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class="vector-toc-numb">2</span> <span>Mechanism of action</span> </div> </a> <ul id="toc-Mechanism_of_action-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Ecology" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Ecology"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Ecology</span> </div> </a> <ul id="toc-Ecology-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Avian_studies" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Avian_studies"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Avian studies</span> </div> </a> <ul id="toc-Avian_studies-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Food_sources" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Food_sources"> <div class="vector-toc-text"> <span 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class="vector-toc-list"> </ul> </li> <li id="toc-Males" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Males"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Males</span> </div> </a> <ul id="toc-Males-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Infant_formula" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Infant_formula"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Infant formula</span> </div> </a> <ul id="toc-Infant_formula-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Ethnopharmacology" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Ethnopharmacology"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Ethnopharmacology</span> </div> </a> <ul id="toc-Ethnopharmacology-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" 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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%A5%D8%B3%D8%AA%D8%B1%D9%88%D8%AC%D9%8A%D9%86_%D9%86%D8%A8%D8%A7%D8%AA%D9%8A" title="إستروجين نباتي – Arabic" lang="ar" hreflang="ar" data-title="إستروجين نباتي" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Fitoestrogen" title="Fitoestrogen – Catalan" lang="ca" hreflang="ca" data-title="Fitoestrogen" 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/Fytoestrogen" title="Fytoestrogen – Czech" lang="cs" hreflang="cs" data-title="Fytoestrogen" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Phyto%C3%B6strogene" title="Phytoöstrogene – German" lang="de" hreflang="de" data-title="Phytoöstrogene" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Fitoestr%C3%B3geno" title="Fitoestrógeno – Spanish" lang="es" hreflang="es" data-title="Fitoestrógeno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%81%DB%8C%D8%AA%D9%88%D8%A7%D8%B3%D8%AA%D8%B1%D9%88%DA%98%D9%86" title="فیتواستروژن – Persian" lang="fa" hreflang="fa" data-title="فیتواستروژن" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Phytoestrog%C3%A8ne" title="Phytoestrogène – French" lang="fr" hreflang="fr" data-title="Phytoestrogène" 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/Fitoestr%C3%B3xeno" title="Fitoestróxeno – Galician" lang="gl" hreflang="gl" data-title="Fitoestróxeno" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Fitoestrogeno" title="Fitoestrogeno – Italian" lang="it" hreflang="it" data-title="Fitoestrogeno" 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%A4%D7%99%D7%98%D7%95%D7%90%D7%A1%D7%98%D7%A8%D7%95%D7%92%D7%9F" title="פיטואסטרוגן – Hebrew" lang="he" hreflang="he" data-title="פיטואסטרוגן" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A4%D0%B8%D1%82%D0%BE%D0%B5%D1%81%D1%82%D1%80%D0%BE%D0%B3%D0%B5%D0%BD" title="Фитоестроген – Macedonian" lang="mk" hreflang="mk" data-title="Фитоестроген" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Fitoestrogen" title="Fitoestrogen – Malay" lang="ms" hreflang="ms" data-title="Fitoestrogen" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Fyto-oestrogenen" title="Fyto-oestrogenen – Dutch" lang="nl" hreflang="nl" data-title="Fyto-oestrogenen" 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%95%E3%82%A3%E3%83%88%E3%82%A8%E3%82%B9%E3%83%88%E3%83%AD%E3%82%B2%E3%83%B3" title="フィトエストロゲン – Japanese" lang="ja" hreflang="ja" data-title="フィトエストロゲン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Fitoestrogeny" title="Fitoestrogeny – Polish" lang="pl" hreflang="pl" data-title="Fitoestrogeny" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Fitoestr%C3%B3geno" title="Fitoestrógeno – Portuguese" lang="pt" hreflang="pt" data-title="Fitoestrógeno" 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/Fitoestrogen" title="Fitoestrogen – Romanian" lang="ro" hreflang="ro" data-title="Fitoestrogen" 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%A4%D0%B8%D1%82%D0%BE%D1%8D%D1%81%D1%82%D1%80%D0%BE%D0%B3%D0%B5%D0%BD%D1%8B" title="Фитоэстрогены – Russian" lang="ru" hreflang="ru" data-title="Фитоэстрогены" 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/Fytoestrog%C3%A9n" title="Fytoestrogén – Slovak" lang="sk" hreflang="sk" data-title="Fytoestrogén" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A4%D0%B8%D1%82%D0%BE%D0%B5%D1%81%D1%82%D1%80%D0%BE%D0%B3%D0%B5%D0%BD%D0%B8" title="Фитоестрогени – Serbian" lang="sr" hreflang="sr" data-title="Фитоестрогени" 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-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Kasviestrogeenit" title="Kasviestrogeenit – Finnish" lang="fi" hreflang="fi" data-title="Kasviestrogeenit" 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/Fyto%C3%B6strogen" title="Fytoöstrogen – Swedish" lang="sv" hreflang="sv" data-title="Fytoöstrogen" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%84%E0%B8%9F%E0%B9%82%E0%B8%95%E0%B9%80%E0%B8%AD%E0%B8%AA%E0%B9%82%E0%B8%95%E0%B8%A3%E0%B9%80%E0%B8%88%E0%B8%99" title="ไฟโตเอสโตรเจน – Thai" lang="th" hreflang="th" data-title="ไฟโตเอสโตรเจน" 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%A4%D1%96%D1%82%D0%BE%D0%B5%D1%81%D1%82%D1%80%D0%BE%D0%B3%D0%B5%D0%BD%D0%B8" title="Фітоестрогени – Ukrainian" lang="uk" hreflang="uk" data-title="Фітоестрогени" data-language-autonym="Українська" 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title="Phytoestrogens">Phytoestrogens</a>)</span></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">Plant-derived xenoestrogen</div> <p>A <b>phytoestrogen</b> is a plant-derived <a href="/wiki/Xenoestrogen" title="Xenoestrogen">xenoestrogen</a> (a type of <a href="/wiki/Estrogen" title="Estrogen">estrogen</a> produced by organisms other than humans) not generated within the <a href="/wiki/Endocrine_system" title="Endocrine system">endocrine system</a>, but consumed by eating plants or manufactured foods.<sup id="cite_ref-lpi_1-0" class="reference"><a href="#cite_note-lpi-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Also called a "dietary estrogen", it is a diverse group of naturally occurring nonsteroidal plant compounds that, because of its structural similarity to <a href="/wiki/Estradiol" title="Estradiol">estradiol</a> (17-β-estradiol), have the ability to cause <a href="/wiki/Estrogenic" class="mw-redirect" title="Estrogenic">estrogenic</a> or antiestrogenic effects.<sup id="cite_ref-Yil_2-0" class="reference"><a href="#cite_note-Yil-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Phytoestrogens are not essential <a href="/wiki/Nutrient" title="Nutrient">nutrients</a> because their absence from the diet does not cause a disease, nor are they known to participate in any normal biological function.<sup id="cite_ref-Yil_2-1" class="reference"><a href="#cite_note-Yil-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Common foods containing phytoestrogens are <a href="/wiki/Soy_protein" title="Soy protein">soy protein</a>, <a href="/wiki/Bean" title="Bean">beans</a>, <a href="/wiki/Oat" title="Oat">oats</a>, <a href="/wiki/Barley" title="Barley">barley</a>, <a href="/wiki/Rice" title="Rice">rice</a>, <a href="/wiki/Coffee" title="Coffee">coffee</a>, <a href="/wiki/Apple" title="Apple">apples</a>, <a href="/wiki/Carrot" title="Carrot">carrots</a> (see Food Sources section below for bigger list). </p><p>Its name comes from the <a href="/wiki/Greek_language" title="Greek language">Greek</a> <i>phyto</i> ("plant") and <i>estrogen</i>, the hormone which gives fertility to <a href="/wiki/Female_mammals" class="mw-redirect" title="Female mammals">female mammals</a>. The word "<a href="/wiki/Estrus" class="mw-redirect" title="Estrus">estrus</a>" (Greek οίστρος) means "<a href="/wiki/Sexual_desire" title="Sexual desire">sexual desire</a>", and "gene" (Greek γόνο) is "to generate". It has been hypothesized that plants use a phytoestrogen as part of their natural defense against the overpopulation of herbivore animals by controlling female fertility.<sup id="cite_ref-pmid3203635_3-0" class="reference"><a href="#cite_note-pmid3203635-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-isbn0-521-64387-2_4-0" class="reference"><a href="#cite_note-isbn0-521-64387-2-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>The similarities, at molecular level, of an <a href="/wiki/Estrogen" title="Estrogen">estrogen</a> and a phytoestrogen allow them to mildly mimic and sometimes act as an antagonist of estrogen.<sup id="cite_ref-Yil_2-2" class="reference"><a href="#cite_note-Yil-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Phytoestrogens were first observed in 1926,<sup id="cite_ref-Yil_2-3" class="reference"><a href="#cite_note-Yil-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><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> but it was unknown if they could have any effect in human or animal metabolism. In the 1940s and early 1950s, it was noticed that some pastures of subterranean clover and <a href="/wiki/Red_clover" class="mw-redirect" title="Red clover">red clover</a> (phytoestrogen-rich plants) had adverse effects on the <a href="/wiki/Fecundity" title="Fecundity">fecundity</a> of grazing sheep.<sup id="cite_ref-Yil_2-4" class="reference"><a href="#cite_note-Yil-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid21028682_6-0" class="reference"><a href="#cite_note-pmid21028682-6"><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><sup id="cite_ref-Jon_8-0" class="reference"><a href="#cite_note-Jon-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Phytoestrogens2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Phytoestrogens2.png/400px-Phytoestrogens2.png" decoding="async" width="400" height="301" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Phytoestrogens2.png/600px-Phytoestrogens2.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/11/Phytoestrogens2.png/800px-Phytoestrogens2.png 2x" data-file-width="2387" data-file-height="1797" /></a><figcaption>Chemical structures of the most common phytoestrogens found in plants (top and middle) compared with estrogen (bottom) found in animals</figcaption></figure> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structure">Structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phytoestrogen&action=edit&section=1" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phytoestrogens mainly belong to a large group of substituted <a href="/wiki/Natural_phenol" class="mw-redirect" title="Natural phenol">natural phenolic</a> compounds: the <a href="/wiki/Coumestan" title="Coumestan">coumestans</a>, <a href="/wiki/Prenylflavonoid" title="Prenylflavonoid">prenylflavonoids</a> and <a href="/wiki/Isoflavone" title="Isoflavone">isoflavones</a> are three of the most active in estrogenic effects in this class.<sup id="cite_ref-lpi_1-1" class="reference"><a href="#cite_note-lpi-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> The best-researched are isoflavones, which are commonly found in <a href="/wiki/Soy" class="mw-redirect" title="Soy">soy</a> and <a href="/wiki/Red_clover" class="mw-redirect" title="Red clover">red clover</a>. <a href="/wiki/Lignan" title="Lignan">Lignans</a> have also been identified as phytoestrogens, although they are not flavonoids.<sup id="cite_ref-Yil_2-5" class="reference"><a href="#cite_note-Yil-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Mycoestrogens" class="mw-redirect" title="Mycoestrogens">Mycoestrogens</a> have similar structures and effects, but are not components of plants; these are mold metabolites of <i><a href="/wiki/Fusarium" title="Fusarium">Fusarium</a></i>, especially common on cereal grains,<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid2961013_10-0" class="reference"><a href="#cite_note-pmid2961013-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid17045381_11-0" class="reference"><a href="#cite_note-pmid17045381-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> but also occurring elsewhere, e.g. on various forages.<sup id="cite_ref-pmid26274974_12-0" class="reference"><a href="#cite_note-pmid26274974-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Although mycoestrogens are rarely taken into account in discussions about phytoestrogens, these are the compounds that initially generated the interest on the topic.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Mechanism_of_action">Mechanism of action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phytoestrogen&action=edit&section=2" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phytoestrogens exert their effects primarily through binding to <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptors</a> (ER).<sup id="cite_ref-pmid17518366_14-0" class="reference"><a href="#cite_note-pmid17518366-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> There are two variants of the estrogen receptor, alpha (<a href="/wiki/Estrogen_receptor_alpha" title="Estrogen receptor alpha">ER-α</a>) and beta (<a href="/wiki/Estrogen_receptor_beta" title="Estrogen receptor beta">ER-β</a>) and many phytoestrogens display somewhat higher <a href="/wiki/Ligand_(biochemistry)#Receptor/ligand_binding_affinity" title="Ligand (biochemistry)">affinity</a> for ER-β compared to ER-α.