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Neurosteroid - Wikipedia

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id="toc-Classification-sublist" class="vector-toc-list"> <li id="toc-Inhibitory_neurosteroids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Inhibitory_neurosteroids"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Inhibitory neurosteroids</span> </div> </a> <ul id="toc-Inhibitory_neurosteroids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Excitatory_neurosteroids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Excitatory_neurosteroids"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Excitatory neurosteroids</span> </div> </a> <ul id="toc-Excitatory_neurosteroids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pheromones" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pheromones"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>Pheromones</span> </div> </a> <ul id="toc-Pheromones-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_neurosteroids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_neurosteroids"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.4</span> <span>Other neurosteroids</span> </div> </a> <ul id="toc-Other_neurosteroids-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Function" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Function"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Function</span> </div> </a> <ul id="toc-Function-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biological_activity" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biological_activity"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Biological activity</span> </div> </a> <button aria-controls="toc-Biological_activity-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Biological activity subsection</span> </button> <ul id="toc-Biological_activity-sublist" class="vector-toc-list"> <li id="toc-Sigma-1_receptor" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Sigma-1_receptor"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Sigma-1 receptor</span> </div> </a> <ul id="toc-Sigma-1_receptor-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Therapeutic_applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Therapeutic_applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Therapeutic applications</span> </div> </a> <button aria-controls="toc-Therapeutic_applications-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Therapeutic applications subsection</span> </button> <ul id="toc-Therapeutic_applications-sublist" class="vector-toc-list"> <li id="toc-Anesthesia" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Anesthesia"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Anesthesia</span> </div> </a> <ul id="toc-Anesthesia-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Ganaxolone" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Ganaxolone"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Ganaxolone</span> </div> </a> <ul id="toc-Ganaxolone-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Catamenial_epilepsy" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Catamenial_epilepsy"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Catamenial epilepsy</span> </div> </a> <ul id="toc-Catamenial_epilepsy-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Allopregnanolone" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Allopregnanolone"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Allopregnanolone</span> </div> </a> <ul id="toc-Allopregnanolone-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_applications" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5</span> <span>Other applications</span> </div> </a> <ul id="toc-Other_applications-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Role_in_antidepressant_action" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Role_in_antidepressant_action"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Role in antidepressant action</span> </div> </a> <ul id="toc-Role_in_antidepressant_action-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Benzodiazepine_effects_on_neurosteroids" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Benzodiazepine_effects_on_neurosteroids"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Benzodiazepine effects on neurosteroids</span> </div> </a> <ul id="toc-Benzodiazepine_effects_on_neurosteroids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>Further reading</span> 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interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Neuroesteroide" title="Neuroesteroide – Catalan" lang="ca" hreflang="ca" data-title="Neuroesteroide" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Neuroesteroide" title="Neuroesteroide – Spanish" lang="es" hreflang="es" data-title="Neuroesteroide" 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%86%D9%88%D8%B1%D9%88%D8%A7%D8%B3%D8%AA%D8%B1%D9%88%D8%A6%DB%8C%D8%AF" title="نورواستروئید – Persian" lang="fa" hreflang="fa" data-title="نورواستروئید" 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/St%C3%A9ro%C3%AFde_neuroactif" title="Stéroïde neuroactif – French" lang="fr" hreflang="fr" data-title="Stéroïde neuroactif" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Neurosteroid" title="Neurosteroid – Indonesian" lang="id" hreflang="id" data-title="Neurosteroid" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Steroide_neuroattivo" title="Steroide neuroattivo – Italian" lang="it" hreflang="it" data-title="Steroide neuroattivo" 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Russian" lang="ru" hreflang="ru" data-title="Нейростероид" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Neuroaktivni_steroid" title="Neuroaktivni steroid – Serbian" lang="sr" hreflang="sr" data-title="Neuroaktivni steroid" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Neuroaktivni_steroid" title="Neuroaktivni steroid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Neuroaktivni steroid" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li> </ul> <div class="after-portlet 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id="mw-content-subtitle"><span class="mw-redirectedfrom">(Redirected from <a href="/w/index.php?title=Neuroactive_steroid&amp;redirect=no" class="mw-redirect" title="Neuroactive steroid">Neuroactive steroid</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">Compounds that affect neuronal excitability through modulation of specific ionotropic receptors</div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Zuranolone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/57/Zuranolone.svg/220px-Zuranolone.svg.png" decoding="async" width="220" height="174" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/57/Zuranolone.svg/330px-Zuranolone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/57/Zuranolone.svg/440px-Zuranolone.svg.png 2x" data-file-width="512" data-file-height="406" /></a><figcaption><a href="/wiki/Zuranolone" title="Zuranolone">Zuranolone</a>, an example of a neurosteroid, used for the treatment of <a href="/wiki/Postpartum_depression" title="Postpartum depression">postpartum depression</a></figcaption></figure> <p><b>Neurosteroids</b>, also known as <b>neuroactive steroids</b>, are <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a> or exogenous <a href="/wiki/Steroid" title="Steroid">steroids</a> that rapidly alter <a href="/wiki/Neuron" title="Neuron">neuronal</a> excitability through interaction with <a href="/wiki/Ligand-gated_ion_channel" title="Ligand-gated ion channel">ligand-gated ion channels</a> and other <a href="/wiki/Cell_surface_receptor" title="Cell surface receptor">cell surface receptors</a>.<sup id="cite_ref-pmid1347506_1-0" class="reference"><a href="#cite_note-pmid1347506-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid7729823_2-0" class="reference"><a href="#cite_note-pmid7729823-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup> The term <i>neurosteroid</i> was coined by the French <a href="/wiki/Physiologist" class="mw-redirect" title="Physiologist">physiologist</a> <a href="/wiki/%C3%89tienne-%C3%89mile_Baulieu" title="Étienne-Émile Baulieu">Étienne-Émile Baulieu</a> and refers to steroids synthesized in the brain.<sup id="cite_ref-pmid21094889_3-0" class="reference"><a href="#cite_note-pmid21094889-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup> The term, <i>neuroactive steroid</i> refers to steroids that can be synthesized in the brain, or are synthesized by an <a href="/wiki/Endocrine_gland" title="Endocrine gland">endocrine gland</a>, that then reach the brain through the bloodstream and have effects on brain function.<sup id="cite_ref-pmid22072656_5-0" class="reference"><a href="#cite_note-pmid22072656-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> The term neuroactive steroids was first coined in 1992 by Steven Paul and Robert Purdy. In addition to their actions on neuronal membrane receptors, some of these steroids may also exert effects on <a href="/wiki/Gene_expression" title="Gene expression">gene expression</a> via nuclear <a href="/wiki/Steroid_hormone_receptor" title="Steroid hormone receptor">steroid hormone receptors</a>. Neurosteroids have a wide range of potential clinical applications from <a href="/wiki/Sedation" title="Sedation">sedation</a> to treatment of <a href="/wiki/Epilepsy" title="Epilepsy">epilepsy</a><sup id="cite_ref-pmid19332335_6-0" class="reference"><a href="#cite_note-pmid19332335-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> and <a href="/wiki/Traumatic_brain_injury" title="Traumatic brain injury">traumatic brain injury</a>.<sup id="cite_ref-pmid17531324_7-0" class="reference"><a href="#cite_note-pmid17531324-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid15694225_8-0" class="reference"><a href="#cite_note-pmid15694225-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Ganaxolone" title="Ganaxolone">Ganaxolone</a>, a synthetic analog of the endogenous neurosteroid <a href="/wiki/Allopregnanolone" title="Allopregnanolone">allopregnanolone</a>, is under investigation for the treatment of epilepsy.<sup id="cite_ref-pmid23219031_9-0" class="reference"><a href="#cite_note-pmid23219031-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Classification">Classification</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Neurosteroid&amp;action=edit&amp;section=1" title="Edit section: Classification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/List_of_neurosteroids" title="List of neurosteroids">List of neurosteroids</a></div> <p>Based on differences in <a href="/wiki/Biological_activity" title="Biological activity">activity</a> and <a href="/wiki/Chemical_structure" title="Chemical structure">structure</a>, neurosteroids can be broadly categorized into several different major groupings.