mw-parser-output .tmulti .trow>.thumbcaption{text-align:center}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .tmulti .multiimageinner img{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .tmulti .multiimageinner img{background-color:white}}</style><div class="thumb tmulti tright"><div class="thumbinner multiimageinner" style="width:242px;max-width:242px"><div class="trow"><div class="tsingle" style="width:110px;max-width:110px"><div class="thumbimage" style="height:170px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Stevens-johnson-syndrome.jpg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Stevens-johnson-syndrome.jpg/108px-Stevens-johnson-syndrome.jpg" decoding="async" width="108" height="170" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Stevens-johnson-syndrome.jpg/162px-Stevens-johnson-syndrome.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/Stevens-johnson-syndrome.jpg/216px-Stevens-johnson-syndrome.jpg 2x" data-file-width="417" data-file-height="658" /></a></span></div><div class="thumbcaption">Person with <a href="/wiki/Stevens%E2%80%93Johnson_syndrome" title="Stevens–Johnson syndrome">Stevens–Johnson syndrome</a></div></div><div class="tsingle" style="width:128px;max-width:128px"><div class="thumbimage" style="height:170px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Urticaria_2.jpg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Urticaria_2.jpg/126px-Urticaria_2.jpg" decoding="async" width="126" height="171" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Urticaria_2.jpg/189px-Urticaria_2.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Urticaria_2.jpg/252px-Urticaria_2.jpg 2x" data-file-width="611" data-file-height="828" /></a></span></div><div class="thumbcaption">Allergic urticaria on the skin induced by an antibiotic</div></div></div></div></div> <p>Sulfonamides have the potential to cause a variety of <a href="/wiki/Adverse_effect" title="Adverse effect">adverse effects</a>, including urinary tract disorders, <a href="/wiki/Haematopoiesis" title="Haematopoiesis">haemopoietic</a> disorders, <a href="/wiki/Porphyria" title="Porphyria">porphyria</a> and hypersensitivity reactions. When used in large doses, they may cause a strong allergic reaction. The most serious of these are classified as <a href="/wiki/Severe_cutaneous_adverse_reactions" title="Severe cutaneous adverse reactions">severe cutaneous adverse reactions</a> (i.e. SCARs) and include the <a href="/wiki/Stevens%E2%80%93Johnson_syndrome" title="Stevens–Johnson syndrome">Stevens–Johnson syndrome</a>, <a href="/wiki/Toxic_epidermal_necrolysis" title="Toxic epidermal necrolysis">toxic epidermal necrolysis</a> (also known as Lyell syndrome), the <a href="/wiki/DRESS_syndrome" class="mw-redirect" title="DRESS syndrome">DRESS syndrome</a>, and a not quite as serious SCARs reaction, <a href="/wiki/Acute_generalized_exanthematous_pustulosis" title="Acute generalized exanthematous pustulosis">acute generalized exanthematous pustulosis</a>. Any one of these SCARs may be triggered by certain sulfonamides.<sup id="cite_ref-allergies.about.com_3-1" class="reference"><a href="#cite_note-allergies.about.com-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Approximately 3% of the general population have adverse reactions when treated with sulfonamide antimicrobials. Of note is the observation that patients with HIV have a much higher prevalence, at about 60%.<sup id="cite_ref-SMJ_17-0" class="reference"><a href="#cite_note-SMJ-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>Hypersensitivity reactions are less common in nonantibiotic sulfonamides, and, though controversial, the available evidence suggests those with hypersensitivity to sulfonamide antibiotics do not have an increased risk of hypersensitivity reaction to the nonantibiotic agents.<sup id="cite_ref-Immun_18-0" class="reference"><a href="#cite_note-Immun-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> A key component to the allergic response to sulfonamide antibiotics is the arylamine group at N4, found in sulfamethoxazole, sulfasalazine, sulfadiazine, and the anti-retrovirals amprenavir and fosamprenavir. Other sulfonamide drugs do not contain this arylamine group; available evidence suggests that patients who are allergic to arylamine sulfonamides do not cross-react to sulfonamides that lack the arylamine group, and may therefore safely take non-arylamine sulfonamides.<sup id="cite_ref-Knowles_19-0" class="reference"><a href="#cite_note-Knowles-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> It has therefore been argued that the terms "sulfonamide allergy" or "sulfa allergy" are misleading and should be replaced by a reference to a specific drug (e.g., "<a href="/wiki/Cotrimoxazole" class="mw-redirect" title="Cotrimoxazole">cotrimoxazole</a> allergy").<sup id="cite_ref-WAMSG_20-0" class="reference"><a href="#cite_note-WAMSG-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>Two regions of the sulfonamide antibiotic chemical structure are implicated in the hypersensitivity reactions associated with the class. </p> <ul><li>The first is the N1 heterocyclic ring, which causes a type I <a href="/wiki/Hypersensitivity" title="Hypersensitivity">hypersensitivity</a> reaction.</li> <li>The second is the N4 amino nitrogen that, in a stereospecific process, forms reactive metabolites that cause either direct cytotoxicity or immunologic response.</li></ul> <p>The nonantibiotic sulfonamides lack both of these structures.<sup id="cite_ref-Cross_21-0" class="reference"><a href="#cite_note-Cross-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p>The most common manifestations of a hypersensitivity reaction to sulfa drugs are <a href="/wiki/Rash" title="Rash">rash</a> and <a href="/wiki/Hives" title="Hives">hives</a>. However, there are several life-threatening manifestations of hypersensitivity to sulfa drugs, including <a href="/wiki/Stevens%E2%80%93Johnson_syndrome" title="Stevens–Johnson syndrome">Stevens–Johnson syndrome</a>, <a href="/wiki/Toxic_epidermal_necrolysis" title="Toxic epidermal necrolysis">toxic epidermal necrolysis</a>, <a href="/wiki/Agranulocytosis" title="Agranulocytosis">agranulocytosis</a>, <a href="/wiki/Hemolytic_anemia" title="Hemolytic anemia">hemolytic anemia</a>, <a href="/wiki/Thrombocytopenia" title="Thrombocytopenia">thrombocytopenia</a>, fulminant hepatic necrosis, and <a href="/wiki/Acute_pancreatitis" title="Acute pancreatitis">acute pancreatitis</a>, among others.