<sup id="cite_ref-pmid17518366_14-1" class="reference"><a href="#cite_note-pmid17518366-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>The key structural elements that enable phytoestrogens to bind with high affinity to estrogen receptors and display estradiol-like effects are:<sup id="cite_ref-Yil_2-6" class="reference"><a href="#cite_note-Yil-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <ul><li>The phenolic ring that is indispensable for binding to estrogen receptor</li> <li>The ring of isoflavones mimicking a ring of estrogens at the receptors binding site</li> <li>Low molecular weight similar to estrogens (MW=272)</li> <li>Distance between two hydroxyl groups at the isoflavones nucleus similar to that occurring in estradiol</li> <li>Optimal hydroxylation pattern</li></ul> <p>In addition to interaction with ERs, phytoestrogens may also modulate the concentration of endogenous estrogens by binding or inactivating some enzymes, and may affect the bioavailability of sex hormones by depressing or stimulating the synthesis of sex hormone-binding globulin (SHBG).<sup id="cite_ref-Jon_8-1" class="reference"><a href="#cite_note-Jon-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>Emerging evidence shows that some phytoestrogens bind to and transactivate <a href="/wiki/Peroxisome_proliferator-activated_receptor" title="Peroxisome proliferator-activated receptor">peroxisome proliferator-activated receptors</a> (PPARs).<sup id="cite_ref-pmid15922618_15-0" class="reference"><a href="#cite_note-pmid15922618-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid19207876_16-0" class="reference"><a href="#cite_note-pmid19207876-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> In vitro studies show an activation of PPARs at concentrations above 1 μM, which is higher than the activation level of ERs.<sup id="cite_ref-pmid12421816_17-0" class="reference"><a href="#cite_note-pmid12421816-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid15068509_18-0" class="reference"><a href="#cite_note-pmid15068509-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> At the concentration below 1 μM, activation of ERs may play a dominant role. At higher concentrations (>1 μM), both ERs and PPARs are activated. Studies have shown that both ERs and PPARs influence each other and therefore induce differential effects in a dose-dependent way. The final biological effects of <a href="/wiki/Genistein" title="Genistein">genistein</a> are determined by the balance among these pleiotrophic actions.<sup id="cite_ref-pmid15922618_15-1" class="reference"><a href="#cite_note-pmid15922618-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid19207876_16-1" class="reference"><a href="#cite_note-pmid19207876-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid12421816_17-1" class="reference"><a href="#cite_note-pmid12421816-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable sortable mw-collapsible mw-collapsed" style="font-size: small; text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist 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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:Affinities_of_estrogen_receptor_ligands_for_the_ER%CE%B1_and_ER%CE%B2" title="Template:Affinities of estrogen receptor ligands for the ERα and ERβ"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Affinities_of_estrogen_receptor_ligands_for_the_ER%CE%B1_and_ER%CE%B2" title="Template talk:Affinities of estrogen receptor ligands for the ERα and ERβ"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Affinities_of_estrogen_receptor_ligands_for_the_ER%CE%B1_and_ER%CE%B2" title="Special:EditPage/Template:Affinities of estrogen receptor ligands for the ERα and ERβ"><abbr title="Edit this template">e</abbr></a></li></ul></div> <span style="font-size:104%;">Affinities of estrogen receptor ligands for the ERα and ERβ</span> </caption> <tbody><tr> <th rowspan="2"><a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">Ligand</a></th> <th rowspan="2" class="unsortable">Other names</th> <th colspan="2"><a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity">Relative binding affinities</a> (RBA, %)<sup>a</sup></th> <th colspan="2"><a href="/wiki/Absolute_binding_affinity" class="mw-redirect" title="Absolute binding affinity">Absolute binding affinities</a> (K<sub>i</sub>, nM)<sup>a</sup></th> <th rowspan="2">Action </th></tr> <tr> <th><a href="/wiki/ER%CE%B1" class="mw-redirect" title="ERα">ERα</a></th> <th><a href="/wiki/ER%CE%B2" class="mw-redirect" title="ERβ">ERβ</a></th> <th><a href="/wiki/ER%CE%B1" class="mw-redirect" title="ERα">ERα</a></th> <th><a href="/wiki/ER%CE%B2" class="mw-redirect" title="ERβ">ERβ</a> </th></tr> <tr> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td>E2; 17β-Estradiol</td> <td>100</td> <td>100</td> <td>0.115 (0.04–0.24)</td> <td>0.15 (0.10–2.08)</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></td> <td>E1; 17-Ketoestradiol</td> <td>16.39 (0.7–60)</td> <td>6.5 (1.36–52)</td> <td>0.445 (0.3–1.01)</td> <td>1.75 (0.35–9.24)</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></td> <td>E3; 16α-OH-17β-E2</td> <td>12.65 (4.03–56)</td> <td>26 (14.0–44.6)</td> <td>0.45 (0.35–1.4)</td> <td>0.7 (0.63–0.7)</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Estetrol_(medication)" title="Estetrol (medication)">Estetrol</a></td> <td>E4; 15α,16α-Di-OH-17β-E2</td> <td>4.0</td> <td>3.0</td> <td>4.9</td> <td>19</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Alfatradiol" title="Alfatradiol">Alfatradiol</a></td> <td>17α-Estradiol</td> <td>20.5 (7–80.1)</td> <td>8.195 (2–42)</td> <td>0.2–0.52</td> <td>0.43–1.2</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/16-Epiestriol" class="mw-redirect" title="16-Epiestriol">16-Epiestriol</a></td> <td>16β-Hydroxy-17β-estradiol</td> <td>7.795 (4.94–63)</td> <td>50</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/17-Epiestriol" class="mw-redirect" title="17-Epiestriol">17-Epiestriol</a></td> <td>16α-Hydroxy-17α-estradiol</td> <td>55.45 (29–103)</td> <td>79–80</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/16,17-Epiestriol" class="mw-redirect" title="16,17-Epiestriol">16,17-Epiestriol</a></td> <td>16β-Hydroxy-17α-estradiol</td> <td>1.0</td> <td>13</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></td> <td>2-OH-E2</td> <td>22 (7–81)</td> <td>11–35</td> <td>2.5</td> <td>1.3</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></td> <td>2-MeO-E2</td> <td>0.0027–2.0</td> <td>1.0</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></td> <td>4-OH-E2</td> <td>13 (8–70)</td> <td>7–56</td> <td>1.0</td> <td>1.9</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></td> <td>4-MeO-E2</td> <td>2.0</td> <td>1.0</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></td> <td>2-OH-E1</td> <td>2.0–4.0</td> <td>0.2–0.4</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/2-Methoxyestrone" title="2-Methoxyestrone">2-Methoxyestrone</a></td> <td>2-MeO-E1</td> <td><0.001–<1</td> <td><1</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a></td> <td>4-OH-E1</td> <td>1.0–2.0</td> <td>1.0</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></td> <td>4-MeO-E1</td> <td><1</td> <td><1</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></td> <td>16α-OH-E1; 17-Ketoestriol</td> <td>2.0–6.5</td> <td>35</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/2-Hydroxyestriol" title="2-Hydroxyestriol">2-Hydroxyestriol</a></td> <td>2-OH-E3</td> <td>2.0</td> <td>1.0</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/4-Methoxyestriol" title="4-Methoxyestriol">4-Methoxyestriol</a></td> <td>4-MeO-E3</td> <td>1.0</td> <td>1.0</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/Estradiol_sulfate" title="Estradiol sulfate">Estradiol sulfate</a></td> <td>E2S; Estradiol 3-sulfate</td> <td><1</td> <td><1</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/Estradiol_disulfate" title="Estradiol disulfate">Estradiol disulfate</a></td> <td>Estradiol 3,17β-disulfate</td> <td>0.0004</td> <td>?</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/Estradiol_3-glucuronide" title="Estradiol 3-glucuronide">Estradiol 3-glucuronide</a></td> <td>E2-3G</td> <td>0.0079</td> <td>?</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/Estradiol_17%CE%B2-glucuronide" class="mw-redirect" title="Estradiol 17β-glucuronide">Estradiol 17β-glucuronide</a></td> <td>E2-17G</td> <td>0.0015</td> <td>?</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/Estradiol_3-glucuronide_17%CE%B2-sulfate" title="Estradiol 3-glucuronide 17β-sulfate">Estradiol 3-gluc. 17β-sulfate</a></td> <td>E2-3G-17S</td> <td>0.0001</td> <td>?</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a></td> <td>E1S; Estrone 3-sulfate</td> <td><1</td> <td><1</td> <td>>10</td> <td>>10</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a></td> <td>EB; Estradiol 3-benzoate</td> <td>10</td> <td>?</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Estradiol_17%CE%B2-benzoate" title="Estradiol 17β-benzoate">Estradiol 17β-benzoate</a></td> <td>E2-17B</td> <td>11.3</td> <td>32.6</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Estrone_methyl_ether" title="Estrone methyl ether">Estrone methyl ether</a></td> <td>Estrone 3-methyl ether</td> <td>0.145</td> <td>?</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Ent-Estradiol" title="Ent-Estradiol"><i>ent</i>-Estradiol</a></td> <td>1-Estradiol</td> <td>1.31–12.34</td> <td>9.44–80.07</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Equilin" title="Equilin">Equilin</a></td> <td>7-Dehydroestrone</td> <td>13 (4.0–28.9)</td> <td>13.0–49</td> <td>0.79</td> <td>0.36</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Equilenin" title="Equilenin">Equilenin</a></td> <td>6,8-Didehydroestrone</td> <td>2.0–15</td> <td>7.0–20</td> <td>0.64</td> <td>0.62</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/17%CE%B2-Dihydroequilin" title="17β-Dihydroequilin">17β-Dihydroequilin</a></td> <td>7-Dehydro-17β-estradiol</td> <td>7.9–113</td> <td>7.9–108</td> <td>0.09</td> <td>0.17</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/17%CE%B1-Dihydroequilin" title="17α-Dihydroequilin">17α-Dihydroequilin</a></td> <td>7-Dehydro-17α-estradiol</td> <td>18.6 (18–41)</td> <td>14–32</td> <td>0.24</td> <td>0.57</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/17%CE%B2-Dihydroequilenin" title="17β-Dihydroequilenin">17β-Dihydroequilenin</a></td> <td>6,8-Didehydro-17β-estradiol</td> <td>35–68</td> <td>90–100</td> <td>0.15</td> <td>0.20</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/17%CE%B1-Dihydroequilenin" title="17α-Dihydroequilenin">17α-Dihydroequilenin</a></td> <td>6,8-Didehydro-17α-estradiol</td> <td>20</td> <td>49</td> <td>0.50</td> <td>0.37</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/8,9-Dehydroestradiol" title="8,9-Dehydroestradiol">Δ<sup>8</sup>-Estradiol</a></td> <td>8,9-Dehydro-17β-estradiol</td> <td>68</td> <td>72</td> <td>0.15</td> <td>0.25</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/8,9-Dehydroestrone" title="8,9-Dehydroestrone">Δ<sup>8</sup>-Estrone</a></td> <td>8,9-Dehydroestrone</td> <td>19</td> <td>32</td> <td>0.52</td> <td>0.57</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></td> <td>EE; 17α-Ethynyl-17β-E2</td> <td>120.9 (68.8–480)</td> <td>44.4 (2.0–144)</td> <td>0.02–0.05</td> <td>0.29–0.81</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></td> <td>EE 3-methyl ether</td> <td>?</td> <td>2.5</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></td> <td>RU-2858; 11β-Methoxy-EE</td> <td>35–43</td> <td>5–20</td> <td>0.5</td> <td>2.6</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></td> <td>17α-Methyl-17β-estradiol</td> <td>70</td> <td>44</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></td> <td>DES; Stilbestrol</td> <td>129.5 (89.1–468)</td> <td>219.63 (61.2–295)</td> <td>0.04</td> <td>0.05</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a></td> <td>Dihydrodiethylstilbestrol</td> <td>153.6 (31–302)</td> <td>60–234</td> <td>0.06</td> <td>0.06</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a></td> <td>Dehydrostilbestrol</td> <td>37 (20.4–223)</td> <td>56–404</td> <td>0.05</td> <td>0.03</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol (B2)</a></td> <td>–</td> <td>114</td> <td>?</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></td> <td>TACE</td> <td>1.74</td> <td>?</td> <td>15.30</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Triphenylethylene" title="Triphenylethylene">Triphenylethylene</a></td> <td>TPE</td> <td>0.074</td> <td>?</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></td> <td>TPBE</td> <td>2.69</td> <td>?</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></td> <td>ICI-46,474</td> <td>3 (0.1–47)</td> <td>3.33 (0.28–6)</td> <td>3.4–9.69</td> <td>2.5</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene</a></td> <td>4-Hydroxytamoxifen; 4-OHT</td> <td>100.1 (1.7–257)</td> <td>10 (0.98–339)</td> <td>2.3 (0.1–3.61)</td> <td>0.04–4.8</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></td> <td>4-Chlorotamoxifen; 4-CT</td> <td>?</td> <td>?</td> <td>7.14–20.3</td> <td>15.4</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a></td> <td>MRL-41</td> <td>25 (19.2–37.2)</td> <td>12</td> <td>0.9</td> <td>1.2</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></td> <td>F-6066; Sexovid</td> <td>151–152</td> <td>243</td> <td>?</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Nafoxidine" title="Nafoxidine">Nafoxidine</a></td> <td>U-11,000A</td> <td>30.9–44</td> <td>16</td> <td>0.3</td> <td>0.8</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></td> <td>–</td> <td>41.2 (7.8–69)</td> <td>5.34 (0.54–16)</td> <td>0.188–0.52</td> <td>20.2</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Arzoxifene" title="Arzoxifene">Arzoxifene</a></td> <td>LY-353,381</td> <td>?</td> <td>?</td> <td>0.179</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></td> <td>CP-336,156</td> <td>10.2–166</td> <td>19.0</td> <td>0.229</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></td> <td>Centchroman</td> <td>?