<sup id="cite_ref-pmid21094889_3-1" class="reference"><a href="#cite_note-pmid21094889-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Inhibitory_neurosteroids">Inhibitory neurosteroids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Neurosteroid&amp;action=edit&amp;section=2" title="Edit section: Inhibitory neurosteroids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>These neurosteroids exert <a href="/wiki/Inhibitory_postsynaptic_potential" title="Inhibitory postsynaptic potential">inhibitory</a> actions on <a href="/wiki/Neurotransmission" title="Neurotransmission">neurotransmission</a>. They act as <a href="/wiki/Positive_allosteric_modulator" class="mw-redirect" title="Positive allosteric modulator">positive allosteric modulators</a> of the <a href="/wiki/GABAA_receptor" title="GABAA receptor">GABA<sub>A</sub> receptor</a> (especially <a href="/wiki/GABRD" title="GABRD">δ subunit</a>-containing <a href="/wiki/Isoform" class="mw-redirect" title="Isoform">isoforms</a>), and possess, in no particular order, <a href="/wiki/Antidepressant" title="Antidepressant">antidepressant</a>, <a href="/wiki/Anxiolytic" title="Anxiolytic">anxiolytic</a>, <a href="/wiki/Stress_(psychological)" class="mw-redirect" title="Stress (psychological)">stress-reducing</a>, <a href="/wiki/Pleasure" title="Pleasure">rewarding</a>,<sup id="cite_ref-pmid12153544_10-0" class="reference"><a href="#cite_note-pmid12153544-10"><span class="cite-bracket">&#91;</span>10<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Prosocial_behavior" title="Prosocial behavior">prosocial</a>,<sup id="cite_ref-pmid19656632_11-0" class="reference"><a href="#cite_note-pmid19656632-11"><span class="cite-bracket">&#91;</span>11<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Serenic" title="Serenic">antiaggressive</a>,<sup id="cite_ref-pmid15677716_12-0" class="reference"><a href="#cite_note-pmid15677716-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Aphrodisiac" title="Aphrodisiac">prosexual</a>,<sup id="cite_ref-pmid19656632_11-1" class="reference"><a href="#cite_note-pmid19656632-11"><span class="cite-bracket">&#91;</span>11<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Sedative" title="Sedative">sedative</a>, <a href="/wiki/Hypnotic" title="Hypnotic">pro-sleep</a>,<sup id="cite_ref-pmid23092405_13-0" class="reference"><a href="#cite_note-pmid23092405-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Cognitive_deficit" class="mw-redirect" title="Cognitive deficit">cognitive</a> and <a href="/wiki/Cognitive_deficit" class="mw-redirect" title="Cognitive deficit">memory-impairing</a>,<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (July 2017)">citation needed</span></a></i>&#93;</sup> <a href="/wiki/Analgesic" title="Analgesic">analgesic</a>,<sup id="cite_ref-pmid23948490_14-0" class="reference"><a href="#cite_note-pmid23948490-14"><span class="cite-bracket">&#91;</span>14<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Anesthetic" title="Anesthetic">anesthetic</a>, <a href="/wiki/Anticonvulsant" title="Anticonvulsant">anticonvulsant</a>, <a href="/wiki/Neuroprotective" class="mw-redirect" title="Neuroprotective">neuroprotective</a>, and <a href="/wiki/Neurogenic" class="mw-redirect" title="Neurogenic">neurogenic</a> effects.<sup id="cite_ref-pmid21094889_3-2" class="reference"><a href="#cite_note-pmid21094889-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> </p><p>Major examples include <a href="/wiki/Tetrahydrodeoxycorticosterone" title="Tetrahydrodeoxycorticosterone">tetrahydrodeoxycorticosterone</a> (THDOC), the <a href="/wiki/Androstane" title="Androstane">androstane</a> <a href="/wiki/3%CE%B1-androstanediol" class="mw-redirect" title="3α-androstanediol">3α-androstanediol</a>, the <a href="/wiki/Cholestane" title="Cholestane">cholestane</a> <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a> and the <a href="/wiki/Pregnane" title="Pregnane">pregnanes</a> <a href="/wiki/Pregnanolone" title="Pregnanolone">pregnanolone</a> (eltanolone), <a href="/wiki/Allopregnanolone" title="Allopregnanolone">allopregnanolone</a> (3α,5α-THP).<sup id="cite_ref-pmid24806926_15-0" class="reference"><a href="#cite_note-pmid24806926-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-LevitanSingh2014_16-0" class="reference"><a href="#cite_note-LevitanSingh2014-16"><span class="cite-bracket">&#91;</span>16<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Excitatory_neurosteroids">Excitatory neurosteroids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Neurosteroid&amp;action=edit&amp;section=3" title="Edit section: Excitatory neurosteroids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>These neurosteroids have <a href="/wiki/Excitatory_postsynaptic_potential" title="Excitatory postsynaptic potential">excitatory</a> effects on neurotransmission. They act as potent <a href="/wiki/Negative_allosteric_modulator" class="mw-redirect" title="Negative allosteric modulator">negative allosteric modulators</a> of the GABA<sub>A</sub> receptor, weak positive allosteric modulators of the <a href="/wiki/NMDA_receptor" title="NMDA receptor">NMDA receptor</a>, and/or <a href="/wiki/Agonist" title="Agonist">agonists</a> of the <a href="/wiki/Sigma-1_receptor" title="Sigma-1 receptor">σ<sub>1</sub> receptor</a>, and mostly have <a href="/wiki/Antidepressant" title="Antidepressant">antidepressant</a>, <a href="/wiki/Anxiogenic" title="Anxiogenic">anxiogenic</a>, <a href="/wiki/Nootropic" title="Nootropic">cognitive</a> and <a href="/wiki/Nootropic" title="Nootropic">memory-enhancing</a>, <a href="/wiki/Convulsant" title="Convulsant">convulsant</a>, <a href="/wiki/Neuroprotective" class="mw-redirect" title="Neuroprotective">neuroprotective</a>, and <a href="/wiki/Neurogenic" class="mw-redirect" title="Neurogenic">neurogenic</a> effects.<sup id="cite_ref-pmid21094889_3-3" class="reference"><a href="#cite_note-pmid21094889-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> </p><p>Major examples include the pregnanes <a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">pregnenolone sulfate</a> (PS), <a href="/wiki/Epipregnanolone" title="Epipregnanolone">epipregnanolone</a>, and <a href="/wiki/Isopregnanolone" title="Isopregnanolone">isopregnanolone</a> (sepranolone), the androstanes <a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">dehydroepiandrosterone</a> (DHEA; <a href="/wiki/Prasterone" title="Prasterone">prasterone</a>), and <a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">dehydroepiandrosterone sulfate</a> (DHEA-S; <a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">prasterone sulfate</a>), and the cholestane <a href="/wiki/24S-hydroxycholesterol" class="mw-redirect" title="24S-hydroxycholesterol">24(<i>S</i>)-hydroxycholesterol</a> (NMDA receptor-selective; very potent).<sup id="cite_ref-PaulDoherty2013_17-0" class="reference"><a href="#cite_note-PaulDoherty2013-17"><span class="cite-bracket">&#91;</span>17<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pheromones">Pheromones</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Neurosteroid&amp;action=edit&amp;section=4" title="Edit section: Pheromones"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Pheromone#Axillary_steroids" title="Pheromone">Pheromone §&#160;Axillary steroids</a></div> <p>Pheromones are neurosteroids that influence brain activity, notably <a href="/wiki/Hypothalamus" title="Hypothalamus">hypothalamic</a> function, via activation of <a href="/wiki/Vomeronasal_receptor" title="Vomeronasal receptor">vomeronasal receptor</a> <a href="/wiki/Cell_(biology)" title="Cell (biology)">cells</a>.<sup id="cite_ref-HawkesDoty2009_18-0" class="reference"><a href="#cite_note-HawkesDoty2009-18"><span class="cite-bracket">&#91;</span>18<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Monti-BlochJennings-White1994_19-0" class="reference"><a href="#cite_note-Monti-BlochJennings-White1994-19"><span class="cite-bracket">&#91;</span>19<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-LiebowitzSalman2014_20-0" class="reference"><a href="#cite_note-LiebowitzSalman2014-20"><span class="cite-bracket">&#91;</span>20<span class="cite-bracket">&#93;</span></a></sup> </p><p>Possible human pheromones include the androstanes <a href="/wiki/Androstadienol" title="Androstadienol">androstadienol</a>, <a href="/wiki/Androstadienone" title="Androstadienone">androstadienone</a>, <a href="/wiki/Androstenol" title="Androstenol">androstenol</a>, and <a href="/wiki/Androstenone" title="Androstenone">androstenone</a> and the estrane <a href="/wiki/Estratetraenol" title="Estratetraenol">estratetraenol</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Other_neurosteroids">Other neurosteroids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Neurosteroid&amp;action=edit&amp;section=5" title="Edit section: Other neurosteroids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Certain other endogenous steroids, such as <a href="/wiki/Pregnenolone" title="Pregnenolone">pregnenolone</a>,<sup id="cite_ref-pmid21756978_21-0" class="reference"><a href="#cite_note-pmid21756978-21"><span class="cite-bracket">&#91;</span>21<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Progesterone" title="Progesterone">progesterone</a>,<sup id="cite_ref-pmid11108866_22-0" class="reference"><a href="#cite_note-pmid11108866-22"><span class="cite-bracket">&#91;</span>22<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid22687885_23-0" class="reference"><a href="#cite_note-pmid22687885-23"><span class="cite-bracket">&#91;</span>23<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>,<sup id="cite_ref-pmid22072656_5-1" class="reference"><a href="#cite_note-pmid22072656-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> and <a href="/wiki/Corticosterone" title="Corticosterone">corticosterone</a> are also neurosteroids. However, unlike those listed above, these neurosteroids do not modulate the GABA<sub>A</sub> or NMDA receptors, and instead affect various other cell surface receptors and non-genomic targets. Also, many endogenous steroids, including pregnenolone, progesterone, corticosterone, <a href="/wiki/Deoxycorticosterone" title="Deoxycorticosterone">deoxycorticosterone</a>, DHEA, and <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a>, are <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> into (other) neurosteroids, effectively functioning as so-called <i>pro</i>neurosteroids. </p> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Neurosteroid&amp;action=edit&amp;section=6" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Neurosteroids are synthesized from <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a>, which is converted into pregnenolone and then into all other endogenous steroids. Neurosteroids are produced in the brain after local synthesis or by conversion of peripherally-derived adrenal steroids or gonadal steroids. They accumulate especially in myelinating glial cells, from cholesterol or steroidal precursors imported from peripheral sources.<sup id="cite_ref-pmid16984997_24-0" class="reference"><a href="#cite_note-pmid16984997-24"><span class="cite-bracket">&#91;</span>24<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid11750861_25-0" class="reference"><a href="#cite_note-pmid11750861-25"><span class="cite-bracket">&#91;</span>25<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/SRD5A1" title="SRD5A1">5α-reductase type I</a> and <a href="/wiki/3%CE%B1-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3α-hydroxysteroid dehydrogenase">3α-hydroxysteroid dehydrogenase</a> are involved in the biosynthesis of inhibitory neurosteroids, while <a href="/wiki/3%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3β-hydroxysteroid dehydrogenase">3β-hydroxysteroid dehydrogenase</a> and <a href="/wiki/Hydroxysteroid_sulfotransferase" class="mw-redirect" title="Hydroxysteroid sulfotransferase">hydroxysteroid sulfotransferases</a> are involved in excitatory neurosteroid production.