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class="vector-toc-link" href="#Anabolic"> <div class="vector-toc-text"> 1.1.1 Anabolic </div> </a> <ul id="toc-Anabolic-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Androgenic" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Androgenic"> <div class="vector-toc-text"> 1.1.2 Androgenic </div> </a> <ul id="toc-Androgenic-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Other"> <div class="vector-toc-text"> 1.1.3 Other </div> </a> <ul id="toc-Other-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Enhancing_performance" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Enhancing_performance"> <div class="vector-toc-text"> 1.2 Enhancing performance </div> </a> <ul id="toc-Enhancing_performance-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dosages" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dosages"> <div class="vector-toc-text"> 1.3 Dosages </div> </a> <ul id="toc-Dosages-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Available_forms" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Available_forms"> <div class="vector-toc-text"> 1.4 Available forms </div> </a> <ul id="toc-Available_forms-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Routes_of_administration" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Routes_of_administration"> <div class="vector-toc-text"> 1.5 Routes of administration </div> </a> <ul id="toc-Routes_of_administration-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Adverse_effects" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Adverse_effects"> <div class="vector-toc-text"> 2 Adverse effects </div> </a> <button aria-controls="toc-Adverse_effects-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Adverse effects subsection </button> <ul id="toc-Adverse_effects-sublist" class="vector-toc-list"> <li id="toc-Physiological" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Physiological"> <div class="vector-toc-text"> 2.1 Physiological </div> </a> <ul id="toc-Physiological-sublist" class="vector-toc-list"> <li id="toc-Cancer" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Cancer"> <div class="vector-toc-text"> 2.1.1 Cancer </div> </a> <ul id="toc-Cancer-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cardiovascular" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Cardiovascular"> <div class="vector-toc-text"> 2.1.2 Cardiovascular </div> </a> <ul id="toc-Cardiovascular-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Growth_defects" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Growth_defects"> <div class="vector-toc-text"> 2.1.3 Growth defects </div> </a> <ul id="toc-Growth_defects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Feminization" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Feminization"> <div class="vector-toc-text"> 2.1.4 Feminization </div> </a> <ul id="toc-Feminization-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Masculinization" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Masculinization"> <div class="vector-toc-text"> 2.1.5 Masculinization </div> </a> <ul id="toc-Masculinization-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Kidney_problems" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Kidney_problems"> <div class="vector-toc-text"> 2.1.6 Kidney problems </div> </a> <ul id="toc-Kidney_problems-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Liver_problems" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Liver_problems"> <div class="vector-toc-text"> 2.1.7 Liver problems </div> </a> <ul id="toc-Liver_problems-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Neuropsychiatric" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Neuropsychiatric"> <div class="vector-toc-text"> 2.2 Neuropsychiatric </div> </a> <ul id="toc-Neuropsychiatric-sublist" class="vector-toc-list"> <li id="toc-Diagnostic_Statistical_Manual_assertion" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Diagnostic_Statistical_Manual_assertion"> <div class="vector-toc-text"> 2.2.1 Diagnostic Statistical Manual assertion </div> </a> <ul id="toc-Diagnostic_Statistical_Manual_assertion-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Personality_profiles" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Personality_profiles"> <div class="vector-toc-text"> 2.2.2 Personality profiles </div> </a> <ul id="toc-Personality_profiles-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mood_and_anxiety" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Mood_and_anxiety"> <div class="vector-toc-text"> 2.2.3 Mood and anxiety </div> </a> <ul id="toc-Mood_and_anxiety-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Aggression_and_hypomania" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Aggression_and_hypomania"> <div class="vector-toc-text"> 2.2.4 Aggression and hypomania </div> </a> <ul id="toc-Aggression_and_hypomania-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Reproductive" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reproductive"> <div class="vector-toc-text"> 2.3 Reproductive </div> </a> <ul id="toc-Reproductive-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Pharmacology" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Pharmacology"> <div class="vector-toc-text"> 3 Pharmacology </div> </a> <button aria-controls="toc-Pharmacology-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Pharmacology subsection </button> <ul id="toc-Pharmacology-sublist" class="vector-toc-list"> <li id="toc-Mechanism_of_action" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Mechanism_of_action"> <div class="vector-toc-text"> 3.1 Mechanism of action </div> </a> <ul id="toc-Mechanism_of_action-sublist" class="vector-toc-list"> <li id="toc-Molecular_interaction_of_AAS_with_androgen_receptors" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Molecular_interaction_of_AAS_with_androgen_receptors"> <div class="vector-toc-text"> 3.1.1 Molecular interaction of AAS with androgen receptors </div> </a> <ul id="toc-Molecular_interaction_of_AAS_with_androgen_receptors-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Anabolic_and_androgenic_effects" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Anabolic_and_androgenic_effects"> <div class="vector-toc-text"> 3.2 Anabolic and androgenic effects </div> </a> <ul id="toc-Anabolic_and_androgenic_effects-sublist" class="vector-toc-list"> <li id="toc-Body_composition_and_strength_improvements" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Body_composition_and_strength_improvements"> <div class="vector-toc-text"> 3.2.1 Body composition and strength improvements </div> </a> <ul id="toc-Body_composition_and_strength_improvements-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Dissociation_of_effects" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dissociation_of_effects"> <div class="vector-toc-text"> 3.3 Dissociation of effects </div> </a> <ul id="toc-Dissociation_of_effects-sublist" class="vector-toc-list"> <li id="toc-Intracellular_metabolism" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Intracellular_metabolism"> <div class="vector-toc-text"> 3.3.1 Intracellular metabolism </div> </a> <ul id="toc-Intracellular_metabolism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Functional_selectivity" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Functional_selectivity"> <div class="vector-toc-text"> 3.3.2 Functional selectivity </div> </a> <ul id="toc-Functional_selectivity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Non-genomic_mechanisms" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Non-genomic_mechanisms"> <div class="vector-toc-text"> 3.3.3 Non-genomic mechanisms </div> </a> <ul id="toc-Non-genomic_mechanisms-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Antigonadotropic_effects" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Antigonadotropic_effects"> <div class="vector-toc-text"> 3.3.4 Antigonadotropic effects </div> </a> <ul id="toc-Antigonadotropic_effects-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-GABAA_receptor_modulation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#GABAA_receptor_modulation"> <div class="vector-toc-text"> 3.4 GABAA receptor modulation </div> </a> <ul id="toc-GABAA_receptor_modulation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Comparison_of_AAS" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Comparison_of_AAS"> <div class="vector-toc-text"> 3.5 Comparison of AAS </div> </a> <ul id="toc-Comparison_of_AAS-sublist" class="vector-toc-list"> <li id="toc-5α-Reductase_and_androgenicity" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#5α-Reductase_and_androgenicity"> <div class="vector-toc-text"> 3.5.1 5α-Reductase and androgenicity </div> </a> <ul id="toc-5α-Reductase_and_androgenicity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Aromatase_and_estrogenicity" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Aromatase_and_estrogenicity"> <div class="vector-toc-text"> 3.5.2 Aromatase and estrogenicity </div> </a> <ul id="toc-Aromatase_and_estrogenicity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Progestogenic_activity" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Progestogenic_activity"> <div class="vector-toc-text"> 3.5.3 Progestogenic activity </div> </a> <ul id="toc-Progestogenic_activity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Oral_activity_and_hepatotoxicity" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Oral_activity_and_hepatotoxicity"> <div class="vector-toc-text"> 3.5.4 Oral activity and hepatotoxicity </div> </a> <ul id="toc-Oral_activity_and_hepatotoxicity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Neurosteroid_activity" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Neurosteroid_activity"> <div class="vector-toc-text"> 3.5.5 Neurosteroid activity </div> </a> <ul id="toc-Neurosteroid_activity-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Chemistry" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> 4 Chemistry </div> </a> <button aria-controls="toc-Chemistry-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Chemistry subsection </button> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> <li id="toc-Structural_conversions_of_anabolic_steroids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Structural_conversions_of_anabolic_steroids"> <div class="vector-toc-text"> 4.1 Structural conversions of anabolic steroids </div> </a> <ul id="toc-Structural_conversions_of_anabolic_steroids-sublist" class="vector-toc-list"> <li id="toc-Testosterone_to_derivatives" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Testosterone_to_derivatives"> <div class="vector-toc-text"> 4.1.1 Testosterone to derivatives </div> </a> <ul id="toc-Testosterone_to_derivatives-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-DHT_to_derivatives" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#DHT_to_derivatives"> <div class="vector-toc-text"> 4.1.2 DHT to derivatives </div> </a> <ul id="toc-DHT_to_derivatives-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nandrolone_to_derivatives" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Nandrolone_to_derivatives"> <div class="vector-toc-text"> 4.1.3 Nandrolone to derivatives </div> </a> <ul id="toc-Nandrolone_to_derivatives-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Detection_in_body_fluids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Detection_in_body_fluids"> <div class="vector-toc-text"> 4.2 Detection in body fluids </div> </a> <ul id="toc-Detection_in_body_fluids-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> 5 History </div> </a> <button aria-controls="toc-History-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle History subsection </button> <ul id="toc-History-sublist" class="vector-toc-list"> <li id="toc-Discovery_of_androgens" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Discovery_of_androgens"> <div class="vector-toc-text"> 5.1 Discovery of androgens </div> </a> <ul id="toc-Discovery_of_androgens-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Development_of_synthetic_AAS" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Development_of_synthetic_AAS"> <div class="vector-toc-text"> 5.2 Development of synthetic AAS </div> </a> <ul id="toc-Development_of_synthetic_AAS-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Society_and_culture" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Society_and_culture"> <div class="vector-toc-text"> 6 Society and culture </div> </a> <button aria-controls="toc-Society_and_culture-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Society and culture subsection </button> <ul id="toc-Society_and_culture-sublist" class="vector-toc-list"> <li id="toc-Etymology" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Etymology"> <div class="vector-toc-text"> 6.1 Etymology </div> </a> <ul id="toc-Etymology-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Legal_status" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Legal_status"> <div class="vector-toc-text"> 6.2 Legal status </div> </a> <ul id="toc-Legal_status-sublist" class="vector-toc-list"> <li id="toc-United_States" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#United_States"> <div class="vector-toc-text"> 6.2.1 United States </div> </a> <ul id="toc-United_States-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-United_Kingdom" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#United_Kingdom"> <div class="vector-toc-text"> 6.2.2 United Kingdom </div> </a> <ul id="toc-United_Kingdom-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Status_in_sports" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Status_in_sports"> <div class="vector-toc-text"> 6.3 Status in sports </div> </a> <ul id="toc-Status_in_sports-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Usage" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Usage"> <div class="vector-toc-text"> 6.4 Usage </div> </a> <ul id="toc-Usage-sublist" class="vector-toc-list"> <li id="toc-Law_enforcement" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Law_enforcement"> <div class="vector-toc-text"> 6.4.1 Law enforcement </div> </a> <ul id="toc-Law_enforcement-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Professional_wrestling" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Professional_wrestling"> <div