</td> <td>?</td> <td>0.313</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Levormeloxifene" title="Levormeloxifene">Levormeloxifene</a></td> <td>6720-CDRI; NNC-460,020</td> <td>1.55</td> <td>1.88</td> <td>?</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></td> <td>Deaminohydroxytoremifene</td> <td>0.82–2.63</td> <td>0.59–1.22</td> <td>?</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></td> <td>–</td> <td>?</td> <td>?</td> <td>0.053</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Etacstil" title="Etacstil">Etacstil</a></td> <td>GW-5638</td> <td>4.30</td> <td>11.5</td> <td>?</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/ICI-164,384" class="mw-redirect" title="ICI-164,384">ICI-164,384</a></td> <td>–</td> <td>63.5 (3.70–97.7)</td> <td>166</td> <td>0.2</td> <td>0.08</td> <td>Antiestrogen </td></tr> <tr> <td><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant</a></td> <td>ICI-182,780</td> <td>43.5 (9.4–325)</td> <td>21.65 (2.05–40.5)</td> <td>0.42</td> <td>1.3</td> <td>Antiestrogen </td></tr> <tr> <td><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></td> <td>PPT</td> <td>49 (10.0–89.1)</td> <td>0.12</td> <td>0.40</td> <td>92.8</td> <td>ERα agonist </td></tr> <tr> <td><a href="/wiki/16%CE%B1-LE2" title="16α-LE2">16α-LE2</a></td> <td>16α-Lactone-17β-estradiol</td> <td>14.6–57</td> <td>0.089</td> <td>0.27</td> <td>131</td> <td>ERα agonist </td></tr> <tr> <td><a href="/wiki/16%CE%B1-Iodo-E2" title="16α-Iodo-E2">16α-Iodo-E2</a></td> <td>16α-Iodo-17β-estradiol</td> <td>30.2</td> <td>2.30</td> <td>?</td> <td>?</td> <td>ERα agonist </td></tr> <tr> <td><a href="/wiki/Methylpiperidinopyrazole" title="Methylpiperidinopyrazole">Methylpiperidinopyrazole</a></td> <td>MPP</td> <td>11</td> <td>0.05</td> <td>?</td> <td>?</td> <td>ERα antagonist </td></tr> <tr> <td><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></td> <td>DPN</td> <td>0.12–0.25</td> <td>6.6–18</td> <td>32.4</td> <td>1.7</td> <td>ERβ agonist </td></tr> <tr> <td><a href="/wiki/8%CE%B2-VE2" title="8β-VE2">8β-VE2</a></td> <td>8β-Vinyl-17β-estradiol</td> <td>0.35</td> <td>22.0–83</td> <td>12.9</td> <td>0.50</td> <td>ERβ agonist </td></tr> <tr> <td><a href="/wiki/Prinaberel" title="Prinaberel">Prinaberel</a></td> <td>ERB-041; WAY-202,041</td> <td>0.27</td> <td>67–72</td> <td>?</td> <td>?</td> <td>ERβ agonist </td></tr> <tr> <td><a href="/wiki/ERB-196" title="ERB-196">ERB-196</a></td> <td>WAY-202,196</td> <td>?</td> <td>180</td> <td>?</td> <td>?</td> <td>ERβ agonist </td></tr> <tr> <td><a href="/wiki/Erteberel" title="Erteberel">Erteberel</a></td> <td>SERBA-1; LY-500,307</td> <td>?</td> <td>?</td> <td>2.68</td> <td>0.19</td> <td>ERβ agonist </td></tr> <tr> <td><a href="/wiki/SERBA-2" title="SERBA-2">SERBA-2</a></td> <td>–</td> <td>?</td> <td>?</td> <td>14.5</td> <td>1.54</td> <td>ERβ agonist </td></tr> <tr> <td><a href="/wiki/Coumestrol" title="Coumestrol">Coumestrol</a></td> <td>–</td> <td>9.225 (0.0117–94)</td> <td>64.125 (0.41–185)</td> <td>0.14–80.0</td> <td>0.07–27.0</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Genistein" title="Genistein">Genistein</a></td> <td>–</td> <td>0.445 (0.0012–16)</td> <td>33.42 (0.86–87)</td> <td>2.6–126</td> <td>0.3–12.8</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Equol" title="Equol">Equol</a></td> <td>–</td> <td>0.2–0.287</td> <td>0.85 (0.10–2.85)</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></td> <td>–</td> <td>0.07 (0.0018–9.3)</td> <td>0.7865 (0.04–17.1)</td> <td>2.0</td> <td>85.3</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Biochanin_A" title="Biochanin A">Biochanin A</a></td> <td>–</td> <td>0.04 (0.022–0.15)</td> <td>0.6225 (0.010–1.2)</td> <td>174</td> <td>8.9</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Kaempferol" title="Kaempferol">Kaempferol</a></td> <td>–</td> <td>0.07 (0.029–0.10)</td> <td>2.2 (0.002–3.00)</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Naringenin" title="Naringenin">Naringenin</a></td> <td>–</td> <td>0.0054 (<0.001–0.01)</td> <td>0.15 (0.11–0.33)</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/8-Prenylnaringenin" title="8-Prenylnaringenin">8-Prenylnaringenin</a></td> <td>8-PN</td> <td>4.4</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></td> <td>–</td> <td><0.001–0.01</td> <td>0.002–0.040</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Ipriflavone" title="Ipriflavone">Ipriflavone</a></td> <td>–</td> <td><0.01</td> <td><0.01</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Miroestrol" title="Miroestrol">Miroestrol</a></td> <td>–</td> <td>0.39</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Deoxymiroestrol" class="mw-redirect" title="Deoxymiroestrol">Deoxymiroestrol</a></td> <td>–</td> <td>2.0</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/%CE%92-Sitosterol" title="Β-Sitosterol">β-Sitosterol</a></td> <td>–</td> <td><0.001–0.0875</td> <td><0.001–0.016</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></td> <td>–</td> <td><0.001–0.0032</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/%CE%91-Zearalenol" title="Α-Zearalenol">α-Zearalenol</a></td> <td>–</td> <td>48 (13–52.5)</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/%CE%92-Zearalenol" title="Β-Zearalenol">β-Zearalenol</a></td> <td>–</td> <td>0.6 (0.032–13)</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Zeranol" title="Zeranol">Zeranol</a></td> <td>α-Zearalanol</td> <td>48–111</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Taleranol" title="Taleranol">Taleranol</a></td> <td>β-Zearalanol</td> <td>16 (13–17.8)</td> <td>14</td> <td>0.8</td> <td>0.9</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Zearalenone" title="Zearalenone">Zearalenone</a></td> <td>ZEN</td> <td>7.68 (2.04–28)</td> <td>9.45 (2.43–31.5)</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Zearalanone" title="Zearalanone">Zearalanone</a></td> <td>ZAN</td> <td>0.51</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Bisphenol_A" title="Bisphenol A">Bisphenol A</a></td> <td>BPA</td> <td>0.0315 (0.008–1.0)</td> <td>0.135 (0.002–4.23)</td> <td>195</td> <td>35</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Endosulfan" title="Endosulfan">Endosulfan</a></td> <td>EDS</td> <td><0.001–<0.01</td> <td><0.01</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Kepone" class="mw-redirect" title="Kepone">Kepone</a></td> <td>Chlordecone</td> <td>0.0069–0.2</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/O,p%27-DDT" class="mw-redirect" title="O,p'-DDT"><i>o,p'</i>-DDT</a></td> <td>–</td> <td>0.0073–0.4</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/P,p%27-DDT" class="mw-redirect" title="P,p'-DDT"><i>p,p'</i>-DDT</a></td> <td>–</td> <td>0.03</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Methoxychlor" title="Methoxychlor">Methoxychlor</a></td> <td><i>p,p'</i>-Dimethoxy-DDT</td> <td>0.01 (<0.001–0.02)</td> <td>0.01–0.13</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/HPTE" title="HPTE">HPTE</a></td> <td>Hydroxychlor; <i>p,p'</i>-OH-DDT</td> <td>1.2–1.7</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">Testosterone</a></td> <td>T; 4-Androstenolone</td> <td><0.0001–<0.01</td> <td><0.002–0.040</td> <td>>5000</td> <td>>5000</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/Androstanolone" title="Androstanolone">Dihydrotestosterone</a></td> <td>DHT; 5α-Androstanolone</td> <td>0.01 (<0.001–0.05)</td> <td>0.0059–0.17</td> <td>221–>5000</td> <td>73–1688</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/Nandrolone" title="Nandrolone">Nandrolone</a></td> <td>19-Nortestosterone; 19-NT</td> <td>0.01</td> <td>0.23</td> <td>765</td> <td>53</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/Prasterone" title="Prasterone">Dehydroepiandrosterone</a></td> <td>DHEA; Prasterone</td> <td>0.038 (<0.001–0.04)</td> <td>0.019–0.07</td> <td>245–1053</td> <td>163–515</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">5-Androstenediol</a></td> <td>A5; Androstenediol</td> <td>6</td> <td>17</td> <td>3.6</td> <td>0.9</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/4-Androstenediol" title="4-Androstenediol">4-Androstenediol</a></td> <td>–</td> <td>0.5</td> <td>0.6</td> <td>23</td> <td>19</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">4-Androstenedione</a></td> <td>A4; Androstenedione</td> <td><0.01</td> <td><0.01</td> <td>>10000</td> <td>>10000</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></td> <td>3α-Adiol</td> <td>0.07</td> <td>0.3</td> <td>260</td> <td>48</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></td> <td>3β-Adiol</td> <td>3</td> <td>7</td> <td>6</td> <td>2</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/Androstanedione" title="Androstanedione">Androstanedione</a></td> <td>5α-Androstanedione</td> <td><0.01</td> <td><0.01</td> <td>>10000</td> <td>>10000</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/Etiocholanedione" title="Etiocholanedione">Etiocholanedione</a></td> <td>5β-Androstanedione</td> <td><0.01</td> <td><0.01</td> <td>>10000</td> <td>>10000</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/Methyltestosterone" title="Methyltestosterone">Methyltestosterone</a></td> <td>17α-Methyltestosterone</td> <td><0.0001</td> <td>?</td> <td>?</td> <td>?</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/Ethinyl-3%CE%B1-androstanediol" class="mw-redirect" title="Ethinyl-3α-androstanediol">Ethinyl-3α-androstanediol</a></td> <td>17α-Ethynyl-3α-adiol</td> <td>4.0</td> <td><0.07</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Ethinyl-3%CE%B2-androstanediol" class="mw-redirect" title="Ethinyl-3β-androstanediol">Ethinyl-3β-androstanediol</a></td> <td>17α-Ethynyl-3β-adiol</td> <td>50</td> <td>5.6</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">Progesterone</a></td> <td>P4; 4-Pregnenedione</td> <td><0.001–0.6</td> <td><0.001–0.010</td> <td>?</td> <td>?</td> <td>Progestogen </td></tr> <tr> <td><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></td> <td>NET; 17α-Ethynyl-19-NT</td> <td>0.085 (0.0015–<0.1)</td> <td>0.1 (0.01–0.3)</td> <td>152</td> <td>1084</td> <td>Progestogen </td></tr> <tr> <td><a href="/wiki/Norethynodrel" class="mw-redirect" title="Norethynodrel">Norethynodrel</a></td> <td>5(10)-Norethisterone</td> <td>0.5 (0.3–0.7)</td> <td><0.1–0.22</td> <td>14</td> <td>53</td> <td>Progestogen </td></tr> <tr> <td><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></td> <td>7α-Methylnorethynodrel</td> <td>0.5 (0.45–2.0)</td> <td>0.2–0.076</td> <td>?</td> <td>?</td> <td>Progestogen </td></tr> <tr> <td><a href="/wiki/%CE%944-Tibolone" title="Δ4-Tibolone">Δ<sup>4</sup>-Tibolone</a></td> <td>7α-Methylnorethisterone</td> <td>0.069–<0.1</td> <td>0.027–<0.1</td> <td>?</td> <td>?</td> <td>Progestogen </td></tr> <tr> <td><a href="/wiki/3%CE%B1-Hydroxytibolone" title="3α-Hydroxytibolone">3α-Hydroxytibolone</a></td> <td>–</td> <td>2.5 (1.06–5.0)</td> <td>0.6–0.8</td> <td>?</td> <td>?</td> <td>Progestogen </td></tr> <tr> <td><a href="/wiki/3%CE%B2-Hydroxytibolone" title="3β-Hydroxytibolone">3β-Hydroxytibolone</a></td> <td>–</td> <td>1.6 (0.75–1.9)</td> <td>0.070–0.1</td> <td>?</td> <td>?</td> <td>Progestogen </td></tr> <tr class="sortbottom"> <td colspan="7" style="width: 1px; background-color:#eaecf0; text-align: center;"><b>Footnotes:</b> <sup>a</sup> = (1) <a href="/wiki/Binding_affinity" class="mw-redirect" title="Binding affinity">Binding affinity</a> values are of the format "median (range)" (# (#–#)), "range" (#–#), or "value" (#) depending on the values available. The full sets of values within the ranges can be found in the Wiki code. (2) Binding affinities were determined via displacement studies in a variety of <i><a href="/wiki/In-vitro" class="mw-redirect" title="In-vitro">in-vitro</a></i> systems with <a href="/wiki/Radiolabel" class="mw-redirect" title="Radiolabel">labeled</a> estradiol and human <a href="/wiki/ER%CE%B1" class="mw-redirect" title="ERα">ERα</a> and <a href="/wiki/ER%CE%B2" class="mw-redirect" title="ERβ">ERβ</a> proteins (except the ERβ values from Kuiper et al. (1997), which are rat ERβ). <b>Sources:</b> See template page. </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Ecology">Ecology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phytoestrogen&action=edit&section=3" title="Edit section: Ecology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phytoestrogens are involved in the synthesis of antifungal <a href="/wiki/Benzofuran" title="Benzofuran">benzofurans</a> and <a href="/wiki/Phytoalexin" title="Phytoalexin">phytoalexins</a>, such as <a href="/wiki/Medicarpin" title="Medicarpin">medicarpin</a> (common in <a href="/wiki/Legume" title="Legume">legumes</a>), and <a href="/wiki/Sesquiterpene" title="Sesquiterpene">sesquiterpenes</a>, such as <a href="/wiki/Capsidiol" title="Capsidiol">capsidiol</a> in tobacco.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Soybeans naturally produce isoflavones, and are therefore a dietary source for isoflavones. </p><p>Phytoestrogens are ancient naturally occurring substances, and as dietary phytochemicals they are considered to have coevolved with mammals. In the human diet, phytoestrogens are not the only source of exogenous estrogens. <a href="/wiki/Xenoestrogens" class="mw-redirect" title="Xenoestrogens">Xenoestrogens</a> (novel, man-made), are found as <a href="/wiki/Food_additive" title="Food additive">food additives</a><sup id="cite_ref-pmid19063592_20-0" class="reference"><a href="#cite_note-pmid19063592-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> and ingredients, and also in cosmetics, plastics, and insecticides. Environmentally, they have similar effects as phytoestrogens, making it difficult to clearly separate the action of these two kind of agents in studies.