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id="toc-History-sublist" class="vector-toc-list"> <li id="toc-Development" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Development"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Development</span> </div> </a> <ul id="toc-Development-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-List_of_tetracycline_antibiotics" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#List_of_tetracycline_antibiotics"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>List of tetracycline antibiotics</span> </div> </a> <ul id="toc-List_of_tetracycline_antibiotics-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Use_as_research_reagents" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Use_as_research_reagents"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Use as research reagents</span> </div> </a> <ul id="toc-Use_as_research_reagents-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Tetracycline antibiotics</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 26 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-26" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">26 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AA%D8%AA%D8%B1%D8%A7%D8%B3%D9%8A%D9%83%D9%84%D9%8A%D9%86%D8%A7%D8%AA" title="تتراسيكلينات – Arabic" lang="ar" hreflang="ar" data-title="تتراسيكلينات" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Tetracykliny" title="Tetracykliny – Czech" lang="cs" hreflang="cs" data-title="Tetracykliny" 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/Tetracyklin-antibiotika" title="Tetracyklin-antibiotika – Danish" lang="da" hreflang="da" data-title="Tetracyklin-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/Tetracycline" title="Tetracycline – German" lang="de" hreflang="de" data-title="Tetracycline" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AA%D8%AA%D8%B1%D8%A7%D8%B3%D8%A7%DB%8C%DA%A9%D9%84%DB%8C%D9%86%E2%80%8C%D9%87%D8%A7" title="تتراسایکلین‌ها – Persian" lang="fa" hreflang="fa" data-title="تتراسایکلین‌ها" 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/Tetracyklin" title="Tetracyklin – Faroese" lang="fo" hreflang="fo" data-title="Tetracyklin" 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/Cyclines_(antibiotiques)" title="Cyclines (antibiotiques) – French" lang="fr" hreflang="fr" data-title="Cyclines (antibiotiques)" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Tetraciclinas" title="Tetraciclinas – Galician" lang="gl" hreflang="gl" data-title="Tetraciclinas" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%85%8C%ED%8A%B8%EB%9D%BC%EC%82%AC%EC%9D%B4%ED%81%B4%EB%A6%B0%EA%B3%84_%ED%95%AD%EC%83%9D%EC%A0%9C" title="테트라사이클린계 항생제 – Korean" lang="ko" hreflang="ko" data-title="테트라사이클린계 항생제" 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%8F%D5%A5%D5%BF%D6%80%D5%A1%D6%81%D5%AB%D5%AF%D5%AC%D5%AB%D5%B6%D5%B6%D5%A5%D6%80" title="Տետրացիկլիններ – Armenian" lang="hy" hreflang="hy" data-title="Տետրացիկլիններ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Tetraciklini" title="Tetraciklini – Croatian" lang="hr" hreflang="hr" data-title="Tetraciklini" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Antibiotik_golongan_tetrasiklina" title="Antibiotik golongan tetrasiklina – Indonesian" lang="id" hreflang="id" data-title="Antibiotik golongan tetrasiklina" 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/Tetracicline" title="Tetracicline – Italian" lang="it" hreflang="it" data-title="Tetracicline" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Tetracyclines" title="Tetracyclines – Dutch" lang="nl" hreflang="nl" data-title="Tetracyclines" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%86%E3%83%88%E3%83%A9%E3%82%B5%E3%82%A4%E3%82%AF%E3%83%AA%E3%83%B3%E7%B3%BB%E6%8A%97%E7%94%9F%E7%89%A9%E8%B3%AA" title="テトラサイクリン系抗生物質 – Japanese" lang="ja" hreflang="ja" data-title="テトラサイクリン系抗生物質" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Tetracykliny" title="Tetracykliny – Polish" lang="pl" hreflang="pl" data-title="Tetracykliny" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Tetraciclin%C4%83_(clas%C4%83)" title="Tetraciclină (clasă) – Romanian" lang="ro" hreflang="ro" data-title="Tetraciclină (clasă)" 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%A2%D0%B5%D1%82%D1%80%D0%B0%D1%86%D0%B8%D0%BA%D0%BB%D0%B8%D0%BD%D1%8B" title="Тетрациклины – Russian" lang="ru" hreflang="ru" data-title="Тетрациклины" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Tetracykl%C3%ADnov%C3%A9_antibiotikum" title="Tetracyklínové antibiotikum – Slovak" lang="sk" hreflang="sk" data-title="Tetracyklínové antibiotikum" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Tetraciklinski_antibiotik" title="Tetraciklinski antibiotik – Slovenian" lang="sl" hreflang="sl" data-title="Tetraciklinski antibiotik" 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/Tetraciklinski_antibiotici" title="Tetraciklinski antibiotici – Serbian" lang="sr" hreflang="sr" data-title="Tetraciklinski antibiotici" 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/Tetraciklinski_antibiotici" title="Tetraciklinski antibiotici – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Tetraciklinski antibiotici" 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/Tetrasykliinit" title="Tetrasykliinit – Finnish" lang="fi" hreflang="fi" data-title="Tetrasykliinit" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Thu%E1%BB%91c_kh%C3%A1ng_sinh_tetracycline" title="Thuốc kháng sinh tetracycline – Vietnamese" lang="vi" hreflang="vi" data-title="Thuốc kháng sinh tetracycline" 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/%E5%9B%9B%E7%8E%AF%E7%B4%A0%E7%B1%BB%E6%8A%97%E7%94%9F%E7%B4%A0" title="四环素类抗生素 – Wu" lang="wuu" hreflang="wuu" data-title="四环素类抗生素" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%9B%9B%E7%8E%AF%E7%B4%A0%E7%B1%BB%E6%8A%97%E7%94%9F%E7%B4%A0" 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<div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Type of broad-spectrum antibiotic</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">This article is about the group of antibiotics known as the tetracyclines. For the specific antibiotic called "tetracycline", see <a href="/wiki/Tetracycline" title="Tetracycline">tetracycline</a>.</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Tetracycline_numbering.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Tetracycline_numbering.svg/300px-Tetracycline_numbering.svg.png" decoding="async" width="300" height="154" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Tetracycline_numbering.svg/450px-Tetracycline_numbering.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Tetracycline_numbering.svg/600px-Tetracycline_numbering.svg.png 2x" data-file-width="512" data-file-height="262" /></a><figcaption>Skeletal formula of <a href="/wiki/Tetracycline" title="Tetracycline">tetracycline</a> with atoms and four rings numbered and labeled.</figcaption></figure> <p><b>Tetracyclines</b> are a group of <a href="/wiki/Broad-spectrum" class="mw-redirect" title="Broad-spectrum">broad-spectrum</a> <a href="/wiki/Antibiotic" title="Antibiotic">antibiotic</a> compounds that have a common basic structure and are either isolated directly from several species of <i><a href="/wiki/Streptomyces" title="Streptomyces">Streptomyces</a></i> <a href="/wiki/Bacteria" title="Bacteria">bacteria</a> or produced semi-synthetically from those isolated compounds.<sup id="cite_ref-Britannica_1-0" class="reference"><a href="#cite_note-Britannica-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Tetracycline molecules comprise a linear fused tetracyclic nucleus (rings designated A, B, C and D) to which a variety of <a href="/wiki/Functional_groups" class="mw-redirect" title="Functional groups">functional groups</a> are attached.<sup id="cite_ref-Chopra_2-0" class="reference"><a href="#cite_note-Chopra-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Tetracyclines are named after their four ("tetra-") hydrocarbon rings ("-cycl-") derivation ("-ine"). They are defined as a subclass of <a href="/wiki/Polyketide" title="Polyketide">polyketides</a>, having an octahydrotetracene-2-carboxamide skeleton and are known as <a href="/wiki/Derivative_(chemistry)" title="Derivative (chemistry)">derivatives</a> of polycyclic naphthacene carboxamide.