<sup id="cite_ref-pmid21094889_3-4" class="reference"><a href="#cite_note-pmid21094889-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Function">Function</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Neurosteroid&amp;action=edit&amp;section=7" title="Edit section: Function"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some major known <a href="/wiki/Function_(biology)" title="Function (biology)">biological functions</a> of neurosteroids include modulation of <a href="/wiki/Neural_plasticity" class="mw-redirect" title="Neural plasticity">neural plasticity</a>,<sup id="cite_ref-pmid17372131_26-0" class="reference"><a href="#cite_note-pmid17372131-26"><span class="cite-bracket">&#91;</span>26<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Learning" title="Learning">learning</a> and <a href="/wiki/Memory" title="Memory">memory</a> processes,<sup id="cite_ref-pmid11599303_27-0" class="reference"><a href="#cite_note-pmid11599303-27"><span class="cite-bracket">&#91;</span>27<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Behavior" title="Behavior">behavior</a>,<sup id="cite_ref-pmid11599304_28-0" class="reference"><a href="#cite_note-pmid11599304-28"><span class="cite-bracket">&#91;</span>28<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid18567641_29-0" class="reference"><a href="#cite_note-pmid18567641-29"><span class="cite-bracket">&#91;</span>29<span class="cite-bracket">&#93;</span></a></sup> and <a href="/wiki/Seizure_threshold" title="Seizure threshold">seizure susceptibility</a>,<sup id="cite_ref-pmid22101060_30-0" class="reference"><a href="#cite_note-pmid22101060-30"><span class="cite-bracket">&#91;</span>30<span class="cite-bracket">&#93;</span></a></sup> as well as responses to <a href="/wiki/Stress_(psychological)" class="mw-redirect" title="Stress (psychological)">stress</a>, <a href="/wiki/Anxiety" title="Anxiety">anxiety</a>, and <a href="/wiki/Depression_(mood)" title="Depression (mood)">depression</a>.<sup id="cite_ref-pmid19656632_11-2" class="reference"><a href="#cite_note-pmid19656632-11"><span class="cite-bracket">&#91;</span>11<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid17597217_31-0" class="reference"><a href="#cite_note-pmid17597217-31"><span class="cite-bracket">&#91;</span>31<span class="cite-bracket">&#93;</span></a></sup> Neurosteroids also appear to play an important role in various <a href="/wiki/Sexual_dimorphism" title="Sexual dimorphism">sexually-dimorphic</a> behaviors and emotional responses.<sup id="cite_ref-pmid18567641_29-1" class="reference"><a href="#cite_note-pmid18567641-29"><span class="cite-bracket">&#91;</span>29<span class="cite-bracket">&#93;</span></a></sup> </p><p>Acute stress elevates the levels of inhibitory neurosteroids like allopregnanolone, and these neurosteroids are known to counteract many of the effects of stress.<sup id="cite_ref-pmid24044974_32-0" class="reference"><a href="#cite_note-pmid24044974-32"><span class="cite-bracket">&#91;</span>32<span class="cite-bracket">&#93;</span></a></sup> This is similar to the case of <a href="/wiki/Endorphin" class="mw-redirect" title="Endorphin">endorphins</a>, which are released in response to stress and physical pain and counteract the negative subjective effects of such states. As such, it has been suggested that one of the biological functions of these <a href="/wiki/Neuromodulator" class="mw-redirect" title="Neuromodulator">neuromodulators</a> may be to help maintain emotional <a href="/wiki/Homeostasis" title="Homeostasis">homeostasis</a>.<sup id="cite_ref-pmid11599304_28-1" class="reference"><a href="#cite_note-pmid11599304-28"><span class="cite-bracket">&#91;</span>28<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid24929099_33-0" class="reference"><a href="#cite_note-pmid24929099-33"><span class="cite-bracket">&#91;</span>33<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Chronic_stress" title="Chronic stress">Chronic stress</a> has been associated with diminished levels of allopregnanolone and altered allopregnanolone stress responsivity, <a href="/wiki/Psychiatric_disorder" class="mw-redirect" title="Psychiatric disorder">psychiatric disorders</a>, and <a href="/wiki/Hypothalamic-pituitary-adrenal_axis" class="mw-redirect" title="Hypothalamic-pituitary-adrenal axis">hypothalamic-pituitary-adrenal axis</a> dysregulation.<sup id="cite_ref-pmid17597217_31-1" class="reference"><a href="#cite_note-pmid17597217-31"><span class="cite-bracket">&#91;</span>31<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid24044974_32-1" class="reference"><a href="#cite_note-pmid24044974-32"><span class="cite-bracket">&#91;</span>32<span class="cite-bracket">&#93;</span></a></sup> </p><p>It is thought that fluctuations in the levels of inhibitory neurosteroids during the <a href="/wiki/Menstrual_cycle" title="Menstrual cycle">menstrual cycle</a> and <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a> play an important role in a variety of <a href="/wiki/Female" title="Female">women's</a> <a href="/wiki/Medical_condition" class="mw-redirect" title="Medical condition">conditions</a>, including <a href="/wiki/Premenstrual_syndrome" title="Premenstrual syndrome">premenstrual syndrome</a> (PMS), <a href="/wiki/Premenstrual_dysphoric_disorder" title="Premenstrual dysphoric disorder">premenstrual dysphoric disorder</a> (PMDD), <a href="/wiki/Postpartum_depression" title="Postpartum depression">postpartum depression</a> (PPD), <a href="/wiki/Postpartum_psychosis" title="Postpartum psychosis">postpartum psychosis</a>, and <a href="/wiki/Catamenial_epilepsy" title="Catamenial epilepsy">catamenial epilepsy</a>.<sup id="cite_ref-pmid14993039_34-0" class="reference"><a href="#cite_note-pmid14993039-34"><span class="cite-bracket">&#91;</span>34<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid18346939_35-0" class="reference"><a href="#cite_note-pmid18346939-35"><span class="cite-bracket">&#91;</span>35<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid21533709_36-0" class="reference"><a href="#cite_note-pmid21533709-36"><span class="cite-bracket">&#91;</span>36<span class="cite-bracket">&#93;</span></a></sup> In addition, it is thought that changes in neurosteroid levels may be involved in the changes in mood, anxiety, and sexual desire that occur during <a href="/wiki/Puberty" title="Puberty">puberty</a> in both sexes and during <a href="/wiki/Menopause" title="Menopause">menopause</a> in women.<sup id="cite_ref-pmid21094889_3-5" class="reference"><a href="#cite_note-pmid21094889-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid10818386_37-0" class="reference"><a href="#cite_note-pmid10818386-37"><span class="cite-bracket">&#91;</span>37<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid21704130_38-0" class="reference"><a href="#cite_note-pmid21704130-38"><span class="cite-bracket">&#91;</span>38<span class="cite-bracket">&#93;</span></a></sup> </p><p>Elevated levels of inhibitory neurosteroids, namely allopregnanolone, can produce paradoxical effects, such as <a href="/wiki/Depression_(mood)" title="Depression (mood)">negative mood</a>, <a href="/wiki/Anxiety" title="Anxiety">anxiety</a>, <a href="/wiki/Irritability" title="Irritability">irritability</a>, and <a href="/wiki/Aggression" title="Aggression">aggression</a>.<sup id="cite_ref-pmid16724185_39-0" class="reference"><a href="#cite_note-pmid16724185-39"><span class="cite-bracket">&#91;</span>39<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid21600269_40-0" class="reference"><a href="#cite_note-pmid21600269-40"><span class="cite-bracket">&#91;</span>40<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid19272715_41-0" class="reference"><a href="#cite_note-pmid19272715-41"><span class="cite-bracket">&#91;</span>41<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid23978486_42-0" class="reference"><a href="#cite_note-pmid23978486-42"><span class="cite-bracket">&#91;</span>42<span class="cite-bracket">&#93;</span></a></sup> This appears to be because these neurosteroids, like other positive allosteric modulators of the GABA<sub>A</sub> receptor such as the <a href="/wiki/Benzodiazepine" title="Benzodiazepine">benzodiazepines</a>, <a href="/wiki/Barbiturate" title="Barbiturate">barbiturates</a>, and <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>,<sup id="cite_ref-pmid14993039_34-1" class="reference"><a href="#cite_note-pmid14993039-34"><span class="cite-bracket">&#91;</span>34<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid23978486_42-1" class="reference"><a href="#cite_note-pmid23978486-42"><span class="cite-bracket">&#91;</span>42<span class="cite-bracket">&#93;</span></a></sup> possess biphasic, U-shaped actions – moderate levels (in the range of 1.5–2 nM/L total alloprogesterone, which are approximately equivalent to <a href="/wiki/Luteal_phase" title="Luteal phase">luteal phase</a> levels) inhibit the activity of the GABA<sub>A</sub> receptor, while lower and higher concentrations facilitate the activity of the receptor.<sup id="cite_ref-pmid21600269_40-1" class="reference"><a href="#cite_note-pmid21600269-40"><span class="cite-bracket">&#91;</span>40<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid19272715_41-1" class="reference"><a href="#cite_note-pmid19272715-41"><span class="cite-bracket">&#91;</span>41<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biological_activity">Biological activity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Neurosteroid&amp;action=edit&amp;section=8" title="Edit section: Biological activity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Sigma-1_receptor">Sigma-1 receptor</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Neurosteroid&amp;action=edit&amp;section=9" title="Edit section: Sigma-1 receptor"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable"> <caption>Neurosteroids at the <a href="/wiki/Sigma-1_receptor" title="Sigma-1 receptor">σ<sub>1</sub> receptor</a><sup id="cite_ref-pmid11744080_43-0" class="reference"><a href="#cite_note-pmid11744080-43"><span class="cite-bracket">&#91;</span>43<span class="cite-bracket">&#93;</span></a></sup> </caption> <tbody><tr> <th>Compound</th> <th>K<sub>i</sub> (nM)</th> <th>Action</th> <th>Species</th> <th>Ref </th></tr> <tr> <td><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></td> <td>268</td> <td>Antagonist</td> <td>Guinea pig</td> <td><sup id="cite_ref-pmid2832949_44-0" class="reference"><a href="#cite_note-pmid2832949-44"><span class="cite-bracket">&#91;</span>44<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid15547787_45-0" class="reference"><a href="#cite_note-pmid15547787-45"><span class="cite-bracket">&#91;</span>45<span class="cite-bracket">&#93;</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Deoxycorticosterone" title="Deoxycorticosterone">Deoxycorticosterone</a></td> <td>938</td> <td>Unknown</td> <td>Guinea pig</td> <td><sup id="cite_ref-pmid2832949_44-1" class="reference"><a href="#cite_note-pmid2832949-44"><span class="cite-bracket">&#91;</span>44<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid15547787_45-1" class="reference"><a href="#cite_note-pmid15547787-45"><span class="cite-bracket">&#91;</span>45<span class="cite-bracket">&#93;</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></td> <td>1,014</td> <td>Unknown</td> <td>Guinea pig</td> <td><sup id="cite_ref-pmid2832949_44-2" class="reference"><a href="#cite_note-pmid2832949-44"><span class="cite-bracket">&#91;</span>44<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid15547787_45-2" class="reference"><a href="#cite_note-pmid15547787-45"><span class="cite-bracket">&#91;</span>45<span class="cite-bracket">&#93;</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></td> <td><abbr title="No data">ND</abbr></td> <td>Agonist</td> <td><abbr title="No data">ND</abbr></td> <td><abbr title="No data">ND</abbr> </td></tr> <tr> <td><a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">Pregnenolone sulfate</a></td> <td>3,198</td> <td>Agonist</td> <td>Guinea pig</td> <td><sup id="cite_ref-pmid2832949_44-3" class="reference"><a href="#cite_note-pmid2832949-44"><span class="cite-bracket">&#91;</span>44<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid15547787_45-3" class="reference"><a href="#cite_note-pmid15547787-45"><span class="cite-bracket">&#91;</span>45<span class="cite-bracket">&#93;</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone"><abbr title="Dehydroepiandrosterone">DHEA</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 Dehydroepiandrosterone</span></td> <td>3,700</td> <td>Agonist</td> <td>?