<sup id="cite_ref-Repro_21-0" class="reference"><a href="#cite_note-Repro-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Avian_studies">Avian studies</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phytoestrogen&action=edit&section=4" title="Edit section: Avian studies"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The consumption of plants with unusual content of phytoestrogens, under drought conditions, has been shown to decrease fertility in <a href="/wiki/Quail" title="Quail">quail</a>.<sup id="cite_ref-pmid1246602_22-0" class="reference"><a href="#cite_note-pmid1246602-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Parrot" title="Parrot">Parrot</a> food as available in nature has shown only weak estrogenic activity. Studies have been conducted on screening methods for environmental estrogens present in manufactured supplementary food, with the purpose of aiding reproduction of endangered species.<sup id="cite_ref-pmid11302429_23-0" class="reference"><a href="#cite_note-pmid11302429-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Food_sources">Food sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phytoestrogen&action=edit&section=5" title="Edit section: Food sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>According to one study of nine common phytoestrogens in a Western diet, foods with the highest relative phytoestrogen content were nuts and oilseeds, followed by soy products, cereals and breads, <a href="/wiki/Legume" title="Legume">legumes</a>, meat products, and other processed foods that may contain soy, vegetables, fruits, alcoholic, and nonalcoholic beverages. <a href="/wiki/Flax" title="Flax">Flax</a> seed and other oilseeds contained the highest total phytoestrogen content, followed by soybeans and <a href="/wiki/Tofu" title="Tofu">tofu</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> The highest concentrations of isoflavones are found in soybeans and soybean products followed by legumes, whereas lignans are the primary source of phytoestrogens found in nuts and oilseeds (e.g. flax) and also found in cereals, legumes, fruits and vegetables. Phytoestrogen content varies in different foods, and may vary significantly within the same group of foods (e.g. soy beverages, tofu) depending on processing mechanisms and type of soybean used. Legumes (in particular soybeans), whole grain cereals, and some seeds are high in phytoestrogens. </p><p>A more comprehensive list of foods known to contain phytoestrogens includes: </p> <style data-mw-deduplicate="TemplateStyles:r1184024115">.mw-parser-output .div-col{margin-top:0.3em;column-width:30em}.mw-parser-output .div-col-small{font-size:90%}.mw-parser-output .div-col-rules{column-rule:1px solid #aaa}.mw-parser-output .div-col dl,.mw-parser-output .div-col ol,.mw-parser-output .div-col ul{margin-top:0}.mw-parser-output .div-col li,.mw-parser-output .div-col dd{page-break-inside:avoid;break-inside:avoid-column}</style><div class="div-col" style="column-width: 20em;"> <ul><li><a href="/wiki/Soybean" title="Soybean">Soybeans</a> and soy products</li> <li><a href="/wiki/Tempeh" title="Tempeh">Tempeh</a></li> <li><a href="/wiki/Flax" title="Flax">Linseed</a> (flax)</li> <li><a href="/wiki/Sesame_seeds" class="mw-redirect" title="Sesame seeds">Sesame seeds</a></li> <li><a href="/wiki/Wheat_berry" title="Wheat berry">Wheat berries</a></li> <li><a href="/wiki/Fenugreek" title="Fenugreek">Fenugreek</a> (contains <a href="/wiki/Diosgenin" title="Diosgenin">diosgenin</a>, but also used to make <a href="/w/index.php?title=Testofen&action=edit&redlink=1" class="new" title="Testofen (page does not exist)">Testofen</a>, a compound taken by men to increase testosterone).</li> <li><a href="/wiki/Oat" title="Oat">Oats</a></li> <li><a href="/wiki/Barley" title="Barley">Barley</a></li> <li><a href="/wiki/Bean" title="Bean">Beans</a></li> <li><a href="/wiki/Lentil" title="Lentil">Lentils</a></li> <li><a href="/wiki/Yam_(vegetable)" title="Yam (vegetable)">Yams</a></li> <li><a href="/wiki/Rice" title="Rice">Rice</a></li> <li><a href="/wiki/Alfalfa" title="Alfalfa">Alfalfa</a></li> <li><a href="/wiki/Mung_bean" title="Mung bean">Mung beans</a></li> <li><a href="/wiki/Apple" title="Apple">Apples</a></li> <li><a href="/wiki/Carrot" title="Carrot">Carrots</a></li> <li><a href="/wiki/Pomegranate" title="Pomegranate">Pomegranates</a><sup id="cite_ref-pmid14732284_25-0" class="reference"><a href="#cite_note-pmid14732284-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Wheat_germ" class="mw-redirect" title="Wheat germ">Wheat germ</a></li> <li><a href="/wiki/Rice_bran" class="mw-redirect" title="Rice bran">Rice bran</a></li> <li><a href="/wiki/Lupin" class="mw-redirect" title="Lupin">Lupin</a></li> <li><a href="/wiki/Kudzu" title="Kudzu">Kudzu</a></li> <li><a href="/wiki/Coffee" title="Coffee">Coffee</a></li> <li><a href="/wiki/Licorice_root" class="mw-redirect" title="Licorice root">Licorice root</a></li> <li><a href="/wiki/Mentha" title="Mentha">Mint</a></li> <li><a href="/wiki/Ginseng" title="Ginseng">Ginseng</a></li> <li><a href="/wiki/Hops" title="Hops">Hops</a>,<sup id="cite_ref-pmid15620245_26-0" class="reference"><a href="#cite_note-pmid15620245-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Bourbon_whiskey" title="Bourbon whiskey">Bourbon whiskey</a></li> <li><a href="/wiki/Beer" title="Beer">Beer</a>,<sup id="cite_ref-pmid8116832_27-0" class="reference"><a href="#cite_note-pmid8116832-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Fennel" title="Fennel">Fennel</a></li> <li><a href="/wiki/Anise" title="Anise">Anise</a>.<sup id="cite_ref-fen_28-0" class="reference"><a href="#cite_note-fen-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Red_clover" class="mw-redirect" title="Red clover">Red clover</a> (sometimes a constituent of <a href="/wiki/Green_manure" title="Green manure">green manure</a>).</li> <li><a href="/wiki/Spinach" title="Spinach">Spinach</a><sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup></li></ul> </div> <ul><li><a href="/wiki/Lavender" class="mw-redirect" title="Lavender">Lavender</a><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup></li></ul> <p>Food content of phytoestrogens is very variable and accurate estimates of intake are therefore difficult and depends on the databases used.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> Data from the <a href="/wiki/European_Prospective_Investigation_into_Cancer_and_Nutrition" title="European Prospective Investigation into Cancer and Nutrition">European Prospective Investigation into Cancer and Nutrition</a> found intakes between 1 mg/d in <a href="/wiki/Mediterranean_Countries" class="mw-redirect" title="Mediterranean Countries">Mediterranean Countries</a> and more than 20 mg/d in the <a href="/wiki/United_Kingdom" title="United Kingdom">United Kingdom</a>.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> The high intake in the UK is partly explained by the use of soy in the <a href="/wiki/Chorleywood_bread_process" title="Chorleywood bread process">Chorleywood bread process</a>.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> A 2001 epidemiological study of women in the United States found that the dietary intake of phytoestrogens in healthy post-menopausal Caucasian women is less than one milligram daily.<sup id="cite_ref-pmid11385074_34-0" class="reference"><a href="#cite_note-pmid11385074-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Effects_on_humans">Effects on humans</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phytoestrogen&action=edit&section=6" title="Edit section: Effects on humans"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Self-contradictory plainlinks metadata ambox ambox-content" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span title="Accuracy dispute"><img alt="Exclamation mark with arrows pointing at each other" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Ambox_contradict.svg/38px-Ambox_contradict.svg.png" decoding="async" width="38" height="38" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Ambox_contradict.svg/57px-Ambox_contradict.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Ambox_contradict.svg/76px-Ambox_contradict.svg.png 2x" data-file-width="620" data-file-height="620" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">This article or section <b>appears to contradict itself</b> <b>on whether humans are affected by phytoestrogens.</b>.<span class="hide-when-compact"> Please see the <a href="/wiki/Talk:Phytoestrogen" title="Talk:Phytoestrogen">talk page</a> for more information.</span> <span class="date-container"><i>(<span class="date">May 2023</span>)</i></span></div></td></tr></tbody></table> <p>In humans, phytoestrogens are digested in the small intestine, poorly absorbed into the circulatory system, circulate in plasma, and are excreted in the urine. Metabolic influence is different from that of grazing animals due to the differences between ruminant versus monogastric digestive systems.<sup id="cite_ref-Repro_21-1" class="reference"><a href="#cite_note-Repro-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p>As of 2020, there is insufficient <a href="/wiki/Evidence-based_medicine" title="Evidence-based medicine">clinical evidence</a> to determine that phytoestrogens have effects in humans.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Females">Females</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phytoestrogen&action=edit&section=7" title="Edit section: Females"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>It is unclear if phytoestrogens have any effect on the cause or prevention of cancer in women.<sup id="cite_ref-lpi_1-2" class="reference"><a href="#cite_note-lpi-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-bilal_36-0" class="reference"><a href="#cite_note-bilal-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> Some epidemiological studies have suggested a protective effect against breast cancer.<sup id="cite_ref-lpi_1-3" class="reference"><a href="#cite_note-lpi-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-bilal_36-1" class="reference"><a href="#cite_note-bilal-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid9329514_37-0" class="reference"><a href="#cite_note-pmid9329514-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> Additionally, other <a href="/wiki/Epidemiology" title="Epidemiology">epidemiological</a> studies found that consumption of soy estrogens is safe for patients with breast cancer, and that it may decrease mortality and recurrence rates.<sup id="cite_ref-lpi_1-4" class="reference"><a href="#cite_note-lpi-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid19996398_38-0" class="reference"><a href="#cite_note-pmid19996398-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-fritz_39-0" class="reference"><a href="#cite_note-fritz-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> It remains unclear if phytoestrogens can minimize some of the deleterious effects of low estrogen levels (<a href="/wiki/Hypoestrogenism" title="Hypoestrogenism">hypoestrogenism</a>) resulting from <a href="/wiki/Oophorectomy" title="Oophorectomy">oophorectomy</a>, <a href="/wiki/Menopause" title="Menopause">menopause</a>, or other causes.<sup id="cite_ref-bilal_36-2" class="reference"><a href="#cite_note-bilal-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> A <a href="/wiki/Cochrane_Library" title="Cochrane Library">Cochrane review</a> of the use of phytoestrogens to relieve the vasomotor symptoms of menopause (<a href="/wiki/Hot_flash" title="Hot flash">hot flashes</a>) stated that there was no conclusive evidence to suggest any benefit to their use, although <a href="/wiki/Genistein" title="Genistein">genistein</a> effects should be further investigated.<sup id="cite_ref-Lethaby_2013_40-0" class="reference"><a href="#cite_note-Lethaby_2013-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Males">Males</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phytoestrogen&action=edit&section=8" title="Edit section: Males"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>It is unclear if phytoestrogens have any effect on male sexuality, with conflicting results about the potential effects of isoflavones originating from soy.<sup id="cite_ref-lpi_1-5" class="reference"><a href="#cite_note-lpi-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Some studies showed that isoflavone supplementation had a positive effect on sperm concentration, count, or <a href="/wiki/Motility" title="Motility">motility</a>, and increased ejaculate volume.<sup id="cite_ref-tox_41-0" class="reference"><a href="#cite_note-tox-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid11352776_42-0" class="reference"><a href="#cite_note-pmid11352776-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> Sperm count decline and increasing rate of testicular cancers in the West may be linked to a higher presence of isoflavone phytoestrogens in the diet while in utero, but such a link has not been definitively proven.<sup id="cite_ref-pmid20347861_43-0" class="reference"><a href="#cite_note-pmid20347861-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> Furthermore, while there is some evidence that phytoestrogens may affect male fertility, more recent reviews of available studies found no link,<sup id="cite_ref-:0_44-0" class="reference"><a href="#cite_note-:0-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_45-0" class="reference"><a href="#cite_note-:1-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> and instead suggests that healthier diets such as the <a href="/wiki/Mediterranean_diet" title="Mediterranean diet">Mediterranean diet</a> might have a positive effect on male fertility.<sup id="cite_ref-:1_45-1" class="reference"><a href="#cite_note-:1-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> Neither isoflavones nor soy have been shown to affect male reproductive hormones in healthy individuals.