<sup id="cite_ref-IUPAC_3-0" class="reference"><a href="#cite_note-IUPAC-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> While all tetracyclines have a common structure, they differ from each other by the presence of <a href="/wiki/Chloro" class="mw-redirect" title="Chloro">chloro</a>, <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a>, and <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> groups. These <a href="/wiki/Chemical_modification" title="Chemical modification">modifications</a> do not change their broad antibacterial activity, but do affect <a href="/wiki/Pharmacological" class="mw-redirect" title="Pharmacological">pharmacological</a> properties such as <a href="/wiki/Half-life" title="Half-life">half-life</a> and binding to <a href="/wiki/Protein" title="Protein">proteins</a> in <a href="/wiki/Serum_(blood)" title="Serum (blood)">serum</a>.<sup id="cite_ref-Britannica_1-1" class="reference"><a href="#cite_note-Britannica-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>Tetracyclines were discovered in the 1940s and exhibited activity against a wide range of <a href="/wiki/Microorganisms" class="mw-redirect" title="Microorganisms">microorganisms</a> including <a href="/wiki/Gram-positive" class="mw-redirect" title="Gram-positive">gram-positive</a> and <a href="/wiki/Gram-negative_bacteria" title="Gram-negative bacteria">gram-negative bacteria</a>, <a href="/wiki/Chlamydiota" title="Chlamydiota">chlamydiota</a>, <a href="/wiki/Mycoplasmatota" title="Mycoplasmatota">mycoplasmatota</a>, <a href="/wiki/Rickettsiae" class="mw-redirect" title="Rickettsiae">rickettsiae</a>, and protozoan <a href="/wiki/Parasite" class="mw-redirect" title="Parasite">parasites</a>.<sup id="cite_ref-Chopra_2-1" class="reference"><a href="#cite_note-Chopra-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Tetracycline itself was discovered later than <a href="/wiki/Chlortetracycline" title="Chlortetracycline">chlortetracycline</a> and <a href="/wiki/Oxytetracycline" title="Oxytetracycline">oxytetracycline</a> but is still considered as the parent compound for nomenclature purposes.<sup id="cite_ref-pdf_4-0" class="reference"><a href="#cite_note-pdf-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Tetracyclines are among the cheapest classes of antibiotics available and have been used extensively in prophylaxis and in treatment of human and animal infections, as well as at subtherapeutic levels in animal feed as growth promoters.<sup id="cite_ref-Chopra_2-2" class="reference"><a href="#cite_note-Chopra-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Tetracyclines are growth inhibitors (<a href="/wiki/Bacteriostatic" class="mw-redirect" title="Bacteriostatic">bacteriostatic</a>) rather than killers of the infectious agent (<a href="/wiki/Bacteriocidal" class="mw-redirect" title="Bacteriocidal">bacteriocidal</a>) and are only effective against multiplying microorganisms.<sup id="cite_ref-Britannica_1-2" class="reference"><a href="#cite_note-Britannica-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> They are short-acting and passively diffuse through <a href="/wiki/Porin_(protein)" title="Porin (protein)">porin channels</a> in the bacterial membrane. They inhibit <a href="/wiki/Protein_synthesis" class="mw-redirect" title="Protein synthesis">protein synthesis</a> by binding reversibly to the bacterial <a href="/wiki/30S_ribosomal_subunit" class="mw-redirect" title="30S ribosomal subunit">30S ribosomal subunit</a> and preventing the <a href="/wiki/Aminoacyl_tRNA" class="mw-redirect" title="Aminoacyl tRNA">aminoacyl tRNA</a> from binding to the A site of the ribosome. They also bind to some extent the bacterial <a href="/wiki/50S_ribosomal_subunit" class="mw-redirect" title="50S ribosomal subunit">50S ribosomal subunit</a> and may alter the <a href="/wiki/Cytoplasmic_membrane" class="mw-redirect" title="Cytoplasmic membrane">cytoplasmic membrane</a> causing <a href="/wiki/Intracellular" class="mw-redirect" title="Intracellular">intracellular</a> components to leak from bacterial cells. </p><p>Tetracyclines all have the same antibacterial spectrum, although there are differences in species' sensitivity to types of tetracyclines. Tetracyclines inhibit protein synthesis in both bacterial and human cells. Bacteria have a system that allows tetracyclines to be transported into the cell, whereas human cells do not. Human cells therefore are spared the effects of tetracycline on protein synthesis.<sup id="cite_ref-Britannica_1-3" class="reference"><a href="#cite_note-Britannica-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>Tetracyclines retain an important role in <a href="/wiki/Medicine" title="Medicine">medicine</a>, although their usefulness has been reduced with the onset of <a href="/wiki/Antimicrobial_resistance" title="Antimicrobial resistance">antibiotic resistance</a>.<sup id="cite_ref-Chopra_2-3" class="reference"><a href="#cite_note-Chopra-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Tetracyclines remain the treatment of choice for some specific indications.<sup id="cite_ref-Chopra_2-4" class="reference"><a href="#cite_note-Chopra-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Because not all of the tetracycline administered orally is <a href="/wiki/Absorption_(pharmacology)" title="Absorption (pharmacology)">absorbed</a> from the <a href="/wiki/Gastrointestinal_tract" title="Gastrointestinal tract">gastrointestinal tract</a>, the bacterial population of the <a href="/wiki/Intestine" class="mw-redirect" title="Intestine">intestine</a> can become resistant to tetracyclines, resulting in overgrowth of resistant organisms. The widespread use of tetracyclines is thought to have contributed to an increase in the number of tetracycline-resistant organisms, in turn rendering certain infections more resilient to treatment.<sup id="cite_ref-Britannica_1-4" class="reference"><a href="#cite_note-Britannica-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Tetracycline resistance is often due to the <a href="/wiki/Horizontal_gene_transfer" title="Horizontal gene transfer">acquisition</a> of new genes, which code for <a href="/wiki/Efflux_(microbiology)" class="mw-redirect" title="Efflux (microbiology)">energy-dependent efflux</a> of tetracyclines or for a protein that protects bacterial ribosomes from the action of tetracyclines. Furthermore, a limited number of bacteria acquire resistance to tetracyclines by mutations.<sup id="cite_ref-Chopra_2-5" class="reference"><a href="#cite_note-Chopra-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Markley-Tetracycline-Inactivating_Enzymes_5-0" class="reference"><a href="#cite_note-Markley-Tetracycline-Inactivating_Enzymes-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tetracycline_antibiotics&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tetracyclines are generally used in the treatment of infections of the urinary tract, respiratory tract, and the intestines and are also used in the treatment of <a href="/wiki/Chlamydia_infection" class="mw-redirect" title="Chlamydia infection">chlamydia</a>, especially in patients allergic to <a href="/wiki/Beta-lactam" class="mw-redirect" title="Beta-lactam">β-lactams</a> and <a href="/wiki/Macrolide" title="Macrolide">macrolides</a>; however, their use for these indications is less popular than it once was due to widespread development of <a href="/wiki/Antibiotic_resistance" class="mw-redirect" title="Antibiotic resistance">resistance</a> in the causative organisms.<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><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> Tetracyclines are widely used in the treatment of moderately severe <a href="/wiki/Acne_vulgaris" class="mw-redirect" title="Acne vulgaris">acne</a> and <a href="/wiki/Rosacea" title="Rosacea">rosacea</a> (<a href="/wiki/Tetracycline" title="Tetracycline">tetracycline</a>, <a href="/wiki/Oxytetracycline" title="Oxytetracycline">oxytetracycline</a>, <a href="/wiki/Doxycycline" title="Doxycycline">doxycycline</a> or <a href="/wiki/Minocycline" title="Minocycline">minocycline</a>).