<sup id="cite_ref-Harrison's_22-0" class="reference"><a href="#cite_note-Harrison's-22"><span class="cite-bracket">[</span>22<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=Sulfonamide_(medicine)&action=edit&section=6" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Dihydropteroate_synthase" title="Dihydropteroate synthase">Dihydropteroate synthase</a></li> <li><a href="/wiki/Elixir_sulfanilamide" title="Elixir sulfanilamide">Elixir sulfanilamide</a></li> <li><a href="/wiki/Hellmuth_Kleinsorge" title="Hellmuth Kleinsorge">Hellmuth Kleinsorge</a> (1920–2001) German medical doctor</li> <li><a href="/wiki/4-Aminobenzoic_acid" title="4-Aminobenzoic acid">PABA</a></li> <li><a href="/wiki/Timeline_of_antibiotics" title="Timeline of antibiotics">Timeline of antibiotics</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=Sulfonamide_(medicine)&action=edit&section=7" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-modeofaction-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-modeofaction_1-0">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFHenry_RJ1943" class="citation journal cs1">Henry RJ (1943). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC440870">"The Mode of Action of Sulfonamides"</a>. <i>Bacteriological Reviews</i>. <b>7</b> (4): 175–262. <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%2FMMBR.7.4.175-262.1943">10.1128/MMBR.7.4.175-262.1943</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/PMC440870">440870</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/16350088">16350088</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bacteriological+Reviews&rft.atitle=The+Mode+of+Action+of+Sulfonamides&rft.volume=7&rft.issue=4&rft.pages=175-262&rft.date=1943&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC440870%23id-name%3DPMC&rft_id=info%3Apmid%2F16350088&rft_id=info%3Adoi%2F10.1128%2FMMBR.7.4.175-262.1943&rft.au=Henry+RJ&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC440870&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASulfonamide+%28medicine%29" class="Z3988"></span></span> </li> <li id="cite_note-chemicalland21-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-chemicalland21_2-0">^</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://chemicalland21.com/info/SULFONAMIDE%20CLASS%20ANTIBIOTICS.htm">"SULFONAMIDE CLASS ANTIBIOTICS"</a>. chemicalland21.com<span class="reference-accessdate">. Retrieved <span class="nowrap">17 January</span> 2014</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=SULFONAMIDE+CLASS+ANTIBIOTICS&rft.pub=chemicalland21.com&rft_id=http%3A%2F%2Fchemicalland21.com%2Finfo%2FSULFONAMIDE%2520CLASS%2520ANTIBIOTICS.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASulfonamide+%28medicine%29" class="Z3988"></span></span> </li> <li id="cite_note-allergies.about.com-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-allergies.about.com_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-allergies.about.com_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 class="citation web cs1"><a rel="nofollow" class="external text" href="http://allergies.about.com/od/medicationallergies/a/sulfa.htm">"Sulfa Drugs Allergy -- Sulfa Bactrim Drug Allergies"</a>. allergies.about.com<span class="reference-accessdate">. Retrieved <span class="nowrap">17 January</span> 2014</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Sulfa+Drugs+Allergy+--+Sulfa+Bactrim+Drug+Allergies&rft.pub=allergies.about.com&rft_id=http%3A%2F%2Fallergies.about.com%2Fod%2Fmedicationallergies%2Fa%2Fsulfa.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASulfonamide+%28medicine%29" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text">M. Madigan, J. Martinko, D. Stahl, D. Clark, <i>Brock Biology of Microorganisms (13th ed.)</i>, Pearson Education, 2012, p. 797 <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780321735515" title="Special:BookSources/9780321735515">9780321735515</a></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="CITEREFLackie2010" class="citation book cs1">Lackie, John (2010). <i>A Dictionary of Biomedicine</i>. Oxford University Press. p. 543. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0199549351" title="Special:BookSources/978-0199549351"><bdi>978-0199549351</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=A+Dictionary+of+Biomedicine&rft.pages=543&rft.pub=Oxford+University+Press&rft.date=2010&rft.isbn=978-0199549351&rft.aulast=Lackie&rft.aufirst=John&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASulfonamide+%28medicine%29" 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="CITEREFOtten_H1986" class="citation journal cs1">Otten H (1986). <a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fjac%2F17.6.689">"Domagk and the development of the sulphonamides"</a>. <i>Journal of Antimicrobial Chemotherapy</i>. <b>17</b> (6): 689–696. <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/10.1093%2Fjac%2F17.6.689">10.1093/jac/17.6.689</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/3525495">3525495</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+Antimicrobial+Chemotherapy&rft.atitle=Domagk+and+the+development+of+the+sulphonamides&rft.volume=17&rft.issue=6&rft.pages=689-696&rft.date=1986&rft_id=info%3Adoi%2F10.1093%2Fjac%2F17.6.689&rft_id=info%3Apmid%2F3525495&rft.au=Otten+H&rft_id=https%3A%2F%2Fdoi.org%2F10.1093%252Fjac%252F17.6.689&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASulfonamide+%28medicine%29" 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="CITEREFHager2006" class="citation book cs1">Hager, Thomas (1 September 2006). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=S32TrACJa6kC&q=demon+under+the+microscope"><i>The Demon Under the Microscope: From Battlefield Hospitals to Nazi Labs, One Doctor's Heroic Search for the World's First Miracle Drug</i></a>. Crown. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-307-35228-6" title="Special:BookSources/978-0-307-35228-6"><bdi>978-0-307-35228-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Demon+Under+the+Microscope%3A+From+Battlefield+Hospitals+to+Nazi+Labs%2C+One+Doctor%27s+Heroic+Search+for+the+World%27s+First+Miracle+Drug&rft.pub=Crown&rft.date=2006-09-01&rft.isbn=978-0-307-35228-6&rft.aulast=Hager&rft.aufirst=Thomas&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DS32TrACJa6kC%26q%3Ddemon%2Bunder%2Bthe%2Bmicroscope&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASulfonamide+%28medicine%29" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text">Cf. 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href="https://web.archive.org/web/20060524135032/http://www.lung.ca/tb/tbhistory/treatment/chemo.html">A History of the Fight Against Tuberculosis in Canada (Chemotherapy)</a></li> <li><a rel="nofollow" class="external text" href="https://www.nobelprize.org/prizes/medicine/1939/ceremony-speech/">Presentation speech</a>, <a href="/wiki/Nobel_Prize_in_Physiology_and_Medicine" class="mw-redirect" title="Nobel Prize in Physiology and Medicine">Nobel Prize in Physiology and Medicine</a>, 1939</li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20100301192707/http://home.att.net/~steinert/wwii.htm">The History of WW II Medicine</a></li> <li><a rel="nofollow" class="external text" href="https://books.google.com/books?id=RicDAAAAMBAJ&pg=PA73&dq=popular+science+1930#v=twopage&q=popular%20science%201930&f=true">"Five Medical Miracles of the Sulfa Drugs"</a>. <i>Popular Science</i>, June 1942, pp. 73–78.</li> <li><a rel="nofollow" class="external text" href="https://science.umd.edu/classroom/bsci424/Chemotherapy/AntibioticsHistory.htm">A history of antibiotics</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 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 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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:Nucleic_acid_inhibitors" title="Template:Nucleic acid inhibitors"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nucleic_acid_inhibitors" title="Template talk:Nucleic acid inhibitors"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nucleic_acid_inhibitors" title="Special:EditPage/Template:Nucleic acid inhibitors"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Antibacterials_that_inhibit_nucleic_acid_(J01E,_J01M)" style="font-size:114%;margin:0 4em"><a href="/wiki/Antibiotics" class="mw-redirect" title="Antibiotics">Antibacterials</a> that <a href="/wiki/Nucleic_acid_inhibitor" title="Nucleic acid inhibitor">inhibit nucleic acid</a> (<a href="/wiki/ATC_code_J01#J01E" title="ATC code J01">J01E</a>, <a href="/wiki/ATC_code_J01#J01M" title="ATC code J01">J01M</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antifolate" title="Antifolate">Antifolates</a><br />(inhibit bacterial<br /><a href="/wiki/Purine_metabolism" title="Purine metabolism">purine metabolism</a>,<br />thereby inhibiting<br />DNA and RNA<br />synthesis)</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/Dihydrofolate_reductase_inhibitor" title="Dihydrofolate reductase inhibitor">DHFR inhibitor</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/2,4-Diaminopyrimidine" title="2,4-Diaminopyrimidine">2,4-Diaminopyrimidine</a> <ul><li><a href="/wiki/Brodimoprim" title="Brodimoprim">Brodimoprim</a></li> <li><a href="/wiki/Iclaprim" title="Iclaprim">Iclaprim</a><sup>†</sup></li> <li><a href="/wiki/Ormetoprim" title="Ormetoprim">Ormetoprim</a></li> <li><a href="/wiki/Pyrimethamine" title="Pyrimethamine">Pyrimethamine</a><sup>#</sup></li> <li><a href="/wiki/Tetroxoprim" title="Tetroxoprim">Tetroxoprim</a></li> <li><a href="/wiki/Trimethoprim" title="Trimethoprim">Trimethoprim</a><sup>#</sup></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Sulfonamides</a><br />(<a href="/wiki/Dihydropteroate_synthetase_inhibitor" class="mw-redirect" title="Dihydropteroate synthetase inhibitor">DHPS inhibitor</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink-fragment" href="#Short-acting">Short-acting</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/Sulfisomidine" title="Sulfisomidine">Sulfaisodimidine</a></li> <li><a href="/wiki/Sulfamethizole" title="Sulfamethizole">Sulfamethizole</a></li> <li><a href="/wiki/Sulfadimidine" title="Sulfadimidine">Sulfadimidine</a></li> <li><a href="/wiki/Sulfapyridine" title="Sulfapyridine">Sulfapyridine</a> (<a href="/wiki/Sulfasalazine" title="Sulfasalazine">Sulfasalazine</a>)</li> <li><a href="/wiki/Sulfafurazole" title="Sulfafurazole">Sulfafurazole</a> (<a href="/w/index.php?title=Acetyl_sulfisoxazole&action=edit&redlink=1" class="new" title="Acetyl sulfisoxazole (page does not exist)">Acetyl sulfisoxazole</a>)</li> <li><a href="/wiki/Sulfanilamide" title="Sulfanilamide">Sulfanilamide</a> <ul><li><a href="/wiki/Prontosil" title="Prontosil">Prontosil</a></li></ul></li> <li><a href="/wiki/Sulfathiazole" title="Sulfathiazole">Sulfathiazole</a> (<a href="/wiki/Phthalylsulfathiazole" title="Phthalylsulfathiazole">Phthalylsulfathiazole</a>, <a href="/wiki/Succinylsulfathiazole" title="Succinylsulfathiazole">Succinylsulfathiazole</a>)</li> <li><a href="/wiki/Sulfathiourea" title="Sulfathiourea">Sulfathiourea</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink-fragment" href="#Intermediate-acting">Intermediate-acting</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/Sulfamethoxazole" title="Sulfamethoxazole">Sulfamethoxazole</a></li> <li><a href="/wiki/Sulfadiazine" title="Sulfadiazine">Sulfadiazine</a><sup>#</sup></li> <li><a href="/wiki/Sulfamoxole" title="Sulfamoxole">Sulfamoxole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink-fragment" href="#Long-acting">Long-acting</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/Sulfadimethoxine" title="Sulfadimethoxine">Sulfadimethoxine</a></li> <li><a href="/wiki/Sulfadoxine" title="Sulfadoxine">Sulfadoxine</a></li> <li><a href="/wiki/Sulfalene" title="Sulfalene">Sulfalene</a></li> <li><a href="/wiki/Sulfametomidine" title="Sulfametomidine">Sulfametomidine</a></li> <li><a href="/wiki/Sulfametoxydiazine" title="Sulfametoxydiazine">Sulfametoxydiazine</a></li> <li><a href="/wiki/Sulfamethoxypyridazine" title="Sulfamethoxypyridazine">Sulfamethoxypyridazine</a></li> <li><a href="/wiki/Sulfaperin" title="Sulfaperin">Sulfaperin</a></li> <li><a