<sup id="cite_ref-:0_44-1" class="reference"><a href="#cite_note-:0-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid33383165_46-0" class="reference"><a href="#cite_note-pmid33383165-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Infant_formula">Infant formula</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phytoestrogen&action=edit&section=9" title="Edit section: Infant formula"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some studies have found that some concentrations of isoflavones may have effects on intestinal cells. At low doses, genistein acted as a weak estrogen and stimulated cell growth; at high doses, it inhibited proliferation and altered cell cycle dynamics. This biphasic response correlates with how genistein is thought to exert its effects.<sup id="cite_ref-pmid15173388_47-0" class="reference"><a href="#cite_note-pmid15173388-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> Some reviews express the opinion that more research is needed to answer the question of what effect phytoestrogens may have on infants,<sup id="cite_ref-pmid14599051_48-0" class="reference"><a href="#cite_note-pmid14599051-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid15189112_49-0" class="reference"><a href="#cite_note-pmid15189112-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> but their authors did not find any adverse effects. Studies conclude there are no adverse effects in human growth, development, or reproduction as a result of the consumption of soy-based infant formula compared to conventional cow-milk formula.<sup id="cite_ref-pmid11497534_50-0" class="reference"><a href="#cite_note-pmid11497534-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid15055353_51-0" class="reference"><a href="#cite_note-pmid15055353-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Nutri_52-0" class="reference"><a href="#cite_note-Nutri-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/American_Academy_of_Pediatrics" title="American Academy of Pediatrics">American Academy of Pediatrics</a> states: "although isolated soy protein-based formulas may be used to provide nutrition for normal growth and development, there are few indications for their use in place of cow milk-based formula. These indications include (a) for infants with galactosemia and hereditary lactase deficiency (rare) and (b) in situations in which a vegetarian diet is preferred."<sup id="cite_ref-pmid18450914_53-0" class="reference"><a href="#cite_note-pmid18450914-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Ethnopharmacology">Ethnopharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phytoestrogen&action=edit&section=10" title="Edit section: Ethnopharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In some countries, phytoestrogenic plants have been used for centuries in the treatment of menstrual and menopausal problems, as well as for fertility problems.<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> Plants used that have been shown to contain phytoestrogens include <i><a href="/wiki/Pueraria_mirifica" title="Pueraria mirifica">Pueraria mirifica</a></i><sup id="cite_ref-pmid12819377_55-0" class="reference"><a href="#cite_note-pmid12819377-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> and its close relative <a href="/wiki/Kudzu" title="Kudzu">kudzu</a>,<sup id="cite_ref-pmid16915857_56-0" class="reference"><a href="#cite_note-pmid16915857-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Angelica" title="Angelica">Angelica</a>,<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Fennel" title="Fennel">fennel</a>,<sup id="cite_ref-fen_28-1" class="reference"><a href="#cite_note-fen-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Anise" title="Anise">anise</a>. In a rigorous study, the use of one such source of phytoestrogen, <a href="/wiki/Trifolium_pratense" title="Trifolium pratense">red clover</a>, has been shown to be safe, but ineffective in relieving menopausal symptoms<sup id="cite_ref-pmid19609225_58-0" class="reference"><a href="#cite_note-pmid19609225-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> (<a href="/wiki/Actaea_racemosa" title="Actaea racemosa">black cohosh</a> is also used for menopausal symptoms, but does not contain phytoestrogens<sup id="cite_ref-pmid12222669_59-0" class="reference"><a href="#cite_note-pmid12222669-59"><span class="cite-bracket">[</span>59<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=Phytoestrogen&action=edit&section=11" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1184024115"><div class="div-col" style="column-width: 20em;"> <ul><li><a href="/wiki/Ethnopharmacology" class="mw-redirect" title="Ethnopharmacology">Ethnopharmacology</a></li> <li><a href="/wiki/Isoflavones" class="mw-redirect" title="Isoflavones">Isoflavones</a></li> <li><a href="/wiki/Lignan" title="Lignan">Lignan</a></li> <li><a href="/wiki/Mycoestrogens" class="mw-redirect" title="Mycoestrogens">Mycoestrogens</a></li> <li><a href="/wiki/Phytoandrogens" class="mw-redirect" title="Phytoandrogens">Phytoandrogens</a></li> <li><a href="/wiki/Plant_hormone" title="Plant hormone">Plant hormone</a></li> <li><a href="/wiki/Soy" class="mw-redirect" title="Soy">Soy</a></li></ul> </div> <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=Phytoestrogen&action=edit&section=12" 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-lpi-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-lpi_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-lpi_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-lpi_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-lpi_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-lpi_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-lpi_1-5"><sup><i><b>f</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://lpi.oregonstate.edu/mic/dietary-factors/phytochemicals/soy-isoflavones">"Isoflavones"</a>. 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Retrieved <span class="nowrap">6 August</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Isoflavones&rft.pub=Micronutrient+Information+Center%2C+Linus+Pauling+Institute%2C+Oregon+State+University%2C+Corvallis&rft.date=2016-10&rft_id=https%3A%2F%2Flpi.oregonstate.edu%2Fmic%2Fdietary-factors%2Fphytochemicals%2Fsoy-isoflavones&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhytoestrogen" class="Z3988"></span></span> </li> <li id="cite_note-Yil-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Yil_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Yil_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Yil_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Yil_2-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Yil_2-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Yil_2-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Yil_2-6"><sup><i><b>g</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFYildiz2005" class="citation book cs1">Yildiz F (2005). <i>Phytoestrogens in Functional Foods</i>. Taylor & Francis Ltd. pp. 3–5, 210–211. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-57444-508-4" title="Special:BookSources/978-1-57444-508-4"><bdi>978-1-57444-508-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Phytoestrogens+in+Functional+Foods&rft.pages=3-5%2C+210-211&rft.pub=Taylor+%26+Francis+Ltd&rft.date=2005&rft.isbn=978-1-57444-508-4&rft.aulast=Yildiz&rft.aufirst=Fatih&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhytoestrogen" class="Z3988"></span></span> </li> <li id="cite_note-pmid3203635-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid3203635_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHughes1988" class="citation journal cs1">Hughes CL (Jun 1988). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1474615">"Phytochemical mimicry of reproductive hormones and modulation of herbivore fertility by phytoestrogens"</a>. <i>Environmental Health Perspectives</i>. <b>78</b>: 171–4. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1289%2Fehp.8878171">10.1289/ehp.8878171</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/PMC1474615">1474615</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/3203635">3203635</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Environmental+Health+Perspectives&rft.atitle=Phytochemical+mimicry+of+reproductive+hormones+and+modulation+of+herbivore+fertility+by+phytoestrogens&rft.volume=78&rft.pages=171-4&rft.date=1988-06&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1474615%23id-name%3DPMC&rft_id=info%3Apmid%2F3203635&rft_id=info%3Adoi%2F10.1289%2Fehp.8878171&rft.aulast=Hughes&rft.aufirst=CL&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1474615&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhytoestrogen" class="Z3988"></span></span> </li> <li id="cite_note-isbn0-521-64387-2-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-isbn0-521-64387-2_4-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBentleyMascie-Taylor2000" class="citation book cs1">Bentley GR, Mascie-Taylor CG (2000). <span class="id-lock-limited" title="Free access subject to limited trial, subscription normally required"><a rel="nofollow" class="external text" href="https://archive.org/details/infertilitymoder00bent"><i>Infertility in the modern world: present and future prospects</i></a></span>. Cambridge, UK: Cambridge University Press. pp. <a rel="nofollow" class="external text" href="https://archive.org/details/infertilitymoder00bent/page/n111">99</a>–100. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-521-64387-0" title="Special:BookSources/978-0-521-64387-0"><bdi>978-0-521-64387-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Infertility+in+the+modern+world%3A+present+and+future+prospects&rft.place=Cambridge%2C+UK&rft.pages=99-100&rft.pub=Cambridge+University+Press&rft.date=2000&rft.isbn=978-0-521-64387-0&rft.aulast=Bentley&rft.aufirst=Gillian+R.&rft.au=Mascie-Taylor%2C+C.+G.+N.&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Finfertilitymoder00bent&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhytoestrogen" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVarnerBonner1966" class="citation book cs1">Varner JE, Bonner J (1966). <i>Plant Biochemistry</i>. Academic Press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-114856-0" title="Special:BookSources/978-0-12-114856-0"><bdi>978-0-12-114856-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Plant+Biochemistry&rft.pub=Academic+Press&rft.date=1966&rft.isbn=978-0-12-114856-0&rft.aulast=Varner&rft.aufirst=JE&rft.au=Bonner%2C+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhytoestrogen" class="Z3988"></span></span> </li> <li id="cite_note-pmid21028682-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid21028682_6-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBennettsUnderwoodShier1946" class="citation journal cs1">Bennetts HW, Underwood EJ, Shier FL (1946). "A specific breeding problem of sheep on subterranean clover pastures in Western Australia". <i>Australian Veterinary Journal</i>. <b>22</b> (1): 2–12. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1751-0813.1946.tb15473.x">10.1111/j.1751-0813.1946.tb15473.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21028682">21028682</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Australian+Veterinary+Journal&rft.atitle=A+specific+breeding+problem+of+sheep+on+subterranean+clover+pastures+in+Western+Australia&rft.volume=22&rft.issue=1&rft.pages=2-12&rft.date=1946&rft_id=info%3Adoi%2F10.1111%2Fj.1751-0813.1946.tb15473.x&rft_id=info%3Apmid%2F21028682&rft.aulast=Bennetts&rft.aufirst=HW&rft.au=Underwood%2C+EJ&rft.au=Shier%2C+FL&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhytoestrogen" 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="CITEREFCunninghamHogan1954" class="citation journal cs1">Cunningham IJ, Hogan KG (1954). 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Phytomedicine&rft.atitle=Analysis+of+thirteen+populations+of+black+cohosh+for+formononetin&rft.volume=9&rft.issue=5&rft.pages=461-467&rft.date=2002-07&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A24786174%23id-name%3DS2CID&rft_id=info%3Apmid%2F12222669&rft_id=info%3Adoi%2F10.1078%2F09447110260571733&rft.aulast=Kennelly&rft.aufirst=EJ&rft.au=Baggett%2C+S&rft.au=Nuntanakorn%2C+P&rft.au=Ososki%2C+AL&rft.au=Mori%2C+SA&rft.au=Duke%2C+J&rft.au=Coleton%2C+M&rft.au=Kronenberg%2C+F&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhytoestrogen" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid 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.navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="Xenoestrogens" 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:Xenoestrogens" title="Template:Xenoestrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Xenoestrogens" title="Template talk:Xenoestrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Xenoestrogens" title="Special:EditPage/Template:Xenoestrogens"><abbr title="Edit this 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title="Naringenin">Naringenin</a></li> <li><a href="/wiki/Pinocembrin" title="Pinocembrin">Pinocembrin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavones" title="Flavones">Flavones</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/Acacetin" title="Acacetin">Acacetin</a></li> <li><a href="/wiki/7,8-Dihydroxyflavone" class="mw-redirect" title="7,8-Dihydroxyflavone">7,8-Dihydroxyflavone</a></li> <li><a href="/wiki/Mirificin" title="Mirificin">Mirificin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Prenylflavonoids" class="mw-redirect" title="Prenylflavonoids">Prenylflavonoids</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/8-Prenylnaringenin" title="8-Prenylnaringenin">8-Prenylnaringenin</a></li> <li><a href="/w/index.php?title=6-Prenylnaringenin&action=edit&redlink=1" class="new" title="6-Prenylnaringenin (page does not exist)">6-Prenylnaringenin</a></li> <li><a