<sup id="cite_ref-Simonart_8-0" class="reference"><a href="#cite_note-Simonart-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Anaerobic bacteria are not as susceptible to tetracyclines as are aerobic bacteria.<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> <a href="/wiki/Doxycycline" title="Doxycycline">Doxycycline</a> is also used as a <a href="/wiki/Prophylactic" class="mw-redirect" title="Prophylactic">prophylactic</a> treatment for infection by <i><a href="/wiki/Bacillus_anthracis" title="Bacillus anthracis">Bacillus anthracis</a></i> (<a href="/wiki/Anthrax" title="Anthrax">anthrax</a>) and is effective against <i><a href="/wiki/Yersinia_pestis" title="Yersinia pestis">Yersinia pestis</a></i>, the infectious agent of <a href="/wiki/Bubonic_plague" title="Bubonic plague">bubonic plague</a>. It is also used for <a href="/wiki/Malaria" title="Malaria">malaria</a> treatment and prophylaxis, as well as treating elephantitis <a href="/wiki/Filariasis" title="Filariasis">filariasis</a>.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Tetracyclines remain the treatment of choice for infections caused by <a href="/wiki/Chlamydia_(bacterium)" class="mw-redirect" title="Chlamydia (bacterium)">chlamydia</a> (<a href="/wiki/Trachoma" title="Trachoma">trachoma</a>, <a href="/wiki/Psittacosis" title="Psittacosis">psittacosis</a>, <a href="/wiki/Salpingitis" title="Salpingitis">salpingitis</a>, <a href="/wiki/Urethritis" title="Urethritis">urethritis</a> and <a href="/wiki/Lymphogranuloma_venereum" title="Lymphogranuloma venereum"><i>L. venereum</i> infection</a>), <a href="/wiki/Rickettsia" title="Rickettsia">Rickettsia</a> (<a href="/wiki/Typhus" title="Typhus">typhus</a>, <a href="/wiki/Rocky_Mountain_spotted_fever" title="Rocky Mountain spotted fever">Rocky Mountain spotted fever</a>), <a href="/wiki/Brucellosis" title="Brucellosis">brucellosis</a> and <a href="/wiki/Spirochete" class="mw-redirect" title="Spirochete">spirochetal infections</a> (<a href="/wiki/Lyme_disease" title="Lyme disease">Lyme disease</a>/<a href="/wiki/Borreliosis" class="mw-redirect" title="Borreliosis">borreliosis</a> and <a href="/wiki/Syphilis" title="Syphilis">syphilis</a>).<sup id="cite_ref-Chopra_2-6" class="reference"><a href="#cite_note-Chopra-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> They are also used in <a href="/wiki/Veterinary_medicine" title="Veterinary medicine">veterinary medicine</a>.<sup id="cite_ref-Chopra_2-7" class="reference"><a href="#cite_note-Chopra-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> They may have a role in reducing the duration and severity of <a href="/wiki/Cholera" title="Cholera">cholera</a>, although drug-resistance is mounting<sup id="cite_ref-ExpertOpinPharmacother2003-Bhattacharya_11-0" class="reference"><a href="#cite_note-ExpertOpinPharmacother2003-Bhattacharya-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> and their effect on overall mortality is questioned.<sup id="cite_ref-PrimCareUpdateObGyns2001-Parsi_12-0" class="reference"><a href="#cite_note-PrimCareUpdateObGyns2001-Parsi-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <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=Tetracycline_antibiotics&action=edit&section=2" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Side-effects from tetracyclines are not common, but of particular note is <a href="/wiki/Phototoxicity" title="Phototoxicity">phototoxicity</a>. It increases the risk of sunburn under exposure to light from the sun or other sources. This may be of particular importance for those intending to take on vacations long-term doxycycline as a malaria prophylaxis. They may cause stomach or bowel upsets, and, on rare occasions, allergic reactions. Very rarely, severe headache and vision problems may be signs of dangerous <a href="/wiki/Idiopathic_intracranial_hypertension" title="Idiopathic intracranial hypertension">secondary intracranial hypertension</a>, also known as <a href="/wiki/Idiopathic_intracranial_hypertension" title="Idiopathic intracranial hypertension">idiopathic intracranial hypertension</a>. Tetracyclines are <a href="/wiki/Teratogenesis" class="mw-redirect" title="Teratogenesis">teratogens</a> due to the likelihood of causing <a href="/wiki/Tooth_(human)#Discoloration" class="mw-redirect" title="Tooth (human)">teeth discolouration</a> in the fetus as they develop in infancy. For this same reason, tetracyclines are contraindicated for use in <a href="/wiki/Children" class="mw-redirect" title="Children">children</a> under 8 years of age. Some adults also experience teeth discoloration (mild grey hue) after use. They are, however, safe to use in the first 18 weeks of pregnancy.<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> Some patients taking tetracyclines require medical supervision because they can cause <a href="/wiki/Steatosis" title="Steatosis">steatosis</a> and <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">liver toxicity</a>.<sup id="cite_ref-Deboysa-steatosis_1989_15-0" class="reference"><a href="#cite_note-Deboysa-steatosis_1989-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Amacher-caninesteatosis_1997_16-0" class="reference"><a href="#cite_note-Amacher-caninesteatosis_1997-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ekwall-steatosis_1982_17-0" class="reference"><a href="#cite_note-Ekwall-steatosis_1982-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cautions">Cautions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tetracycline_antibiotics&action=edit&section=3" title="Edit section: Cautions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tetracyclines should be used with caution by those with liver impairment. Also, because the molecules are soluble in water it can worsen <a href="/wiki/Kidney_failure" title="Kidney failure">kidney failure</a> (this is not true of the lipid-soluble agents doxycycline and <a href="/wiki/Minocycline" title="Minocycline">minocycline</a>). They may increase muscle weakness in <a href="/wiki/Myasthenia_gravis" title="Myasthenia gravis">myasthenia gravis</a> and exacerbate <a href="/wiki/Systemic_lupus_erythematosus" class="mw-redirect" title="Systemic lupus erythematosus">systemic lupus erythematosus</a>. Antacids containing aluminium and calcium reduce the absorption of all tetracyclines, and dairy products reduce absorption greatly for all but <a href="/wiki/Minocycline" title="Minocycline">minocycline</a>. The breakdown products of tetracyclines are toxic and can cause <a href="/wiki/Fanconi_syndrome" title="Fanconi syndrome">Fanconi syndrome</a>, a potentially fatal disease affecting proximal tubular function in the nephrons of the kidney. Prescriptions of these drugs should be discarded once expired because they can cause hepatotoxicity. It was once believed that tetracycline antibiotics impair the effectiveness of many types of <a href="/wiki/Hormonal_contraception" title="Hormonal contraception">hormonal contraception</a>. Recent research has shown no significant loss of effectiveness in oral contraceptives while using most tetracyclines. Despite these studies, many physicians still recommend the use of barrier contraception for people taking any tetracyclines to prevent unwanted pregnancy.<sup id="cite_ref-pmid12063491_18-0" class="reference"><a href="#cite_note-pmid12063491-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid15564203_19-0" class="reference"><a href="#cite_note-pmid15564203-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid12436822_20-0" class="reference"><a href="#cite_note-pmid12436822-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> In tetracycline preparation, stability must be considered in order to avoid formation of toxic epi-anhydrotetracyclines.<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. (March 2023)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Contraindications">Contraindications</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tetracycline_antibiotics&action=edit&section=4" title="Edit section: Contraindications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tetracycline use should be avoided in pregnant or lactating women, and in children with developing teeth because they may result in permanent staining (dark yellow-gray teeth with a darker horizontal band that goes across the top and bottom rows of teeth), and possibly affect the growth of teeth and bones. Usage during the first 12 weeks of pregnancy does not appear to increase the risk of any major birth defects.