</td> <td><sup id="cite_ref-pmid15547787_45-4" class="reference"><a href="#cite_note-pmid15547787-45"><span class="cite-bracket">&#91;</span>45<span class="cite-bracket">&#93;</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate"><abbr title="Dehydroepiandrosterone sulfate">DHEA-S</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 Dehydroepiandrosterone sulfate</span></td> <td><abbr title="No data">ND</abbr></td> <td>Agonist</td> <td><abbr title="No data">ND</abbr></td> <td><abbr title="No data">ND</abbr> </td></tr> <tr> <td><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></td> <td>4,074</td> <td>Unknown</td> <td>Guinea pig</td> <td><sup id="cite_ref-pmid2832949_44-4" class="reference"><a href="#cite_note-pmid2832949-44"><span class="cite-bracket">&#91;</span>44<span class="cite-bracket">&#93;</span></a></sup> </td></tr> </tbody></table> <div class="mw-heading mw-heading2"><h2 id="Therapeutic_applications">Therapeutic applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Neurosteroid&amp;action=edit&amp;section=10" title="Edit section: Therapeutic applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Neuroactive_steroids.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Neuroactive_steroids.png/220px-Neuroactive_steroids.png" decoding="async" width="220" height="206" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Neuroactive_steroids.png/330px-Neuroactive_steroids.png 1.5x, //upload.wikimedia.org/wikipedia/commons/7/73/Neuroactive_steroids.png 2x" data-file-width="366" data-file-height="342" /></a><figcaption>Older clinically used synthetic neuroactive steroids.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Anesthesia">Anesthesia</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Neurosteroid&amp;action=edit&amp;section=11" title="Edit section: Anesthesia"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Several synthetic neurosteroids have been used as <a href="/wiki/Sedative" title="Sedative">sedatives</a> for the purpose of <a href="/wiki/General_anaesthesia" title="General anaesthesia">general anaesthesia</a> for carrying out surgical procedures. The best known of these are <a href="/wiki/Alphaxolone" class="mw-redirect" title="Alphaxolone">alphaxolone</a>, <a href="/wiki/Althesin" class="mw-redirect" title="Althesin">alphadolone</a>, <a href="/wiki/Hydroxydione" title="Hydroxydione">hydroxydione</a>, and <a href="/wiki/Minaxolone" title="Minaxolone">minaxolone</a>. The first of these to be introduced was hydroxydione, which is the esterified 21-hydroxy derivative of 5β-pregnanedione. Hydroxydione proved to be a useful anaesthetic drug with a good safety profile, but was painful and irritating when injected probably due to poor water solubility. This led to the development of newer neuroactive steroids. The next drug from this family to be marketed was a mixture of alphaxolone and alphadolone, known as <a href="/wiki/Althesin" class="mw-redirect" title="Althesin">Althesin</a>. This was withdrawn from human use due to rare but serious toxic reactions, but is still used in <a href="/wiki/Veterinary_medicine" title="Veterinary medicine">veterinary medicine</a>. The next neurosteroid anaesthetic introduced into human medicine was the newer drug minaxolone, which is around three times more potent than althesin and retains the favourable safety profile, without the toxicity problems seen with althesin. However this drug was also ultimately withdrawn, not because of problems in clinical use, but because animal studies suggested potential carcinogenicity and since alternative agents were available it was felt that the possible risk outweighed the benefit of keeping the drug on the market. </p> <div class="mw-heading mw-heading3"><h3 id="Ganaxolone">Ganaxolone</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Neurosteroid&amp;action=edit&amp;section=12" title="Edit section: Ganaxolone"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Ganaxolone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Ganaxolone.svg/220px-Ganaxolone.svg.png" decoding="async" width="220" height="163" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Ganaxolone.svg/330px-Ganaxolone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Ganaxolone.svg/440px-Ganaxolone.svg.png 2x" data-file-width="512" data-file-height="379" /></a><figcaption>Ganaxolone, a neuroactive steroid currently in clinical development.</figcaption></figure> <p>The neurosteroid <a href="/wiki/Ganaxolone" title="Ganaxolone">ganaxolone</a>, an analog of the progesterone metabolite allopregnanolone, has been extensively investigated in animal models and is currently in clinical trials for the treatment of <a href="/wiki/Epilepsy" title="Epilepsy">epilepsy</a>. Neurosteroids, including ganaxolone have a broad spectrum of activity in animal models.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">&#91;</span>46<span class="cite-bracket">&#93;</span></a></sup> They may have advantages over other GABA<sub>A</sub> receptor modulators, notably benzodiazepines, in that tolerance does not appear to occur with extended use.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">&#91;</span>47<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">&#91;</span>48<span class="cite-bracket">&#93;</span></a></sup> </p><p>A randomized, placebo controlled, 10-week phase 2 clinical trial of orally administered ganaxolone in adults with partial onset seizure demonstrated that the treatment is safe, well tolerated and efficacious.<sup id="cite_ref-pmid23219031_9-1" class="reference"><a href="#cite_note-pmid23219031-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup> The drug continued to demonstrate efficacy in a 104-week open label extension. Data from non-clinical studies suggest that ganaxolone may have low risk for use in pregnancy. In addition to use in the treatment of epilepsy, the drug has potential in the treatment of a broad range of neurological and psychiatric conditions. Proof-of-concept studies are currently underway in posttraumatic stress disorder and fragile X syndrome. Ganaxolone was approved for medical use in the United States in March 2022. </p> <div class="mw-heading mw-heading3"><h3 id="Catamenial_epilepsy">Catamenial epilepsy</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Neurosteroid&amp;action=edit&amp;section=13" title="Edit section: Catamenial epilepsy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Researchers have suggested the use of so-called "neurosteroid replacement therapy" as a way of treating <a href="/wiki/Catamenial_epilepsy" title="Catamenial epilepsy">catamenial epilepsy</a> with neuroactive steroids such as ganaxolone during the period of the <a href="/wiki/Menstrual_cycle" title="Menstrual cycle">menstrual cycle</a> when <a href="/wiki/Seizure" title="Seizure">seizure</a> frequency increases.<sup id="cite_ref-pmid19332335_6-1" class="reference"><a href="#cite_note-pmid19332335-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Micronized_progesterone" class="mw-redirect" title="Micronized progesterone">Micronized progesterone</a>, which behaves reliably as a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> to allopregnanolone, has been suggested as a treatment for catamenial epilepsy in the same manner.<sup id="cite_ref-DevinskySchachter2005_49-0" class="reference"><a href="#cite_note-DevinskySchachter2005-49"><span class="cite-bracket">&#91;</span>49<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Allopregnanolone">Allopregnanolone</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Neurosteroid&amp;action=edit&amp;section=14" title="Edit section: Allopregnanolone"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Allopregnanolone (SAGE-547) is under development as an <a href="/wiki/Intravenous_therapy" title="Intravenous therapy">intravenous therapy</a> for the treatment of <a href="/wiki/Super-refractory_status_epilepticus" class="mw-redirect" title="Super-refractory status epilepticus">super-refractory status epilepticus</a>, <a href="/wiki/Postpartum_depression" title="Postpartum depression">postpartum depression</a>, and <a href="/wiki/Essential_tremor" title="Essential tremor">essential tremor</a>.<sup id="cite_ref-AdisInsight-1_50-0" class="reference"><a href="#cite_note-AdisInsight-1-50"><span class="cite-bracket">&#91;</span>50<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Other_applications">Other applications</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Neurosteroid&amp;action=edit&amp;section=15" title="Edit section: Other applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/4,16-Androstadien-3%CE%B2-ol" class="mw-redirect" title="4,16-Androstadien-3β-ol">4,16-Androstadien-3β-ol</a> (PH94B, Aloradine) is a synthetic pheromone, or <i><a href="/wiki/Pherine" title="Pherine">pherine</a></i>, neurosteroid which is under investigation for the treatment of <a href="/wiki/Anxiety_disorder" title="Anxiety disorder">anxiety disorders</a> in women.<sup id="cite_ref-Monti-BlochJennings-White1994_19-1" class="reference"><a href="#cite_note-Monti-BlochJennings-White1994-19"><span class="cite-bracket">&#91;</span>19<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-LiebowitzSalman2014_20-1" class="reference"><a href="#cite_note-LiebowitzSalman2014-20"><span class="cite-bracket">&#91;</span>20<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-GriebelHolmes2013_51-0" class="reference"><a href="#cite_note-GriebelHolmes2013-51"><span class="cite-bracket">&#91;</span>51<span class="cite-bracket">&#93;</span></a></sup> </p><p><a href="/wiki/3%CE%B2-Methoxypregnenolone" title="3β-Methoxypregnenolone">3β-Methoxypregnenolone</a> (MAP-4343), or pregnenolone 3β-methyl ether, is a synthetic neuroactive steroid and pregnenolone derivative that interacts with <a href="/wiki/Microtubule-associated_protein_2" title="Microtubule-associated protein 2">microtubule-associated protein 2</a> (MAP2) in a similar manner to pregnenolone and is under development for potential clinical use for indications such as the treatment of <a href="/wiki/Brain_injury" title="Brain injury">brain</a> and <a href="/wiki/Spinal_cord_injury" title="Spinal cord injury">spinal cord injury</a> and <a href="/wiki/Depressive_disorder" class="mw-redirect" title="Depressive disorder">depressive disorders</a>.