href="/w/index.php?title=8-Geranylnaringenin&action=edit&redlink=1" class="new" title="8-Geranylnaringenin (page does not exist)">8-Geranylnaringenin</a></li> <li><a href="/w/index.php?title=6,8-Diprenylnaringenin&action=edit&redlink=1" class="new" title="6,8-Diprenylnaringenin (page does not exist)">6,8-Diprenylnaringenin</a></li> <li><a href="/w/index.php?title=Icaritin&action=edit&redlink=1" class="new" title="Icaritin (page does not exist)">Icaritin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Isoflavones" class="mw-redirect" title="Isoflavones">Isoflavones</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/Biochanin_A" title="Biochanin A">Biochanin A</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/Daidzin" title="Daidzin">Daidzin</a></li> <li><a href="/wiki/Formononetin" title="Formononetin">Formononetin</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/wiki/Genistin" title="Genistin">Genistin</a></li> <li><a href="/wiki/Glycitein" title="Glycitein">Glycitein</a></li> <li><a href="/wiki/Ononin" title="Ononin">Ononin</a></li> <li><a href="/wiki/Prunetin" title="Prunetin">Prunetin</a></li> <li><a href="/wiki/Puerarin" title="Puerarin">Puerarin</a></li> <li><a href="/wiki/Tectorigenin" title="Tectorigenin">Tectorigenin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Isoflavanes" class="mw-redirect" title="Isoflavanes">Isoflavanes</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/Equol" title="Equol">Equol</a> (<a href="/wiki/S-Equol" class="mw-redirect" title="S-Equol"><i>S</i>-Equol</a>)</li> <li><a href="/wiki/Glabridin" title="Glabridin">Glabridin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Dihydrochalcone" title="Dihydrochalcone">Dihydrochalcones</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/Phloretin" title="Phloretin">Phloretin</a></li> <li><a href="/wiki/Phlorizin" title="Phlorizin">Phlorizin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Isoflavenes" class="mw-redirect" title="Isoflavenes">Isoflavenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/wiki/Glabrene" title="Glabrene">Glabrene</a></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Coumestans" class="mw-redirect" title="Coumestans">Coumestans</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/Coumestan" title="Coumestan">Coumestan</a></li> <li><a href="/wiki/Coumestrol" title="Coumestrol">Coumestrol</a></li> <li><a href="/w/index.php?title=Desmethylwedelolactone&action=edit&redlink=1" class="new" title="Desmethylwedelolactone (page does not exist)">Desmethylwedelolactone</a></li> <li><a href="/wiki/Wedelolactone" title="Wedelolactone">Wedelolactone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lignans" class="mw-redirect" title="Lignans">Lignans</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/Enterodiol" title="Enterodiol">Enterodiol</a></li> <li><a href="/wiki/Enterolactone" title="Enterolactone">Enterolactone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavonolignans" class="mw-redirect" title="Flavonolignans">Flavonolignans</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/Silybin" class="mw-redirect" title="Silybin">Silybin</a></li> <li><a href="/wiki/Cinchonain-Ib" title="Cinchonain-Ib">Cinchonain-Ib</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavonol" class="mw-redirect" title="Flavonol">Flavonols</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/Quercetin" title="Quercetin">Quercetin</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/Deoxymiroestrol" class="mw-redirect" title="Deoxymiroestrol">Deoxymiroestrol</a></li> <li><a href="/wiki/Miroestrol" title="Miroestrol">Miroestrol</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/w/index.php?title=%CE%91-Isosparteine&action=edit&redlink=1" class="new" title="Α-Isosparteine (page does not exist)">α-Isosparteine</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/Mycoestrogen" title="Mycoestrogen">Mycoestrogens</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/Zearalanone" title="Zearalanone">Zearalanone</a></li> <li><a href="/wiki/Zearalenone" title="Zearalenone">Zearalenone</a></li> <li><a href="/wiki/Zeranol" title="Zeranol">α-Zearalanol (zeranol)</a></li> <li><a href="/wiki/Alpha-zearalenol" class="mw-redirect" title="Alpha-zearalenol">α-Zearalenol</a></li> <li><a href="/wiki/%CE%92-Zearalanol" class="mw-redirect" title="Β-Zearalanol">β-Zearalanol</a></li> <li><a href="/wiki/%CE%92-Zearalenol" title="Β-Zearalenol">β-Zearalenol</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Derivatives" scope="row" class="navbox-group" style="width:1%">Derivatives</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/Penicillamine" title="Penicillamine"><small>D</small>-Penicillamine</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Synthetic</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/Alkylphenol" title="Alkylphenol">Alkylphenols</a></li> <li><a href="/wiki/Atrazine" title="Atrazine">Atrazine</a></li> <li><a href="/wiki/Butylated_hydroxyanisole" title="Butylated hydroxyanisole">BHA</a></li> <li><a href="/wiki/Bisphenol_A" title="Bisphenol A">Bisphenol A</a></li> <li><a href="/wiki/Bisphenol_F" title="Bisphenol F">Bisphenol F</a></li> <li><a href="/wiki/Bisphenol_S" title="Bisphenol S">Bisphenol S</a></li> <li><a href="/wiki/Dichlorodiphenyldichloroethylene" title="Dichlorodiphenyldichloroethylene">DDE</a></li> <li><a href="/wiki/Dichlorodiphenyltrichloroethane" class="mw-redirect" title="Dichlorodiphenyltrichloroethane">DDT</a></li> <li><a href="/wiki/Dieldrin" title="Dieldrin">Dieldrin</a></li> <li><a href="/wiki/Dioxins_and_dioxin-like_compounds" title="Dioxins and dioxin-like compounds">Dioxins</a></li> <li><a href="/wiki/Endosulfan" title="Endosulfan">Endosulfan</a></li> <li><a href="/wiki/Enzacamene" title="Enzacamene">Enzacamene</a></li> <li><a href="/wiki/Erythrosine" title="Erythrosine">Erythrosine</a></li> <li><a href="/wiki/Heptachlor" title="Heptachlor">Heptachlor</a></li> <li><a href="/wiki/Lindane" title="Lindane">Lindane</a></li> <li><a href="/wiki/Methoxychlor" title="Methoxychlor">Methoxychlor</a></li> <li><a href="/wiki/Nonylphenol" title="Nonylphenol">Nonylphenol</a></li> <li><a href="/wiki/Paraben" title="Paraben">Parabens</a></li> <li><a href="/wiki/Polybrominated_biphenyl" title="Polybrominated biphenyl">PBBs</a></li> <li><a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a></li> <li><a href="/wiki/Pentachlorophenol" title="Pentachlorophenol">Pentachlorophenol</a></li> <li><a href="/wiki/4-Hydroxybenzoic_acid" title="4-Hydroxybenzoic acid">PHBA</a></li> <li><a href="/wiki/Phthalates" title="Phthalates">Phthalates</a></li> <li><a href="/wiki/Propyl_gallate" title="Propyl gallate">Propyl gallate</a></li> <li><a href="/wiki/Perfluorinated_compound" title="Perfluorinated compound">Perfluorinated compound</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Metalloestrogen" title="Metalloestrogen">Metalloestrogens</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>Aluminium</li> <li>Antimony</li> <li>Arsenite</li> <li>Barium</li> <li>Cadmium</li> <li><a href="/wiki/Chromium" title="Chromium">Chromium</a></li> <li><a href="/wiki/Cobalt" title="Cobalt">Cobalt</a></li> <li><a href="/wiki/Copper" title="Copper">Copper</a></li> <li>Lead</li> <li>Mercury</li> <li>Nickel</li> <li>Selenite</li> <li>Tin</li> <li>Vanadate</li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" 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href="/wiki/Special:EditPage/Template:Estrogen_receptor_modulators" title="Special:EditPage/Template:Estrogen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogen_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor">Estrogen receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</span></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:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Steroidal:</i> <a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/3-Methyl-19-methyleneandrosta-3,5-dien-17%CE%B2-ol" title="3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol">3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/w/index.php?title=3%CE%B1,5%CE%B1-Dihydrolevonorgestrel&action=edit&redlink=1" class="new" title="3α,5α-Dihydrolevonorgestrel (page does not exist)">3α,5α-Dihydrolevonorgestrel</a></li> <li><a href="/w/index.php?title=3%CE%B2,5%CE%B1-Dihydrolevonorgestrel&action=edit&redlink=1" class="new" title="3β,5α-Dihydrolevonorgestrel (page does not exist)">3β,5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/3%CE%B1-Hydroxytibolone" title="3α-Hydroxytibolone">3α-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Hydroxytibolone" title="3β-Hydroxytibolone">3β-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/4-Androstenediol" title="4-Androstenediol">4-Androstenediol</a></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">4-Androstenedione</a></li> <li><a href="/wiki/4-Fluoroestradiol" title="4-Fluoroestradiol">4-Fluoroestradiol</a></li> <li><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></li> <li><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a></li> <li><a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></li> <li><a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">5-Androstenediol</a></li> <li><a href="/wiki/7-Keto-DHEA" title="7-Keto-DHEA">7-Oxo-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxy-DHEA" title="7α-Hydroxy-DHEA">7α-Hydroxy-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Methylestradiol" title="7α-Methylestradiol">7α-Methylestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/8,9-Dehydroestradiol" title="8,9-Dehydroestradiol">8,9-Dehydroestradiol</a></li> <li><a href="/wiki/8,9-Dehydroestrone" title="8,9-Dehydroestrone">8,9-Dehydroestrone</a></li> <li><a href="/wiki/8%CE%B2-VE2" title="8β-VE2">8β-VE2</a></li> <li><a href="/wiki/10%CE%B2,17%CE%B2-Dihydroxyestra-1,4-dien-3-one" title="10β,17β-Dihydroxyestra-1,4-dien-3-one">10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)</a></li> <li><a href="/wiki/11%CE%B2-Chloromethylestradiol" title="11β-Chloromethylestradiol">11β-Chloromethylestradiol</a></li> <li><a href="/wiki/11%CE%B2-Methoxyestradiol" title="11β-Methoxyestradiol">11β-Methoxyestradiol</a></li> <li><a href="/wiki/15%CE%B1-Hydroxyestradiol" title="15α-Hydroxyestradiol">15α-Hydroxyestradiol</a></li> <li><a href="/wiki/16-Ketoestradiol" title="16-Ketoestradiol">16-Ketoestradiol</a></li> <li><a href="/wiki/16-Ketoestrone" title="16-Ketoestrone">16-Ketoestrone</a></li> <li><a href="/wiki/16%CE%B1-Fluoroestradiol" class="mw-redirect" title="16α-Fluoroestradiol">16α-Fluoroestradiol</a></li> <li><a href="/wiki/16%CE%B1-Hydroxy-DHEA" title="16α-Hydroxy-DHEA">16α-Hydroxy-DHEA</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B1-Iodoestradiol" class="mw-redirect" title="16α-Iodoestradiol">16α-Iodoestradiol</a></li> <li><a href="/wiki/16%CE%B1-LE2" title="16α-LE2">16α-LE2</a></li> <li><a href="/wiki/16%CE%B2-Hydroxyestrone" title="16β-Hydroxyestrone">16β-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B2,17%CE%B1-Epiestriol" title="16β,17α-Epiestriol">16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Estradiol" title="17α-Estradiol">17α-Estradiol</a> (<a href="/wiki/Alfatradiol" title="Alfatradiol">alfatradiol</a>)</li> <li><a href="/wiki/17%CE%B1-Dihydroequilenin" title="17α-Dihydroequilenin">17α-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B1-Dihydroequilin" title="17α-Dihydroequilin">17α-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B1-Epiestriol" title="17α-Epiestriol">17α-Epiestriol (16α-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B1-androstanediol" title="17α-Ethynyl-3α-androstanediol">17α-Ethynyl-3α-androstanediol</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B2-androstanediol" title="17α-Ethynyl-3β-androstanediol">17α-Ethynyl-3β-androstanediol</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilenin" title="17β-Dihydroequilenin">17β-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilin" title="17β-Dihydroequilin">17β-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B2-Methyl-17%CE%B1-dihydroequilenin" title="17β-Methyl-17α-dihydroequilenin">17β-Methyl-17α-dihydroequilenin</a></li> <li><a href="/wiki/Abiraterone" class="mw-redirect" title="Abiraterone">Abiraterone</a></li> <li><a href="/wiki/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a></li> <li><a href="/wiki/Alestramustine" title="Alestramustine">Alestramustine</a></li> <li><a href="/wiki/Almestrone" title="Almestrone">Almestrone</a></li> <li><a href="/wiki/Anabolic_steroid" title="Anabolic steroid">Anabolic steroids</a> (e.g., <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> and <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">esters</a>, <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone (methandrostenolone)</a>, <a href="/wiki/Nandrolone" title="Nandrolone">nandrolone</a> and <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">esters</a>, many others; via estrogenic metabolites)</li> <li><a href="/wiki/Atrimustine" title="Atrimustine">Atrimustine</a></li> <li><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a></li> <li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li> <li><a href="/wiki/Butolame" title="Butolame">Butolame</a></li> <li><a href="/wiki/Clomestrone" title="Clomestrone">Clomestrone</a></li> <li><a href="/wiki/Cloxestradiol" title="Cloxestradiol">Cloxestradiol</a> <ul><li><a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li></ul></li> <li><a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Cyclodiol" title="Cyclodiol">Cyclodiol</a></li> <li><a href="/wiki/Cyclotriol" title="Cyclotriol">Cyclotriol</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA-S</a></li> <li><a href="/wiki/Ent-Estradiol" title="Ent-Estradiol"><i>ent</i>-Estradiol</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Equilenin" title="Equilenin">Equilenin</a></li> <li><a href="/wiki/Equilin" title="Equilin">Equilin</a></li> <li><a