<sup id="cite_ref-otis_21-0" class="reference"><a href="#cite_note-otis-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> There may be a small increased risk for minor birth defects such as an <a href="/wiki/Inguinal_hernia" title="Inguinal hernia">inguinal hernia</a>, but the number of reports is too small to be sure if there actually is any risk.<sup id="cite_ref-otis_21-1" class="reference"><a href="#cite_note-otis-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Mechanism_of_action">Mechanism of action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tetracycline_antibiotics&action=edit&section=5" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tetracycline antibiotics are <a href="/wiki/Protein_synthesis_inhibitor" title="Protein synthesis inhibitor">protein synthesis inhibitors</a>.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> They inhibit the initiation of translation in variety of ways by binding to the <a href="/wiki/30S_ribosomal_subunit" class="mw-redirect" title="30S ribosomal subunit">30S ribosomal subunit</a>, which is made up of 16S rRNA and 21 proteins. They inhibit the binding of <a href="/wiki/Aminoacyl-tRNA" title="Aminoacyl-tRNA">aminoacyl-tRNA</a> to the <a href="/wiki/MRNA_translation" class="mw-redirect" title="MRNA translation">mRNA translation</a> complex. Some studies have shown that tetracyclines may bind to both 16S and 23S rRNAs.<sup id="cite_ref-Chukwudi_23-0" class="reference"><a href="#cite_note-Chukwudi-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Tetracyclines also have been found to inhibit <a href="/wiki/Matrix_metalloproteinases" class="mw-redirect" title="Matrix metalloproteinases">matrix metalloproteinases</a>. This mechanism does not add to their antibiotic effects, but has led to extensive research on chemically modified tetracyclines or CMTs (like <a href="/wiki/Incyclinide" title="Incyclinide">incyclinide</a>) for the treatment of <a href="/wiki/Rosacea" title="Rosacea">rosacea</a>, <a href="/wiki/Acne" title="Acne">acne</a>, <a href="/wiki/Diabetes" title="Diabetes">diabetes</a> and various types of <a href="/wiki/Neoplasm" title="Neoplasm">neoplasms</a>.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ryan_2001_26-0" class="reference"><a href="#cite_note-Ryan_2001-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> It has been shown that tetracyclines are not only active against broad spectrum of bacteria, but also against viruses, protozoa that lack mitochondria and some noninfectious conditions. The binding of tetracyclines to cellular dsRNA (double stranded RNA) may be an explanation for their wide range of effect. It can also be attributed to the nature of ribosomal protein synthesis pathways among bacteria.<sup id="cite_ref-Chukwudi_23-1" class="reference"><a href="#cite_note-Chukwudi-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Incyclinide was announced to be ineffective for rosacea in September 2007.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> Several trials have examined modified and unmodified tetracyclines for the treatment of human cancers; of those, very promising results were achieved with CMT-3 for patients with <a href="/wiki/Kaposi_Sarcoma" class="mw-redirect" title="Kaposi Sarcoma">Kaposi Sarcoma</a>.<sup id="cite_ref-Richards_2011_28-0" class="reference"><a href="#cite_note-Richards_2011-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Structure-activity_relationship">Structure-activity relationship</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tetracycline_antibiotics&action=edit&section=6" title="Edit section: Structure-activity relationship"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tetracyclines are composed of a rigid skeleton of 4 fused rings.<sup id="cite_ref-Chopra_2-8" class="reference"><a href="#cite_note-Chopra-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The rings structure of tetracyclines is divided into an upper modifiable region and a lower non modifiable region.<sup id="cite_ref-Saleha_29-0" class="reference"><a href="#cite_note-Saleha-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuoco_30-0" class="reference"><a href="#cite_note-Fuoco-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> An active tetracycline requires a C10 phenol as well as a C11-C12 keto-enol substructure in conjugation with a 12a-OH group and a C1-C3 diketo substructure.<sup id="cite_ref-Chopra_2-9" class="reference"><a href="#cite_note-Chopra-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fuoco_30-1" class="reference"><a href="#cite_note-Fuoco-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Saleha_29-1" class="reference"><a href="#cite_note-Saleha-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> Removal of the dimethylamine group at C4 reduces antibacterial activity.<sup id="cite_ref-Fuoco_30-2" class="reference"><a href="#cite_note-Fuoco-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Saleha_29-2" class="reference"><a href="#cite_note-Saleha-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> Replacement of the carboxylamine group at C2 results in reduced antibacterial activity but it is possible to add substituents to the amide nitrogen to get more soluble analogs like the prodrug <a href="/wiki/Lymecycline" title="Lymecycline">lymecycline</a>.<sup id="cite_ref-Chopra_2-10" class="reference"><a href="#cite_note-Chopra-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The simplest tetracycline with measurable antibacterial activity is 6-deoxy-6-demethyltetracycline and its structure is often considered to be the minimum pharmacophore for the tetracycle class of antibiotics.<sup id="cite_ref-Chopra_2-11" class="reference"><a href="#cite_note-Chopra-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Bristol_31-0" class="reference"><a href="#cite_note-Bristol-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> C5-C9 can be modified to make derivatives with varying antibacterial activity.<sup id="cite_ref-Fuoco_30-3" class="reference"><a href="#cite_note-Fuoco-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Saleha_29-3" class="reference"><a href="#cite_note-Saleha-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Mechanism_of_resistance">Mechanism of resistance</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tetracycline_antibiotics&action=edit&section=7" title="Edit section: Mechanism of resistance"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cells can become <a href="/wiki/Antimicrobial_resistance" title="Antimicrobial resistance">resistant</a> to tetracycline by <a href="/wiki/Enzyme" title="Enzyme">enzymatic</a> inactivation of tetracycline, <a href="/wiki/Efflux_(microbiology)" class="mw-redirect" title="Efflux (microbiology)">efflux</a>, ribosomal protection,<sup id="cite_ref-Chopra_2-12" class="reference"><a href="#cite_note-Chopra-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> reduced permeability and ribosome mutation.<sup id="cite_ref-Markley-Tetracycline-Inactivating_Enzymes_5-1" class="reference"><a href="#cite_note-Markley-Tetracycline-Inactivating_Enzymes-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Inactivation is the rarest type of resistance,<sup id="cite_ref-Forsberg_32-0" class="reference"><a href="#cite_note-Forsberg-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> where NADPH-dependent <a href="/wiki/Oxidoreductase" title="Oxidoreductase">oxidoreductase</a>, a class of antibiotic destructase, modifies the tetracycline antibiotic at their oxidative soft spot leading to an inactivation of the tetracycline antibiotic. For example, the oxireductase makes a modification on the C11a site of oxytetracycline. Both Mg<sup>2+ </sup>chelation and ribosome binding are required for the <a href="/wiki/Biological_activity" title="Biological activity">biological activity</a> of oxytetracycline and the modification attenuate the binding, leading to inactivation of the oxytetracycline antibiotic.