<sup id="cite_ref-AdisInsight-2_52-0" class="reference"><a href="#cite_note-AdisInsight-2-52"><span class="cite-bracket">&#91;</span>52<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid21704982_53-0" class="reference"><a href="#cite_note-pmid21704982-53"><span class="cite-bracket">&#91;</span>53<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid22307636_54-0" class="reference"><a href="#cite_note-pmid22307636-54"><span class="cite-bracket">&#91;</span>54<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid26251072_55-0" class="reference"><a href="#cite_note-pmid26251072-55"><span class="cite-bracket">&#91;</span>55<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Role_in_antidepressant_action">Role in antidepressant action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Neurosteroid&amp;action=edit&amp;section=16" title="Edit section: Role in antidepressant action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Certain <a href="/wiki/Antidepressant" title="Antidepressant">antidepressant</a> drugs such as <a href="/wiki/Fluoxetine" title="Fluoxetine">fluoxetine</a> and <a href="/wiki/Fluvoxamine" title="Fluvoxamine">fluvoxamine</a>, which are generally thought to affect depression by acting as <a href="/wiki/Selective_serotonin_reuptake_inhibitor" title="Selective serotonin reuptake inhibitor">selective serotonin reuptake inhibitors</a> (SSRIs), have also been found to normalize the levels of certain neurosteroids (which are frequently deficient in depressed patients) at doses that are inactive in affecting the <a href="/wiki/Reuptake" title="Reuptake">reuptake</a> of <a href="/wiki/Serotonin" title="Serotonin">serotonin</a>. This suggests that other actions involving neurosteroids may also be at play in the effectiveness of these drugs against depression.<sup id="cite_ref-pmid9501247_56-0" class="reference"><a href="#cite_note-pmid9501247-56"><span class="cite-bracket">&#91;</span>56<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid16432684_57-0" class="reference"><a href="#cite_note-pmid16432684-57"><span class="cite-bracket">&#91;</span>57<span class="cite-bracket">&#93;</span></a></sup> </p><p>The <a href="/wiki/3%CE%B1-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3α-hydroxysteroid dehydrogenase">3α-hydroxysteroid dehydrogenase</a> (3α-HSD) enzyme is <a href="/wiki/Enzyme_inducer" title="Enzyme inducer">induced</a> by certain (SSRIs), including <a href="/wiki/Fluoxetine" title="Fluoxetine">fluoxetine</a>, <a href="/wiki/Fluvoxamine" title="Fluvoxamine">fluvoxamine</a>, <a href="/wiki/Sertraline" title="Sertraline">sertraline</a>, and <a href="/wiki/Paroxetine" title="Paroxetine">paroxetine</a>, as well as by certain other <a href="/wiki/Antidepressant" title="Antidepressant">antidepressants</a> like <a href="/wiki/Venlafaxine" title="Venlafaxine">venlafaxine</a> and <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>, and these antidepressants have been found to increase inhibitory neurosteroid levels.<sup id="cite_ref-Reddy2010_58-0" class="reference"><a href="#cite_note-Reddy2010-58"><span class="cite-bracket">&#91;</span>58<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid10557352_59-0" class="reference"><a href="#cite_note-pmid10557352-59"><span class="cite-bracket">&#91;</span>59<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid20716970_60-0" class="reference"><a href="#cite_note-pmid20716970-60"><span class="cite-bracket">&#91;</span>60<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid16344854_61-0" class="reference"><a href="#cite_note-pmid16344854-61"><span class="cite-bracket">&#91;</span>61<span class="cite-bracket">&#93;</span></a></sup> Enhancement of biosynthesis of inhibitory neurosteroids has been implicated in the <a href="/wiki/Antidepressant" title="Antidepressant">antidepressant</a> and <a href="/wiki/Anxiolytic" title="Anxiolytic">anxiolytic</a> effects of some of the SSRIs.<sup id="cite_ref-Reddy2010_58-1" class="reference"><a href="#cite_note-Reddy2010-58"><span class="cite-bracket">&#91;</span>58<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Benzodiazepine_effects_on_neurosteroids">Benzodiazepine effects on neurosteroids</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Neurosteroid&amp;action=edit&amp;section=17" title="Edit section: Benzodiazepine effects on neurosteroids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Benzodiazepines" class="mw-redirect" title="Benzodiazepines">Benzodiazepines</a> may influence neurosteroid metabolism by virtue of their actions on <a href="/wiki/Translocator_protein" title="Translocator protein">translocator protein</a> (TSPO; "peripheral benzodiazepine receptor").<sup id="cite_ref-pmid22014182_62-0" class="reference"><a href="#cite_note-pmid22014182-62"><span class="cite-bracket">&#91;</span>62<span class="cite-bracket">&#93;</span></a></sup> The <a href="/wiki/Pharmacological" class="mw-redirect" title="Pharmacological">pharmacological</a> actions of benzodiazepines at the GABA<sub>A</sub> receptor are similar to those of <a href="/wiki/Neurosteroids" class="mw-redirect" title="Neurosteroids">neurosteroids</a>. Factors which affect the ability of individual benzodiazepines to alter neurosteroid levels may depend upon whether the individual benzodiazepine drug interacts with TSPO. Some benzodiazepines may also inhibit neurosteroidogenic enzymes reducing neurosteroid synthesis.<sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">&#91;</span>63<span class="cite-bracket">&#93;</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=Neurosteroid&amp;action=edit&amp;section=18" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/List_of_neurosteroids" title="List of neurosteroids">List of neurosteroids</a></li> <li><a href="/wiki/Neurosteroidogenesis_inhibitor" title="Neurosteroidogenesis inhibitor">Neurosteroidogenesis inhibitor</a></li> <li><a href="/wiki/Membrane_steroid_receptor" title="Membrane steroid receptor">Membrane steroid receptor</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Neurosteroid&amp;action=edit&amp;section=19" 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-pmid1347506-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid1347506_1-0">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFPaulPurdy1992" class="citation journal cs1">Paul SM, Purdy RH (March 1992). <a rel="nofollow" class="external text" href="https://doi.org/10.1096%2Ffasebj.6.6.1347506">"Neuroactive steroids"</a>. <i>FASEB Journal</i>. <b>6</b> (6): 2311–22. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1096%2Ffasebj.6.6.1347506">10.1096/fasebj.6.6.1347506</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/1347506">1347506</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a>&#160;<a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:221753076">221753076</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=FASEB+Journal&amp;rft.atitle=Neuroactive+steroids&amp;rft.volume=6&amp;rft.issue=6&amp;rft.pages=2311-22&amp;rft.date=1992-03&amp;rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A221753076%23id-name%3DS2CID&amp;rft_id=info%3Apmid%2F1347506&amp;rft_id=info%3Adoi%2F10.1096%2Ffasebj.6.6.1347506&amp;rft.aulast=Paul&amp;rft.aufirst=SM&amp;rft.au=Purdy%2C+RH&amp;rft_id=https%3A%2F%2Fdoi.org%2F10.1096%252Ffasebj.6.6.1347506&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ANeurosteroid" class="Z3988"></span></span> </li> <li id="cite_note-pmid7729823-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid7729823_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLanGee1994" class="citation journal cs1">Lan NC, Gee KW (December 1994). "Neuroactive steroid actions at the GABAA receptor". <i>Hormones and Behavior</i>. <b>28</b> (4): 537–44. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1006%2Fhbeh.1994.1052">10.1006/hbeh.1994.1052</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/7729823">7729823</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a>&#160;<a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:40697424">40697424</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Hormones+and+Behavior&amp;rft.atitle=Neuroactive+steroid+actions+at+the+GABAA+receptor&amp;rft.volume=28&amp;rft.issue=4&amp;rft.pages=537-44&amp;rft.date=1994-12&amp;rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A40697424%23id-name%3DS2CID&amp;rft_id=info%3Apmid%2F7729823&amp;rft_id=info%3Adoi%2F10.1006%2Fhbeh.1994.1052&amp;rft.aulast=Lan&amp;rft.aufirst=NC&amp;rft.au=Gee%2C+KW&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ANeurosteroid" class="Z3988"></span></span> </li> <li id="cite_note-pmid21094889-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid21094889_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid21094889_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid21094889_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-pmid21094889_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-pmid21094889_3-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-pmid21094889_3-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFReddy2010" class="citation book cs1">Reddy DS (2010). "Neurosteroids". <i>Sex Differences in the Human Brain, their Underpinnings and Implications</i>. Progress in Brain Research. Vol.&#160;186. pp.&#160;113–37. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FB978-0-444-53630-3.00008-7">10.1016/B978-0-444-53630-3.00008-7</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/9780444536303" title="Special:BookSources/9780444536303"><bdi>9780444536303</bdi></a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a>&#160;<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3139029">3139029</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21094889">21094889</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=bookitem&amp;rft.atitle=Neurosteroids&amp;rft.btitle=Sex+Differences+in+the+Human+Brain%2C+their+Underpinnings+and+Implications&amp;rft.series=Progress+in+Brain+Research&amp;rft.pages=113-37&amp;rft.date=2010&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3139029%23id-name%3DPMC&amp;rft_id=info%3Apmid%2F21094889&amp;rft_id=info%3Adoi%2F10.1016%2FB978-0-444-53630-3.00008-7&amp;rft.isbn=9780444536303&amp;rft.aulast=Reddy&amp;rft.aufirst=DS&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ANeurosteroid" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFReddyRogawski2012" class="citation book cs1">Reddy DS, Rogawski MA (2012). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/books/NBK98218/">"Neurosteroids — Endogenous Regulators of Seizure Susceptibility and Role in the Treatment of Epilepsy"</a>. 