href="/wiki/ERA-63" title="ERA-63">ERA-63 (ORG-37663)</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol" title="Estetrol">Estetrol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a></li> <li><a href="/wiki/Lipoidal_estradiol" title="Lipoidal estradiol">Lipoidal estradiol</a></li> <li><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a></li></ul></li> <li><a href="/wiki/Estramustine" title="Estramustine">Estramustine</a></li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a></li> <li><a href="/wiki/Estrapronicate" title="Estrapronicate">Estrapronicate</a></li> <li><a href="/wiki/Estrazinol" title="Estrazinol">Estrazinol</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a></li> <li><a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">Polyestriol phosphate</a></li></ul></li> <li><a href="/wiki/Estrofurate" title="Estrofurate">Estrofurate</a></li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estromustine" title="Estromustine">Estromustine</a></li> <li><a href="/wiki/Estrone" title="Estrone">Estrone</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a></li> <li><a href="/wiki/Estrone_methyl_ether" title="Estrone methyl ether">Estrone methyl ether</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate</a></li></ul></li> <li><a href="/wiki/Etamestrol" title="Etamestrol">Etamestrol (eptamestrol)</a></li> <li><a href="/wiki/Ethinylandrostenediol" title="Ethinylandrostenediol">Ethinylandrostenediol</a> <ul><li><a href="/wiki/Ethandrostate" title="Ethandrostate">Ethandrostate</a></li></ul></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a> <ul><li><a href="/wiki/Ethinylestradiol_3-benzoate" class="mw-redirect" title="Ethinylestradiol 3-benzoate">Ethinylestradiol 3-benzoate</a></li> <li><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li> <li><a href="/wiki/Ethinylestriol" title="Ethinylestriol">Ethinylestriol</a></li> <li><a href="/wiki/Ethylestradiol" title="Ethylestradiol">Ethylestradiol</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a></li> <li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li> <li><a href="/wiki/Hexolame" title="Hexolame">Hexolame</a></li> <li><a href="/wiki/Hippulin" title="Hippulin">Hippulin</a></li> <li><a href="/wiki/Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</a></li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a></li> <li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li> <li><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></li> <li><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></li> <li><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></li> <li><a href="/wiki/Mytatrienediol" title="Mytatrienediol">Mytatrienediol</a></li> <li><a href="/wiki/Nilestriol" title="Nilestriol">Nilestriol</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Orestrate" title="Orestrate">Orestrate</a></li> <li><a href="/wiki/Pentolame" title="Pentolame">Pentolame</a></li> <li><a href="/wiki/Prodiame" title="Prodiame">Prodiame</a></li> <li><a href="/wiki/Prolame" title="Prolame">Prolame</a></li> <li><a href="/wiki/Promestriene" title="Promestriene">Promestriene</a></li> <li><a href="/wiki/RU-16117" title="RU-16117">RU-16117</a></li> <li><a href="/wiki/Quinestradol" title="Quinestradol">Quinestradol</a></li> <li><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/(S,S)-Tetrahydrochrysene" title="(S,S)-Tetrahydrochrysene">(S,S)-THC</a></li> <li><a href="/wiki/2,8-Dihydroxyhexahydrochrysene" title="2,8-Dihydroxyhexahydrochrysene">2,8-DHHHC</a></li> <li><a href="/w/index.php?title=%CE%92-LGND1&action=edit&redlink=1" class="new" title="Β-LGND1 (page does not exist)">β-LGND1</a></li> <li><a href="/wiki/%CE%92-LGND2" title="Β-LGND2">β-LGND2 (GTx-878)</a></li> <li><a href="/w/index.php?title=AC-186&action=edit&redlink=1" class="new" title="AC-186 (page does not exist)">AC-186</a></li> <li><a href="/wiki/Allenestrol" title="Allenestrol">Allenestrol</a></li> <li><a href="/wiki/Allenolic_acid" title="Allenolic acid">Allenolic acid</a></li> <li><a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Bisdehydrodoisynolic_acid" title="Bisdehydrodoisynolic acid">Bisdehydrodoisynolic acid</a></li> <li><a href="/wiki/Butestrol" title="Butestrol">Butestrol</a></li> <li><a href="/wiki/Carbestrol" title="Carbestrol">Carbestrol</a></li> <li><a href="/wiki/D-15414" title="D-15414">D-15414</a></li> <li><a href="/wiki/DCW234" title="DCW234">DCW234</a></li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> <ul><li><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a></li></ul></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Diethylstilbestrol_esters" title="List of estrogen esters">Diethylstilbestrol esters</a></li></ul></li> <li><a href="/wiki/Dimestrol" title="Dimestrol">Dimestrol (dianisylhexene)</a></li> <li><a href="/wiki/Dimethylstilbestrol" title="Dimethylstilbestrol">Dimethylstilbestrol</a></li> <li><a href="/wiki/Doisynoestrol" title="Doisynoestrol">Doisynoestrol (fenocycline)</a></li> <li><a href="/wiki/Doisynolic_acid" title="Doisynolic acid">Doisynolic acid</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Elacestrant" title="Elacestrant">Elacestrant</a></li> <li><a href="/wiki/ERB-196" title="ERB-196">ERB-196 (WAY-202196)</a></li> <li><a href="/wiki/Erteberel" title="Erteberel">Erteberel (SERBA-1, LY-500307)</a></li> <li><a href="/wiki/Estrobin" title="Estrobin">Estrobin (DBE)</a></li> <li><a href="/wiki/Fenestrel" title="Fenestrel">Fenestrel</a></li> <li><a href="/wiki/FERb_033" title="FERb 033">FERb 033</a></li> <li><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol (diethylstilbestrol diphosphate)</a></li> <li><a href="/wiki/Furostilbestrol" title="Furostilbestrol">Furostilbestrol (diethylstilbestrol difuroate)</a></li> <li><a href="/wiki/GTx-758" title="GTx-758">GTx-758</a></li> <li><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Hexestrol_esters" title="List of estrogen esters">Hexestrol esters</a></li></ul></li> <li><a href="/wiki/ICI-85966" title="ICI-85966">ICI-85966 (Stilbostat)</a></li> <li><a href="/wiki/M2613" title="M2613">M2613</a></li> <li><a href="/wiki/Meso-Butestrol" title="Meso-Butestrol"><i>meso</i>-Butestrol</a></li> <li><a href="/wiki/Meso-Hexestrol" class="mw-redirect" title="Meso-Hexestrol"><i>meso</i>-Hexestrol</a></li> <li><a href="/wiki/Mestilbol" title="Mestilbol">Mestilbol</a></li> <li><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a></li> <li><a href="/wiki/Methestrol" title="Methestrol">Methestrol</a></li> <li><a href="/wiki/Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate</a></li> <li><a href="/wiki/Paroxypropione" title="Paroxypropione">Paroxypropione</a></li> <li><a href="/wiki/Pentafluranol" title="Pentafluranol">Pentafluranol</a></li> <li><a href="/wiki/Phenestrol" title="Phenestrol">Phenestrol</a></li> <li><a href="/wiki/Prinaberel" title="Prinaberel">Prinaberel (ERB-041, WAY-202041)</a></li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></li> <li><a href="/w/index.php?title=SC-3296&action=edit&redlink=1" class="new" title="SC-3296 (page does not exist)">SC-3296</a></li> <li><a href="/wiki/SC-4289" title="SC-4289">SC-4289</a></li> <li><a href="/wiki/SERBA-2" title="SERBA-2">SERBA-2</a></li> <li><a href="/wiki/SKF-82,958" title="SKF-82,958">SKF-82,958</a></li> <li><a href="/wiki/Terfluranol" title="Terfluranol">Terfluranol</a></li> <li><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></li> <li><a href="/wiki/Triphenylchloroethylene" title="Triphenylchloroethylene">Triphenylchloroethylene</a></li> <li><a href="/wiki/Triphenyliodoethylene" title="Triphenyliodoethylene">Triphenyliodoethylene</a></li> <li><a href="/wiki/Triphenylmethylethylene" title="Triphenylmethylethylene">Triphenylmethylethylene (triphenylpropene)</a></li> <li><a href="/wiki/WAY-166818" title="WAY-166818">WAY-166818</a></li> <li><a href="/w/index.php?title=WAY-169916&action=edit&redlink=1" class="new" title="WAY-169916 (page does not exist)">WAY-169916</a></li> <li><a href="/wiki/WAY-200070" title="WAY-200070">WAY-200070</a></li> <li><a href="/wiki/WAY-204688" title="WAY-204688">WAY-204688 (SIM-688)</a></li> <li><a href="/wiki/WAY-214156" title="WAY-214156">WAY-214156</a></li></ul> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/ERB-26" title="ERB-26">ERB-26</a></li> <li><a href="/wiki/ERA-45" title="ERA-45">ERA-45</a></li> <li><a href="/wiki/ERB-79" title="ERB-79">ERB-79</a></li> <li><a href="/wiki/ZK-283197" title="ZK-283197">ZK-283197</a></li></ul> <ul><li><i>Xenoestrogens:</i> <a href="/wiki/Anise" title="Anise">Anise</a>-related (e.g., <a href="/wiki/Anethole" title="Anethole">anethole</a>, <a href="/wiki/Anol" title="Anol">anol</a>, <a href="/wiki/Dianethole" title="Dianethole">dianethole</a>, <a href="/wiki/Dianol" title="Dianol">dianol</a>, <a href="/wiki/Photoanethole" title="Photoanethole">photoanethole</a>)</li> <li><a href="/wiki/Chalconoid" title="Chalconoid">Chalconoids</a> (e.g., <a href="/wiki/Isoliquiritigenin" title="Isoliquiritigenin">isoliquiritigenin</a>, <a href="/wiki/Phloretin" title="Phloretin">phloretin</a>, <a href="/wiki/Phlorizin" title="Phlorizin">phlorizin (phloridzin)</a>, <a href="/wiki/Wedelolactone" title="Wedelolactone">wedelolactone</a>)</li> <li><a href="/wiki/Coumestan" title="Coumestan">Coumestans</a> (e.g., <a href="/wiki/Coumestrol" title="Coumestrol">coumestrol</a>, <a href="/wiki/Psoralidin" title="Psoralidin">psoralidin</a>)</li> <li><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a> (incl. <a href="/wiki/7,8-Dihydroxyflavone" class="mw-redirect" title="7,8-Dihydroxyflavone">7,8-DHF</a>, <a href="/wiki/8-Prenylnaringenin" title="8-Prenylnaringenin">8-prenylnaringenin</a>, <a href="/wiki/Apigenin" title="Apigenin">apigenin</a>, <a href="/wiki/Baicalein" title="Baicalein">baicalein</a>, <a href="/wiki/Baicalin" title="Baicalin">baicalin</a>, <a href="/wiki/Biochanin_A" title="Biochanin A">biochanin A</a>, <a href="/wiki/Calycosin" title="Calycosin">calycosin</a>, <a href="/wiki/Catechin" title="Catechin">catechin</a>, <a href="/wiki/Daidzein" title="Daidzein">daidzein</a>, <a href="/wiki/Daidzin" title="Daidzin">daidzin</a>, <a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">ECG</a>, <a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">EGCG</a>, <a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">epicatechin</a>, <a href="/wiki/Equol" title="Equol">equol</a>, <a href="/wiki/Formononetin" title="Formononetin">formononetin</a>, <a href="/wiki/Glabrene" title="Glabrene">glabrene</a>, <a href="/wiki/Glabridin" title="Glabridin">glabridin</a>, <a href="/wiki/Genistein" title="Genistein">genistein</a>, <a href="/wiki/Genistin" title="Genistin">genistin</a>, <a href="/wiki/Glycitein" title="Glycitein">glycitein</a>, <a href="/wiki/Kaempferol" title="Kaempferol">kaempferol</a>, <a href="/wiki/Liquiritigenin" title="Liquiritigenin">liquiritigenin</a>, <a href="/wiki/Mirificin" title="Mirificin">mirificin</a>, <a href="/wiki/Myricetin" title="Myricetin">myricetin</a>, <a href="/wiki/Naringenin" title="Naringenin">naringenin</a>, <a href="/w/index.php?title=Penduletin&action=edit&redlink=1" class="new" title="Penduletin (page does not exist)">penduletin</a>, <a href="/wiki/Pinocembrin" title="Pinocembrin">pinocembrin</a>, <a href="/wiki/Prunetin" title="Prunetin">prunetin</a>, <a href="/wiki/Puerarin" title="Puerarin">puerarin</a>, <a href="/wiki/Quercetin" title="Quercetin">quercetin</a>, <a href="/wiki/Tectoridin" title="Tectoridin">tectoridin</a>, <a href="/wiki/Tectorigenin" title="Tectorigenin">tectorigenin</a>)</li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/wiki/Lignan" title="Lignan">Lignans</a> (e.g., <a href="/wiki/Enterodiol" title="Enterodiol">enterodiol</a>, <a href="/wiki/Enterolactone" title="Enterolactone">enterolactone</a>, <a href="/wiki/Nyasol" title="Nyasol">nyasol (<i>cis</i>-hinokiresinol)</a>)</li> <li><a href="/wiki/Metalloestrogen" title="Metalloestrogen">Metalloestrogens</a> (e.g., <a href="/wiki/Cadmium" title="Cadmium">cadmium</a>)</li> <li><a href="/wiki/Pesticide" title="Pesticide">Pesticides</a> (e.g., <a href="/wiki/Alternariol" title="Alternariol">alternariol</a>, <a href="/wiki/Dieldrin" title="Dieldrin">dieldrin</a>, <a href="/wiki/Endosulfan" title="Endosulfan">endosulfan</a>, <a href="/wiki/Fenarimol" title="Fenarimol">fenarimol</a>, <a href="/wiki/HPTE" title="HPTE">HPTE</a>, <a href="/wiki/Methiocarb" title="Methiocarb">methiocarb</a>, <a href="/wiki/Methoxychlor" title="Methoxychlor">methoxychlor</a>, <a href="/wiki/Triclocarban" title="Triclocarban">triclocarban</a>, <a href="/wiki/Triclosan" title="Triclosan">triclosan</a>)</li> <li><a href="/wiki/Phytosteroid" title="Phytosteroid">Phytosteroids</a> (e.g., <a href="/wiki/Digitoxin" title="Digitoxin">digitoxin</a> (<a href="/wiki/Digitalis" title="Digitalis">digitalis</a>), <a href="/wiki/Diosgenin" title="Diosgenin">diosgenin</a>, <a href="/wiki/Guggulsterone" title="Guggulsterone">guggulsterone</a>)</li> <li><a href="/wiki/Phytosterol" title="Phytosterol">Phytosterols</a> (e.g., <a href="/wiki/%CE%92-sitosterol" class="mw-redirect" title="Β-sitosterol">β-sitosterol</a>, <a href="/wiki/Campesterol" title="Campesterol">campesterol</a>, <a href="/wiki/Stigmasterol" title="Stigmasterol">stigmasterol</a>)</li> <li><a href="/wiki/Resorcylic_acid_lactone" title="Resorcylic acid lactone">Resorcylic acid lactones</a> (e.g., <a href="/wiki/Zearalanone" title="Zearalanone">zearalanone</a>, <a href="/wiki/%CE%91-zearalenol" class="mw-redirect" title="Α-zearalenol">α-zearalenol</a>, <a href="/wiki/%CE%92-zearalenol" class="mw-redirect" title="Β-zearalenol">β-zearalenol</a>, <a href="/wiki/Zearalenone" title="Zearalenone">zearalenone</a>, <a href="/wiki/Zeranol" title="Zeranol">zeranol (α-zearalanol)</a>, <a href="/wiki/Taleranol" title="Taleranol">taleranol (teranol, β-zearalanol)</a>)</li> <li><a href="/wiki/Steroid" title="Steroid">Steroid</a>-like (e.g., <a