<sup id="cite_ref-Markley-Tetracycline-Inactivating_Enzymes_5-2" class="reference"><a href="#cite_note-Markley-Tetracycline-Inactivating_Enzymes-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>In the most common mechanism of reaction, efflux,<sup id="cite_ref-Chukwudi_23-2" class="reference"><a href="#cite_note-Chukwudi-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> various resistance genes encode a membrane protein that actively pumps tetracycline out of the cell by exchanging a proton for a tetracycline cation complex. This exchange leads to a reduced cytoplasmic concentration of tetracycline.<sup id="cite_ref-Marilyn_Roberts_33-0" class="reference"><a href="#cite_note-Marilyn_Roberts-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p><p>In ribosomal protection, a resistance gene encodes a protein that can have several effects, depending on what <a href="/wiki/Gene" title="Gene">gene</a> is transferred.<sup id="cite_ref-Grossman_34-0" class="reference"><a href="#cite_note-Grossman-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> Twelve classes of ribosomal protection genes/proteins have been found.<sup id="cite_ref-Warburton_35-0" class="reference"><a href="#cite_note-Warburton-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p><p>Possible mechanisms of action of these protective proteins include: </p> <ol><li>blocking tetracyclines from binding to the ribosome<sup id="cite_ref-Li_36-0" class="reference"><a href="#cite_note-Li-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup></li> <li>binding to the ribosome and distorting the structure to still allow t-RNA binding while tetracycline is bound<sup id="cite_ref-Donhofer_37-0" class="reference"><a href="#cite_note-Donhofer-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup></li> <li>binding to the ribosome and dislodging tetracycline<sup id="cite_ref-Li_36-1" class="reference"><a href="#cite_note-Li-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Connell_38-0" class="reference"><a href="#cite_note-Connell-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup></li></ol> <div class="mw-heading mw-heading2"><h2 id="Administration">Administration</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tetracycline_antibiotics&action=edit&section=8" title="Edit section: Administration"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>When ingested, it is usually recommended that the more <a href="/wiki/Water-soluble" class="mw-redirect" title="Water-soluble">water-soluble</a>, short-acting tetracyclines (plain tetracycline, chlortetracycline, <a href="/wiki/Oxytetracycline" title="Oxytetracycline">oxytetracycline</a>, <a href="/wiki/Demeclocycline" title="Demeclocycline">demeclocycline</a> and <a href="/wiki/Methacycline" class="mw-redirect" title="Methacycline">methacycline</a>) be taken with a full glass of water, either two hours after eating or two hours before eating. This is partly because most tetracyclines bind with food and also easily with <a href="/wiki/Magnesium" title="Magnesium">magnesium</a>, <a href="/wiki/Aluminium" title="Aluminium">aluminium</a>, <a href="/wiki/Iron" title="Iron">iron</a> and <a href="/wiki/Calcium" title="Calcium">calcium</a>, which reduces their ability to be completely <a href="/wiki/Absorption_(pharmacology)" title="Absorption (pharmacology)">absorbed</a> by the body. Dairy products, <a href="/wiki/Antacids" class="mw-redirect" title="Antacids">antacids</a> and preparations containing iron should be avoided near the time of taking the drug. Partial exceptions to these rules occur for <a href="/wiki/Doxycycline" title="Doxycycline">doxycycline</a> and <a href="/wiki/Minocycline" title="Minocycline">minocycline</a>, which may be taken with food (though not iron, antacids, or calcium supplements). <a href="/wiki/Minocycline" title="Minocycline">Minocycline</a> can be taken with dairy products because it does not chelate calcium as readily, although dairy products do decrease absorption of minocycline slightly.<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </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=Tetracycline_antibiotics&action=edit&section=9" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The history of the tetracyclines involves the collective contributions of thousands of dedicated researchers, scientists, clinicians, and business executives. Tetracyclines were discovered in the 1940s, first reported in scientific literature in 1948, and exhibited activity against a wide range of microorganisms. The first members of the tetracycline group to be described were chlortetracycline and oxytetracycline.<sup id="cite_ref-Chopra_2-13" class="reference"><a href="#cite_note-Chopra-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Nelson_40-0" class="reference"><a href="#cite_note-Nelson-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Chlortetracycline" title="Chlortetracycline">Chlortetracycline</a> (Aureomycin) was first discovered as an ordinary item in 1945 and initially endorsed in 1948<sup id="cite_ref-Essays_41-0" class="reference"><a href="#cite_note-Essays-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> by <a href="/wiki/Benjamin_Minge_Duggar" title="Benjamin Minge Duggar">Benjamin Minge Duggar</a>, a 73-year-old emeritus professor of botany employed by American Cyanamid – Lederle Laboratories, under the leadership of <a href="/wiki/Yellapragada_Subbarow" title="Yellapragada Subbarow">Yellapragada Subbarow</a>. Duggar derived the substance from a Missouri soil sample, golden-colored, fungus-like, soil-dwelling bacterium named <a href="/wiki/Streptomyces_aureofaciens" class="mw-redirect" title="Streptomyces aureofaciens">Streptomyces aureofaciens</a>.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> About the same time as Lederle discovered aureomycin, <a href="/wiki/Pfizer" title="Pfizer">Pfizer</a> was scouring the globe for new antibiotics. Soil samples were collected from jungles, deserts, mountaintops, and oceans. But ultimately <a href="/wiki/Oxytetracycline" title="Oxytetracycline">oxytetracycline</a> (terramycin) was isolated in 1949 by Alexander Finlay from a soil sample collected on the grounds of a factory in Terre Haute, Indiana.<sup id="cite_ref-Lin_43-0" class="reference"><a href="#cite_note-Lin-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> It came from a similar soil bacterium named Streptomyces rimosus.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> From the beginning, terramycin was a molecule enveloped in controversy. It was the subject of the first mass-marketing campaign by a modern pharmaceutical company. <a href="/wiki/Pfizer" title="Pfizer">Pfizer</a> advertised the drug heavily in medical journals, eventually spending twice as much on marketing as it did to discover and develop terramycin. Still, it turned <a href="/wiki/Pfizer" title="Pfizer">Pfizer</a>, then a small company, into a pharmaceutical giant.<sup id="cite_ref-Lin_43-1" class="reference"><a href="#cite_note-Lin-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Pfizer" title="Pfizer">Pfizer</a> group, led by Francis A. Hochstein, in loose collaboration with and Robert Burns Woodward, determined the structure of <a href="/wiki/Oxytetracycline" title="Oxytetracycline">oxytetracycline</a>, enabling Lloyd H. Conover to successfully produce <a href="/wiki/Tetracycline" title="Tetracycline">tetracycline</a> itself as a synthetic product.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> In 1955, Conover discovered that hydrogenolysis of aureomycin gives a deschloro product that is just as active as the original product. This proved for the first time that chemically modified antibiotics could have biological activity. Within a few years, a number of semisynthetic tetracyclines had entered the market, and now most antibiotic discoveries are of novel active derivatives of older compounds.<sup id="cite_ref-Lin_43-2" class="reference"><a href="#cite_note-Lin-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> Other tetracyclines were identified later, either as naturally occurring molecules, e.g., tetracycline from S. aureofaciens, S. rimosus, and S. viridofaciens and dimethyl-chlortetracycline from S. aureofaciens, or as products of semisynthetic approaches, e.g., methacycline, doxycycline, and minocycline.