class="vector-toc-text"> 6.4.2 Professional wrestling </div> </a> <ul id="toc-Professional_wrestling-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Economics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Economics"> <div class="vector-toc-text"> 6.5 Economics </div> </a> <ul id="toc-Economics-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Research" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Research"> <div class="vector-toc-text"> 7 Research </div> </a> <ul id="toc-Research-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> 8 See also </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"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> 9 References </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"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> 10 Further reading </div> </a> <ul id="toc-Further_reading-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> 11 External links </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" > Toggle the table of contents </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading">Anabolic steroid</h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" 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Available in 44 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-44" aria-hidden="true" > 44 languages </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%B3%D8%AA%D9%8A%D8%B1%D9%88%D9%8A%D8%AF_%D8%A7%D8%A8%D8%AA%D9%86%D8%A7%D8%A6%D9%8A" title="ستيرويد ابتنائي – Arabic" lang="ar" hreflang="ar" data-title="ستيرويد ابتنائي" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target">العربية</a></li><li class="interlanguage-link interwiki-hyw mw-list-item"><a href="https://hyw.wikipedia.org/wiki/%D4%BF%D5%A1%D5%BC%D5%B8%D6%82%D6%81%D5%B8%D5%B2%D5%A1%D5%AF%D5%A1%D5%B6_%D5%84%D5%B2%D6%85%D5%B6%D5%B6%D5%A5%D6%80" title="Կառուցողական Մղօններ – Western Armenian" lang="hyw" hreflang="hyw" data-title="Կառուցողական Մղօններ" data-language-autonym="Արեւմտահայերէն" data-language-local-name="Western Armenian" class="interlanguage-link-target">Արեւմտահայերէն</a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%90%D0%BD%D0%B0%D0%B1%D0%BE%D0%BB%D0%B5%D0%BD_%D1%81%D1%82%D0%B5%D1%80%D0%BE%D0%B8%D0%B4" title="Анаболен стероид – Bulgarian" lang="bg" hreflang="bg" data-title="Анаболен стероид" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target">Български</a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Anaboli%C4%8Dki_steroid" title="Anabolički steroid – Bosnian" lang="bs" hreflang="bs" data-title="Anabolički steroid" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target">Bosanski</a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Esteroide_anab%C3%B2lic" title="Esteroide anabòlic – Catalan" lang="ca" hreflang="ca" data-title="Esteroide anabòlic" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target">Català</a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Anabolick%C3%A9_steroidy" title="Anabolické steroidy – Czech" lang="cs" hreflang="cs" data-title="Anabolické steroidy" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target">Čeština</a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Anabolt_steroid" title="Anabolt steroid – Danish" lang="da" hreflang="da" data-title="Anabolt steroid" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target">Dansk</a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Anabole_Steroide" title="Anabole Steroide – German" lang="de" hreflang="de" data-title="Anabole Steroide" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%91%CE%BD%CE%B1%CE%B2%CE%BF%CE%BB%CE%B9%CE%BA%CF%8C_%CF%83%CF%84%CE%B5%CF%81%CE%BF%CE%B5%CE%B9%CE%B4%CE%AD%CF%82" title="Αναβολικό στεροειδές – Greek" lang="el" hreflang="el" data-title="Αναβολικό στεροειδές" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target">Ελληνικά</a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Esteroide_anab%C3%B3lico" title="Esteroide anabólico – Spanish" lang="es" hreflang="es" data-title="Esteroide anabólico" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target">Español</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%B3%D8%AA%D8%B1%D9%88%D8%A6%DB%8C%D8%AF_%D8%A2%D9%86%D8%A7%D8%A8%D9%88%D9%84%DB%8C%DA%A9" title="استروئید آنابولیک – Persian" lang="fa" hreflang="fa" data-title="استروئید آنابولیک" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-fo mw-list-item"><a href="https://fo.wikipedia.org/wiki/Anabolskar_steroidir" title="Anabolskar steroidir – Faroese" lang="fo" hreflang="fo" data-title="Anabolskar steroidir" data-language-autonym="Føroyskt" data-language-local-name="Faroese" class="interlanguage-link-target">Føroyskt</a></li><li class="interlanguage-link interwiki-fr badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://fr.wikipedia.org/wiki/St%C3%A9ro%C3%AFde_anabolisant" title="Stéroïde anabolisant – French" lang="fr" hreflang="fr" data-title="Stéroïde anabolisant" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Esteroide_anab%C3%B3lico" title="Esteroide anabólico – Galician" lang="gl" hreflang="gl" data-title="Esteroide anabólico" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target">Galego</a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%8B%A8%EB%B0%B1%EB%8F%99%ED%99%94_%EC%8A%A4%ED%85%8C%EB%A1%9C%EC%9D%B4%EB%93%9C" title="단백동화 스테로이드 – Korean" lang="ko" hreflang="ko" data-title="단백동화 스테로이드" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target">한국어</a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B1%D5%B6%D5%A1%D5%A2%D5%B8%D5%AC%D5%AB%D5%AF_%D5%A1%D5%B6%D5%A4%D6%80%D5%B8%D5%A3%D5%A5%D5%B6%D5%A1%D5%B5%D5%AB%D5%B6_%D5%BD%D5%BF%D5%A5%D6%80%D5%B8%D5%AB%D5%A4%D5%B6%D5%A5%D6%80" title="Անաբոլիկ անդրոգենային ստերոիդներ – Armenian" lang="hy" hreflang="hy" data-title="Անաբոլիկ անդրոգենային ստերոիդներ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target">Հայերեն</a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%90%E0%A4%A8%E0%A4%AC%E0%A4%BE%E0%A4%B2%E0%A4%BF%E0%A4%95_%E0%A4%B8%E0%A5%8D%E0%A4%9F%E0%A5%87%E0%A4%B0%E0%A5%89%E0%A4%AF%E0%A4%A1" title="ऐनबालिक स्टेरॉयड – Hindi" lang="hi" hreflang="hi" data-title="ऐनबालिक स्टेरॉयड" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target">हिन्दी</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Steroid_anabolik" title="Steroid anabolik – Indonesian" lang="id" hreflang="id" data-title="Steroid anabolik" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target">Bahasa Indonesia</a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Vefaukandi_sterar" title="Vefaukandi sterar – Icelandic" lang="is" hreflang="is" data-title="Vefaukandi sterar" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target">Íslenska</a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Steroide_anabolizzante" title="Steroide anabolizzante – Italian" lang="it" hreflang="it" data-title="Steroide anabolizzante" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target">Italiano</a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A1%D7%98%D7%A8%D7%95%D7%90%D7%99%D7%93%D7%99%D7%9D_%D7%90%D7%A0%D7%90%D7%91%D7%95%D7%9C%D7%99%D7%99%D7%9D" title="סטרואידים אנאבוליים – Hebrew" lang="he" hreflang="he" data-title="סטרואידים אנאבוליים" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target">עברית</a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%B8%E0%B2%82%E0%B2%B5%E0%B2%B0%E0%B3%8D%E0%B2%A7%E0%B2%95_%E0%B2%B8%E0%B3%8D%E0%B2%9F%E0%B3%80%E0%B2%B0%E0%B2%BE%E0%B2%AF%E0%B3%8D%E0%B2%A1%E0%B3%8D" title="ಸಂವರ್ಧಕ ಸ್ಟೀರಾಯ್ಡ್ – Kannada" lang="kn" hreflang="kn" data-title="ಸಂವರ್ಧಕ ಸ್ಟೀರಾಯ್ಡ್" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target">ಕನ್ನಡ</a></li><li class="interlanguage-link interwiki-sw mw-list-item"><a href="https://sw.wikipedia.org/wiki/Steroidi_anaboliki" title="Steroidi anaboliki – Swahili" lang="sw" hreflang="sw" data-title="Steroidi anaboliki" data-language-autonym="Kiswahili" data-language-local-name="Swahili" class="interlanguage-link-target">Kiswahili</a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Anaboliskie_stero%C4%ABdi" title="Anaboliskie steroīdi – Latvian" lang="lv" hreflang="lv" data-title="Anaboliskie steroīdi" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target">Latviešu</a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Anaboliniai_steroidai" title="Anaboliniai steroidai – Lithuanian" lang="lt" hreflang="lt" data-title="Anaboliniai steroidai" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target">Lietuvių</a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Steroid_anabolik" title="Steroid anabolik – Malay" lang="ms" hreflang="ms" data-title="Steroid anabolik" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target">Bahasa Melayu</a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Anabole_stero%C3%AFden" title="Anabole steroïden – Dutch" lang="nl" hreflang="nl" data-title="Anabole steroïden" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target">Nederlands</a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A2%E3%83%8A%E3%83%9C%E3%83%AA%E3%83%83%E3%82%AF%E3%82%B9%E3%83%86%E3%83%AD%E3%82%A4%E3%83%89" title="アナボリックステロイド – Japanese" lang="ja" hreflang="ja" data-title="アナボリックステロイド" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target">日本語</a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Anabole_androgene_steroider" title="Anabole androgene steroider – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Anabole androgene steroider" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target">Norsk bokmål</a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Steroidy_anaboliczno-androgenne" title="Steroidy anaboliczno-androgenne – Polish" lang="pl" hreflang="pl" data-title="Steroidy anaboliczno-androgenne" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target">Polski</a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Esteroide_anabolizante" title="Esteroide anabolizante – Portuguese" lang="pt" hreflang="pt" data-title="Esteroide anabolizante" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target">Português</a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Steroid_anabolizant" title="Steroid anabolizant – Romanian" lang="ro" hreflang="ro" data-title="Steroid anabolizant" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target">Română</a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%90%D0%BD%D0%B0%D0%B1%D0%BE%D0%BB%D0%B8%D1%87%D0%B5%D1%81%D0%BA%D0%B8%D0%B5_%D1%81%D1%82%D0%B5%D1%80%D0%BE%D0%B8%D0%B4%D1%8B" title="Анаболические стероиды – Russian" lang="ru" hreflang="ru" data-title="Анаболические стероиды" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Anabolic_steroid" title="Anabolic steroid – Simple English" lang="en-simple" hreflang="en-simple" data-title="Anabolic steroid" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target">Simple English</a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Anabolick%C3%BD_steroid" title="Anabolický steroid – Slovak" lang="sk" hreflang="sk" data-title="Anabolický steroid" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target">Slovenčina</a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D8%B3%D8%AA%D8%B1%DB%86%DB%8C%DB%8C%D8%AF%DB%8C_%D8%A6%D8%A7%D9%86%D8%A7%D8%A8%DB%86%D9%84%DB%8C%DA%A9" title="سترۆییدی ئانابۆلیک – Central Kurdish" lang="ckb" hreflang="ckb" data-title="سترۆییدی ئانابۆلیک" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target">کوردی</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%90%D0%BD%D0%B0%D0%B1%D0%BE%D0%BB%D0%B8%D1%87%D0%BA%D0%B8_%D1%81%D1%82%D0%B5%D1%80%D0%BE%D0%B8%D0%B4" title="Анаболички стероид – Serbian" lang="sr" hreflang="sr" data-title="Анаболички стероид" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target">Српски / srpski</a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Anaboli%C4%8Dki_steroid" title="Anabolički steroid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Anabolički steroid" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target">Srpskohrvatski / српскохрватски</a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Anaboliset_steroidit" title="Anaboliset steroidit – Finnish" lang="fi" hreflang="fi" data-title="Anaboliset steroidit" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target">Suomi</a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Anabola_steroider" title="Anabola steroider – Swedish" lang="sv" hreflang="sv" data-title="Anabola steroider" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target">Svenska</a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Anabolik_steroid" title="Anabolik steroid – Turkish" lang="tr" hreflang="tr" data-title="Anabolik steroid" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target">Türkçe</a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%90%D0%BD%D0%B0%D0%B1%D0%BE%D0%BB%D1%96%D1%87%D0%BD%D1%96_%D1%81%D1%82%D0%B5%D1%80%D0%BE%D1%97%D0%B4%D0%B8" title="Анаболічні стероїди – Ukrainian" lang="uk" hreflang="uk" data-title="Анаболічні стероїди" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target">Українська</a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Steroid_%C4%91%E1%BB%93ng_h%C3%B3a" title="Steroid đồng hóa – Vietnamese" lang="vi" hreflang="vi" data-title="Steroid đồng hóa" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target">Tiếng Việt</a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%90%8C%E5%8C%96%E9%A1%9E%E5%9B%BA%E9%86%87" title="同化類固醇 – Chinese" lang="zh" hreflang="zh" data-title="同化類固醇" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target">中文</a></li> </ul> <div class="after-portlet after-portlet-lang"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q309438#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Anabolic_steroid" title="View the content page [c]" accesskey="c">Article</a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Talk:Anabolic_steroid" rel="discussion" title="Discuss improvements to the content page [t]" accesskey="t">Talk</a></li> </ul> </div> </div> <div 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class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Class of drugs</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">This article is about exogenously administered androgens. For androgens as natural hormones, see <a href="/wiki/Androgen" title="Androgen">Androgen</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox"><tbody><tr><th colspan="2" class="infobox-above" style="background-color: #ddbbee">Anabolic–androgenic steroids</th></tr><tr><td colspan="2" class="infobox-subheader"><a href="/wiki/Drug_class" title="Drug class">Drug class</a></td></tr><tr><td colspan="2" class="infobox-image"><a href="/wiki/File:Testosteron.