href="/wiki/Sulfamerazine" title="Sulfamerazine">Sulfamerazine</a></li> <li><a href="/wiki/Sulfaphenazole" title="Sulfaphenazole">Sulfaphenazole</a></li> <li><a href="/wiki/Sulfamazone" title="Sulfamazone">Sulfamazone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other/ungrouped</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/Mafenide" title="Mafenide">Mafenide</a></li> <li><a href="/wiki/Sulfacetamide" title="Sulfacetamide">Sulfacetamide</a></li> <li><a href="/w/index.php?title=Sulfaclozine&action=edit&redlink=1" class="new" title="Sulfaclozine (page does not exist)">Sulfaclozine</a></li> <li><a href="/wiki/Sulfadicramide" title="Sulfadicramide">Sulfadicramide</a></li> <li><a href="/wiki/Sulfaguanidine" title="Sulfaguanidine">Sulfaguanidine</a></li> <li><a href="/wiki/Sulfametrole" title="Sulfametrole">Sulfametrole</a></li> <li><a href="/wiki/Sulfanitran" title="Sulfanitran">Sulfanitran</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Combinations</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/Trimethoprim/sulfamethoxazole" title="Trimethoprim/sulfamethoxazole">Trimethoprim/sulfamethoxazole</a><sup>#</sup></li> <li><a href="/wiki/Sulfadimethoxine#with_ormetoprim" title="Sulfadimethoxine">Ormetoprim/sulfadimethoxine</a></li> <li><a href="/w/index.php?title=Pyrimethamine/dapsone&action=edit&redlink=1" class="new" title="Pyrimethamine/dapsone (page does not exist)">Pyrimethamine/dapsone</a></li> <li><a href="/w/index.php?title=Pyrimethamine/sulfadoxine&action=edit&redlink=1" class="new" title="Pyrimethamine/sulfadoxine (page does not exist)">Pyrimethamine/sulfadoxine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other DHPS inhibitors</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/Acediasulfone" title="Acediasulfone">Acediasulfone</a></li> <li><a href="/wiki/Dapsone" title="Dapsone">Dapsone</a></li> <li><a href="/wiki/Solasulfone" title="Solasulfone">Solasulfone</a></li> <li><a href="/wiki/Sulfoxone" title="Sulfoxone">Sulfoxone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Quinolone_antibiotic" title="Quinolone antibiotic">Quinolones</a><br />(inhibit bacterial<br /><a href="/wiki/Topoisomerase_inhibitor" title="Topoisomerase inhibitor">topoisomerase</a><br />and/or <a href="/wiki/DNA_gyrase" title="DNA gyrase">DNA gyrase</a>,<br />thereby inhibiting<br /><a href="/wiki/DNA_replication" title="DNA replication">DNA replication</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/Quinolone_antibiotic#First_generation" title="Quinolone antibiotic">1st generation</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cinoxacin" title="Cinoxacin">Cinoxacin</a><sup>‡</sup></li> <li><a href="/wiki/Flumequine" title="Flumequine">Flumequine</a><sup>‡</sup></li> <li><a href="/wiki/Nalidixic_acid" title="Nalidixic acid">Nalidixic acid</a><sup>‡</sup></li> <li><a href="/wiki/Oxolinic_acid" title="Oxolinic acid">Oxolinic acid</a><sup>‡</sup></li> <li><a href="/wiki/Pipemidic_acid" title="Pipemidic acid">Pipemidic acid</a><sup>‡</sup></li> <li><a href="/wiki/Piromidic_acid" title="Piromidic acid">Piromidic acid</a><sup>‡</sup></li> <li><a href="/wiki/Rosoxacin" title="Rosoxacin">Rosoxacin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Quinolone_antibiotic" title="Quinolone antibiotic">Fluoroquinolones</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Quinolone_antibiotic#Second_generation" title="Quinolone antibiotic">2nd generation</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ciprofloxacin" title="Ciprofloxacin">Ciprofloxacin</a><sup>#</sup></li> <li><a href="/wiki/Ofloxacin" title="Ofloxacin">Ofloxacin</a></li> <li><a href="/wiki/Enoxacin" title="Enoxacin">Enoxacin</a><sup>‡</sup></li> <li><a href="/wiki/Fleroxacin" title="Fleroxacin">Fleroxacin</a><sup>‡</sup></li> <li><a href="/wiki/Lomefloxacin" title="Lomefloxacin">Lomefloxacin</a><sup>‡</sup></li> <li><a href="/wiki/Nadifloxacin" title="Nadifloxacin">Nadifloxacin</a><sup>‡</sup>/<a href="/wiki/Levonadifloxacin" title="Levonadifloxacin">Levonadifloxacin</a>/<a href="/wiki/Alalevonadifloxacin" title="Alalevonadifloxacin">Alalevonadifloxacin</a></li> <li><a href="/wiki/Norfloxacin" title="Norfloxacin">Norfloxacin</a><sup>‡</sup></li> <li><a href="/wiki/Pefloxacin" title="Pefloxacin">Pefloxacin</a><sup>‡</sup></li> <li><a href="/wiki/Rufloxacin" title="Rufloxacin">Rufloxacin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Quinolone_antibiotic#Third_generation" title="Quinolone antibiotic">3rd generation</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Levofloxacin" title="Levofloxacin">Levofloxacin</a><sup>#</sup></li> <li><a href="/wiki/Balofloxacin" title="Balofloxacin">Balofloxacin</a><sup>‡</sup></li> <li><a href="/wiki/Grepafloxacin" title="Grepafloxacin">Grepafloxacin</a><sup>‡</sup></li> <li><a href="/wiki/Pazufloxacin" title="Pazufloxacin">Pazufloxacin</a><sup>‡</sup></li> <li><a href="/wiki/Sparfloxacin" title="Sparfloxacin">Sparfloxacin</a><sup>‡</sup></li> <li><a href="/wiki/Temafloxacin" title="Temafloxacin">Temafloxacin</a><sup>‡</sup></li> <li><a href="/wiki/Tosufloxacin" title="Tosufloxacin">Tosufloxacin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Quinolone_antibiotic#Fourth_generation" title="Quinolone antibiotic">4th generation</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Besifloxacin" title="Besifloxacin">Besifloxacin</a></li> <li><a href="/wiki/Delafloxacin" title="Delafloxacin">Delafloxacin</a></li> <li><a href="/wiki/Gatifloxacin" title="Gatifloxacin">Gatifloxacin</a></li> <li><a href="/wiki/Finafloxacin" title="Finafloxacin">Finafloxacin</a></li> <li><a href="/wiki/Gemifloxacin" title="Gemifloxacin">Gemifloxacin</a></li> <li><a href="/wiki/Moxifloxacin" title="Moxifloxacin">Moxifloxacin</a><sup>#</sup></li> <li><a href="/wiki/Clinafloxacin" title="Clinafloxacin">Clinafloxacin</a><sup>†</sup></li> <li><a href="/wiki/Garenoxacin" title="Garenoxacin">Garenoxacin</a><sup>‡</sup></li> <li><a href="/wiki/Prulifloxacin" title="Prulifloxacin">Prulifloxacin</a><sup>‡</sup></li> <li><a href="/wiki/Sitafloxacin" title="Sitafloxacin">Sitafloxacin</a><sup>‡</sup></li> <li><a href="/wiki/Trovafloxacin" title="Trovafloxacin">Trovafloxacin</a><sup>‡</sup>/<a