<sup id="cite_ref-Chopra_2-14" class="reference"><a href="#cite_note-Chopra-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Essays_41-1" class="reference"><a href="#cite_note-Essays-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p><p>Research conducted by <a href="/wiki/Anthropology" title="Anthropology">anthropologist</a> <a href="/wiki/George_J._Armelagos" title="George J. Armelagos">George J. Armelagos</a> and his team at <a href="/wiki/Emory_University" title="Emory University">Emory University</a> showed that ancient <a href="/wiki/Nubia" title="Nubia">Nubians</a> from the post-<a href="/wiki/Mero%C3%AB" title="Meroë">Meroitic</a> period (around AD 350) had deposits of tetracycline in their bones, detectable through analyses of cross-sections through <a href="/wiki/Ultraviolet" title="Ultraviolet">ultraviolet</a> light – the deposits are fluorescent, just as are modern ones. Armelagos suggested that this was due to ingestion of the local <a href="/wiki/History_of_beer#Early_beers" title="History of beer">ancient beer</a> (very much like the Egyptian beer<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup>), made from contaminated stored grains.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Development">Development</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tetracycline_antibiotics&action=edit&section=10" title="Edit section: Development"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tetracyclines were noted for their broad spectrum antibacterial activity and were commercialized with clinical success beginning in the late 1940s to the early 1950s. The second-generation semisynthetic analogs and more recent third-generation compounds show the continued evolution of the tetracycline platform towards derivatives with increased potency as well as efficacy against tetracycline-resistant bacteria, with improved pharmacokinetic and chemical properties.<sup id="cite_ref-Nelson_40-1" class="reference"><a href="#cite_note-Nelson-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> Shortly after the introduction of tetracycline therapy, the first tetracycline-resistant bacterial pathogen was identified. Since then, tetracycline-resistant bacterial pathogens have continued to be identified, limiting tetracycline's effectiveness in treatment of bacterial disease.<sup id="cite_ref-Eliopoulos_48-0" class="reference"><a href="#cite_note-Eliopoulos-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p><p>Glycylcyclines and fluorocyclines are new classes of antibiotics derived from tetracycline.<sup id="cite_ref-Zhanel_49-0" class="reference"><a href="#cite_note-Zhanel-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-JAMA_50-0" class="reference"><a href="#cite_note-JAMA-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Eliopoulos_48-1" class="reference"><a href="#cite_note-Eliopoulos-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> These tetracycline analogues are specifically designed to overcome two common mechanisms of tetracycline resistance, namely resistance mediated by acquired efflux pumps and/or ribosomal protection. In 2005, <a href="/wiki/Tigecycline" title="Tigecycline">tigecycline</a>, the first member of a new subgroup of tetracyclines named glycylcyclines, was introduced to treat infections that are resistant to other antimicrobials.<sup id="cite_ref-pmid16723578_51-0" class="reference"><a href="#cite_note-pmid16723578-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> Although it is structurally related to <a href="/wiki/Minocycline" title="Minocycline">minocycline</a>, alterations to the molecule resulted in its expanded spectrum of activity and decreased susceptibility to the development of resistance when compared with other tetracycline antibiotics. Like <a href="/wiki/Minocycline" title="Minocycline">minocycline</a>, <a href="/wiki/Tigecycline" title="Tigecycline">tigecycline</a> binds to the bacterial 30S ribosome, blocking the entry of transfer RNA. This ultimately prevents protein synthesis and thus inhibiting bacterial growth. However, the addition of an N,N,-dimethylglycylamido group at the 9 position of the minocycline molecule increases the affinity of <a href="/wiki/Tigecycline" title="Tigecycline">tigecycline</a> for the ribosomal target up to 5 times when compared with <a href="/wiki/Minocycline" title="Minocycline">minocycline</a> or <a href="/wiki/Tetracycline" title="Tetracycline">tetracycline</a>. This allows for an expanded spectrum of activity and decreased susceptibility to the development of resistance.<sup id="cite_ref-Eliopoulos_48-2" class="reference"><a href="#cite_note-Eliopoulos-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> While <a href="/wiki/Tigecycline" title="Tigecycline">tigecycline</a> was the first tetracycline approved in over 20 years, other, newer versions of tetracyclines are currently in human clinical trials.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="List_of_tetracycline_antibiotics">List of tetracycline antibiotics</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tetracycline_antibiotics&action=edit&section=11" title="Edit section: List of tetracycline antibiotics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable sortable"> <tbody><tr> <th>Antibiotic (<a href="/wiki/International_nonproprietary_name" title="International nonproprietary name">INN</a>)</th> <th>Source<sup id="cite_ref-Nelson_40-2" class="reference"><a href="#cite_note-Nelson-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup></th> <th>Half-life<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup></th> <th>Notes </th></tr> <tr> <td><a href="/wiki/Tetracycline" title="Tetracycline">Tetracycline</a></td> <td rowspan="4">Naturally occurring</td> <td>6–8 hours (short)</td> <td> </td></tr> <tr> <td><a href="/wiki/Chlortetracycline" title="Chlortetracycline">Chlortetracycline</a></td> <td>6–8 hours (short)</td> <td> </td></tr> <tr> <td><a href="/wiki/Oxytetracycline" title="Oxytetracycline">Oxytetracycline</a></td> <td>6–8 hours (short)</td> <td> </td></tr> <tr> <td><a href="/wiki/Demeclocycline" title="Demeclocycline">Demeclocycline</a></td> <td>12 hours (intermediate)</td> <td> </td></tr> <tr> <td><a href="/wiki/Lymecycline" title="Lymecycline">Lymecycline</a></td> <td rowspan="6">Semi-synthetic</td> <td>6–8 hours (short)</td> <td> </td></tr> <tr> <td><a href="/wiki/Meclocycline" title="Meclocycline">Meclocycline</a></td> <td>6–8 hours (short)</td> <td>(no longer marketed) </td></tr> <tr> <td><a href="/wiki/Methacycline" class="mw-redirect" title="Methacycline">Methacycline</a></td> <td>12 hours (intermediate)</td> <td> </td></tr> <tr> <td><a href="/wiki/Minocycline" title="Minocycline">Minocycline</a></td> <td>16+ hours (long)</td> <td> </td></tr> <tr> <td><a href="/wiki/Rolitetracycline" title="Rolitetracycline">Rolitetracycline</a></td> <td>6–8 hours (short)</td> <td> </td></tr> <tr> <td><a href="/wiki/Doxycycline" title="Doxycycline">Doxycycline</a></td> <td>16+ hours (long)</td> <td> </td></tr> <tr> <td><a href="/wiki/Tigecycline" title="Tigecycline">Tigecycline</a></td> <td>Glycylcyclines</td> <td>16+ hours (long)</td> <td> </td></tr> <tr> <td><a href="/wiki/Eravacycline" title="Eravacycline">Eravacycline</a></td> <td rowspan="3">Newer</td> <td>16+ hours (long)</td> <td>(formerly known as TP-434) received FDA approval on August 27, 2018, for treatment of complicated intra-abdominal infections.<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Sarecycline" title="Sarecycline">Sarecycline</a></td> <td>16+ hours (long)</td> <td>(formerly known as WC 3035) received FDA approval on October 1, 2018, for treatment of moderate to severe <a href="/wiki/Acne_vulgaris" class="mw-redirect" title="Acne vulgaris">acne vulgaris</a>.<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> Sarecycline is a <a href="/wiki/Narrow-spectrum_antibiotic" title="Narrow-spectrum antibiotic">narrow-spectrum</a> antibiotic.<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid30397052_57-0" class="reference"><a href="#cite_note-pmid30397052-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Omadacycline" title="Omadacycline">Omadacycline</a></td> <td>16+ hours (long)</td> <td>(formerly known as PTK-0796<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup>) received <a href="/wiki/FDA" class="mw-redirect" title="FDA">FDA</a> approval on October 2, 2018, for treatment of <a href="/wiki/Community-acquired_pneumonia" title="Community-acquired pneumonia">community-acquired pneumonia</a><sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> and acute <a href="/wiki/Skin_and_skin_structure_infection" title="Skin and skin structure infection">skin and skin structure infections</a>.