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Testosteron.svg/225px-Testosteron.svg.png" decoding="async" width="225" height="150" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Testosteron.svg/338px-Testosteron.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Testosteron.svg/450px-Testosteron.svg.png 2x" data-file-width="512" data-file-height="341" /></a><div class="infobox-caption">Chemical structure of the natural AAS <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a> (androst-4-en-17β-ol-3-one).</div></td></tr><tr><th colspan="2" class="infobox-header" style="background: #e8e8e8;">Class identifiers</th></tr><tr><th scope="row" class="infobox-label"><a href="/wiki/Synonym" title="Synonym">Synonyms</a></th><td class="infobox-data">Anabolic steroids; Androgens</td></tr><tr><th scope="row" class="infobox-label">Use</th><td class="infobox-data"><a href="#Medical_uses">Various</a></td></tr><tr><th scope="row" class="infobox-label"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><a href="/wiki/ATC_code_A14A" class="mw-redirect" title="ATC code A14A">A14A</a></td></tr><tr><th scope="row" class="infobox-label"><a href="/wiki/Biological_target" title="Biological target">Biological target</a></th><td class="infobox-data"><a href="/wiki/Androgen_receptor" title="Androgen receptor">Androgen receptor</a> (AR)</td></tr><tr><th scope="row" class="infobox-label"><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">Chemical class</a></th><td class="infobox-data"><a href="/wiki/Steroid" title="Steroid">Steroids</a>; <a href="/wiki/Androstane" title="Androstane">Androstanes</a>; <a href="/wiki/Estrane" title="Estrane">Estranes</a></td></tr><tr><th colspan="2" class="infobox-header" style="background: #e8e8e8;">Clinical data</th></tr><tr><th scope="row" class="infobox-label"><a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://www.drugs.com/drug-class/androgens-and-anabolic-steroids.html">Drug Classes</a></td></tr><tr><th colspan="2" class="infobox-header" style="background: #e8e8e8;">External links</th></tr><tr><th scope="row" class="infobox-label"><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://meshb.nlm.nih.gov/record/ui?ui=D045165">D045165</a></td></tr><tr><th colspan="2" class="infobox-header" style="background: #e8e8e8;">Legal status</th></tr><tr><th scope="row" class="infobox-label"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"> <ul><li><abbr class="country-name" title="Canada">CA</abbr>: <a href="/wiki/Controlled_Drugs_and_Substances_Act#Schedule_IV" title="Controlled Drugs and Substances Act">Schedule IV</a></li> <li><abbr class="country-name" title="United Kingdom">UK</abbr>: <a href="/wiki/Drugs_controlled_by_the_UK_Misuse_of_Drugs_Act#Class_C_drugs" class="mw-redirect" title="Drugs controlled by the UK Misuse of Drugs Act">Class C</a></li> <li><abbr class="country-name" title="United States">US</abbr>: <a href="/wiki/Controlled_Substances_Act#Schedule_III_drugs" title="Controlled Substances Act">Schedule III</a></li> <li>Controlled in many countries</li></ul></div> </td></tr><tr><td colspan="2" class="infobox-below" style="background: #e8e8e8; text-align: center"><a href="https://www.wikidata.org/wiki/Q309438" class="extiw" title="d:Q309438">In Wikidata</a></td></tr></tbody></table> Anabolic steroids, also known as anabolic-androgenic steroids (AAS), are a class of drugs that are structurally related to <a href="/wiki/Testosterone" title="Testosterone">testosterone</a>, the main male <a href="/wiki/Sex_hormone" title="Sex hormone">sex hormone</a>, and produce effects by binding to the <a href="/wiki/Androgen_receptor" title="Androgen receptor">androgen receptor</a> (AR). Anabolic steroids have a number of medical uses,<a href="#cite_note-pmid29494025-1">[1]</a> but are also used by athletes to increase muscle size, strength, and performance. Health risks can be produced by long-term use or excessive doses of AAS.<a href="#cite_note-pmid7556805-2">[2]</a><a href="#cite_note-pmid16606610-3">[3]</a> These effects include harmful changes in <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a> levels (increased <a href="/wiki/Low-density_lipoprotein" title="Low-density lipoprotein">low-density lipoprotein</a> and decreased <a href="/wiki/High-density_lipoprotein" title="High-density lipoprotein">high-density lipoprotein</a>), <a href="/wiki/Acne" title="Acne">acne</a>, <a href="/wiki/High_blood_pressure" class="mw-redirect" title="High blood pressure">high blood pressure</a>, <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">liver damage</a> (mainly with most oral AAS), and <a href="/wiki/Left_ventricular_hypertrophy" title="Left ventricular hypertrophy">left ventricular hypertrophy</a>.<a href="#cite_note-pmid1917226-4">[4]</a> These risks are further increased when athletes take steroids alongside other drugs, causing significantly more damage to their bodies.<a href="#cite_note-pmid19751025-5">[5]</a> The effect of anabolic steroids on the heart can cause <a href="/wiki/Myocardial_infarction" title="Myocardial infarction">myocardial infarction</a> and <a href="/wiki/Stroke" title="Stroke">strokes</a>.<a href="#cite_note-pmid19751025-5">[5]</a> Conditions pertaining to <a href="/wiki/Hormonal_imbalance" class="mw-redirect" title="Hormonal imbalance">hormonal imbalances</a> such as <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a> and <a href="/wiki/Hypogonadism" title="Hypogonadism">testicular size reduction</a> may also be caused by AAS.<a href="#cite_note-pmid21443513-6">[6]</a> In women and children, AAS can cause irreversible <a href="/wiki/Masculinization" class="mw-redirect" title="Masculinization">masculinization</a>.<a href="#cite_note-pmid21443513-6">[6]</a> <a href="/wiki/Ergogenic" class="mw-redirect" title="Ergogenic">Ergogenic</a> uses for AAS in sports, <a href="/wiki/Racing" title="Racing">racing</a>, and <a href="/wiki/Bodybuilding" title="Bodybuilding">bodybuilding</a> as <a href="/wiki/Performance-enhancing_drugs" class="mw-redirect" title="Performance-enhancing drugs">performance-enhancing drugs</a> are controversial because of their adverse effects and the potential to gain advantage in physical competitions. Their use is referred to as <a href="/wiki/Use_of_performance-enhancing_drugs_in_sport" class="mw-redirect" title="Use of performance-enhancing drugs in sport">doping</a> and banned by most major sporting bodies. Athletes have been looking for drugs to enhance their athletic abilities since the Olympics started in Ancient Greece.<a href="#cite_note-pmid19751025-5">[5]</a> For many years, AAS have been by far the most detected doping substances in <a href="/wiki/IOC" class="mw-redirect" title="IOC">IOC</a>-accredited laboratories.<a href="#cite_note-pmid15248788-7">[7]</a><a href="#cite_note-pmid12880534-8">[8]</a> Anabolic steroids are classified as <a href="/wiki/Schedule_III_controlled_substances" class="mw-redirect" title="Schedule III controlled substances">Schedule III controlled substances</a> in many countries,<a href="#cite_note-Powers-2011-9">[9]</a> meaning that AAS have recognized medical use but are also recognized as having a potential for abuse and dependence, leading to their regulation and control. In countries where AAS are <a href="/wiki/Controlled_substances" class="mw-redirect" title="Controlled substances">controlled substances</a>, there is often a <a href="/wiki/Black_market" title="Black market">black market</a> in which smuggled, <a href="https://en.wiktionary.org/wiki/clandestine" class="extiw" title="wikt:clandestine">clandestinely</a> manufactured or even <a href="/wiki/Counterfeit_drugs" class="mw-redirect" title="Counterfeit drugs">counterfeit drugs</a> are sold to users. <style data-mw-deduplicate="TemplateStyles:r886046785">.mw-parser-output .toclimit-2 .toclevel-1 ul,.mw-parser-output .toclimit-3 .toclevel-2 ul,.mw-parser-output .toclimit-4 .toclevel-3 ul,.mw-parser-output .toclimit-5 .toclevel-4 ul,.mw-parser-output .toclimit-6 .toclevel-5 ul,.mw-parser-output .toclimit-7 .toclevel-6 ul{display:none}</style><div class="toclimit-3"><meta property="mw:PageProp/toc" /></div> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=1" title="Edit section: Uses">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Medical">Medical</h3>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=2" title="Edit section: Medical">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Anabolicsteroids41.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/Anabolicsteroids41.jpg/220px-Anabolicsteroids41.jpg" decoding="async" width="220" height="133" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/d/dc/Anabolicsteroids41.jpg 1.5x" data-file-width="253" data-file-height="153" /></a><figcaption>Various AAS and related compounds</figcaption></figure> Since the discovery and synthesis of testosterone in the 1930s, AAS have been used by physicians for many purposes, with varying degrees of success. These can broadly be grouped into anabolic, androgenic, and other uses. <div class="mw-heading mw-heading4"><h4 id="Anabolic">Anabolic</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=3" title="Edit section: Anabolic">edit</a>]</div> <ul><li><a href="/wiki/Bone_marrow" title="Bone marrow">Bone marrow</a> stimulation: For decades, AAS were the mainstay of therapy for <a href="/wiki/Hypoplastic" class="mw-redirect" title="Hypoplastic">hypoplastic</a> <a href="/wiki/Anemia" title="Anemia">anemias</a> due to <a href="/wiki/Leukemia" title="Leukemia">leukemia</a>, <a href="/wiki/Kidney_failure" title="Kidney failure">kidney failure</a> or <a href="/wiki/Aplastic_anemia" title="Aplastic anemia">aplastic anemia</a>.<a href="#cite_note-pmid11701661-10">[10]</a></li> <li><a href="/wiki/Human_development_(biology)" class="mw-redirect" title="Human development (biology)">Growth</a> stimulation: AAS can be used by <a href="/wiki/Pediatric_endocrinology" title="Pediatric endocrinology">pediatric endocrinologists</a> to treat children with <a href="/wiki/Growth_failure" class="mw-redirect" title="Growth failure">growth failure</a>.<a href="#cite_note-pmid2429792-11">[11]</a> However, the availability of synthetic <a href="/wiki/Growth_hormone_treatment" class="mw-redirect" title="Growth hormone treatment">growth hormone</a>, which has fewer side effects, makes this a secondary treatment.[<a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)">medical citation needed</a>]</li> <li>Stimulation of <a href="/wiki/Appetite" title="Appetite">appetite</a> and preservation and increase of <a href="/wiki/Muscle" title="Muscle">muscle</a> mass: AAS have been given to people with <a href="/wiki/Cachexia" title="Cachexia">chronic wasting conditions</a> such as <a href="/wiki/Cancer" title="Cancer">cancer</a> and <a href="/wiki/AIDS" class="mw-redirect" title="AIDS">AIDS</a>.<a href="#cite_note-pmid16540931-12">[12]</a><a href="#cite_note-pmid8970686-13">[13]</a></li> <li>Stimulation of lean body mass and prevention of <a href="/wiki/Bone_resorption" title="Bone resorption">bone loss</a> in elderly men, as some studies indicate.<a href="#cite_note-pmid11320105-14">[14]</a><a href="#cite_note-pmid17824721-15">[15]</a><a href="#cite_note-pmid11730258-16">[16]</a> However, a 2006 placebo-controlled trial of low-dose testosterone supplementation in elderly men with low levels of testosterone found no benefit on body composition, physical performance, <a href="/wiki/Insulin_sensitivity" class="mw-redirect" title="Insulin sensitivity">insulin sensitivity</a>, or <a href="/wiki/Quality_of_life" title="Quality of life">quality of life</a>.<a href="#cite_note-pmid17050889-17">[17]</a></li> <li>Prevention or treatment of <a href="/wiki/Osteoporosis" title="Osteoporosis">osteoporosis</a> in <a href="/wiki/Postmenopausal" class="mw-redirect" title="Postmenopausal">postmenopausal</a> women.<a href="#cite_note-Mangus-2005-18">[18]</a><a href="#cite_note-London1999-19">[19]</a> <a href="/wiki/Nandrolone_decanoate" title="Nandrolone decanoate">Nandrolone decanoate</a> is approved for this use.<a href="#cite_note-pmid10418991-20">[20]</a> Although they have been indicated for this indication, AAS saw very little use for this purpose due to their virilizing side effects.<a href="#cite_note-Mangus-2005-18">[18]</a><a href="#cite_note-McFarland-2002-21">[21]</a></li> <li>Aiding <a href="/wiki/Weight_gain" title="Weight gain">weight gain</a> following <a href="/wiki/Surgery" title="Surgery">surgery</a> or <a href="/wiki/Physical_trauma" class="mw-redirect" title="Physical trauma">physical trauma</a>, during <a href="/wiki/Chronic_infection" class="mw-redirect" title="Chronic infection">chronic infection</a>, or in the context of unexplained <a href="/wiki/Weight_loss" title="Weight loss">weight loss</a>.<a href="#cite_note-UpsherSmithLabel-22">[22]</a><a href="#cite_note-BTGLabel-23">[23]</a></li> <li>Counteracting the <a href="/wiki/Catabolic" class="mw-redirect" title="Catabolic">catabolic</a> effect of long-term <a href="/wiki/Corticosteroid" title="Corticosteroid">corticosteroid</a> therapy.<a href="#cite_note-UpsherSmithLabel-22">[22]</a><a href="#cite_note-BTGLabel-23">[23]</a></li> <li><a href="/wiki/Oxandrolone" title="Oxandrolone">Oxandrolone</a> improves both short-term and long-term outcomes in people recovering from <a href="/wiki/Severe_burns" class="mw-redirect" title="Severe burns">severe burns</a>, and is well-established as a safe treatment for this indication.<a href="#cite_note-pmid26454425-24">[24]</a><a href="#cite_note-pmid23121414-25">[25]</a></li> <li>Treatment of <a href="/wiki/Idiopathic_short_stature" title="Idiopathic short stature">idiopathic short stature</a>, <a href="/wiki/Hereditary_angioedema" title="Hereditary angioedema">hereditary angioedema</a>, <a href="/wiki/Alcoholic_hepatitis" title="Alcoholic hepatitis">alcoholic hepatitis</a>, and <a href="/wiki/Hypogonadism" title="Hypogonadism">hypogonadism</a>.