href="/wiki/Alatrofloxacin" title="Alatrofloxacin">Alatrofloxacin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Quinolone_antibiotic#Veterinary_use" title="Quinolone antibiotic">Veterinary</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Danofloxacin" title="Danofloxacin">Danofloxacin</a></li> <li><a href="/wiki/Difloxacin" title="Difloxacin">Difloxacin</a></li> <li><a href="/wiki/Enrofloxacin" title="Enrofloxacin">Enrofloxacin</a></li> <li><a href="/wiki/Ibafloxacin" title="Ibafloxacin">Ibafloxacin</a></li> <li><a href="/wiki/Marbofloxacin" title="Marbofloxacin">Marbofloxacin</a></li> <li><a href="/wiki/Orbifloxacin" title="Orbifloxacin">Orbifloxacin</a></li> <li><a href="/wiki/Pradofloxacin" title="Pradofloxacin">Pradofloxacin</a></li> <li><a href="/wiki/Sarafloxacin" title="Sarafloxacin">Sarafloxacin</a><sup>‡</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Newer non-fluorinated</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/Nemonoxacin" title="Nemonoxacin">Nemonoxacin</a></li> <li><a href="/wiki/Ozenoxacin" title="Ozenoxacin">Ozenoxacin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related (<a href="/wiki/DNA_gyrase" title="DNA gyrase">DG</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/Aminocoumarin" title="Aminocoumarin">Aminocoumarins</a>: <a href="/wiki/Novobiocin" title="Novobiocin">Novobiocin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anaerobic_organism" title="Anaerobic organism">Anaerobic</a> DNA<br /><a href="/wiki/Nucleic_acid_inhibitor#DNA_inhibitors" title="Nucleic acid inhibitor">inhibitors</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 id="Nitroimidazole_derivatives" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitroimidazole" title="Nitroimidazole">Nitroimidazole</a> derivatives</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/Secnidazole" title="Secnidazole">Secnidazole</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/RNA" title="RNA">RNA</a> synthesis</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/Rifamycin" title="Rifamycin">Rifamycins</a>/<br /><a href="/wiki/RNA-dependent_RNA_polymerase" title="RNA-dependent RNA polymerase">RNA polymerase</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/Rifampicin" title="Rifampicin">Rifampicin</a><sup>#</sup></li> <li><a href="/wiki/Rifabutin" title="Rifabutin">Rifabutin</a><sup>#</sup></li> <li><a href="/wiki/Rifapentine" title="Rifapentine">Rifapentine</a><sup>#</sup></li> <li><a href="/wiki/Rifaximin" title="Rifaximin">Rifaximin</a></li> <li><a href="/wiki/Rifalazil" title="Rifalazil">Rifalazil</a><sup>§</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lipiarmycin" class="mw-redirect" title="Lipiarmycin">Lipiarmycins</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/Fidaxomicin" title="Fidaxomicin">Fidaxomicin</a></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 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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Anticonvulsants_(N03)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Anticonvulsants" title="Template:Anticonvulsants"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Anticonvulsants" title="Template talk:Anticonvulsants"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Anticonvulsants" title="Special:EditPage/Template:Anticonvulsants"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Anticonvulsants_(N03)" style="font-size:114%;margin:0 4em"><a href="/wiki/Anticonvulsant" title="Anticonvulsant">Anticonvulsants</a> (<a href="/wiki/ATC_code_N03" title="ATC code N03">N03</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/GABAergic" title="GABAergic">GABAergics</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/GABAA_receptor" title="GABAA receptor">GABA<sub>A</sub>R</a> <a href="/wiki/Allosteric_modulator" title="Allosteric modulator">PAMs</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a>:</b> <a href="/wiki/Barbexaclone" title="Barbexaclone">Barbexaclone</a></li> <li><a href="/wiki/Metharbital" title="Metharbital">Metharbital</a></li> <li><a href="/wiki/Methylphenobarbital" title="Methylphenobarbital">Methylphenobarbital</a></li> <li><a href="/wiki/Pentobarbital" title="Pentobarbital">Pentobarbital</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a><sup>#</sup></li> <li><a href="/wiki/Primidone" title="Primidone">Primidone</a>; <b><a href="/wiki/Carbamate" title="Carbamate">Carbamates</a></b>: <a href="/wiki/Cenobamate" title="Cenobamate">Cenobamate</a></li> <li><a href="/wiki/Felbamate" title="Felbamate">Felbamate</a>; <b><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a></b>: <a href="/wiki/Clobazam" title="Clobazam">Clobazam</a></li> <li><a href="/wiki/Clonazepam" title="Clonazepam">Clonazepam</a></li> <li><a href="/wiki/Clorazepate" title="Clorazepate">Clorazepate</a></li> <li><a href="/wiki/Diazepam" title="Diazepam">Diazepam</a><sup>#</sup></li> <li><a href="/wiki/Lorazepam" title="Lorazepam">Lorazepam</a><sup>#</sup></li> <li><a href="/wiki/Midazolam" title="Midazolam">Midazolam</a></li> <li><a href="/wiki/Nimetazepam" title="Nimetazepam">Nimetazepam</a></li> <li><a href="/wiki/Nitrazepam" title="Nitrazepam">Nitrazepam</a></li> <li><a href="/wiki/Temazepam" title="Temazepam">Temazepam</a>; <b>Others:</b> <a href="/wiki/Bromide" title="Bromide">Bromide</a> (<a href="/wiki/Potassium_bromide" title="Potassium bromide">potassium bromide</a>, <a href="/wiki/Sodium_bromide" title="Sodium bromide">sodium bromide</a>)</li> <li><a href="/wiki/Imepitoin" title="Imepitoin">Imepitoin</a></li> <li><a href="/wiki/Paraldehyde" title="Paraldehyde">Paraldehyde</a></li> <li><a href="/wiki/Stiripentol" title="Stiripentol">Stiripentol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/GABA_transaminase_inhibitor" title="GABA transaminase inhibitor">GABA-T inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/Fatty_acid" title="Fatty acid">Fatty acids</a> (and related):</b> <a href="/wiki/Valproate" title="Valproate">Valproate</a></li> <li><a href="/wiki/Valpromide" title="Valpromide">Valpromide</a></li> <li><a href="/wiki/Valproate_pivoxil" title="Valproate pivoxil">Valproate pivoxil</a></li> <li><a href="/wiki/Vigabatrin" title="Vigabatrin">Vigabatrin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/GABA_receptor_agonist" title="GABA receptor agonist">GABAR