<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Use_as_research_reagents">Use as research reagents</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tetracycline_antibiotics&action=edit&section=12" title="Edit section: Use as research reagents"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Members of the tetracycline class of antibiotics are often used as research <a href="/wiki/Reagent" title="Reagent">reagents</a> in <i>in vitro</i> and <i>in vivo</i> biomedical research experiments involving bacteria as well in experiments in eukaryotic cells and organisms with inducible protein expression systems using <a href="/wiki/Tetracycline-controlled_transcriptional_activation" title="Tetracycline-controlled transcriptional activation">tetracycline-controlled transcriptional activation</a>.<sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> The mechanism of action for the antibacterial effect of tetracyclines relies on disrupting protein translation in bacteria, thereby damaging the ability of microbes to grow and repair; however protein translation is also disrupted in eukaryotic <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a> leading to effects that may <a href="/wiki/Confound" class="mw-redirect" title="Confound">confound</a> experimental results.<sup id="cite_ref-pmid25772356_62-0" class="reference"><a href="#cite_note-pmid25772356-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid26475870_63-0" class="reference"><a href="#cite_note-pmid26475870-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> It can be used as an artificial <a href="/wiki/Biomarker" title="Biomarker">biomarker</a> in wildlife to check if wild animals are consuming a bait that contains a <a href="/wiki/Vaccine" title="Vaccine">vaccine</a> or medication. Since it is <a href="/wiki/Fluorescent" class="mw-redirect" title="Fluorescent">fluorescent</a> and binds to <a href="/wiki/Calcium" title="Calcium">calcium</a>, a UV lamp can be used to check if it is in a tooth pulled from an animal. For example, it was used to check uptake of oral <a href="/wiki/Rabies_vaccine" title="Rabies vaccine">rabies vaccine</a> baits by <a href="/wiki/Raccoon" title="Raccoon">raccoons</a> in the USA. However, this is an invasive procedure for the animal and labour-intensive for the researcher. Therefore, other dyes such as <a href="/wiki/Rhodamine_B" title="Rhodamine B">rhodamine B</a> that can be detected in hair and whiskers are preferred.<sup id="cite_ref-aphis_wildlife_64-0" class="reference"><a href="#cite_note-aphis_wildlife-64"><span class="cite-bracket">[</span>64<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=Tetracycline_antibiotics&action=edit&section=13" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Glycylcycline" title="Glycylcycline">Glycylcycline</a></li> <li><a href="/wiki/Eravacycline" title="Eravacycline">Eravacycline</a></li> <li><a href="/wiki/Tetracycline_controlled_transcriptional_activation" class="mw-redirect" title="Tetracycline controlled transcriptional activation">Tetracycline controlled transcriptional activation</a></li> <li><a href="/wiki/Animal_Drug_Availability_Act_1996" title="Animal Drug Availability Act 1996">Animal Drug Availability Act 1996</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=Tetracycline_antibiotics&action=edit&section=14" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-Britannica-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Britannica_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Britannica_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Britannica_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Britannica_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Britannica_1-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.britannica.com/science/tetracycline">"Tetracycline"</a>. <i>Encyclopedia Britannica</i><span class="reference-accessdate">. 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Archived from <a rel="nofollow" class="external text" href="https://docs.google.com/viewer?a=v&q=cache%3ApirPMTK4diYJ%3Awww.aspenpharma.com.au%2Fproduct_info%2Fpi%2FPI_Achromycin.pdf+&hl=tr&gl=tr&pid=bl&srcid=ADGEESglhms2KnMNxqTQggqA1NFIZ5bCPuVLdnVkcqcQBZHQ7GvUg6eP_aE3BuPXrboyT3ww9GhDSuuuDWSY9l81b0HjWhxqheQ6K3oQVWtigcxfcKKhVfC7K-qDg-o_jKhPoG0DDjVj&sig=AHIEtbShF40Ty8nx5wadZwoCT_gqW8Ycww">the original</a> on 2016-04-09<span class="reference-accessdate">. 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Retrieved <span class="nowrap">2017-05-03</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+12th+Wildlife+Damage+Management+Conference&rft.atitle=A+Review+of+Biomarkers+Used+For+Wildlife+Damage+and+Disease+Management&rft.pages=%3Cspan+class%3D%22nowrap%22%3E217-%3C%2Fspan%3E222&rft.date=2007&rft.aulast=Fry&rft.aufirst=TL&rft.au=Dunbar%2C+MR&rft_id=https%3A%2F%2Fwww.aphis.usda.gov%2Fwildlife_damage%2Fnwrc%2Fpublications%2F07pubs%2Ffry071.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATetracycline+antibiotics" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tetracycline_antibiotics&action=edit&section=15" title="Edit section: External links"><span>edit</span></a><span 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id="Antibacterials_that_inhibit_protein_synthesis_(J01A,_J01B,_J01F,_J01G,_QJ01XQ)575" style="font-size:114%;margin:0 4em"><a href="/wiki/Antibiotic" title="Antibiotic">Antibacterials</a> that <a href="/wiki/Protein_synthesis_inhibitor" title="Protein synthesis inhibitor">inhibit protein synthesis</a> (<a href="/wiki/ATC_code_J01#J01A" title="ATC code J01">J01A</a>, <a href="/wiki/ATC_code_J01#J01B" title="ATC code J01">J01B</a>, <a href="/wiki/ATC_code_J01#J01F" title="ATC code J01">J01F</a>, <a href="/wiki/ATC_code_J01#J01G" title="ATC code J01">J01G</a>, <a href="/wiki/ATC_code_J01#QJ01XQ" title="ATC code J01">QJ01XQ</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/30S" class="mw-redirect" title="30S">30S</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/Aminoglycoside" title="Aminoglycoside">Aminoglycosides</a><br />(<a href="/wiki/Bacterial_translation#Initiation" title="Bacterial translation">initiation</a> inhibitors)</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%">-mycin (<i><a href="/wiki/Streptomyces" title="Streptomyces">Streptomyces</a></i>)</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/Streptomycin" title="Streptomycin">Streptomycin</a><sup>#</sup></li> <li><a href="/wiki/Dihydrostreptomycin" title="Dihydrostreptomycin">Dihydrostreptomycin</a></li></ul> <ul><li><a href="/wiki/Neomycin" title="Neomycin">Neomycin</a><sup>#</sup> <ul><li><a href="/wiki/Framycetin" class="mw-redirect" title="Framycetin">Framycetin</a></li> <li><a href="/wiki/Paromomycin" title="Paromomycin">Paromomycin</a><sup>#</sup></li> <li><a href="/wiki/Ribostamycin" title="Ribostamycin">Ribostamycin</a></li></ul></li></ul> <ul><li><a href="/wiki/Kanamycin" class="mw-redirect" title="Kanamycin">Kanamycin</a> <ul><li><a href="/wiki/Amikacin" title="Amikacin">Amikacin</a><sup>#</sup></li> <li><a href="/wiki/Arbekacin" title="Arbekacin">Arbekacin</a></li> <li><a href="/wiki/Bekanamycin" title="Bekanamycin">Bekanamycin</a></li> <li><a href="/wiki/Dibekacin" title="Dibekacin">Dibekacin</a></li></ul></li></ul> <ul><li><a href="/wiki/Tobramycin" title="Tobramycin">Tobramycin</a> (<a href="/wiki/Loteprednol/tobramycin" title="Loteprednol/tobramycin">+loteprednol</a>)</li> <li><a href="/wiki/Spectinomycin" title="Spectinomycin">Spectinomycin</a><sup>#</sup></li> <li><a href="/wiki/Hygromycin_B" title="Hygromycin B">Hygromycin B</a></li> <li><a href="/wiki/Totomycin" title="Totomycin">Totomycin</a></li> <li><a href="/wiki/Apramycin" title="Apramycin">Apramycin</a></li> <li><a href="/wiki/Nourseothricin" title="Nourseothricin">Nourseothricin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">-micin (<i><a