<a href="#cite_note-pmid22729959-26">[26]</a><a href="#cite_note-pmid22541704-27">[27]</a></li> <li>Methyltestosterone is used in the treatment of <a href="/wiki/Delayed_puberty" title="Delayed puberty">delayed puberty</a>, <a href="/wiki/Hypogonadism" title="Hypogonadism">hypogonadism</a>, <a href="/wiki/Cryptorchidism" title="Cryptorchidism">cryptorchidism</a>, and <a href="/wiki/Erectile_dysfunction" title="Erectile dysfunction">erectile dysfunction</a> in males, and in low doses to treat <a href="/wiki/Menopause" title="Menopause">menopausal symptoms</a> (specifically for <a href="/wiki/Osteoporosis" title="Osteoporosis">osteoporosis</a>, <a href="/wiki/Hot_flash" title="Hot flash">hot flashes</a>, and to increase <a href="/wiki/Libido" title="Libido">libido</a> and <a href="/wiki/Energy_(psychological)" title="Energy (psychological)">energy</a>), <a href="/wiki/Postpartum" class="mw-redirect" title="Postpartum">postpartum</a> <a href="/wiki/Breast_pain" title="Breast pain">breast pain</a> and <a href="/wiki/Engorgement" class="mw-redirect" title="Engorgement">engorgement</a>, and <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> in women.<a href="#cite_note-Ebadi2007-28">[28]</a><a href="#cite_note-Yagiela-2010-29">[29]</a><a href="#cite_note-Android-Label-30">[30]</a></li> <li><a href="/wiki/Growth_hormone" title="Growth hormone">Growth hormones</a> used in veterinary medicine (e.g. <a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">trenbolone acetate</a>) are also used in <a href="/wiki/Intensive_animal_farming" title="Intensive animal farming">intensive animal farming</a> for faster gains in muscle mass for higher yields of meat from livestock and higher milk production in the <a href="/wiki/Dairy_farming" title="Dairy farming">dairy industry</a>.<a href="#cite_note-31">[31]</a></li></ul> <div class="mw-heading mw-heading4"><h4 id="Androgenic">Androgenic</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=4" title="Edit section: Androgenic">edit</a>]</div> <ul><li><a href="/wiki/Androgen_replacement_therapy" title="Androgen replacement therapy">Androgen replacement therapy</a> for men with low levels of testosterone, such as those associated with <a href="/wiki/Late-onset_hypogonadism" title="Late-onset hypogonadism">late-onset hypogonadism</a>;<a href="#cite_note-pmid35266057-32">[32]</a> also effective in improving libido for elderly males.<a href="#cite_note-pmid17403329-33">[33]</a><a href="#cite_note-pmid17367445-34">[34]</a><a href="#cite_note-pmid9497881-35">[35]</a><a href="#cite_note-pmid10619981-36">[36]</a></li> <li>Induction of male <a href="/wiki/Puberty" title="Puberty">puberty</a>: Androgens are given to many boys distressed about extreme <a href="/wiki/Delayed_puberty" title="Delayed puberty">delay of puberty</a>. Testosterone is now nearly the only androgen used for this purpose and has been shown to increase height, weight, and fat-free mass in boys with delayed puberty.<a href="#cite_note-pmid9329341-37">[37]</a></li> <li><a href="/wiki/Masculinizing_hormone_therapy" title="Masculinizing hormone therapy">Masculinizing hormone therapy</a> for <a href="/wiki/Transgender_men" class="mw-redirect" title="Transgender men">transgender men</a>, other <a href="/wiki/Transmasculine" class="mw-redirect" title="Transmasculine">transmasculine</a> people, and <a href="/wiki/Intersex" title="Intersex">intersex</a> people, by producing masculine secondary sexual characteristics such as a <a href="/wiki/Voice_deepening" class="mw-redirect" title="Voice deepening">voice deepening</a>, increased bone and muscle mass, <a href="/wiki/Android_fat_distribution" title="Android fat distribution">masculine fat distribution</a>, facial and body hair, and <a href="/wiki/Clitoral_enlargement" class="mw-redirect" title="Clitoral enlargement">clitoral enlargement</a>, as well as mental changes such as alleviation of <a href="/wiki/Gender_dysphoria" title="Gender dysphoria">gender dysphoria</a> and increased sex drive.<a href="#cite_note-pmid12915619-38">[38]</a><a href="#cite_note-ieet.org-39">[39]</a><a href="#cite_note-www.sfgate.com-40">[40]</a><a href="#cite_note-pmid15649098-41">[41]</a><a href="#cite_note-interactyouth.org-42">[42]</a></li></ul> <div class="mw-heading mw-heading4"><h4 id="Other">Other</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=5" title="Edit section: Other">edit</a>]</div> <ul><li>Treatment of <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> in women, although they are now very rarely used for this purpose due to their marked virilizing side effects.<a href="#cite_note-Perry-2012-43">[43]</a><a href="#cite_note-Mangus-2005-18">[18]</a><a href="#cite_note-pmid3909420-44">[44]</a></li> <li>In low doses as a component of <a href="/wiki/Hormone_replacement_therapy" title="Hormone replacement therapy">hormone therapy</a> for <a href="/wiki/Postmenopausal" class="mw-redirect" title="Postmenopausal">postmenopausal</a> and <a href="/wiki/Transgender_women" class="mw-redirect" title="Transgender women">transgender women</a>, for instance to increase <a href="/wiki/Energy_(psychological)" title="Energy (psychological)">energy</a>, <a href="/wiki/Well-being" title="Well-being">well-being</a>, <a href="/wiki/Libido" title="Libido">libido</a>, and <a href="/wiki/Quality_of_life" title="Quality of life">quality of life</a>, as well as to reduce <a href="/wiki/Hot_flash" title="Hot flash">hot flashes</a>.<a href="#cite_note-pmid10076169-45">[45]</a><a href="#cite_note-pmid17087613-46">[46]</a><a href="#cite_note-pmid18488873-47">[47]</a><a href="#cite_note-pmid16794424-48">[48]</a> Testosterone is usually used for this purpose, although <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a> is also used.<a href="#cite_note-pmid16794424-48">[48]</a><a href="#cite_note-pmid11304877-49">[49]</a></li> <li><a href="/wiki/Male_hormonal_contraception" class="mw-redirect" title="Male hormonal contraception">Male hormonal contraception</a>; currently experimental, but potential for use as effective, safe, reliable, and reversible male contraceptives.<a href="#cite_note-pmid20933120-50">[50]</a></li> <li>Assistant in the treatment of <a href="/wiki/Raynaud%27s_Phenomenon" class="mw-redirect" title="Raynaud's Phenomenon">Raynaud's Phenomenon</a> and peripheral <a href="/wiki/Acrocyanosis" title="Acrocyanosis">acrocyanosis</a>. Testosterone and other anabolics tend to be potent <a href="/wiki/Vasodilators" class="mw-redirect" title="Vasodilators">vasodilators</a>, which can significantly improve bloodflow in individuals prone to vasoconstriction.<a href="#cite_note-Baalmann-2017-51">[51]</a></li></ul> <div class="mw-heading mw-heading3"><h3 id="Enhancing_performance">Enhancing performance</h3>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=6" title="Edit section: Enhancing performance">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Ergogenic_use_of_anabolic_steroids" title="Ergogenic use of anabolic steroids">Ergogenic use of anabolic steroids</a></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Rawdealsteroids4.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Rawdealsteroids4.jpg/220px-Rawdealsteroids4.jpg" decoding="async" width="220" height="155" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Rawdealsteroids4.jpg/330px-Rawdealsteroids4.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Rawdealsteroids4.jpg/440px-Rawdealsteroids4.jpg 2x" data-file-width="794" data-file-height="558" /></a><figcaption>Numerous vials of injectable AAS</figcaption></figure> Most steroid users are not athletes.<a href="#cite_note-Reuters-2007-52">[52]</a> In the United States, between 1 million and 3 million people (1% of the population) are thought to have used AAS.<a href="#cite_note-pmid18514731-53">[53]</a> Studies in the United States have shown that AAS users tend to be mostly middle-class men with a <a href="/wiki/Median" title="Median">median</a> age of about 25 who are noncompetitive bodybuilders and non-athletes and use the drugs for cosmetic purposes.<a href="#cite_note-pmid8355384-54">[54]</a> "Among 12- to 17-year-old boys, use of steroids and similar drugs jumped 25 percent from 1999 to 2000, with 20 percent saying they use them for looks rather than sports, a study by insurer Blue Cross Blue Shield found."<a href="#cite_note-55">[55]</a> Another study found that non-medical use of AAS among college students was at or less than 1%.<a href="#cite_note-pmid17512138-56">[56]</a> According to a recent survey, 78.4% of steroid users were noncompetitive bodybuilders and non-athletes, while about 13% reported unsafe injection practices such as reusing needles, sharing needles, and sharing multidose vials,<a href="#cite_note-pmid16679978-57">[57]</a> though a 2007 study found that sharing of needles was extremely uncommon among individuals using AAS for non-medical purposes, less than 1%.<a href="#cite_note-pmid17931410-58">[58]</a> Another 2007 study found that 74% of non-medical AAS users had post-secondary degrees and more had completed college and fewer had failed to complete high school than is expected from the general populace.<a href="#cite_note-pmid17931410-58">[58]</a> The same study found that individuals using AAS for non-medical purposes had a higher employment rate and a higher household income than the general population.<a href="#cite_note-pmid17931410-58">[58]</a> AAS users tend to research the drugs they are taking more than other controlled-substance users;[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] however, the major sources consulted by steroid users include friends, non-medical handbooks, internet-based forums, blogs, and fitness magazines, which can provide questionable or inaccurate information.<a href="#cite_note-pmid9549549-59">[59]</a> AAS users tend to be unhappy with the portrayal of AAS as deadly in the media and in politics.<a href="#cite_note-Eastley-2006-60">[60]</a> According to one study, AAS users also distrust their physicians and in the sample 56% had not disclosed their AAS use to their physicians.<a href="#cite_note-pmid15317640-61">[61]</a> Another 2007 study had similar findings, showing that, while 66% of individuals using AAS for non-medical purposes were willing to seek medical supervision for their steroid use, 58% lacked trust in their physicians, 92% felt that the medical community's knowledge of non-medical AAS use was lacking, and 99% felt that the public has an exaggerated view of the side-effects of AAS use.<a href="#cite_note-pmid17931410-58">[58]</a> A recent study has also shown that long term AAS users were more likely to have symptoms of <a href="/wiki/Muscle_dysmorphia" title="Muscle dysmorphia">muscle dysmorphia</a> and also showed stronger endorsement of more conventional male roles.<a href="#cite_note-pmid16585446-62">[62]</a> A recent study in the Journal of Health Psychology showed that many users believed that steroids used in moderation were safe.<a href="#cite_note-pmid17035257-63">[63]</a> AAS have been used by men and women in many different kinds of professional sports to attain a competitive edge or to assist in recovery from injury. These sports include <a href="/wiki/Bodybuilding" title="Bodybuilding">bodybuilding</a>, <a href="/wiki/Olympic_weightlifting" title="Olympic weightlifting">weightlifting</a>, <a href="/wiki/Shot_put" title="Shot put">shot put</a> and other <a href="/wiki/Track_and_field" title="Track and field">track and field</a>, <a href="/wiki/Cycle_sport" title="Cycle sport">cycling</a>, <a href="/wiki/Baseball" title="Baseball">baseball</a>, <a href="/wiki/Wrestling" title="Wrestling">wrestling</a>, <a href="/wiki/Mixed_martial_arts" title="Mixed martial arts">mixed martial arts</a>, <a href="/wiki/Boxing" title="Boxing">boxing</a>, <a href="/wiki/Football" title="Football">football</a>, and <a href="/wiki/Cricket" title="Cricket">cricket</a>. Such use is prohibited by the rules of the governing bodies of most sports. AAS use occurs among adolescents, especially by those participating in competitive sports. It has been suggested that the prevalence of use among high-school students in the U.S. may be as high as 2.7%.<a href="#cite_note-pmid2199753-64">[64]</a> <div class="mw-heading mw-heading3"><h3 id="Dosages">Dosages</h3>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=7" title="Edit section: Dosages">edit</a>]</div> <table class="wikitable sortable floatright" style="margin: 1em auto;"> <caption class="nowrap">General dosage ranges of anabolic steroids </caption> <tbody><tr> <th scope="col">Medication </th> <th scope="col">Route </th> <th scope="col">Dosage range<a href="#cite_note-65">[a]</a> </th></tr> <tr> <td><a href="/wiki/Danazol" title="Danazol">Danazol</a></td> <td><a href="/wiki/Oral_administration" title="Oral administration">Oral</a></td> <td>100–800 mg/day </td></tr> <tr> <td><a href="/wiki/Drostanolone_propionate" title="Drostanolone propionate">Drostanolone propionate</a></td> <td><a href="/wiki/Injection_(medicine)" title="Injection (medicine)">Injection</a></td> <td>100 mg 3 times/week </td></tr> <tr> <td><a href="/wiki/Ethylestrenol" title="Ethylestrenol">Ethylestrenol</a></td> <td>Oral</td> <td>2–8 mg/day </td></tr> <tr> <td><a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">Fluoxymesterone</a></td> <td>Oral</td> <td>2–40 mg/day </td></tr> <tr> <td><a href="/wiki/Mesterolone" title="Mesterolone">Mesterolone</a></td> <td>Oral</td> <td>25–150 mg/day </td></tr> <tr> <td><a href="/wiki/Metandienone" title="Metandienone">Metandienone</a></td> <td>Oral</td> <td>2.5–15 mg/day </td></tr> <tr> <td><a href="/wiki/Metenolone_acetate" title="Metenolone acetate">Metenolone acetate</a></td> <td>Oral</td> <td>10–150 mg/day </td></tr> <tr> <td><a href="/wiki/Metenolone_enanthate" title="Metenolone enanthate">Metenolone enanthate</a></td> <td>Injection</td> <td>25–100 mg/week </td></tr> <tr> <td><a href="/wiki/Methyltestosterone" title="Methyltestosterone">Methyltestosterone</a></td> <td>Oral</td> <td>1.5–200 mg/day </td></tr> <tr> <td><a href="/wiki/Nandrolone_decanoate" title="Nandrolone decanoate">Nandrolone decanoate</a></td> <td>Injection</td> <td>12.5–200 mg/week<a href="#cite_note-div-66">[b]</a> </td></tr> <tr> <td><a href="/wiki/Nandrolone_phenylpropionate" title="Nandrolone phenylpropionate">Nandrolone phenylpropionate</a></td> <td>Injection</td> <td>6.25–200 mg/week<a href="#cite_note-div-66">[b]</a> </td></tr> <tr> <td><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a></td> <td>Oral</td> <td>20–30 mg/day </td></tr> <tr> <td><a