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href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22014182">22014182</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=British+Journal+of+Pharmacology&amp;rft.atitle=Role+of+neurosteroids+in+the+anticonvulsant+activity+of+midazolam&amp;rft.volume=165&amp;rft.issue=8&amp;rft.pages=2684-91&amp;rft.date=2012-04&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3423249%23id-name%3DPMC&amp;rft_id=info%3Apmid%2F22014182&amp;rft_id=info%3Adoi%2F10.1111%2Fj.1476-5381.2011.01733.x&amp;rft.aulast=Dhir&amp;rft.aufirst=A&amp;rft.au=Rogawski%2C+MA&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3423249&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ANeurosteroid" class="Z3988"></span></span> </li> <li id="cite_note-63"><span class="mw-cite-backlink"><b><a href="#cite_ref-63">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFUsamiYamamotoShintaniIshikura2002" class="citation journal cs1">Usami N, Yamamoto T, Shintani S, Ishikura S, Higaki Y, Katagiri Y, Hara A (April 2002). <a rel="nofollow" class="external text" href="http://www.jstage.jst.go.jp/article/bpb/25/4/441/_pdf">"Substrate specificity of human 3(20)alpha-hydroxysteroid dehydrogenase for neurosteroids and its inhibition by benzodiazepines"</a> <span class="cs1-format">(pdf)</span>. <i>Biological &amp; Pharmaceutical Bulletin</i>. <b>25</b> (4): 441–5. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1248%2Fbpb.25.441">10.1248/bpb.25.441</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11995921">11995921</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Biological+%26+Pharmaceutical+Bulletin&amp;rft.atitle=Substrate+specificity+of+human+3%2820%29alpha-hydroxysteroid+dehydrogenase+for+neurosteroids+and+its+inhibition+by+benzodiazepines&amp;rft.volume=25&amp;rft.issue=4&amp;rft.pages=441-5&amp;rft.date=2002-04&amp;rft_id=info%3Adoi%2F10.1248%2Fbpb.25.441&amp;rft_id=info%3Apmid%2F11995921&amp;rft.aulast=Usami&amp;rft.aufirst=N&amp;rft.au=Yamamoto%2C+T&amp;rft.au=Shintani%2C+S&amp;rft.au=Ishikura%2C+S&amp;rft.au=Higaki%2C+Y&amp;rft.au=Katagiri%2C+Y&amp;rft.au=Hara%2C+A&amp;rft_id=http%3A%2F%2Fwww.jstage.jst.go.jp%2Farticle%2Fbpb%2F25%2F4%2F441%2F_pdf&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ANeurosteroid" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Neurosteroid&amp;action=edit&amp;section=20" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239549316">.mw-parser-output .refbegin{margin-bottom:0.5em}.mw-parser-output .refbegin-hanging-indents>ul{margin-left:0}.mw-parser-output .refbegin-hanging-indents>ul>li{margin-left:0;padding-left:3.2em;text-indent:-3.2em}.mw-parser-output .refbegin-hanging-indents ul,.mw-parser-output .refbegin-hanging-indents ul li{list-style:none}@media(max-width:720px){.mw-parser-output .refbegin-hanging-indents>ul>li{padding-left:1.6em;text-indent:-1.6em}}.mw-parser-output .refbegin-columns{margin-top:0.3em}.mw-parser-output .refbegin-columns ul{margin-top:0}.mw-parser-output .refbegin-columns li{page-break-inside:avoid;break-inside:avoid-column}@media screen{.mw-parser-output .refbegin{font-size:90%}}</style><div class="refbegin refbegin-columns references-column-width" style="column-width: 30em"> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAkkShuWangSteinbach2005" class="citation journal cs1">Akk G, Shu HJ, Wang C, Steinbach JH, Zorumski CF, Covey DF, Mennerick S (December 2005). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6726021">"Neurosteroid access to the GABAA receptor"</a>. <i>The Journal of Neuroscience</i>. <b>25</b> (50): 11605–13. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1523%2FJNEUROSCI.4173-05.2005">10.1523/JNEUROSCI.4173-05.2005</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a>&#160;<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6726021">6726021</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16354918">16354918</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=The+Journal+of+Neuroscience&amp;rft.atitle=Neurosteroid+access+to+the+GABAA+receptor&amp;rft.volume=25&amp;rft.issue=50&amp;rft.pages=11605-13&amp;rft.date=2005-12&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6726021%23id-name%3DPMC&amp;rft_id=info%3Apmid%2F16354918&amp;rft_id=info%3Adoi%2F10.1523%2FJNEUROSCI.4173-05.2005&amp;rft.aulast=Akk&amp;rft.aufirst=G&amp;rft.au=Shu%2C+HJ&amp;rft.au=Wang%2C+C&amp;rft.au=Steinbach%2C+JH&amp;rft.au=Zorumski%2C+CF&amp;rft.au=Covey%2C+DF&amp;rft.au=Mennerick%2C+S&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6726021&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ANeurosteroid" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWangJohnstonBallBrinton2005" class="citation journal cs1">Wang JM, Johnston PB, Ball BG, Brinton RD (May 2005). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6724768">"The neurosteroid allopregnanolone promotes proliferation of rodent and human neural progenitor cells and regulates cell-cycle gene and protein expression"</a>. <i>The Journal of Neuroscience</i>. <b>25</b> (19): 4706–18. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1523%2FJNEUROSCI.4520-04.2005">10.1523/JNEUROSCI.4520-04.2005</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a>&#160;<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6724768">6724768</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15888646">15888646</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=The+Journal+of+Neuroscience&amp;rft.atitle=The+neurosteroid+allopregnanolone+promotes+proliferation+of+rodent+and+human+neural+progenitor+cells+and+regulates+cell-cycle+gene+and+protein+expression&amp;rft.volume=25&amp;rft.issue=19&amp;rft.pages=4706-18&amp;rft.date=2005-05&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6724768%23id-name%3DPMC&amp;rft_id=info%3Apmid%2F15888646&amp;rft_id=info%3Adoi%2F10.1523%2FJNEUROSCI.4520-04.2005&amp;rft.aulast=Wang&amp;rft.aufirst=JM&amp;rft.au=Johnston%2C+PB&amp;rft.au=Ball%2C+BG&amp;rft.au=Brinton%2C+RD&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6724768&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ANeurosteroid" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDongMatsumotoUzunovaSugaya2001" class="citation journal cs1">Dong E, Matsumoto K, Uzunova V, Sugaya I, Takahata H, Nomura H, Watanabe H, Costa E, Guidotti A (February 2001). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC30228">"Brain 5alpha-dihydroprogesterone and allopregnanolone synthesis in a mouse model of protracted social isolation"</a>. <i>Proceedings of the National Academy of Sciences of the United States of America</i>. <b>98</b> (5): 2849–54. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2001PNAS...98.2849D">2001PNAS...98.2849D</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1073%2Fpnas.051628598">10.1073/pnas.051628598</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a>&#160;<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC30228">30228</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11226329">11226329</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Proceedings+of+the+National+Academy+of+Sciences+of+the+United+States+of+America&amp;rft.atitle=Brain+5alpha-dihydroprogesterone+and+allopregnanolone+synthesis+in+a+mouse+model+of+protracted+social+isolation&amp;rft.volume=98&amp;rft.issue=5&amp;rft.pages=2849-54&amp;rft.date=2001-02&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC30228%23id-name%3DPMC&amp;rft_id=info%3Apmid%2F11226329&amp;rft_id=info%3Adoi%2F10.1073%2Fpnas.051628598&amp;rft_id=info%3Abibcode%2F2001PNAS...98.2849D&amp;rft.aulast=Dong&amp;rft.aufirst=E&amp;rft.au=Matsumoto%2C+K&amp;rft.au=Uzunova%2C+V&amp;rft.au=Sugaya%2C+I&amp;rft.au=Takahata%2C+H&amp;rft.au=Nomura%2C+H&amp;rft.au=Watanabe%2C+H&amp;rft.au=Costa%2C+E&amp;rft.au=Guidotti%2C+A&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC30228&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ANeurosteroid" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMelcangiCelottiMartini1994" class="citation journal cs1">Melcangi RC, Celotti F, Martini L (March 1994). "Progesterone 5-alpha-reduction in neuronal and in different types of glial cell cultures: type 1 and 2 astrocytes and oligodendrocytes". <i>Brain Research</i>. <b>639</b> (2): 202–6. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0006-8993%2894%2991731-0">10.1016/0006-8993(94)91731-0</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/8205473">8205473</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a>&#160;<a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:37105244">37105244</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Brain+Research&amp;rft.atitle=Progesterone+5-alpha-reduction+in+neuronal+and+in+different+types+of+glial+cell+cultures%3A+type+1+and+2+astrocytes+and+oligodendrocytes&amp;rft.volume=639&amp;rft.issue=2&amp;rft.pages=202-6&amp;rft.date=1994-03&amp;rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A37105244%23id-name%3DS2CID&amp;rft_id=info%3Apmid%2F8205473&amp;rft_id=info%3Adoi%2F10.1016%2F0006-8993%2894%2991731-0&amp;rft.aulast=Melcangi&amp;rft.aufirst=RC&amp;rft.au=Celotti%2C+F&amp;rft.au=Martini%2C+L&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ANeurosteroid" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCorpéchotRobelAxelsonSjövall1981" class="citation journal cs1">Corpéchot C, Robel P, Axelson M, Sjövall J, Baulieu EE (August 1981). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC320231">"Characterization and measurement of dehydroepiandrosterone sulfate in rat brain"</a>. <i>Proceedings of the National Academy of Sciences of the United States of America</i>. <b>78</b> (8): 4704–7. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1981PNAS...78.4704C">1981PNAS...78.4704C</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1073%2Fpnas.78.8.4704">10.1073/pnas.78.8.4704</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a>&#160;<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC320231">320231</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6458035">6458035</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Proceedings+of+the+National+Academy+of+Sciences+of+the+United+States+of+America&amp;rft.atitle=Characterization+and+measurement+of+dehydroepiandrosterone+sulfate+in+rat+brain&amp;rft.volume=78&amp;rft.issue=8&amp;rft.pages=4704-7&amp;rft.date=1981-08&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC320231%23id-name%3DPMC&amp;rft_id=info%3Apmid%2F6458035&amp;rft_id=info%3Adoi%2F10.1073%2Fpnas.78.8.4704&amp;rft_id=info%3Abibcode%2F1981PNAS...78.4704C&amp;rft.aulast=Corp%C3%A9chot&amp;rft.aufirst=C&amp;rft.au=Robel%2C+P&amp;rft.au=Axelson%2C+M&amp;rft.au=Sj%C3%B6vall%2C+J&amp;rft.au=Baulieu%2C+EE&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC320231&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ANeurosteroid" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFReddyRogawski2012" class="citation book cs1">Reddy D, Rogawski MA (2012). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/books/NBK98218">"Neurosteroids — Endogenous regulators of seizure susceptibility and role in the treatment of epilepsy"</a>. In Noebels JL, Avoli M, Rogawski MA, et&#160;al. (eds.). <i>Jasper's Basic Mechanisms of the Epilepsies</i> (4th&#160;ed.). Bethesda (MD): National Center for Biotechnology Information. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22787590">22787590</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=bookitem&amp;rft.atitle=Neurosteroids+%E2%80%94+Endogenous+regulators+of+seizure+susceptibility+and+role+in+the+treatment+of+epilepsy&amp;rft.btitle=Jasper%27s+Basic+Mechanisms+of+the+Epilepsies&amp;rft.place=Bethesda+%28MD%29&amp;rft.edition=4th&amp;rft.pub=National+Center+for+Biotechnology+Information&amp;rft.date=2012&amp;rft_id=info%3Apmid%2F22787590&amp;rft.aulast=Reddy&amp;rft.aufirst=D&amp;rft.au=Rogawski%2C+MA&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fbooks%2FNBK98218&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ANeurosteroid" class="Z3988"></span></li></ul> </div> <div class="navbox-styles"><style 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.navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="Endogenous_steroids" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style 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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:Steroid_hormones" title="Template:Steroid hormones"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Steroid_hormones" title="Template talk:Steroid hormones"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Steroid_hormones" title="Special:EditPage/Template:Steroid hormones"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Endogenous_steroids" style="font-size:114%;margin:0 4em"><a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">Endogenous</a> <a href="/wiki/Steroid" title="Steroid">steroids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">Precursors</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/Cholesterol" title="Cholesterol">Cholesterol</a></li> <li><a href="/wiki/22R-Hydroxycholesterol" title="22R-Hydroxycholesterol">22<i>R</i>-Hydroxycholesterol</a></li> <li><a href="/wiki/20%CE%B1,22R-Dihydroxycholesterol" title="20α,22R-Dihydroxycholesterol">20α,22<i>R</i>-Dihydroxycholesterol</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/w/index.php?title=11%CE%B2-Hydroxypregnenolone&amp;action=edit&amp;redlink=1" class="new" title="11β-Hydroxypregnenolone (page does not exist)">11β-Hydroxypregnenolone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxypregnenolone" title="17α-Hydroxypregnenolone">17α-Hydroxypregnenolone</a></li> <li><a href="/wiki/21-Hydroxypregnenolone" title="21-Hydroxypregnenolone">21-Hydroxypregnenolone</a></li> <li><a href="/w/index.php?title=17%CE%B1,21-Dihydroxypregnenolone&amp;action=edit&amp;redlink=1" class="new" title="17α,21-Dihydroxypregnenolone (page does not exist)">17α,21-Dihydroxypregnenolone</a></li> <li><a href="/w/index.php?title=11%CE%B2,17%CE%B1,21-Trihydroxypregnenolone&amp;action=edit&amp;redlink=1" class="new" title="11β,17α,21-Trihydroxypregnenolone (page does not exist)">11β,17α,21-Trihydroxypregnenolone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Corticosteroid" title="Corticosteroid">Corticosteroids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glucocorticoid" title="Glucocorticoid">Glucocorticoids</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/Tetrahydrocorticosterone" title="Tetrahydrocorticosterone">3α,5α-Tetrahydrocorticosterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydrocorticosterone" title="5α-Dihydrocorticosterone">5α-Dihydrocorticosterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol</a></li> <li><a href="/wiki/11-Ketoprogesterone" title="11-Ketoprogesterone">11-Ketoprogesterone</a></li> <li><a href="/wiki/21-Deoxycortisol" title="21-Deoxycortisol">21-Deoxycortisol</a></li> <li><a href="/wiki/21-Deoxycortisone" title="21-Deoxycortisone">21-Deoxycortisone</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></li> <li><a href="/wiki/Cortisol" title="Cortisol">Cortisol</a></li> <li><a href="/wiki/Cortisone" title="Cortisone">Cortisone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxypregnenolone" title="17α-Hydroxypregnenolone">17α-Hydroxypregnenolone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li></ul> <ul><li><i>Metabolites:</i> <a href="/wiki/5%CE%B1-Dihydrocortisol" title="5α-Dihydrocortisol">5α-Dihydrocortisol</a></li> <li><a href="/w/index.php?title=3%CE%B1,5%CE%B1-Tetrahydrocortisol&amp;action=edit&amp;redlink=1" class="new" title="3α,5α-Tetrahydrocortisol (page does not exist)">3α,5α-Tetrahydrocortisol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mineralocorticoid" title="Mineralocorticoid">Mineralocorticoids</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/5%CE%B1-Dihydroaldosterone" title="5α-Dihydroaldosterone">5α-Dihydroaldosterone</a></li> <li><a href="/wiki/11-Dehydrocorticosterone" title="11-Dehydrocorticosterone">11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)</a></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/11%CE%B2-Hydroxyprogesterone" title="11β-Hydroxyprogesterone">11β-Hydroxyprogesterone (21-deoxycorticosterone)</a></li> <li><a href="/wiki/18-Hydroxy-11-deoxycorticosterone" title="18-Hydroxy-11-deoxycorticosterone">18-Hydroxy-11-deoxycorticosterone</a></li> <li><a href="/wiki/18-Hydroxycorticosterone" title="18-Hydroxycorticosterone">18-Hydroxycorticosterone</a></li> <li><a href="/w/index.php?title=18-Hydroxyprogesterone&amp;action=edit&amp;redlink=1" class="new" title="18-Hydroxyprogesterone (page does not exist)">18-Hydroxyprogesterone</a></li> <li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></li> <li><a href="/wiki/Cortisol" title="Cortisol">Cortisol</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/Sex_steroid" class="mw-redirect" title="Sex steroid">Sex steroids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Androgen" title="Androgen">Androgens</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/11-Ketodihydrotestosterone" title="11-Ketodihydrotestosterone">11-Ketodihydrotestosterone</a></li> <li><a href="/wiki/11-Ketotestosterone" title="11-Ketotestosterone">11-Ketotestosterone</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/11%CE%B2-Hydroxyandrostenedione" title="11β-Hydroxyandrostenedione">11β-Hydroxyandrostenedione</a></li> <li><a href="/wiki/Adrenosterone" title="Adrenosterone">Adrenosterone (11-ketoandrostenedione)</a></li> <li><a href="/wiki/Androstenediol" title="Androstenediol">Androstenediol</a></li> <li><a href="/wiki/Androstenedione" title="Androstenedione">Androstenedione</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li><a href="/wiki/Dehydroandrosterone" title="Dehydroandrosterone">Dehydroandrosterone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA sulfate</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">Dihydrotestosterone</a></li> <li><a href="/wiki/Epiandrosterone" title="Epiandrosterone">Epiandrosterone</a></li> <li><a href="/wiki/Epitestosterone" title="Epitestosterone">Epitestosterone</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyandrostenedione" title="16α-Hydroxyandrostenedione">16α-Hydroxyandrostenedione</a></li> <li><a href="/wiki/16-Hydroxydehydroepiandrosterone" class="mw-redirect" title="16-Hydroxydehydroepiandrosterone">16α-Hydroxy-DHEA</a></li> <li><a href="/wiki/16-Hydroxydehydroepiandrosterone_sulfate" class="mw-redirect" title="16-Hydroxydehydroepiandrosterone sulfate">16α-Hydroxy-DHEA sulfate</a></li> <li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></li></ul> <ul><li><i>Metabolites:</i> <a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol_glucuronide" class="mw-redirect" title="3α-Androstanediol glucuronide">3α-Androstanediol glucuronide</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/5%CE%B2-Dihydrotestosterone" title="5β-Dihydrotestosterone">5β-Dihydrotestosterone</a></li> <li><a href="/wiki/3%CE%B1-Etiocholanediol" title="3α-Etiocholanediol">3α-Etiocholanediol</a></li> <li><a href="/wiki/3%CE%B2-Etiocholanediol" title="3β-Etiocholanediol">3β-Etiocholanediol</a></li> <li><a href="/w/index.php?title=Androstanetriol&amp;action=edit&amp;redlink=1" class="new" title="Androstanetriol (page does not exist)">Androstanetriols</a></li> <li><a href="/wiki/Androstenediol_sulfate" title="Androstenediol sulfate">Androstenediol sulfate</a></li> <li><a href="/wiki/Androstenetriol" title="Androstenetriol">Androstenetriol</a></li> <li><a href="/wiki/Androsterone_glucuronide" title="Androsterone glucuronide">Androsterone glucuronide</a></li> <li><a href="/wiki/Androsterone_sulfate" title="Androsterone sulfate">Androsterone sulfate</a></li> <li><a href="/w/index.php?title=Dihydrotestosterone_glucuronide&amp;action=edit&amp;redlink=1" class="new" title="Dihydrotestosterone glucuronide (page does not exist)">Dihydrotestosterone glucuronide</a></li> <li><a href="/w/index.php?title=Dihydrotestosterone_sulfate&amp;action=edit&amp;redlink=1" class="new" title="Dihydrotestosterone sulfate (page does not exist)">Dihydrotestosterone sulfate</a></li> <li><a href="/wiki/Etiocholanedione" title="Etiocholanedione">Etiocholanedione</a></li> <li><a href="/wiki/Etiocholanolone" title="Etiocholanolone">Etiocholanolone</a></li> <li><a href="/wiki/Etiocholanolone_glucuronide" title="Etiocholanolone glucuronide">Etiocholanolone glucuronide</a></li> <li><a href="/wiki/Epietiocholanolone" title="Epietiocholanolone">Epietiocholanolone</a></li> <li><a href="/wiki/Testosterone_glucuronide" title="Testosterone glucuronide">Testosterone glucuronide</a></li> <li><a href="/wiki/Testosterone_sulfate" title="Testosterone sulfate">Testosterone sulfate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Estrogen" title="Estrogen">Estrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Estranes:</i> <a href="/wiki/Estetrol" title="Estetrol">Estetrol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Estrone" title="Estrone">Estrone</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a></li> <li><a href="/wiki/17%CE%B1-Estradiol" title="17α-Estradiol">17α-Estradiol</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">16β-Epiestriol (16β-hydroxyestradiol)</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/16%CE%B2,17%CE%B1-Epiestriol" title="16β,17α-Epiestriol">16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestriol" title="2-Hydroxyestriol">2-Hydroxyestriol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></li> <li><a href="/wiki/4-Hydroxyestriol" title="4-Hydroxyestriol">4-Hydroxyestriol</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/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B2-Hydroxyestrone" title="16β-Hydroxyestrone">16β-Hydroxyestrone</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></ul> <ul><li><i>Others:</i> <a href="/wiki/27-Hydroxycholesterol" title="27-Hydroxycholesterol">27-Hydroxycholesterol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">4-Androstenedione</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">5-Androstenediol</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA sulfate</a></li> <li><a href="/wiki/7-Keto-DHEA" title="7-Keto-DHEA">7-Keto-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/16-Hydroxydehydroepiandrosterone" class="mw-redirect" title="16-Hydroxydehydroepiandrosterone">16α-Hydroxy-DHEA</a></li></ul> <ul><li><i>Metabolites:</i> <a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></li> <li><a href="/wiki/2-Methoxyestrone" title="2-Methoxyestrone">2-Methoxyestrone</a></li> <li><a href="/wiki/2-Methoxyestriol" title="2-Methoxyestriol">2-Methoxyestriol</a></li> <li><a href="/wiki/4-Methoxyestriol" title="4-Methoxyestriol">4-Methoxyestriol</a></li> <li><a href="/wiki/Estradiol_disulfate" title="Estradiol disulfate">Estradiol disulfate</a></li> <li><a href="/wiki/Estradiol_glucuronide" title="Estradiol glucuronide">Estradiol glucuronide</a></li> <li><a href="/wiki/Estradiol_3-glucuronide" title="Estradiol 3-glucuronide">Estradiol 3-glucuronide</a></li> <li><a href="/wiki/Estradiol_3-glucuronide_17%CE%B2-sulfate" title="Estradiol 3-glucuronide 17β-sulfate">Estradiol 3-glucuronide 17β-sulfate</a></li> <li><a