agonists</a></b>: <a href="/wiki/Progabide" title="Progabide">Progabide</a>; <b><a href="/wiki/GABA_reuptake_inhibitor" title="GABA reuptake inhibitor">GAT-1 inhibitors</a>:</b> <a href="/wiki/Tiagabine" title="Tiagabine">Tiagabine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Channel_modulator" title="Channel modulator">Channel<br />modulators</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sodium_channel_blocker" title="Sodium channel blocker">Sodium blockers</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/Hydantoin" title="Hydantoin">Hydantoins</a>:</b> <a href="/wiki/Ethotoin" title="Ethotoin">Ethotoin</a></li> <li><a href="/wiki/Fosphenytoin" title="Fosphenytoin">Fosphenytoin</a></li> <li><a href="/wiki/Mephenytoin" title="Mephenytoin">Mephenytoin</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a><sup>#</sup>; <b><a href="/wiki/Acylurea" title="Acylurea">Ureides</a>:</b> <a href="/w/index.php?title=Acetylpheneturide&action=edit&redlink=1" class="new" title="Acetylpheneturide (page does not exist)">Acetylpheneturide</a></li> <li><a href="/wiki/Chlorphenacemide" title="Chlorphenacemide">Chlorphenacemide</a></li> <li><a href="/wiki/Phenacemide" title="Phenacemide">Phenacemide</a><sup>‡</sup></li> <li><a href="/wiki/Pheneturide" title="Pheneturide">Pheneturide</a>; <b><a href="/wiki/Fatty_acid" title="Fatty acid">Fatty acids</a>:</b> <a href="/wiki/Valproate" title="Valproate">Valproate</a></li> <li><a href="/wiki/Valpromide" title="Valpromide">Valpromide</a></li> <li><a href="/wiki/Valproate_pivoxil" title="Valproate pivoxil">Valproate pivoxil</a>; <b><a href="/wiki/Carboxamide" class="mw-redirect" title="Carboxamide">Carboxamides</a>:</b></li> <li><a href="/wiki/Carbamazepine" title="Carbamazepine">Carbamazepine</a><sup>#</sup></li> <li><a href="/wiki/Eslicarbazepine_acetate" title="Eslicarbazepine acetate">Eslicarbazepine acetate</a></li> <li><a href="/wiki/Oxcarbazepine" title="Oxcarbazepine">Oxcarbazepine</a>; <b>Others:</b> <a href="/wiki/Lacosamide" title="Lacosamide">Lacosamide</a></li> <li><a href="/wiki/Lamotrigine" title="Lamotrigine">Lamotrigine</a><sup>#</sup></li> <li><a href="/wiki/Rufinamide" title="Rufinamide">Rufinamide</a></li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><a href="/wiki/Zonisamide" title="Zonisamide">Zonisamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Calcium_channel_blocker" title="Calcium channel blocker">Calcium blockers</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/2,4-Oxazolidinedione" title="2,4-Oxazolidinedione">Oxazolidinediones</a>:</b> <a href="/wiki/Ethadione" title="Ethadione">Ethadione</a></li> <li><a href="/wiki/Paramethadione" title="Paramethadione">Paramethadione</a></li> <li><a href="/wiki/Trimethadione" title="Trimethadione">Trimethadione</a>; <b><a href="/wiki/Succinimide" title="Succinimide">Succinimides</a></b>: <a href="/wiki/Ethosuximide" title="Ethosuximide">Ethosuximide</a><sup>#</sup></li> <li><a href="/wiki/Mesuximide" title="Mesuximide">Mesuximide</a></li> <li><a href="/wiki/Phensuximide" title="Phensuximide">Phensuximide</a>; <b><a href="/wiki/Gabapentinoid" title="Gabapentinoid">Gabapentinoids</a>:</b> <a href="/wiki/Gabapentin" title="Gabapentin">Gabapentin</a></li> <li><a href="/wiki/Pregabalin" title="Pregabalin">Pregabalin</a>; <b>Others:</b> <a href="/wiki/Imepitoin" title="Imepitoin">Imepitoin</a></li> <li><a href="/wiki/Lamotrigine" title="Lamotrigine">Lamotrigine</a><sup>#</sup></li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><a href="/wiki/Zonisamide" title="Zonisamide">Zonisamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Potassium_channel_opener" title="Potassium channel opener">Potassium openers</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Retigabine" title="Retigabine">Retigabine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonic_anhydrase_inhibitor" title="Carbonic anhydrase inhibitor">CA inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b><a class="mw-selflink-fragment" href="#Anticonvulsant">Sulfonamides</a>:</b> <a href="/wiki/Acetazolamide" title="Acetazolamide">Acetazolamide</a></li> <li><a href="/wiki/Ethoxzolamide" title="Ethoxzolamide">Ethoxzolamide</a></li> <li><a href="/wiki/Sultiame" title="Sultiame">Sultiame</a></li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><a href="/wiki/Zonisamide" title="Zonisamide">Zonisamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Albutoin" title="Albutoin">Albutoin</a></li> <li><a href="/wiki/Beclamide" title="Beclamide">Beclamide</a></li> <li><a href="/wiki/Brivaracetam" title="Brivaracetam">Brivaracetam</a></li> <li><a href="/wiki/Cannabidiol" title="Cannabidiol">Cannabidiol</a></li> <li><a href="/wiki/Carisbamate" title="Carisbamate">Carisbamate</a></li> <li><a href="/wiki/Etiracetam" title="Etiracetam">Etiracetam</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a></li> <li><a href="/wiki/Ganaxolone" title="Ganaxolone">Ganaxolone</a></li> <li><a href="/wiki/Levetiracetam" title="Levetiracetam">Levetiracetam</a></li> <li><a href="/wiki/Perampanel" title="Perampanel">Perampanel</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: transparent; padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Antibiotics_and_chemotherapeutics_for_dermatological_use_(D06)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Antibiotics_and_chemotherapeutics_for_dermatological_use" title="Template:Antibiotics and chemotherapeutics for dermatological use"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Antibiotics_and_chemotherapeutics_for_dermatological_use" title="Template talk:Antibiotics and chemotherapeutics for dermatological use"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Antibiotics_and_chemotherapeutics_for_dermatological_use" title="Special:EditPage/Template:Antibiotics and chemotherapeutics for dermatological use"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Antibiotics_and_chemotherapeutics_for_dermatological_use_(D06)" style="font-size:114%;margin:0 4em"><a href="/wiki/Antibiotic" title="Antibiotic">Antibiotics</a> and <a href="/wiki/Chemotherapeutics" class="mw-redirect" title="Chemotherapeutics">chemotherapeutics</a> for <a href="/wiki/Dermatological" class="mw-redirect" title="Dermatological">dermatological</a> use (<a href="/wiki/ATC_code_D06" title="ATC code D06">D06</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antibiotic" title="Antibiotic">Antibiotics</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/Tetracycline" title="Tetracycline">Tetracycline</a> and derivatives</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/Demeclocycline" title="Demeclocycline">Demeclocycline</a></li> <li><a href="/wiki/Chlortetracycline" title="Chlortetracycline">Chlortetracycline</a></li> <li><a href="/wiki/Oxytetracycline" title="Oxytetracycline">Oxytetracycline</a></li> <li><a href="/wiki/Tetracycline" title="Tetracycline">Tetracycline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amphenicol" title="Amphenicol">Amphenicol</a>: <a href="/wiki/Chloramphenicol" title="Chloramphenicol">Chloramphenicol</a></li></ul> <ul><li><a href="/wiki/Aminoglycoside" title="Aminoglycoside">Aminoglycosides</a>: <a href="/wiki/Neomycin" title="Neomycin">Neomycin</a></li> <li><a href="/wiki/Gentamicin" title="Gentamicin">Gentamicin</a></li> <li><a href="/wiki/Amikacin" title="Amikacin">Amikacin</a></li></ul> <ul><li><a href="/wiki/Quinolone_antibiotic" title="Quinolone antibiotic">Quinolones</a>: <a href="/wiki/Nadifloxacin" title="Nadifloxacin">Nadifloxacin</a></li></ul> <ul><li><a href="/wiki/Streptogramin" title="Streptogramin">Streptogramin</a>: <a href="/wiki/Virginiamycin" title="Virginiamycin">Virginiamycin</a></li></ul> <ul><li><a href="/wiki/Rifamycin" title="Rifamycin">Rifamycin</a>: <a href="/wiki/Rifaximin" title="Rifaximin">Rifaximin</a></li></ul> <ul><li><i>other:</i> <a href="/wiki/Fusidic_acid" title="Fusidic acid">Fusidic acid</a></li> <li><a href="/wiki/Bacitracin" title="Bacitracin">Bacitracin</a></li> <li><a href="/wiki/Tyrothricin" title="Tyrothricin">Tyrothricin</a></li> <li><a href="/wiki/Mupirocin" title="Mupirocin">Mupirocin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chemotherapy" title="Chemotherapy">Chemotherapeutics</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 class="mw-selflink selflink">Sulfonamides</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/Silver_sulfadiazine" title="Silver sulfadiazine">Silver sulfadiazine</a></li> <li><a href="/wiki/Sulfathiazole" title="Sulfathiazole">Sulfathiazole</a></li> <li><a href="/wiki/Mafenide" title="Mafenide">Mafenide</a></li> <li><a href="/wiki/Sulfamethizole" title="Sulfamethizole">Sulfamethizole</a></li> <li><a href="/wiki/Sulfanilamide" title="Sulfanilamide">Sulfanilamide</a></li> <li><a href="/wiki/Sulfamerazine" title="Sulfamerazine">Sulfamerazine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antiviral_drug" title="Antiviral drug">Antivirals</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/Aciclovir" title="Aciclovir">Aciclovir</a></li> <li><a href="/wiki/Penciclovir" title="Penciclovir">Penciclovir</a></li> <li><a href="/wiki/Idoxuridine" title="Idoxuridine">Idoxuridine</a></li> <li><a href="/wiki/Edoxudine" title="Edoxudine">Edoxudine</a></li> <li><a href="/wiki/Imiquimod" title="Imiquimod">Imiquimod</a></li> <li><a href="/wiki/Resiquimod" title="Resiquimod">Resiquimod</a></li> <li><a href="/wiki/Podophyllotoxin" title="Podophyllotoxin">Podophyllotoxin</a></li> <li><a href="/wiki/Docosanol" class="mw-redirect" title="Docosanol">Docosanol</a></li> <li><a href="/wiki/Tromantadine" title="Tromantadine">Tromantadine</a></li> <li><a href="/wiki/Inosine" title="Inosine">Inosine</a></li> <li><a href="/wiki/Lysozyme" title="Lysozyme">Lysozyme</a></li> <li><a href="/wiki/Ibacitabine" title="Ibacitabine">Ibacitabine</a></li> <li><a href="/wiki/Lysine" title="Lysine">Lysine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ingenol_mebutate" title="Ingenol mebutate">Ingenol mebutate</a></li> <li><a href="/wiki/Metronidazole" title="Metronidazole">Metronidazole</a></li> <li><a href="/wiki/Tirbanibulin" title="Tirbanibulin">Tirbanibulin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Diuretics_(C03)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Diuretics" title="Template:Diuretics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Diuretics" title="Template talk:Diuretics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Diuretics" title="Special:EditPage/Template:Diuretics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Diuretics_(C03)" style="font-size:114%;margin:0 4em"><a href="/wiki/Diuretic" title="Diuretic">Diuretics</a> (<a href="/wiki/ATC_code_C03" title="ATC code C03">C03</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Sulfonamides</a><br />(and <a href="/wiki/Etacrynic_acid" title="Etacrynic acid">etacrynic acid</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/Carbonic_anhydrase_inhibitor" title="Carbonic anhydrase inhibitor">CA inhibitors</a> (at <a href="/wiki/Proximal_tubule" title="Proximal tubule">PT</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/Acetazolamide" title="Acetazolamide">Acetazolamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Loop_diuretic" title="Loop diuretic">Loop</a> (<a href="/wiki/Na-K-Cl_cotransporter" class="mw-redirect" title="Na-K-Cl cotransporter">Na-K-Cl</a> at <a href="/wiki/Thick_ascending_limb_of_loop_of_Henle" class="mw-redirect" title="Thick ascending limb of loop of Henle">AL</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/Furosemide" title="Furosemide">Furosemide</a><sup>#</sup></li> <li><a href="/wiki/Azosemide" title="Azosemide">Azosemide</a></li> <li><a href="/wiki/Bumetanide" title="Bumetanide">Bumetanide</a></li> <li><a href="/wiki/Etacrynic_acid" title="Etacrynic acid">Etacrynic acid</a></li> <li><a href="/wiki/Etozolin" title="Etozolin">Etozolin</a></li> <li><a href="/wiki/Indacrinone" title="Indacrinone">Indacrinone</a></li> <li><a href="/wiki/Muzolimine" title="Muzolimine">Muzolimine</a></li> <li><a href="/wiki/Ozolinone" title="Ozolinone">Ozolinone</a></li> <li><a href="/wiki/Piretanide" title="Piretanide">Piretanide</a></li> <li><a href="/wiki/Tienilic_acid" title="Tienilic acid">Tienilic acid</a><sup>‡</sup></li> <li><a href="/wiki/Torasemide" title="Torasemide">Torasemide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Thiazide" title="Thiazide">Thiazides</a> (<a href="/wiki/Sodium-chloride_symporter" title="Sodium-chloride symporter">Na-Cl</a> at <a href="/wiki/Distal_convoluted_tubule" title="Distal convoluted tubule">DCT</a>,<br /><a href="/wiki/Diuretic#Calcium-sparing_diuretics" title="Diuretic">Calcium-sparing</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/Altizide" title="Altizide">Altizide</a></li> <li><a href="/wiki/Bendroflumethiazide" title="Bendroflumethiazide">Bendroflumethiazide</a></li> <li><a href="/wiki/Butizide" title="Butizide">Butizide</a></li> <li><a href="/wiki/Chlorothiazide" title="Chlorothiazide">Chlorothiazide</a></li> <li><a href="/wiki/Cyclopenthiazide" title="Cyclopenthiazide">Cyclopenthiazide</a></li> <li><a href="/wiki/Cyclothiazide" title="Cyclothiazide">Cyclothiazide</a></li> <li><a href="/wiki/Epitizide" title="Epitizide">Epitizide</a></li> <li><a href="/wiki/Hydrochlorothiazide" title="Hydrochlorothiazide">Hydrochlorothiazide</a></li> <li><a href="/wiki/Hydroflumethiazide" title="Hydroflumethiazide">Hydroflumethiazide</a></li> <li><a href="/wiki/Mebutizide" title="Mebutizide">Mebutizide</a></li> <li><a href="/wiki/Methyclothiazide" title="Methyclothiazide">Methyclothiazide</a></li> <li><a href="/wiki/Polythiazide" title="Polythiazide">Polythiazide</a></li> <li><a href="/wiki/Trichlormethiazide" title="Trichlormethiazide">Trichlormethiazide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Thiazide-like_diuretic" title="Thiazide-like diuretic">Thiazide-likes</a> (primarily <a href="/wiki/Distal_convoluted_tubule" title="Distal convoluted tubule">DCT</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/Chlortalidone" title="Chlortalidone">Chlortalidone</a></li> <li><a href="/wiki/Clofenamide" title="Clofenamide">Clofenamide</a></li> <li><a href="/wiki/Clopamide" title="Clopamide">Clopamide</a></li> <li><a href="/wiki/Clorexolone" title="Clorexolone">Clorexolone</a></li> <li><a href="/wiki/Fenquizone" title="Fenquizone">Fenquizone</a></li> <li><a href="/wiki/Indapamide" title="Indapamide">Indapamide</a></li> <li><a href="/wiki/Mefruside" title="Mefruside">Mefruside</a></li> <li><a href="/wiki/Meticrane" title="Meticrane">Meticrane</a></li> <li><a href="/wiki/Metolazone" title="Metolazone">Metolazone</a></li> <li><a href="/wiki/Quinethazone" title="Quinethazone">Quinethazone</a></li> <li><a href="/wiki/Xipamide" title="Xipamide">Xipamide</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Potassium-sparing_diuretic" title="Potassium-sparing diuretic">Potassium-sparing</a> (at <a href="/wiki/Collecting_duct_system" title="Collecting duct system">CD</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/Epithelial_sodium_channel_blocker" title="Epithelial sodium channel blocker">ESC blockers</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amiloride" title="Amiloride">Amiloride</a><sup>#</sup></li> <li><a href="/wiki/Benzamil" title="Benzamil">Benzamil</a></li> <li><a href="/wiki/Triamterene" title="Triamterene">Triamterene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antimineralocorticoid" class="mw-redirect" title="Antimineralocorticoid">Aldosterone antagonists</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/Spirolactone" title="Spirolactone">Spirolactones</a></i> <ul><li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a><sup>#</sup></li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a></li> <li><a href="/wiki/Eplerenone" title="Eplerenone">Eplerenone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Potassium canrenoate</a></li></ul></li></ul> <ul><li><i><a href="/wiki/Nonsteroidal" title="Nonsteroidal">Nonsteroidal</a></i> <ul><li><a href="/wiki/Finerenone" title="Finerenone">Finerenone</a></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/Osmotic_diuretic" title="Osmotic diuretic">Osmotic diuretics</a> (<a href="/wiki/Proximal_tubule" title="Proximal tubule">PT</a>, <a href="/wiki/Descending_limb_of_loop_of_Henle" title="Descending limb of loop of Henle">DL</a>)</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/Mannitol" title="Mannitol">Mannitol</a><sup>#</sup></li> <li><a href="/wiki/Glycerol" title="Glycerol">Glycerol</a></li> <li><a href="/wiki/Urea" title="Urea">Urea</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vasopressin_receptor_antagonist" title="Vasopressin receptor antagonist">Vasopressin receptor inhibitors</a><br />(<a href="/wiki/Distal_convoluted_tubule" title="Distal convoluted tubule">DCT</a> and <a href="/wiki/Collecting_duct" class="mw-redirect" title="Collecting duct">CD</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><i><a href="/wiki/Vasopressin_receptor_antagonist#Vaptans" title="Vasopressin receptor antagonist">Vaptans</a></i> <ul><li><a href="/wiki/Conivaptan" title="Conivaptan">Conivaptan</a></li> <li><a href="/wiki/Mozavaptan" title="Mozavaptan">Mozavaptan</a></li> <li><a href="/wiki/Satavaptan" title="Satavaptan">Satavaptan</a></li> <li><a href="/wiki/Tolvaptan" title="Tolvaptan">Tolvaptan</a></li></ul></li></ul> <ul><li><i><a href="/wiki/Vasopressin_receptor_antagonist#Demeclocycline_and_lithium" title="Vasopressin receptor antagonist">Others</a></i> <ul><li><a href="/wiki/Demeclocycline" title="Demeclocycline">Demeclocycline</a></li> <li><a href="/wiki/Lithium_carbonate" title="Lithium carbonate">Lithium carbonate</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a>, <a href="/wiki/Isopropanol" class="mw-redirect" title="Isopropanol">Isopropanol</a>, <a href="/wiki/Tert-Amyl_alcohol" title="Tert-Amyl alcohol">2M2B</a></li> <li><i><a href="/wiki/Mercurial_diuretic" title="Mercurial diuretic">mercurial diuretics</a></i> (<a href="/wiki/Chlormerodrin" title="Chlormerodrin">Chlormerodrin</a>, <a href="/wiki/Mersalyl" title="Mersalyl">Mersalyl</a>, <a href="/wiki/Meralluride" title="Meralluride">Meralluride</a>)</li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a></li> <li><a href="/wiki/Cicletanine" title="Cicletanine">Cicletanine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Combination products</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/Hydrochlorothiazide/triamterene" title="Hydrochlorothiazide/triamterene">Hydrochlorothiazide/triamterene</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: transparent; padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> 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