href="/wiki/Oxandrolone" title="Oxandrolone">Oxandrolone</a></td> <td>Oral</td> <td>2.5–20 mg/day </td></tr> <tr> <td><a href="/wiki/Oxymetholone" title="Oxymetholone">Oxymetholone</a></td> <td>Oral</td> <td>1–5 mg/kg/day or 50–150 mg/day </td></tr> <tr> <td rowspan="2"><a href="/wiki/Stanozolol" title="Stanozolol">Stanozolol</a></td> <td>Oral</td> <td>2–6 mg/day </td></tr> <tr> <td>Injection</td> <td>50 mg up to every two weeks </td></tr> <tr> <td rowspan="2"><a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">Testosterone</a></td> <td>Oral<a href="#cite_note-67">[c]</a></td> <td>400–800 mg/day<a href="#cite_note-div-66">[b]</a> </td></tr> <tr> <td>Injection</td> <td>25–100 mg up to three times weekly </td></tr> <tr> <td><a href="/wiki/Testosterone_cypionate" title="Testosterone cypionate">Testosterone cypionate</a></td> <td>Injection</td> <td>50–400 mg up to every four weeks </td></tr> <tr> <td><a href="/wiki/Testosterone_enanthate" title="Testosterone enanthate">Testosterone enanthate</a></td> <td>Injection</td> <td>50–400 mg up to every four weeks </td></tr> <tr> <td><a href="/wiki/Testosterone_propionate" title="Testosterone propionate">Testosterone propionate</a></td> <td>Injection</td> <td>25–50 mg up to three times weekly </td></tr> <tr> <td rowspan="2"><a href="/wiki/Testosterone_undecanoate" title="Testosterone undecanoate">Testosterone undecanoate</a></td> <td>Oral</td> <td>80–240 mg/day<a href="#cite_note-div-66">[b]</a> </td></tr> <tr> <td>Injection</td> <td>750–1000 mg up to every 10 weeks </td></tr> <tr> <td><a href="/wiki/Trenbolone_hexahydrobenzylcarbonate" title="Trenbolone hexahydrobenzylcarbonate">Trenbolone <abbr title="hexahydrobenzylcarbonate">HBC</abbr></a></td> <td>Injection</td> <td>75 mg every 10 days </td></tr> <tr class="sortbottom"> <td colspan="5" style="width:1px; background:#eaecf0; text-align:center;">Sources: <a href="#cite_note-Drugs@FDA-68">[65]</a><a href="#cite_note-HamiltonDuffy2014-69">[66]</a><a href="#cite_note-FordRoach2010-70">[67]</a><a href="#cite_note-LemkeWilliams2012-71">[68]</a><a href="#cite_note-Mangus-2005-18">[18]</a><a href="#cite_note-Thomas2012-72">[69]</a><a href="#cite_note-Llewellyn2011-73">[70]</a><a href="#cite_note-Burkett-1984-74">[71]</a><a href="#cite_note-BainSchill2012-75">[72]</a><a href="#cite_note-pmid6372655-76">[73]</a> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-lower-alpha"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-65"><a href="#cite_ref-65">^</a> Unless otherwise noted, given as a once daily/weekly dose </li> <li id="cite_note-div-66">^ <a href="#cite_ref-div_66-0">a</a> <a href="#cite_ref-div_66-1">b</a> <a href="#cite_ref-div_66-2">c</a> <a href="#cite_ref-div_66-3">d</a> In divided doses </li> <li id="cite_note-67"><a href="#cite_ref-67">^</a> Studied for human use but never marketed, for comparison only </li> </ol></div></div> </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Available_forms">Available forms</h3>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=8" title="Edit section: Available forms">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/List_of_androgens/anabolic_steroids" class="mw-redirect" title="List of androgens/anabolic steroids">List of androgens/anabolic steroids</a></div> The AAS that have been used most commonly in medicine are <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a> and its many <a href="/wiki/Testosterone_ester" class="mw-redirect" title="Testosterone ester">esters</a> (but most typically <a href="/wiki/Testosterone_undecanoate" title="Testosterone undecanoate">testosterone undecanoate</a>, <a href="/wiki/Testosterone_enanthate" title="Testosterone enanthate">testosterone enanthate</a>, <a href="/wiki/Testosterone_cypionate" title="Testosterone cypionate">testosterone cypionate</a>, and <a href="/wiki/Testosterone_propionate" title="Testosterone propionate">testosterone propionate</a>),<a href="#cite_note-Becker-2001-77">[74]</a> <a href="/wiki/Nandrolone" title="Nandrolone">nandrolone</a> <a href="/wiki/Nandrolone_ester" class="mw-redirect" title="Nandrolone ester">esters</a> (typically <a href="/wiki/Nandrolone_decanoate" title="Nandrolone decanoate">nandrolone decanoate</a> and <a href="/wiki/Nandrolone_phenylpropionate" title="Nandrolone phenylpropionate">nandrolone phenylpropionate</a>), <a href="/wiki/Stanozolol" title="Stanozolol">stanozolol</a>, and <a href="/wiki/Metandienone" title="Metandienone">metandienone</a> (methandrostenolone).<a href="#cite_note-pmid18500378-78">[75]</a> Others that have also been available and used commonly but to a lesser extent include <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Oxandrolone" title="Oxandrolone">oxandrolone</a>, <a href="/wiki/Mesterolone" title="Mesterolone">mesterolone</a>, and <a href="/wiki/Oxymetholone" title="Oxymetholone">oxymetholone</a>, as well as <a href="/wiki/Drostanolone_propionate" title="Drostanolone propionate">drostanolone propionate</a> (dromostanolone propionate), <a href="/wiki/Metenolone" title="Metenolone">metenolone</a> (methylandrostenolone) esters (specifically <a href="/wiki/Metenolone_acetate" title="Metenolone acetate">metenolone acetate</a> and <a href="/wiki/Metenolone_enanthate" title="Metenolone enanthate">metenolone enanthate</a>), and <a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">fluoxymesterone</a>.<a href="#cite_note-pmid18500378-78">[75]</a> <a href="/wiki/Androstanolone" title="Androstanolone">Dihydrotestosterone</a> (DHT), known as androstanolone or stanolone when used medically, and its <a href="/wiki/Dihydrotestosterone_ester" class="mw-redirect" title="Dihydrotestosterone ester">esters</a> are also notable, although they are not widely used in medicine.<a href="#cite_note-Llewellyn2011-73">[70]</a> <a href="/wiki/Boldenone_undecylenate" title="Boldenone undecylenate">Boldenone undecylenate</a> and <a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">trenbolone acetate</a> are used in <a href="/wiki/Veterinary_medicine" title="Veterinary medicine">veterinary medicine</a>.<a href="#cite_note-pmid18500378-78">[75]</a> <a href="/wiki/Designer_steroid" class="mw-redirect" title="Designer steroid">Designer steroids</a> are AAS that have not been approved and marketed for medical use but have been distributed through the black market.<a href="#cite_note-pmid25684733-79">[76]</a> Examples of notable designer steroids include <a href="/wiki/1-testosterone" class="mw-redirect" title="1-testosterone">1-testosterone</a> (dihydroboldenone), <a href="/wiki/Methasterone" title="Methasterone">methasterone</a>, <a href="/wiki/Trenbolone_enanthate" title="Trenbolone enanthate">trenbolone enanthate</a>, <a href="/wiki/Desoxymethyltestosterone" title="Desoxymethyltestosterone">desoxymethyltestosterone</a>, <a href="/wiki/Tetrahydrogestrinone" title="Tetrahydrogestrinone">tetrahydrogestrinone</a>, and <a href="/wiki/Methylstenbolone" title="Methylstenbolone">methylstenbolone</a>.<a href="#cite_note-pmid25684733-79">[76]</a> <div class="mw-heading mw-heading3"><h3 id="Routes_of_administration">Routes of administration</h3>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=9" title="Edit section: Routes of administration">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Depo-testosterone_200_mg_ml.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Depo-testosterone_200_mg_ml.jpg/170px-Depo-testosterone_200_mg_ml.jpg" decoding="async" width="170" height="238" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Depo-testosterone_200_mg_ml.jpg/255px-Depo-testosterone_200_mg_ml.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Depo-testosterone_200_mg_ml.jpg/340px-Depo-testosterone_200_mg_ml.jpg 2x" data-file-width="2000" data-file-height="2800" /></a><figcaption>A vial of injectable testosterone cypionate</figcaption></figure> There are four common forms in which AAS are administered: oral pills; injectable steroids; creams/gels for topical application; and skin patches. Oral administration is the most convenient. Testosterone administered by mouth is rapidly absorbed, but it is largely converted to inactive metabolites, and only about one-sixth is available in active form. In order to be sufficiently active when given by mouth, testosterone derivatives are alkylated at the 17α position, e.g. <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a> and <a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">fluoxymesterone</a>. This modification reduces the liver's ability to break down these compounds before they reach the systemic circulation. Testosterone can be administered <a href="/wiki/Parenteral_medication" class="mw-redirect" title="Parenteral medication">parenterally</a>, but it has more irregular prolonged absorption time and greater activity in muscle in <a href="/wiki/Enanthate" class="mw-redirect" title="Enanthate">enanthate</a>, <a href="/wiki/Undecanoate" class="mw-redirect" title="Undecanoate">undecanoate</a>, or <a href="/wiki/Cypionate" class="mw-redirect" title="Cypionate">cypionate</a> <a href="/wiki/Ester" title="Ester">ester</a> form. These derivatives are hydrolyzed to release free testosterone at the site of injection; absorption rate (and thus injection schedule) varies among different esters, but medical injections are normally done anywhere between semi-weekly to once every 12 weeks. A more frequent schedule may be desirable in order to maintain a more constant level of hormone in the system.<a href="#cite_note-Chrousos-2012-80">[77]</a> Injectable steroids are typically administered into the muscle, not into the vein, to avoid sudden changes in the amount of the drug in the bloodstream. In addition, because estered testosterone is dissolved in oil, intravenous injection has the potential to cause a dangerous <a href="/wiki/Embolism" title="Embolism">embolism</a> (clot) in the bloodstream. <a href="/wiki/Transdermal_patch" title="Transdermal patch">Transdermal patches</a> (adhesive patches placed on the skin) may also be used to deliver a steady dose through the skin and into the bloodstream. Testosterone-containing creams and gels that are applied daily to the skin are also available, but absorption is inefficient (roughly 10%, varying between individuals) and these treatments tend to be more expensive. Individuals who are especially physically active and/or bathe often may not be good candidates, since the medication can be washed off and may take up to six hours to be fully absorbed. There is also the risk that an intimate partner or child may come in contact with the application site and inadvertently dose themselves; children and women are highly sensitive to testosterone and can develop unintended masculinization and health effects, even from small doses. Injection is the most common method used by individuals administering AAS for non-medical purposes.<a href="#cite_note-pmid17931410-58">[58]</a> The traditional routes of administration do not have differential effects on the efficacy of the drug. Studies indicate that the anabolic properties of AAS are relatively similar despite the differences in pharmacokinetic principles such as <a href="/wiki/First-pass_metabolism" class="mw-redirect" title="First-pass metabolism">first-pass metabolism</a>. However, the orally available forms of AAS may cause <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">liver damage</a> in high doses.<a href="#cite_note-pmid12880534-8">[8]</a><a href="#cite_note-pmid11366379-81">[78]</a> <div class="mw-heading mw-heading2"><h2 id="Adverse_effects">Adverse effects</h2>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=10" title="Edit section: Adverse effects">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:HarmCausedByDrugsTable.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2c/HarmCausedByDrugsTable.svg/300px-HarmCausedByDrugsTable.svg.png" decoding="async" width="300" height="232" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2c/HarmCausedByDrugsTable.svg/450px-HarmCausedByDrugsTable.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2c/HarmCausedByDrugsTable.svg/600px-HarmCausedByDrugsTable.svg.png 2x" data-file-width="990" data-file-height="765" /></a><figcaption>Table from the 2010 ISCD study ranking various drugs (legal and illegal) based on statements by drug-harm experts. Anabolic steroids was found to be the 15th overall most dangerous drug.<a href="#cite_note-Nutt_2010-82">[79]</a></figcaption></figure> Known possible <a href="/wiki/Side_effect" title="Side effect">side effects</a> of AAS include:<a href="#cite_note-pmid21443513-6">[6]</a><a href="#cite_note-pmid17723870-83">[80]</a><a href="#cite_note-pmid24423981-84">[81]</a><a href="#cite_note-pmid19028512-85">[82]</a><a href="#cite_note-pmid25805894-86">[83]</a> <ul><li><a href="/wiki/Cutaneous_condition" class="mw-redirect" title="Cutaneous condition">Dermatological</a>/<a href="/wiki/Integumentary_system" title="Integumentary system">integumental</a>: <a href="/wiki/Oily_skin" class="mw-redirect" title="Oily skin">oily skin</a>, <a href="/wiki/Acne_vulgaris" class="mw-redirect" title="Acne vulgaris">acne vulgaris</a>, <a href="/wiki/Acne_conglobata" title="Acne conglobata">acne conglobata</a>, <a href="/wiki/Seborrhea" class="mw-redirect" title="Seborrhea">seborrhea</a>, <a href="/wiki/Stretch_mark" class="mw-redirect" title="Stretch mark">stretch marks</a> (due to rapid <a href="/wiki/Muscle_hypertrophy" title="Muscle hypertrophy">muscle enlargement</a>), <a href="/wiki/Hypertrichosis" title="Hypertrichosis">hypertrichosis</a> (excessive body hair growth), <a href="/wiki/Androgenic_alopecia" class="mw-redirect" title="Androgenic alopecia">androgenic alopecia</a> (pattern hair loss; scalp baldness), <a href="/wiki/Water_retention_(medicine)" class="mw-redirect" title="Water retention (medicine)">fluid retention</a>/<a href="/wiki/Edema" title="Edema">edema</a>.</li> <li><a href="/wiki/Reproductive_system_disease" title="Reproductive system disease">Reproductive</a>/<a href="/wiki/Endocrine_disease" title="Endocrine disease">endocrine</a>: <a href="/wiki/Libido" title="Libido">libido</a> changes, reversible <a href="/wiki/Infertility" title="Infertility">infertility</a>, <a href="/wiki/Hypogonadotropic_hypogonadism" title="Hypogonadotropic hypogonadism">hypogonadotropic hypogonadism</a>.