href="/wiki/Estradiol_sulfate" title="Estradiol sulfate">Estradiol sulfate</a></li> <li><a href="/wiki/Estradiol_17%CE%B2-sulfate" title="Estradiol 17β-sulfate">Estradiol 17β-sulfate</a></li> <li><a href="/wiki/Estrone_glucuronide" title="Estrone glucuronide">Estrone glucuronide</a></li> <li><a href="/wiki/Estrone_sulfate" title="Estrone sulfate">Estrone sulfate</a></li> <li><a href="/wiki/Estriol_glucuronide" title="Estriol glucuronide">Estriol glucuronide</a></li> <li><a href="/wiki/Estriol_sulfate" title="Estriol sulfate">Estriol sulfate</a></li> <li><a href="/wiki/Lipoidal_estradiol" title="Lipoidal estradiol">Lipoidal estradiol</a> (e.g., <a href="/wiki/Estradiol_stearate" title="Estradiol stearate">estradiol stearate</a>, <a href="/wiki/Estradiol_palmitate" title="Estradiol palmitate">estradiol palmitate</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Progestogen" title="Progestogen">Progestogens</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/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyprogesterone" title="16α-Hydroxyprogesterone">16α-Hydroxyprogesterone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/20%CE%B1-Dihydroprogesterone" title="20α-Dihydroprogesterone">20α-Dihydroprogesterone</a></li> <li><a href="/wiki/20%CE%B2-Dihydroprogesterone" title="20β-Dihydroprogesterone">20β-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/Dihydrodeoxycorticosterone" title="Dihydrodeoxycorticosterone">5α-DHDOC</a></li></ul> <ul><li><i>Metabolites:</i> <a href="/wiki/Allopregnanediol" title="Allopregnanediol">Allopregnanediol</a></li> <li><a href="/wiki/Pregnanediol" title="Pregnanediol">Pregnanediol</a></li> <li><a href="/wiki/Pregnanediol_glucuronide" title="Pregnanediol glucuronide">Pregnanediol glucuronide</a></li> <li><a href="/wiki/Pregnanetriol" title="Pregnanetriol">Pregnanetriol</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/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neurosteroids</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><i>Cholestanes:</i> <a href="/wiki/24S-hydroxycholesterol" class="mw-redirect" title="24S-hydroxycholesterol">24<i>S</i>-Hydroxycholesterol</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li></ul> <ul><li><i>Pregnanes:</i> <a href="/wiki/3%CE%B1-Dihydroprogesterone" title="3α-Dihydroprogesterone">3α-Dihydroprogesterone</a></li> <li><a href="/wiki/3%CE%B2-Dihydroprogesterone" title="3β-Dihydroprogesterone">3β-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydrocorticosterone" title="5α-Dihydrocorticosterone">5α-Dihydrocorticosterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">5β-Dihydroprogesterone</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></li> <li><a href="/wiki/Dihydrocorticosterone" class="mw-redirect" title="Dihydrocorticosterone">DHC</a></li> <li><a href="/wiki/Dihydrodeoxycorticosterone" title="Dihydrodeoxycorticosterone">DHDOC</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/Epipregnanolone" title="Epipregnanolone">Epipregnanolone</a></li> <li><a href="/wiki/Isopregnanolone" title="Isopregnanolone">Isopregnanolone</a></li> <li><a href="/wiki/Pregnanolone" title="Pregnanolone">Pregnanolone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">Pregnenolone sulfate</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Tetrahydrocorticosterone" title="Tetrahydrocorticosterone">THB</a></li> <li><a href="/wiki/Tetrahydrodeoxycorticosterone" title="Tetrahydrodeoxycorticosterone">THDOC</a></li></ul> <ul><li><i>Androstanes:</i> <a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/3%CE%B1-Androstenol" class="mw-redirect" title="3α-Androstenol">3α-Androstenol</a></li> <li><a href="/wiki/7-Keto-DHEA" title="7-Keto-DHEA">7-Keto-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%B2-Hydroxy-DHEA" title="7β-Hydroxy-DHEA">7β-Hydroxy-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxyepiandrosterone" title="7α-Hydroxyepiandrosterone">7α-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA sulfate</a></li> <li><a href="/wiki/Etiocholanolone" title="Etiocholanolone">Etiocholanolone</a></li></ul> <ul><li><b><a href="/wiki/Pheromone" title="Pheromone">Pheromones</a>:</b> <a href="/wiki/3%CE%B1-Androstenol" class="mw-redirect" title="3α-Androstenol">3α-Androstenol</a></li> <li><a href="/wiki/3%CE%B2-Androstenol" title="3β-Androstenol">3β-Androstenol</a></li> <li><a href="/wiki/Androstadienol" title="Androstadienol">Androstadienol</a></li> <li><a href="/wiki/Androstadienone" title="Androstadienone">Androstadienone</a></li> <li><a href="/wiki/Androstenone" title="Androstenone">Androstenone</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li><a href="/wiki/Estratetraenol" title="Estratetraenol">Estratetraenol</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 hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/Vitamin_D" title="Vitamin D">Vitamin D</a>:</b> <a href="/wiki/7-Dehydrocholesterol" title="7-Dehydrocholesterol">7-Dehydrocholesterol</a></li> <li><a href="/wiki/Calcifediol" title="Calcifediol">Calcidiol/Calcifediol</a></li> <li><a href="/wiki/Calcitriol" title="Calcitriol">Calcitriol</a></li> <li><a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a></li></ul> <ul><li><b>Others:</b> <a href="/wiki/7%CE%B1-Hydroxycholesterol" title="7α-Hydroxycholesterol">7α-Hydroxycholesterol</a></li> <li><a href="/wiki/11%CE%B1-Hydroxyprogesterone" title="11α-Hydroxyprogesterone">11α-Hydroxyprogesterone</a></li> <li><a href="/wiki/11%CE%B2-Hydroxyprogesterone" title="11β-Hydroxyprogesterone">11β-Hydroxyprogesterone</a></li> <li><a href="/wiki/Cholesterol_sulfate" title="Cholesterol sulfate">Cholesterol sulfate</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="General_anesthetics_(N01A)" 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:General_anesthetics" title="Template:General anesthetics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:General_anesthetics" title="Template talk:General anesthetics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:General_anesthetics" title="Special:EditPage/Template:General anesthetics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="General_anesthetics_(N01A)" style="font-size:114%;margin:0 4em"><a href="/wiki/General_anaesthetic" title="General anaesthetic">General anesthetics</a> (<a href="/wiki/ATC_code_N01#N01A" title="ATC code N01">N01A</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Inhalational_anesthetic" title="Inhalational anesthetic">Inhalational</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/Chloroform" title="Chloroform">Chloroform</a><sup>‡</sup></li> <li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a><sup>‡</sup></li> <li><a href="/wiki/Desflurane" title="Desflurane">Desflurane</a></li> <li><a href="/wiki/Diethyl_ether" title="Diethyl ether">Diethyl ether</a><sup>‡</sup></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a><sup>‡</sup></li> <li><a href="/wiki/Fluroxene" title="Fluroxene">Fluroxene</a><sup>‡</sup></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a><sup>#</sup></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a><sup>#</sup></li> <li><a href="/wiki/Methoxyflurane" title="Methoxyflurane">Methoxyflurane</a></li> <li><a href="/wiki/Methoxypropane" title="Methoxypropane">Methoxypropane</a><sup>‡</sup></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a><sup>#</sup></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</a></li> <li><a href="/wiki/Trichloroethylene" title="Trichloroethylene">Trichloroethylene</a><sup>‡</sup></li> <li><a href="/wiki/Divinyl_ether" title="Divinyl ether">Vinyl ether</a><sup>‡</sup></li> <li><a href="/wiki/Xenon" title="Xenon">Xenon</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/General_anaesthetic#Injection" title="General anaesthetic">Injection</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenols" title="Phenols">Phenols</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/Ciprofol" title="Ciprofol">Ciprofol</a><sup>†</sup></li> <li><a href="/wiki/Fospropofol" title="Fospropofol">Fospropofol</a></li> <li><a href="/wiki/Propofol" title="Propofol">Propofol</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</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/Amobarbital" title="Amobarbital">Amobarbital</a></li> <li><a href="/wiki/Hexobarbital" title="Hexobarbital">Hexobarbital</a></li> <li><a href="/wiki/Methohexital" title="Methohexital">Methohexital</a></li> <li><a href="/wiki/Narcobarbital" title="Narcobarbital">Narcobarbital</a></li> <li><a href="/wiki/Thiamylal" title="Thiamylal">Thiamylal</a></li> <li><a href="/wiki/Sodium_thiopental" title="Sodium thiopental">Thiopental</a><sup>#</sup></li> <li><a href="/wiki/Thiotetrabarbital" title="Thiotetrabarbital">Thiotetrabarbital</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</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/Midazolam" title="Midazolam">Midazolam</a><sup>#</sup></li> <li><a href="/wiki/Diazepam" title="Diazepam">Diazepam</a><sup>#</sup></li> <li><a href="/wiki/Lorazepam" title="Lorazepam">Lorazepam</a><sup>#</sup></li> <li><a href="/wiki/Remimazolam" title="Remimazolam">Remimazolam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Opioid" title="Opioid">Opioids</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/Morphine" title="Morphine">Morphine</a><sup>#</sup></li> <li><a href="/wiki/Oxycodone" title="Oxycodone">Oxycodone</a></li> <li><a href="/wiki/Anileridine" title="Anileridine">Anileridine</a><sup>‡</sup></li> <li><a href="/wiki/Embutramide" title="Embutramide">Embutramide</a><sup>‡</sup></li> <li><a href="/wiki/Fentanyl" title="Fentanyl">Fentanyl</a><sup>#</sup></li> <li><a href="/wiki/Alfentanil" title="Alfentanil">Alfentanil</a></li> <li><a href="/wiki/Phenoperidine" title="Phenoperidine">Phenoperidine</a></li> <li><a href="/wiki/Remifentanil" title="Remifentanil">Remifentanil</a>÷</li> <li><a href="/wiki/Sufentanil" title="Sufentanil">Sufentanil</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arylcyclohexylamine" title="Arylcyclohexylamine">Arylcyclohexylamines</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/Esketamine" title="Esketamine">Esketamine</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a><sup>#</sup></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a><sup>‡</sup></li> <li><a href="/wiki/Tiletamine" title="Tiletamine">Tiletamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Neuroactive steroids</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/Alfadolone" title="Alfadolone">Alfadolone</a></li> <li><a href="/wiki/Alfaxalone" title="Alfaxalone">Alfaxalone</a></li> <li><a href="/wiki/Hydroxydione" title="Hydroxydione">Hydroxydione</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/Etomidate" title="Etomidate">Etomidate</a></li> <li><a href="/wiki/Propanidid" title="Propanidid">Propanidid</a><sup>‡</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <p class="mw-empty-elt"> </p> <!-- NewPP limit report Parsed by mw‐web.codfw.main‐f69cdc8f6‐5z8dw Cached time: 20241122143206 Cache expiry: 2592000 Reduced expiry: false Complications: [vary‐revision‐sha1, show‐toc] CPU time usage: 0.769 seconds Real time usage: 0.967 seconds Preprocessor visited node count: 4483/1000000 Post‐expand include size: 245221/2097152 bytes Template argument size: 2524/2097152 bytes Highest expansion depth: 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