href="/wiki/Micromonospora" title="Micromonospora">Micromonospora</a></i>)</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/Gentamicin" title="Gentamicin">Gentamicin</a><sup>#</sup> <ul><li><a href="/wiki/Netilmicin" title="Netilmicin">Netilmicin</a></li> <li><a href="/wiki/Sisomicin" title="Sisomicin">Sisomicin</a></li> <li><a href="/wiki/Micronomicin" title="Micronomicin">Micronomicin</a></li> <li><a href="/wiki/Plazomicin" title="Plazomicin">Plazomicin</a><sup>#</sup></li> <li><a href="/wiki/Isepamicin" title="Isepamicin">Isepamicin</a></li></ul></li></ul> <ul><li><a href="/wiki/Verdamicin" title="Verdamicin">Verdamicin</a></li> <li><a href="/wiki/Astromicin" title="Astromicin">Astromicin</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/Butirosin" title="Butirosin">Butirosin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Tetracycline antibiotics</a><br />(<a href="/wiki/Transfer_RNA" title="Transfer RNA">tRNA</a> binding)</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%">Tetracyclines</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/Doxycycline" title="Doxycycline">Doxycycline</a><sup>#</sup></li> <li><a href="/wiki/Chlortetracycline" title="Chlortetracycline">Chlortetracycline</a></li> <li><a href="/wiki/Clomocycline" title="Clomocycline">Clomocycline</a></li> <li><a href="/wiki/Demeclocycline" title="Demeclocycline">Demeclocycline</a></li> <li><a href="/wiki/Eravacycline" title="Eravacycline">Eravacycline</a></li> <li><a href="/wiki/Lymecycline" title="Lymecycline">Lymecycline</a></li> <li><a href="/wiki/Meclocycline" title="Meclocycline">Meclocycline</a><sup>‡</sup></li> <li><a href="/wiki/Metacycline" title="Metacycline">Metacycline</a></li> <li><a href="/wiki/Minocycline" title="Minocycline">Minocycline</a></li> <li><a href="/wiki/Omadacycline" title="Omadacycline">Omadacycline</a></li> <li><a href="/wiki/Oxytetracycline" title="Oxytetracycline">Oxytetracycline</a></li> <li><a href="/wiki/Penimepicycline" title="Penimepicycline">Penimepicycline</a></li> <li><a href="/wiki/Rolitetracycline" title="Rolitetracycline">Rolitetracycline</a></li> <li><a href="/wiki/Sarecycline" title="Sarecycline">Sarecycline</a></li> <li><a href="/wiki/Tetracycline" title="Tetracycline">Tetracycline</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glycylcycline" title="Glycylcycline">Glycylcyclines</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/Tigecycline" title="Tigecycline">Tigecycline</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/50S" class="mw-redirect" title="50S">50S</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/2-Oxazolidone" class="mw-redirect" title="2-Oxazolidone">Oxazolidinone</a><br />(<a href="/wiki/Bacterial_translation#Initiation" title="Bacterial translation">initiation</a> inhibitors)</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/Eperezolid" title="Eperezolid">Eperezolid</a></li> <li><a href="/wiki/Linezolid" title="Linezolid">Linezolid</a><sup>#</sup></li> <li><a href="/wiki/Posizolid" title="Posizolid">Posizolid</a></li> <li><a href="/wiki/Radezolid" title="Radezolid">Radezolid</a></li> <li><a href="/wiki/Ranbezolid" title="Ranbezolid">Ranbezolid</a></li> <li><a href="/wiki/Sutezolid" title="Sutezolid">Sutezolid</a></li> <li><a href="/wiki/Tedizolid" title="Tedizolid">Tedizolid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Peptidyl_transferase" class="mw-redirect" title="Peptidyl transferase">Peptidyl transferase</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 id="Amphenicols15" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Amphenicol" title="Amphenicol">Amphenicols</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/Chloramphenicol" title="Chloramphenicol">Chloramphenicol</a><sup>#</sup></li> <li><a href="/wiki/Azidamfenicol" title="Azidamfenicol">Azidamfenicol</a></li> <li><a href="/wiki/Thiamphenicol" title="Thiamphenicol">Thiamphenicol</a></li> <li><a href="/wiki/Florfenicol" title="Florfenicol">Florfenicol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">MLS (<a href="/wiki/Bacterial_translation#Elongation" title="Bacterial translation">transpeptidation/translocation</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/Macrolide" title="Macrolide">Macrolides</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/Azithromycin" title="Azithromycin">Azithromycin</a><sup>#</sup></li> <li><a href="/wiki/Boromycin" title="Boromycin">Boromycin</a></li> <li><a href="/wiki/Carbomycin" title="Carbomycin">Carbomycin</a></li> <li><a href="/wiki/Carrimycin" title="Carrimycin">Carrimycin</a></li> <li><a href="/wiki/Clarithromycin" title="Clarithromycin">Clarithromycin</a><sup>#</sup></li> <li><a href="/wiki/Dirithromycin" title="Dirithromycin">Dirithromycin</a></li> <li><a href="/wiki/Erythromycin" title="Erythromycin">Erythromycin</a><sup>#</sup></li> <li><a href="/wiki/Flurithromycin" title="Flurithromycin">Flurithromycin</a></li> <li><a href="/wiki/Gamithromycin" title="Gamithromycin">Gamithromycin</a></li> <li><a href="/wiki/Josamycin" title="Josamycin">Josamycin</a></li> <li><a href="/wiki/Kitasamycin" title="Kitasamycin">Kitasamycin</a></li> <li><a href="/wiki/Midecamycin" title="Midecamycin">Midecamycin</a></li> <li><a href="/wiki/Miocamycin" title="Miocamycin">Miocamycin</a></li> <li><a href="/wiki/Nafithromycin" title="Nafithromycin">Nafithromycin</a></li> <li><a href="/wiki/Oleandomycin" title="Oleandomycin">Oleandomycin</a></li> <li><a href="/wiki/Rokitamycin" title="Rokitamycin">Rokitamycin</a></li> <li><a href="/wiki/Roxithromycin" title="Roxithromycin">Roxithromycin</a></li> <li><a href="/wiki/Solithromycin" title="Solithromycin">Solithromycin</a></li> <li><a href="/wiki/Spiramycin" title="Spiramycin">Spiramycin</a></li> <li><a href="/wiki/Telithromycin" title="Telithromycin">Telithromycin</a></li> <li><a href="/wiki/Tildipirosin" title="Tildipirosin">Tildipirosin</a></li> <li><a href="/wiki/Tilmicosin" title="Tilmicosin">Tilmicosin</a></li> <li><a href="/wiki/Troleandomycin" title="Troleandomycin">Troleandomycin</a></li> <li><a href="/wiki/Tulathromycin" title="Tulathromycin">Tulathromycin</a></li> <li><a href="/wiki/Tylosin" title="Tylosin">Tylosin</a></li> <li><a href="/wiki/Tylvalosin" title="Tylvalosin">Tylvalosin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ketolide" title="Ketolide">Ketolides</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/Telithromycin" title="Telithromycin">Telithromycin</a><sup>‡</sup></li> <li><a href="/wiki/Cethromycin" title="Cethromycin">Cethromycin</a></li> <li><a href="/wiki/Solithromycin" title="Solithromycin">Solithromycin</a><sup>†</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lincosamides" title="Lincosamides">Lincosamides</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/Clindamycin" title="Clindamycin">Clindamycin</a><sup>#</sup></li> <li><a href="/wiki/Lincomycin" title="Lincomycin">Lincomycin</a></li> <li><a href="/wiki/Pirlimycin" title="Pirlimycin">Pirlimycin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Streptogramin" title="Streptogramin">Streptogramins</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/Pristinamycin" title="Pristinamycin">Pristinamycin</a> (<a href="/wiki/Pristinamycin_IA" title="Pristinamycin IA">IA</a>, <a href="/wiki/Pristinamycin_IIA" title="Pristinamycin IIA">IIA</a>, <a href="/wiki/Pristinamycin_IIB" title="Pristinamycin IIB">IIB</a>)</li> <li><a href="/wiki/NXL103" class="mw-redirect" title="NXL103">NXL103</a> (<a href="/wiki/Flopristin" title="Flopristin">Flopristin</a>, <a href="/wiki/Linopristin" title="Linopristin">Linopristin</a>)</li> <li><a href="/wiki/Quinupristin/dalfopristin" title="Quinupristin/dalfopristin">Quinupristin/dalfopristin</a> (<a href="/wiki/Dalfopristin" title="Dalfopristin">Dalfopristin</a>, <a href="/wiki/Quinupristin" title="Quinupristin">Quinupristin</a>)</li> <li><a href="/wiki/Streptogramin_A" title="Streptogramin A">Streptogramin A</a></li> <li><a href="/wiki/Streptogramin_B" title="Streptogramin B">Streptogramin B</a></li> <li><a href="/wiki/Virginiamycin" title="Virginiamycin">Virginiamycin</a> (<a href="/wiki/Virginiamycin_S1" title="Virginiamycin S1">S1</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="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 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