</li> <li>Male-specific: <a href="/wiki/Spontaneous_erection" class="mw-redirect" title="Spontaneous erection">spontaneous erections</a>, <a href="/wiki/Nocturnal_emission" title="Nocturnal emission">nocturnal emissions</a>, <a href="/wiki/Priapism" title="Priapism">priapism</a>, <a href="/wiki/Erectile_dysfunction" title="Erectile dysfunction">erectile dysfunction</a>, <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a> (mostly only with <a href="/wiki/Aromatase" title="Aromatase">aromatizable</a> and hence <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogenic</a> AAS), <a href="/wiki/Oligospermia" title="Oligospermia">oligospermia</a>/<a href="/wiki/Azoospermia" title="Azoospermia">azoospermia</a>, <a href="/wiki/Testicular_atrophy" title="Testicular atrophy">testicular atrophy</a>, <a href="/wiki/Intratesticular_leiomyosarcoma" class="mw-redirect" title="Intratesticular leiomyosarcoma">intratesticular leiomyosarcoma</a>, <a href="/wiki/Prostate_hypertrophy" class="mw-redirect" title="Prostate hypertrophy">prostate hypertrophy</a>, <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a>.</li> <li>Female-specific: <a href="/wiki/Masculinization" class="mw-redirect" title="Masculinization">masculinization</a>, irreversible <a href="/wiki/Voice_deepening" class="mw-redirect" title="Voice deepening">voice deepening</a>, <a href="/wiki/Hirsutism" title="Hirsutism">hirsutism</a> (excessive facial/body hair growth), <a href="/wiki/Menstrual_disturbances" class="mw-redirect" title="Menstrual disturbances">menstrual disturbances</a> (e.g., <a href="/wiki/Anovulation" title="Anovulation">anovulation</a>, <a href="/wiki/Oligomenorrhea" title="Oligomenorrhea">oligomenorrhea</a>, <a href="/wiki/Amenorrhea" title="Amenorrhea">amenorrhea</a>, <a href="/wiki/Dysmenorrhea" title="Dysmenorrhea">dysmenorrhea</a>), <a href="/wiki/Clitoral_enlargement" class="mw-redirect" title="Clitoral enlargement">clitoral enlargement</a>, <a href="/wiki/Breast_atrophy" title="Breast atrophy">breast atrophy</a>, <a href="/wiki/Uterine_atrophy" class="mw-redirect" title="Uterine atrophy">uterine atrophy</a>, <a href="/wiki/Teratogenicity" class="mw-redirect" title="Teratogenicity">teratogenicity</a> (in female <a href="/wiki/Fetus" title="Fetus">fetuses</a>).</li> <li>Child-specific: premature <a href="/wiki/Epiphyseal_closure" class="mw-redirect" title="Epiphyseal closure">epiphyseal closure</a> and associated <a href="/wiki/Short_stature" title="Short stature">short stature</a>, <a href="/wiki/Precocious_puberty" title="Precocious puberty">precocious puberty</a> in boys, <a href="/wiki/Delayed_puberty" title="Delayed puberty">delayed puberty</a> and <a href="/wiki/Contrasexual_precocity" class="mw-redirect" title="Contrasexual precocity">contrasexual precocity</a> in girls.</li> <li><a href="/wiki/Emotional_and_behavioral_disorders" title="Emotional and behavioral disorders">Psychiatric</a>/<a href="/wiki/Neurological_disorder" title="Neurological disorder">neurological</a>: <a href="/wiki/Mood_swing" title="Mood swing">mood swings</a>, <a href="/wiki/Irritability" title="Irritability">irritability</a>, <a href="/wiki/Aggression" title="Aggression">aggression</a>, <a href="/wiki/Violent_behavior" class="mw-redirect" title="Violent behavior">violent behavior</a>, <a href="/wiki/Impulsivity" title="Impulsivity">impulsivity</a>/<a href="/wiki/Recklessness_(psychology)" title="Recklessness (psychology)">recklessness</a>, <a href="/wiki/Hypomania" title="Hypomania">hypomania</a>/<a href="/wiki/Mania" title="Mania">mania</a>, <a href="/wiki/Euphoria" title="Euphoria">euphoria</a>, <a href="/wiki/Depression_(mood)" title="Depression (mood)">depression</a>, <a href="/wiki/Anxiety" title="Anxiety">anxiety</a>, <a href="/wiki/Dysphoria" title="Dysphoria">dysphoria</a>, <a href="/wiki/Suicidality" class="mw-redirect" title="Suicidality">suicidality</a>, <a href="/wiki/Delusion" title="Delusion">delusions</a>, <a href="/wiki/Psychosis" title="Psychosis">psychosis</a>, <a href="/wiki/Drug_withdrawal" title="Drug withdrawal">withdrawal</a>, <a href="/wiki/Drug_dependence" class="mw-redirect" title="Drug dependence">dependence</a>, <a href="/wiki/Neurotoxicity" title="Neurotoxicity">neurotoxicity</a>, <a href="/wiki/Cognitive_impairment" title="Cognitive impairment">cognitive impairment</a>.<a href="#cite_note-pmid16000671-87">[84]</a><a href="#cite_note-pmid15984895-88">[85]</a></li> <li><a href="/wiki/Musculoskeletal_disorder" title="Musculoskeletal disorder">Musculoskeletal</a>: <a href="/wiki/Muscle_hypertrophy" title="Muscle hypertrophy">muscle hypertrophy</a>, <a href="/wiki/Muscle_strain" class="mw-redirect" title="Muscle strain">muscle strains</a>, <a href="/wiki/Tendon_rupture" title="Tendon rupture">tendon ruptures</a>, <a href="/wiki/Rhabdomyolysis" title="Rhabdomyolysis">rhabdomyolysis</a>.</li> <li><a href="/wiki/Cardiovascular_disease" title="Cardiovascular disease">Cardiovascular</a>: <a href="/wiki/Dyslipidemia" title="Dyslipidemia">dyslipidemia</a> (e.g., increased <a href="/wiki/Low-density_lipoprotein" title="Low-density lipoprotein"><abbr title="low-density lipoprotein">LDL</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 low-density lipoprotein levels, decreased <a href="/wiki/High-density_lipoprotein" title="High-density lipoprotein"><abbr title="high-density lipoprotein">HDL</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 high-density lipoprotein levels, reduced <a href="/wiki/Apolipoprotein_A1" class="mw-redirect" title="Apolipoprotein A1"><abbr title="apolipoprotein A1">apo-A1</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 apolipoprotein A1 levels), <a href="/wiki/Atherosclerosis" title="Atherosclerosis">atherosclerosis</a>, elevated <a href="/wiki/Hematocrit" title="Hematocrit">hematocrit</a>, <a href="/wiki/Hypertension" title="Hypertension">hypertension</a>, <a href="/wiki/Left_ventricular_hypertrophy" title="Left ventricular hypertrophy">left ventricular hypertrophy</a>, <a href="/wiki/Cardiomyopathy" title="Cardiomyopathy">cardiomyopathy</a>, <a href="/wiki/Myocardial_hypertrophy" class="mw-redirect" title="Myocardial hypertrophy">myocardial hypertrophy</a>, <a href="/wiki/Polycythemia" title="Polycythemia">polycythemia</a>/<a href="/wiki/Erythrocytosis" class="mw-redirect" title="Erythrocytosis">erythrocytosis</a>, <a href="/wiki/Arrhythmia" title="Arrhythmia">arrhythmias</a>, <a href="/wiki/Thrombosis" title="Thrombosis">thrombosis</a> (e.g., <a href="/wiki/Embolism" title="Embolism">embolism</a>, <a href="/wiki/Stroke" title="Stroke">stroke</a>), <a href="/wiki/Myocardial_infarction" title="Myocardial infarction">myocardial infarction</a>, <a href="/wiki/Sudden_cardiac_death" class="mw-redirect" title="Sudden cardiac death">sudden death</a>.<a href="#cite_note-pmid20020375-89">[86]</a><a href="#cite_note-pmid20816133-90">[87]</a></li> <li><a href="/wiki/Liver_disease" title="Liver disease">Hepatic</a>: elevated <a href="/wiki/Liver_function_test" class="mw-redirect" title="Liver function test">liver function tests</a> (<a href="/wiki/Aspartate_aminotransferase" class="mw-redirect" title="Aspartate aminotransferase"><abbr title="aspartate aminotransferase">AST</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 aspartate aminotransferase, <a href="/wiki/Alanine_aminotransferase" class="mw-redirect" title="Alanine aminotransferase"><abbr title="alanine aminotransferase">ALT</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 alanine aminotransferase, <a href="/wiki/Bilirubin" title="Bilirubin">bilirubin</a>, <a href="/wiki/Lactic_dehydrogenase" class="mw-redirect" title="Lactic dehydrogenase"><abbr title="lactic dehydrogenase">LDH</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 lactic dehydrogenase, <a href="/wiki/Alkaline_phosphatase" title="Alkaline phosphatase"><abbr title="alkaline phosphatase">ALP</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 alkaline phosphatase), <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">hepatotoxicity</a>, <a href="/wiki/Jaundice" title="Jaundice">jaundice</a>, <a href="/wiki/Hepatic_steatosis" class="mw-redirect" title="Hepatic steatosis">hepatic steatosis</a>, <a href="/wiki/Hepatocellular_adenoma" title="Hepatocellular adenoma">hepatocellular adenoma</a>, <a href="/wiki/Hepatocellular_carcinoma" title="Hepatocellular carcinoma">hepatocellular carcinoma</a>, <a href="/wiki/Cholestasis" title="Cholestasis">cholestasis</a>, <a href="/wiki/Peliosis_hepatis" title="Peliosis hepatis">peliosis hepatis</a>; all mostly or exclusively with 17α-alkylated AAS.<a href="#cite_note-pmid28379599-91">[88]</a></li> <li><a href="/wiki/Renal_disease" class="mw-redirect" title="Renal disease">Renal</a>: <a href="/wiki/Renal_hypertrophy" class="mw-redirect" title="Renal hypertrophy">renal hypertrophy</a>, <a href="/wiki/Nephropathy" class="mw-redirect" title="Nephropathy">nephropathy</a>, <a href="/wiki/Acute_renal_failure" class="mw-redirect" title="Acute renal failure">acute renal failure</a> (secondary to rhabdomyolysis), <a href="/wiki/Focal_segmental_glomerulosclerosis" title="Focal segmental glomerulosclerosis">focal segmental glomerulosclerosis</a>, <a href="/wiki/Renal_cell_carcinoma" title="Renal cell carcinoma">renal cell carcinoma</a>.</li> <li>Others: <a href="/wiki/Glucose_intolerance" class="mw-redirect" title="Glucose intolerance">glucose intolerance</a>, <a href="/wiki/Insulin_resistance" title="Insulin resistance">insulin resistance</a>, <a href="/wiki/Immune_dysfunction" class="mw-redirect" title="Immune dysfunction">immune dysfunction</a>.<a href="#cite_note-pmid21443507-92">[89]</a></li></ul> <div class="mw-heading mw-heading3"><h3 id="Physiological">Physiological</h3>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=11" title="Edit section: Physiological">edit</a>]</div> Depending on the length of drug use, there is a chance that the immune system can be damaged. Most of these side-effects are dose-dependent, the most common being elevated <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a>, especially in those with pre-existing <a href="/wiki/Hypertension" title="Hypertension">hypertension</a>.<a href="#cite_note-pmid14609147-93">[90]</a> In addition to morphological changes of the heart which may have a permanent adverse effect on cardiovascular efficiency. AAS have been shown to alter fasting blood sugar and glucose tolerance tests.<a href="#cite_note-Dailymed.nlm.nih.gov-94">[91]</a> AAS such as testosterone also increase the risk of <a href="/wiki/Cardiovascular_disease" title="Cardiovascular disease">cardiovascular disease</a><a href="#cite_note-pmid7556805-2">[2]</a> or <a href="/wiki/Coronary_artery_disease" title="Coronary artery disease">coronary artery disease</a>.<a href="#cite_note-pmid1586105-95">[92]</a><a href="#cite_note-pmid8821428-96">[93]</a> <a href="/wiki/Acne" title="Acne">Acne</a> is fairly common among AAS users, mostly due to stimulation of the <a href="/wiki/Sebaceous_gland" title="Sebaceous gland">sebaceous glands</a> by increased testosterone levels.<a href="#cite_note-pmid15248788-7">[7]</a><a href="#cite_note-pmid17274777-97">[94]</a> Conversion of testosterone to DHT can accelerate the rate of premature <a href="/wiki/Baldness" class="mw-redirect" title="Baldness">baldness</a> for males genetically predisposed, but testosterone itself can produce baldness in females.<a href="#cite_note-pmid12870172-98">[95]</a> A number of severe side effects can occur if adolescents use AAS. For example, AAS may prematurely stop the lengthening of bones (premature <a href="/wiki/Epiphyseal_plate" title="Epiphyseal plate">epiphyseal fusion</a> through increased levels of <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a> <a href="/wiki/Metabolite" title="Metabolite">metabolites</a>), resulting in <a href="/wiki/Stunted_growth" title="Stunted growth">stunted growth</a>. Other effects include, but are not limited to, accelerated <a href="/wiki/Bone_maturation" class="mw-redirect" title="Bone maturation">bone maturation</a>, increased frequency and duration of erections, and premature sexual development. AAS use in adolescence is also <a href="/wiki/Correlated" class="mw-redirect" title="Correlated">correlated</a> with poorer attitudes related to health.<a href="#cite_note-pmid11927236-99">[96]</a> <div class="mw-heading mw-heading4"><h4 id="Cancer">Cancer</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=12" title="Edit section: Cancer">edit</a>]</div> WHO organization <a href="/wiki/International_Agency_for_Research_on_Cancer" title="International Agency for Research on Cancer">International Agency for Research on Cancer</a> (IARC) list AAS under <a href="/wiki/List_of_IARC_Group_2A_carcinogens" class="mw-redirect" title="List of IARC Group 2A carcinogens">Group 2A</a>: Probably carcinogenic to humans.<a href="#cite_note-url_ACS_known_carcinogens-100">[97]</a> <div class="mw-heading mw-heading4"><h4 id="Cardiovascular">Cardiovascular</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=13" title="Edit section: Cardiovascular">edit</a>]</div> Other side-effects can include alterations in the structure of the <a href="/wiki/Heart" title="Heart">heart</a>, such as <a href="/wiki/Left_ventricular_hypertrophy" title="Left ventricular hypertrophy">enlargement and thickening of the left ventricle</a>, which impairs its contraction and <a href="/wiki/Diastolic" class="mw-redirect" title="Diastolic">relaxation</a>, and therefore reducing ejected blood volume.<a href="#cite_note-pmid1917226-4">[4]</a> Possible effects of these alterations in the heart are hypertension, <a href="/wiki/Cardiac_arrhythmia" class="mw-redirect" title="Cardiac arrhythmia">cardiac arrhythmias</a>, <a href="/wiki/Congestive_heart_failure" class="mw-redirect" title="Congestive heart failure">congestive heart failure</a>, <a href="/wiki/Heart_attacks" class="mw-redirect" title="Heart attacks">heart attacks</a>, and <a href="/wiki/Sudden_cardiac_death" class="mw-redirect" title="Sudden cardiac death">sudden cardiac death</a>.<a href="#cite_note-pmid10499702-101">[98]</a> These changes are also seen in non-drug-using <a href="/wiki/Athletes" class="mw-redirect" title="Athletes">athletes</a>, but steroid use may accelerate this process.