href="/wiki/Deoxymiroestrol" class="mw-redirect" title="Deoxymiroestrol">deoxymiroestrol</a>, <a href="/wiki/Miroestrol" title="Miroestrol">miroestrol</a>)</li> <li><a href="/wiki/Stilbenoid" title="Stilbenoid">Stilbenoids</a> (e.g., <a href="/wiki/Resveratrol" title="Resveratrol">resveratrol</a>, <a href="/wiki/Rhaponticin" title="Rhaponticin">rhaponticin</a>)</li> <li><a href="/wiki/Synthetic_xenoestrogen" class="mw-redirect" title="Synthetic xenoestrogen">Synthetic xenoestrogens</a> (e.g., <a href="/wiki/Alkylphenol" title="Alkylphenol">alkylphenols</a>, <a href="/wiki/Bisphenol" title="Bisphenol">bisphenols</a> (e.g., <a href="/wiki/Bisphenol_A" title="Bisphenol A">BPA</a>, <a href="/wiki/Bisphenol_F" title="Bisphenol F">BPF</a>, <a href="/wiki/Bisphenol_S" title="Bisphenol S">BPS</a>), <a href="/wiki/Dichlorodiphenyltrichloroethane" class="mw-redirect" title="Dichlorodiphenyltrichloroethane">DDT</a>, <a href="/wiki/Paraben" title="Paraben">parabens</a>, <a href="/wiki/Polybrominated_biphenyl" title="Polybrominated biphenyl">PBBs</a>, <a href="/wiki/4-hydroxybenzoic_acid" class="mw-redirect" title="4-hydroxybenzoic acid">PHBA</a>, <a href="/wiki/Phthalate" class="mw-redirect" title="Phthalate">phthalates</a>, <a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a>)</li> <li>Others (e.g., <a href="/wiki/Agnuside" title="Agnuside">agnuside</a>, <a href="/w/index.php?title=Rotundifuran&action=edit&redlink=1" class="new" title="Rotundifuran (page does not exist)">rotundifuran</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Mixed<br />(<a href="/wiki/Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="Selective estrogen receptor modulators">SERMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective estrogen receptor modulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Phenylbenzofuran" title="2-Phenylbenzofuran">2-Phenylbenzofuran</a></li> <li><a href="/w/index.php?title=2-Phenylbenzothiophene&action=edit&redlink=1" class="new" title="2-Phenylbenzothiophene (page does not exist)">2-Phenylbenzothiophene</a></li> <li><a href="/wiki/4%27-Hydroxynorendoxifen" title="4'-Hydroxynorendoxifen">4'-Hydroxynorendoxifen</a></li> <li><a href="/wiki/27-Hydroxycholesterol" title="27-Hydroxycholesterol">27-Hydroxycholesterol</a></li> <li><a href="/wiki/Acefluranol" title="Acefluranol">Acefluranol</a></li> <li><a href="/wiki/Acolbifene" title="Acolbifene">Acolbifene</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene</a></li> <li><a href="/wiki/Anordiol" title="Anordiol">Anordiol</a></li> <li><a href="/wiki/Anordrin" title="Anordrin">Anordrin</a></li> <li><a href="/wiki/Arzoxifene" title="Arzoxifene">Arzoxifene</a></li> <li><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></li> <li><a href="/wiki/Brilanestrant" title="Brilanestrant">Brilanestrant</a></li> <li><a href="/wiki/Broparestrol" title="Broparestrol">Broparestrol</a></li> <li><a href="/wiki/Camizestrant" title="Camizestrant">Camizestrant</a></li> <li><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></li> <li><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a></li> <li><a href="/wiki/Clomifenoxide" title="Clomifenoxide">Clomifenoxide</a></li> <li><a href="/w/index.php?title=CN-55945-27&action=edit&redlink=1" class="new" title="CN-55945-27 (page does not exist)">CN-55945-27</a></li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/w/index.php?title=D-15413&action=edit&redlink=1" class="new" title="D-15413 (page does not exist)">D-15413</a></li> <li><a href="/wiki/Desmethylchlorotrianisene" title="Desmethylchlorotrianisene">Desmethylchlorotrianisene</a></li> <li><a href="/wiki/Droloxifene" title="Droloxifene">Droloxifene</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a></li> <li><a href="/wiki/Endoxifen" title="Endoxifen">Endoxifen</a></li> <li><a href="/wiki/Etacstil" title="Etacstil">Etacstil (GW-5638, DPC-974)</a></li> <li><a href="/wiki/Ethamoxytriphetol" title="Ethamoxytriphetol">Ethamoxytriphetol (MER-25)</a></li> <li><a href="/wiki/Femarelle" title="Femarelle">Femarelle</a></li> <li><a href="/wiki/Fispemifene" title="Fispemifene">Fispemifene</a></li> <li><a href="/w/index.php?title=GW-7604&action=edit&redlink=1" class="new" title="GW-7604 (page does not exist)">GW-7604</a></li> <li><a href="/wiki/ICI-55548" class="mw-redirect" title="ICI-55548">ICI-55548</a></li> <li><a href="/wiki/Idoxifene" title="Idoxifene">Idoxifene</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Levormeloxifene" title="Levormeloxifene">Levormeloxifene</a></li> <li><a href="/wiki/LN-1643" class="mw-redirect" title="LN-1643">LN-1643</a></li> <li><a href="/wiki/LN-2299" class="mw-redirect" title="LN-2299">LN-2299</a></li> <li><a href="/w/index.php?title=LY-117018&action=edit&redlink=1" class="new" title="LY-117018 (page does not exist)">LY-117018</a></li> <li><a href="/wiki/Menerba" title="Menerba">Menerba</a></li> <li><a href="/wiki/Miproxifene" title="Miproxifene">Miproxifene</a></li> <li><a href="/wiki/Miproxifene_phosphate" title="Miproxifene phosphate">Miproxifene phosphate</a></li> <li><a href="/w/index.php?title=MRL-37&action=edit&redlink=1" class="new" title="MRL-37 (page does not exist)">MRL-37</a></li> <li><a href="/wiki/Nafoxidine" title="Nafoxidine">Nafoxidine</a></li> <li><a href="/wiki/Nitromifene" title="Nitromifene">Nitromifene</a></li> <li><a href="/wiki/NNC_45-0095" title="NNC 45-0095">NNC 45-0095</a></li> <li><a href="/w/index.php?title=NNC_45-0320&action=edit&redlink=1" class="new" title="NNC 45-0320 (page does not exist)">NNC 45-0320</a></li> <li><a href="/w/index.php?title=NNC_45-0781&action=edit&redlink=1" class="new" title="NNC 45-0781 (page does not exist)">NNC 45-0781</a></li> <li><a href="/w/index.php?title=NNC_45-1506&action=edit&redlink=1" class="new" title="NNC 45-1506 (page does not exist)">NNC 45-1506</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li> <li><a href="/wiki/Panomifene" title="Panomifene">Panomifene</a></li> <li><a href="/wiki/Pipendoxifene" title="Pipendoxifene">Pipendoxifene</a></li> <li><a href="/w/index.php?title=Promensil&action=edit&redlink=1" class="new" title="Promensil (page does not exist)">Promensil</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Rimostil" title="Rimostil">Rimostil (P-081)</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/w/index.php?title=SS1010&action=edit&redlink=1" class="new" title="SS1010 (page does not exist)">SS1010</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/TAS-108" title="TAS-108">TAS-108 (SR-16234)</a></li> <li><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></li> <li><a href="/wiki/Trioxifene" title="Trioxifene">Trioxifene</a></li> <li><a href="/w/index.php?title=TZE-5323&action=edit&redlink=1" class="new" title="TZE-5323 (page does not exist)">TZE-5323</a></li> <li><a href="/w/index.php?title=U-11555A&action=edit&redlink=1" class="new" title="U-11555A (page does not exist)">U-11555A</a></li> <li><a href="/w/index.php?title=U-11634&action=edit&redlink=1" class="new" title="U-11634 (page does not exist)">U-11634</a></li> <li><a href="/w/index.php?title=Y-134&action=edit&redlink=1" class="new" title="Y-134 (page does not exist)">Y-134</a></li> <li><a href="/wiki/Zindoxifene" title="Zindoxifene">Zindoxifene</a></li> <li><a href="/wiki/Zuclomifene" title="Zuclomifene">Zuclomifene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/7%CE%B2-Hydroxy-DHEA" title="7β-Hydroxy-DHEA">7β-Hydroxy-DHEA</a></li> <li><a href="/w/index.php?title=Chloroindazole&action=edit&redlink=1" class="new" title="Chloroindazole (page does not exist)">Chloroindazole</a></li> <li><a href="/wiki/Cytestrol_acetate" title="Cytestrol acetate">Cytestrol acetate</a></li> <li><a href="/w/index.php?title=EM-800&action=edit&redlink=1" class="new" title="EM-800 (page does not exist)">EM-800 (SCH-57050)</a></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/w/index.php?title=ERA-90&action=edit&redlink=1" class="new" title="ERA-90 (page does not exist)">ERA-90</a></li> <li><a href="/w/index.php?title=ERB-88&action=edit&redlink=1" class="new" title="ERB-88 (page does not exist)">ERB-88</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/wiki/Glyceollin" title="Glyceollin">Glyceollins</a> (<a href="/wiki/Glyceollin_I" title="Glyceollin I">I</a>, <a href="/w/index.php?title=Glyceollin_II&action=edit&redlink=1" class="new" title="Glyceollin II (page does not exist)">II</a>, <a href="/wiki/Glyceollin_III" title="Glyceollin III">III</a>, <a href="/w/index.php?title=Glyceollin_IV&action=edit&redlink=1" class="new" title="Glyceollin IV (page does not exist)">IV</a>)</li> <li><a href="/wiki/ICI-164384" title="ICI-164384">ICI-164384</a></li> <li><a href="/w/index.php?title=MDL-101906&action=edit&redlink=1" class="new" title="MDL-101906 (page does not exist)">MDL-101906</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Methylepitiostanol" title="Methylepitiostanol">Methylepitiostanol</a></li> <li><a href="/wiki/Methylpiperidinopyrazole" title="Methylpiperidinopyrazole">Methylpiperidinopyrazole</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li> <li><a href="/w/index.php?title=Oxabicycloheptene_sulfonate&action=edit&redlink=1" class="new" title="Oxabicycloheptene sulfonate (page does not exist)">Oxabicycloheptene sulfonate</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/PHTPP" title="PHTPP">PHTPP</a></li> <li><a href="/wiki/Prochloraz" title="Prochloraz">Prochloraz</a></li> <li><a href="/w/index.php?title=RU-39411&action=edit&redlink=1" class="new" title="RU-39411 (page does not exist)">RU-39411</a></li> <li><a href="/w/index.php?title=RU-58668&action=edit&redlink=1" class="new" title="RU-58668 (page does not exist)">RU-58668</a></li> <li><a href="/w/index.php?title=SS1020&action=edit&redlink=1" class="new" title="SS1020 (page does not exist)">SS1020</a></li> <li><a href="/wiki/TAS-108" title="TAS-108">TAS-108 (SR-16234)</a></li> <li><a href="/wiki/ZB716" title="ZB716">ZB716</a></li> <li><a href="/w/index.php?title=ZK-164015&action=edit&redlink=1" class="new" title="ZK-164015 (page does not exist)">ZK-164015</a></li> <li><a href="/w/index.php?title=ZK-191703&action=edit&redlink=1" class="new" title="ZK-191703 (page does not exist)">ZK-191703</a></li></ul> <ul><li><i>Coregulator-binding modulators:</i> <a href="/wiki/ERX-11" title="ERX-11">ERX-11</a></li></ul> <ul><li><i>Noncompetitive inhibitors:</i> <a href="/wiki/Trilostane" title="Trilostane">Trilostane</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/G_protein-coupled_estrogen_receptor" class="mw-redirect" title="G protein-coupled estrogen receptor"><abbr title="G protein-coupled estrogen receptor">GPER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip G protein-coupled estrogen receptor</span></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:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene (4-hydroxytamoxifen)</a></li> <li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a href="/wiki/Atrazine" title="Atrazine">Atrazine</a></li> <li><a href="/wiki/Bisphenol_A" title="Bisphenol A">Bisphenol A</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/DDT" title="DDT">DDT</a> (<a href="/wiki/P,p%27-DDT" class="mw-redirect" title="P,p'-DDT">p,p'-DDT</a>, <a href="/w/index.php?title=O%27,p%27-DDE&action=edit&redlink=1" class="new" title="O',p'-DDE (page does not exist)">o',p'-DDE</a>)</li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Equol" title="Equol">Equol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/w/index.php?title=G-1_(drug)&action=edit&redlink=1" class="new" title="G-1 (drug) (page does not exist)">G-1</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/w/index.php?title=GPER-L1&action=edit&redlink=1" class="new" title="GPER-L1 (page does not exist)">GPER-L1</a></li> <li><a href="/w/index.php?title=GPER-L2&action=edit&redlink=1" class="new" title="GPER-L2 (page does not exist)">GPER-L2</a></li> <li><a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol</a></li> <li><a href="/wiki/Kepone" class="mw-redirect" title="Kepone">Kepone</a></li> <li><a href="/wiki/Niacin" title="Niacin">Niacin</a></li> <li><a href="/wiki/Niacinamide" class="mw-redirect" title="Niacinamide">Niacinamide</a></li> <li><a href="/wiki/Nonylphenol" title="Nonylphenol">Nonylphenol</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li> <li><a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a> (<a href="/w/index.php?title=2,2%27,5%27-PCB-4-OH&action=edit&redlink=1" class="new" title="2,2',5'-PCB-4-OH (page does not exist)">2,2',5'-PCB-4-OH</a>)</li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/w/index.php?title=STX_(drug)&action=edit&redlink=1" class="new" title="STX (drug) (page does not exist)">STX</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/Tectoridin" title="Tectoridin">Tectoridin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CCL18" title="CCL18">CCL18</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a></li> <li><a href="/w/index.php?title=G-15_(drug)&action=edit&redlink=1" class="new" title="G-15 (drug) (page does not exist)">G-15</a></li> <li><a href="/w/index.php?title=G-36_(drug)&action=edit&redlink=1" class="new" title="G-36 (drug) (page does not exist)">G-36</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Unknown</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></li> <li><a href="/wiki/Zearalenone" title="Zearalenone">Zearalenone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens">Estrogens and antiestrogens</a></dd> <dd><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators">Androgen receptor modulators</a></dd> <dd><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators">Progesterone receptor modulators</a></dd> <dd><a href="/wiki/List_of_steroidal_estrogens" class="mw-redirect" title="List of steroidal estrogens">List of estrogens</a></dd></dl> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" 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