<a href="#cite_note-pmid9778553-102">[99]</a><a href="#cite_note-pmid1829849-103">[100]</a> However, both the connection between changes in the structure of the left ventricle and decreased cardiac function, as well as the connection to steroid use have been disputed.<a href="#cite_note-pmid9113423-104">[101]</a><a href="#cite_note-pmid4079743-105">[102]</a> AAS use can cause harmful changes in <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a> levels: Some steroids cause an increase in <a href="/wiki/LDL_cholesterol" class="mw-redirect" title="LDL cholesterol">LDL cholesterol</a> and a decrease in <a href="/wiki/HDL_cholesterol" class="mw-redirect" title="HDL cholesterol">HDL cholesterol</a>.<a href="#cite_note-Tokar-2006-106">[103]</a> <div class="mw-heading mw-heading4"><h4 id="Growth_defects">Growth defects</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=14" title="Edit section: Growth defects">edit</a>]</div> AAS use in adolescents quickens bone maturation and may reduce adult height in high doses.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] Low doses of AAS such as <a href="/wiki/Oxandrolone" title="Oxandrolone">oxandrolone</a> are used in the treatment of <a href="/wiki/Idiopathic_short_stature" title="Idiopathic short stature">idiopathic short stature</a>, but this may only quicken maturation rather than increasing adult height.<a href="#cite_note-pmid26051296-107">[104]</a> <div class="mw-heading mw-heading4"><h4 id="Feminization">Feminization</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=15" title="Edit section: Feminization">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:GynecomastiaFrontalAsymSevere.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9c/GynecomastiaFrontalAsymSevere.jpg/220px-GynecomastiaFrontalAsymSevere.jpg" decoding="async" width="220" height="132" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9c/GynecomastiaFrontalAsymSevere.jpg/330px-GynecomastiaFrontalAsymSevere.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9c/GynecomastiaFrontalAsymSevere.jpg/440px-GynecomastiaFrontalAsymSevere.jpg 2x" data-file-width="1000" data-file-height="600" /></a><figcaption>22-year-old man with gynecomastia not due to AAS use. Before and after gynecomastia surgery.</figcaption></figure> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Feminization_(biology)" title="Feminization (biology)">Feminization (biology)</a></div> Although all anabolic steroids have <a href="/wiki/Androgenic" class="mw-redirect" title="Androgenic">androgenic</a> effects, some of them paradoxically results in feminization, such as breast tissue in males, a condition called <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a>. These side effect are caused by the natural conversion of testosterone into <a href="/wiki/Estrogen" title="Estrogen">estrogen</a> and <a href="/wiki/Estradiol" title="Estradiol">estradiol</a> by the action of <a href="/wiki/Aromatase" title="Aromatase">aromatase</a> enzyme, encoded by the CYP19A1 gene.<a href="#cite_note-pmid779604-108">[105]</a> Prolonged use of androgenic-anabolic steroids by men results in temporary shut down of their natural testosterone production due to an inhibition of the <a href="/wiki/Hypothalamic%E2%80%93pituitary%E2%80%93gonadal_axis" title="Hypothalamic–pituitary–gonadal axis">hypothalamic–pituitary–gonadal axis</a>. This manifests in <a href="/wiki/Testicular_atrophy" title="Testicular atrophy">testicular atrophy</a>, inhibition of the <a href="/wiki/Spermatogenesis" title="Spermatogenesis">production of sperm</a>, <a href="/wiki/Sexual_function" title="Sexual function">sexual function</a> and <a href="/wiki/Infertility" title="Infertility">infertility</a>.<a href="#cite_note-pmid2104626-109">[106]</a><a href="#cite_note-Hoffman-2006-110">[107]</a><a href="#cite_note-pmid12185103-111">[108]</a> A short (1–2 months) use of androgenic-anabolic steroids by men followed by a course of testosterone-boosting therapy (e.g. <a href="/wiki/Clomifene" title="Clomifene">clomifene</a> and <a href="/wiki/Human_chorionic_gonadotropin" title="Human chorionic gonadotropin">human chorionic gonadotropin</a>) usually results in return to normal testosterone production.<a href="#cite_note-pmid2991700-112">[109]</a>) <div class="mw-heading mw-heading4"><h4 id="Masculinization">Masculinization</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=16" title="Edit section: Masculinization">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Virilization" title="Virilization">Virilization</a></div> Female-specific side effects include <a href="/wiki/Hirsutism" title="Hirsutism">increases in body hair</a>, permanent deepening of the voice, <a href="/wiki/Clitoral_hypertrophy" class="mw-redirect" title="Clitoral hypertrophy">enlarged clitoris</a>, and temporary decreases in <a href="/wiki/Menstrual_cycle" title="Menstrual cycle">menstrual cycles</a>. Alteration of <a href="/wiki/Fertility" title="Fertility">fertility</a> and ovarian cysts can also occur in females.<a href="#cite_note-pmid9216474-113">[110]</a> When taken during pregnancy, AAS can affect <a href="/wiki/Fetal_development" class="mw-redirect" title="Fetal development">fetal development</a> by causing the development of male features in the female fetus and female features in the male fetus.<a href="#cite_note-pmid14576190-114">[111]</a> <div class="mw-heading mw-heading4"><h4 id="Kidney_problems">Kidney problems</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=17" title="Edit section: Kidney problems">edit</a>]</div> Kidney tests revealed that nine of the ten steroid users developed a condition called <a href="/wiki/Focal_segmental_glomerulosclerosis" title="Focal segmental glomerulosclerosis">focal segmental glomerulosclerosis</a>, a type of scarring within the kidneys. The kidney damage in the bodybuilders has similarities to that seen in morbidly obese patients, but appears to be even more severe.<a href="#cite_note-Herlitz-2009-115">[112]</a> <div class="mw-heading mw-heading4"><h4 id="Liver_problems">Liver problems</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=18" title="Edit section: Liver problems">edit</a>]</div> High doses of oral AAS compounds can cause <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">liver damage</a>.<a href="#cite_note-pmid16606610-3">[3]</a> <a href="/wiki/Peliosis_hepatis" title="Peliosis hepatis">Peliosis hepatis</a> has been increasingly recognised with the use of AAS. <div class="mw-heading mw-heading3"><h3 id="Neuropsychiatric">Neuropsychiatric</h3>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=19" title="Edit section: Neuropsychiatric">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Rational_harm_assessment_of_drugs_radar_plot.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Rational_harm_assessment_of_drugs_radar_plot.svg/220px-Rational_harm_assessment_of_drugs_radar_plot.svg.png" decoding="async" width="220" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Rational_harm_assessment_of_drugs_radar_plot.svg/330px-Rational_harm_assessment_of_drugs_radar_plot.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Rational_harm_assessment_of_drugs_radar_plot.svg/440px-Rational_harm_assessment_of_drugs_radar_plot.svg.png 2x" data-file-width="900" data-file-height="900" /></a><figcaption>Addiction experts in psychiatry, chemistry, pharmacology, forensic science, epidemiology, and the police and legal services engaged in <a href="/wiki/Delphi_method" title="Delphi method">delphic analysis</a> regarding 20 popular recreational drugs. AAS were ranked 19th in dependence, 9th in physical harm, and 15th in social harm.<a href="#cite_note-pmid17382831-116">[113]</a></figcaption></figure> A 2005 review in <a href="/wiki/CNS_Drugs" class="mw-redirect" title="CNS Drugs">CNS Drugs</a> determined that "significant psychiatric symptoms including aggression and violence, <a href="/wiki/Mania" title="Mania">mania</a>, and less frequently <a href="/wiki/Psychosis" title="Psychosis">psychosis</a> and suicide have been associated with steroid <a href="/wiki/Drug_abuse" class="mw-redirect" title="Drug abuse">abuse</a>. Long-term steroid abusers may develop symptoms of <a href="/wiki/Substance_dependence" title="Substance dependence">dependence</a> and <a href="/wiki/Drug_withdrawal" title="Drug withdrawal">withdrawal</a> on discontinuation of AAS".<a href="#cite_note-pmid15984895-88">[85]</a> High concentrations of AAS, comparable to those likely sustained by many recreational AAS users, produce <a href="/wiki/Apoptotic" class="mw-redirect" title="Apoptotic">apoptotic</a> effects on <a href="/wiki/Neuron" title="Neuron">neurons</a>,[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] raising the specter of possibly irreversible neurotoxicity. Recreational AAS use appears to be associated with a range of potentially prolonged psychiatric effects, including dependence syndromes, <a href="/wiki/Mood_disorder" title="Mood disorder">mood disorders</a>, and progression to other forms of substance use, but the prevalence and severity of these various effects remains poorly understood.<a href="#cite_note-pmid18599224-117">[114]</a> There is no evidence that steroid dependence develops from therapeutic use of AAS to treat medical disorders, but instances of AAS dependence have been reported among weightlifters and bodybuilders who chronically administered supraphysiologic doses.<a href="#cite_note-pmid12230967-118">[115]</a> Mood disturbances (e.g. depression, [hypo-]mania, psychotic features) are likely to be dose- and drug-dependent, but AAS dependence or withdrawal effects seem to occur only in a small number of AAS users.<a href="#cite_note-pmid15248788-7">[7]</a> Large-scale long-term studies of psychiatric effects on AAS users are not currently available.<a href="#cite_note-pmid18599224-117">[114]</a> <div class="mw-heading mw-heading4"><h4 id="Diagnostic_Statistical_Manual_assertion">Diagnostic Statistical Manual assertion</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=20" title="Edit section: Diagnostic Statistical Manual assertion">edit</a>]</div> <a href="/wiki/DSM-IV" class="mw-redirect" title="DSM-IV">DSM-IV</a> lists <a href="/wiki/Personality_disorder#Diagnosis" title="Personality disorder">General diagnostic criteria</a>[<a href="/wiki/MOS:BROKENSECTIONLINKS" class="mw-redirect" title="MOS:BROKENSECTIONLINKS">broken anchor</a>] for a personality disorder guideline that "The pattern must not be better accounted for as a manifestation of another mental disorder, or to the direct physiological effects of a substance (e.g. drug or medication) or a general medical condition (e.g. head trauma).". As a result, AAS users may get misdiagnosed by a psychiatrist not told about their habit.<a href="#cite_note-Rashid-2007-119">[116]</a> <div class="mw-heading mw-heading4"><h4 id="Personality_profiles">Personality profiles</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=21" title="Edit section: Personality profiles">edit</a>]</div> Cooper, Noakes, Dunne, Lambert, and Rochford identified that AAS-using individuals are more likely to score higher on <a href="/wiki/Borderline_personality_disorder" title="Borderline personality disorder">borderline</a> (4.7 times), <a href="/wiki/Anti-social_behaviour" title="Anti-social behaviour">antisocial</a> (3.8 times), <a href="/wiki/Paranoid_personality_disorder" title="Paranoid personality disorder">paranoid</a> (3.4 times), <a href="/wiki/Schizotypal" class="mw-redirect" title="Schizotypal">schizotypal</a> (3.1 times), <a href="/wiki/Histrionic_personality_disorder" title="Histrionic personality disorder">histrionic</a> (2.9 times), <a href="/wiki/Passive-aggressive_personality_disorder" class="mw-redirect" title="Passive-aggressive personality disorder">passive-aggressive</a> (2.4 times), and <a href="/wiki/Narcissistic_personality_disorder" title="Narcissistic personality disorder">narcissistic</a> (1.6 times) personality profiles than non-users.<a href="#cite_note-pmid8889121-120">[117]</a> Other studies have suggested that antisocial personality disorder is slightly more likely among AAS users than among non-users (Pope & Katz, 1994).<a href="#cite_note-Rashid-2007-119">[116]</a> <a href="/wiki/Bipolar_disorder" title="Bipolar disorder">Bipolar</a> dysfunction,<a href="#cite_note-Vitalquests.org-121">[118]</a> <a href="/wiki/Substance_dependency" class="mw-redirect" title="Substance dependency">substance dependency</a>, and <a href="/wiki/Conduct_disorder" title="Conduct disorder">conduct disorder</a> have also been associated with AAS use.<a href="#cite_note-pmid19922565-122">[119]</a> <div class="mw-heading mw-heading4"><h4 id="Mood_and_anxiety">Mood and anxiety</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=22" title="Edit section: Mood and anxiety">edit</a>]</div> Affective disorders have long been recognised as a complication of AAS use. Case reports describe both hypomania and mania, along with irritability, elation, recklessness, racing thoughts and feelings of power and invincibility that did not meet the criteria for mania/hypomania.<a href="#cite_note-Eisenberg-1992-123">[120]</a> Of 53 bodybuilders who used AAS, 27 (51%) reported unspecified mood disturbance.<a href="#cite_note-pmid2351927-124">[121]</a> <div class="mw-heading mw-heading4"><h4 id="Aggression_and_hypomania">Aggression and hypomania</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=23" title="Edit section: Aggression and hypomania">edit</a>]</div> From the mid-1980s onward, the media reported "roid rage" as a side effect of AAS.<a href="#cite_note-Lenahan-2003-125">[122]</a>: 23  A 2005 review determined that some, but not all, randomized controlled studies have found that AAS use correlates with <a href="/wiki/Hypomania" title="Hypomania">hypomania</a> and increased aggressiveness, but pointed out that attempts to determine whether AAS use triggers violent behavior have failed, primarily because of high rates of non-participation.<a href="#cite_note-pmid15660958-126">[123]</a> A 2008 study on a nationally representative sample of young adult males in the United States found an association between lifetime and past-year self-reported AAS use and involvement in violent acts. Compared with individuals that did not use steroids, young adult males that used AAS reported greater involvement in violent behaviors even after controlling for the effects of key demographic variables, previous violent behavior, and polydrug use.<a href="#cite_note-pmid18923108-127">[124]</a> A 1996 review examining the <a href="/wiki/Blinded_experiment" title="Blinded experiment">blind studies</a> available at that time also found that these had demonstrated a link between aggression and steroid use, but pointed out that with estimates of over one million past or current steroid users in the United States at that time, an extremely small percentage of those using steroids appear to have experienced mental disturbance severe enough to result in clinical treatments or medical case reports.<a href="#cite_note-pmid8969015-128">[125]</a> The relationship between AAS use and depression is inconclusive. A 1992 review[<a href="/wiki/Wikipedia:Manual_of_Style/Dates_and_numbers#Chronological_items" title="Wikipedia:Manual of Style/Dates and numbers">needs update</a>] found that AAS may both relieve and cause depression, and that cessation or diminished use of AAS may also result in depression, but called for additional studies due to disparate data.<a href="#cite_note-pmid1551042-129">[126]</a> <div class="mw-heading mw-heading3"><h3 id="Reproductive">Reproductive</h3>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=24" title="Edit section: Reproductive">edit</a>]</div> <a href="/wiki/Androgen" title="Androgen">Androgens</a> such as <a href="/wiki/Testosterone" title="Testosterone">testosterone</a>, <a href="/wiki/Androstenedione" title="Androstenedione">androstenedione</a> and <a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">dihydrotestosterone</a> are required for the development of organs in the <a href="/wiki/Male_reproductive_system" title="Male reproductive system">male reproductive system</a>, including the <a href="/wiki/Seminal_vesicles" title="Seminal vesicles">seminal vesicles</a>, <a href="/wiki/Epididymis" title="Epididymis">epididymis</a>, <a href="/wiki/Vas_deferens" title="Vas deferens">vas deferens</a>, <a href="/wiki/Penis" title="Penis">penis</a> and <a href="/wiki/Prostate" title="Prostate">prostate</a>.<a href="#cite_note-pmid26855782-130">[127]</a> AAS are testosterone derivatives designed to maximize the <a href="/wiki/Anabolic" class="mw-redirect" title="Anabolic">anabolic</a> effects of testosterone.<a href="#cite_note-pmid18500378-78">[75]</a> AAS are consumed by <a href="/wiki/Elite_athletes" class="mw-redirect" title="Elite athletes">elite athletes</a> competing in <a href="/wiki/Sports" class="mw-redirect" title="Sports">sports</a> like <a href="/wiki/Olympic_weightlifting" title="Olympic weightlifting">weightlifting</a>, <a href="/wiki/Bodybuilding" title="Bodybuilding">bodybuilding</a>, and <a href="/wiki/Track_and_field" title="Track and field">track and field</a>.<a href="#cite_note-pmid4437350-131">[128]</a> Male recreational athletes take AAS to achieve an "enhanced" <a href="/wiki/Physical_appearance" class="mw-redirect" title="Physical appearance">physical appearance</a>.<a href="#cite_note-pmid24582699-132">[129]</a> AAS consumption disrupts the <a href="/wiki/Hypothalamic%E2%80%93pituitary%E2%80%93gonadal_axis" title="Hypothalamic–pituitary–gonadal axis">hypothalamic–pituitary–gonadal axis</a> (HPG axis) in males.<a href="#cite_note-pmid26855782-130">[127]</a> In the HPG axis, <a href="/wiki/Gonadotropin-releasing_hormone" title="Gonadotropin-releasing hormone">gonadotropin-releasing hormone</a> (GnRH) is secreted from the <a href="/wiki/Arcuate_nucleus" class="mw-redirect" title="Arcuate nucleus">arcuate nucleus</a> of the <a href="/wiki/Hypothalamus" title="Hypothalamus">hypothalamus</a> and stimulates the <a href="/wiki/Anterior_pituitary" title="Anterior pituitary">anterior pituitary</a> to secrete the two <a href="/wiki/Gonadotropin" title="Gonadotropin">gonadotropins</a>, <a href="/wiki/Follicle_stimulating_hormone" class="mw-redirect" title="Follicle stimulating hormone">follicle stimulating hormone</a> (FSH) and <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">luteinizing hormone</a> (LH).<a href="#cite_note-pmid28258581-133">[130]</a> In adult males, LH stimulates the <a href="/wiki/Leydig_cells" class="mw-redirect" title="Leydig cells">Leydig cells</a> in the <a href="/wiki/Testes" class="mw-redirect" title="Testes">testes</a> to produce testosterone which is required to form new <a href="/wiki/Sperm" title="Sperm">sperm</a> through <a href="/wiki/Spermatogenesis" title="Spermatogenesis">spermatogenesis</a>.<a href="#cite_note-pmid26855782-130">[127]</a> AAS consumption leads to dose-dependent suppression of gonadotropin release through suppression of GnRH from the hypothalamus (long-loop mechanism) or from direct <a href="/wiki/Negative_feedback" title="Negative feedback">negative feedback</a> on the anterior pituitary to inhibit gonadotropin release (short-loop mechanism), leading to AAS-induced <a href="/wiki/Hypogonadism" title="Hypogonadism">hypogonadism</a>.<a href="#cite_note-pmid26855782-130">[127]</a> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=25" title="Edit section: Pharmacology">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Mechanism_of_action">Mechanism of action</h3>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=26" title="Edit section: Mechanism of action">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Steroid_hormone" title="Steroid hormone">Steroid hormone</a></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Steroid_receptor.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Steroid_receptor.png/220px-Steroid_receptor.png" decoding="async" width="220" height="153" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Steroid_receptor.png/330px-Steroid_receptor.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Steroid_receptor.png/440px-Steroid_receptor.png 2x" data-file-width="800" data-file-height="558" /></a><figcaption>The human <a href="/wiki/Androgen_receptor" title="Androgen receptor">androgen receptor</a> bound to <a href="/wiki/Testosterone" title="Testosterone">testosterone</a><a href="#cite_note-pmid16641486-134">[131]</a> The protein is shown as a <a href="/wiki/Ribbon_diagram" title="Ribbon diagram">ribbon diagram</a> in red, green, and blue, with the steroid shown in white.</figcaption></figure> The <a href="/wiki/Pharmacodynamics" title="Pharmacodynamics">pharmacodynamics</a> of AAS are unlike <a href="/wiki/Peptide_hormone" title="Peptide hormone">peptide hormones</a>. Water-soluble peptide hormones cannot penetrate the fatty <a href="/wiki/Cell_membrane" title="Cell membrane">cell membrane</a> and only indirectly affect the <a href="/wiki/Cell_nucleus" title="Cell nucleus">nucleus</a> of target <a href="/wiki/Cell_(biology)" title="Cell (biology)">cells</a> through their interaction with the cell's surface <a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">receptors</a>. However, as fat-soluble hormones, AAS are membrane-permeable and influence the nucleus of cells by direct action. The pharmacodynamic action of AAS begin when the exogenous hormone penetrates the membrane of the target cell and binds to an <a href="/wiki/Androgen_receptor" title="Androgen receptor">androgen receptor</a> (AR) located in the <a href="/wiki/Cytoplasm" title="Cytoplasm">cytoplasm</a> of that cell. From there, the compound hormone-receptor diffuses into the nucleus, where it either alters the <a href="/wiki/Gene_expression" title="Gene expression">expression</a> of <a href="/wiki/Gene" title="Gene">genes</a><a href="#cite_note-pmid16238547-135">[132]</a> or activates processes that <a href="/wiki/Signal_transduction" title="Signal transduction">send signals</a> to other parts of the cell.<a href="#cite_note-pmid15352158-136">[133]</a> Different types of AAS bind to the AAR with different <a href="/wiki/Dissociation_constant" title="Dissociation constant">affinities</a>, depending on their chemical structure.<a href="#cite_note-pmid15248788-7">[7]</a> The effect of AAS on muscle mass is caused in at least two ways:<a href="#cite_note-pmid8855787-137">[134]</a> first, they increase the <a href="/wiki/Protein_biosynthesis" title="Protein biosynthesis">production of proteins</a>; second, they reduce recovery time by blocking the effects of stress hormone <a href="/wiki/Cortisol" title="Cortisol">cortisol</a> on muscle tissue, so that <a href="/wiki/Catabolism" title="Catabolism">catabolism</a> of muscle is greatly reduced. It has been <a href="/wiki/Hypothesized" class="mw-redirect" title="Hypothesized">hypothesized</a> that this reduction in muscle breakdown may occur through AAS inhibiting the action of other steroid hormones called <a href="/wiki/Glucocorticoid" title="Glucocorticoid">glucocorticoids</a> that promote the breakdown of muscles.<a href="#cite_note-pmid2199753-64">[64]</a> AAS also affect the number of cells that develop into fat-storage cells, by favouring <a href="/wiki/Cellular_differentiation" title="Cellular differentiation">cellular differentiation</a> into muscle cells instead.<a href="#cite_note-pmid12960001-138">[135]</a> <div class="mw-heading mw-heading4"><h4 id="Molecular_interaction_of_AAS_with_androgen_receptors">Molecular interaction of AAS with androgen receptors</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=27" title="Edit section: Molecular interaction of AAS with androgen receptors">edit</a>]</div> Anabolic steroids interact with ARs across various tissues, including muscle, bone, and reproductive systems.<a href="#cite_note-pmid15082523-139">[136]</a> Upon binding to the AR, anabolic steroids trigger a translocation of the hormone-receptor complex to the cell nucleus, where they either alter gene expression or activate cellular signaling pathways; this results in increased protein synthesis, enhanced muscle growth, and reduced muscle catabolism.<a href="#cite_note-140">[137]</a> Anabolic steroids influence cellular differentiation while favoring the development of muscle cells over fat-storage cells.<a href="#cite_note-141">[138]</a> Research in this field has shown that structural modifications in anabolic steroids are critical in determining their binding affinity to ARs and their resulting anabolic and androgenic activities.<a href="#cite_note-pmid19028512-85">[82]</a> These modifications affect a steroid's ability to influence gene expression and cellular processes, highlighting the complex biophysical interactions of anabolic steroids at the cellular level.<a href="#cite_note-pmid15082523-139">[136]</a> <div class="mw-heading mw-heading3"><h3 id="Anabolic_and_androgenic_effects">Anabolic and androgenic effects</h3>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=28" title="Edit section: Anabolic and androgenic effects">edit</a>]</div> <table class="wikitable floatright mw-collapsible" style="text-align:left; border:none;"> <caption class="nowrap"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · ";font-weight:bold}.mw-parser-output .hlist dd:last-child::after,.mw-parser-output .hlist dt:last-child::after,.mw-parser-output .hlist li:last-child::after{content:none}.mw-parser-output .hlist dd dd:first-child::before,.mw-parser-output .hlist dd dt:first-child::before,.mw-parser-output .hlist dd li:first-child::before,.mw-parser-output .hlist dt dd:first-child::before,.mw-parser-output .hlist dt dt:first-child::before,.mw-parser-output .hlist dt li:first-child::before,.mw-parser-output .hlist li dd:first-child::before,.mw-parser-output .hlist li dt:first-child::before,.mw-parser-output .hlist li li:first-child::before{content:" (";font-weight:normal}.mw-parser-output .hlist dd dd:last-child::after,.mw-parser-output .hlist dd dt:last-child::after,.mw-parser-output .hlist dd li:last-child::after,.mw-parser-output .hlist dt dd:last-child::after,.mw-parser-output .hlist dt dt:last-child::after,.mw-parser-output .hlist dt li:last-child::after,.mw-parser-output .hlist li dd:last-child::after,.mw-parser-output .hlist li dt:last-child::after,.mw-parser-output .hlist li li:last-child::after{content:")";font-weight:normal}.mw-parser-output .hlist ol{counter-reset:listitem}.mw-parser-output .hlist ol>li{counter-increment:listitem}.mw-parser-output .hlist ol>li::before{content:" "counter(listitem)"\a0 "}.mw-parser-output .hlist dd ol>li:first-child::before,.mw-parser-output .hlist dt ol>li:first-child::before,.mw-parser-output .hlist li ol>li:first-child::before{content:" ("counter(listitem)"\a0 "}</style><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Relative_androgenic_to_anabolic_activity_in_animals" title="Template:Relative androgenic to anabolic activity in animals"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Relative_androgenic_to_anabolic_activity_in_animals" title="Template talk:Relative androgenic to anabolic activity in animals"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Relative_androgenic_to_anabolic_activity_in_animals" title="Special:EditPage/Template:Relative androgenic to anabolic activity in animals"><abbr title="Edit this template">e</abbr></a></li></ul></div> Androgenic vs. anabolic activity ratio of androgens/anabolic steroids </caption> <tbody><tr> <th>Medication</th> <th>Ratioa </th></tr> <tr> <td><a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">Testosterone</a></td> <td>~1:1 </td></tr> <tr> <td><a href="/wiki/Androstanolone" title="Androstanolone">Androstanolone (<abbr title="dihydrotestosterone">DHT</abbr>)</a></td> <td>~1:1 </td></tr> <tr> <td><a href="/wiki/Methyltestosterone" title="Methyltestosterone">Methyltestosterone</a></td> <td>~1:1 </td></tr> <tr> <td><a href="/wiki/Methandriol" title="Methandriol">Methandriol</a></td> <td>~1:1 </td></tr> <tr> <td><a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">Fluoxymesterone</a></td> <td>1:1–1:15 </td></tr> <tr> <td><a href="/wiki/Metandienone" title="Metandienone">Metandienone</a></td> <td>1:1–1:8 </td></tr> <tr> <td><a href="/wiki/Drostanolone" title="Drostanolone">Drostanolone</a></td> <td>1:3–1:4 </td></tr> <tr> <td><a href="/wiki/Metenolone" title="Metenolone">Metenolone</a></td> <td>1:2–1:30 </td></tr> <tr> <td><a href="/wiki/Oxymetholone" title="Oxymetholone">Oxymetholone</a></td> <td>1:2–1:9 </td></tr> <tr> <td><a href="/wiki/Oxandrolone" title="Oxandrolone">Oxandrolone</a></td> <td>1:3–1:13 </td></tr> <tr> <td><a href="/wiki/Stanozolol" title="Stanozolol">Stanozolol</a></td> <td>1:1–1:30 </td></tr> <tr> <td><a href="/wiki/Nandrolone" title="Nandrolone">Nandrolone</a></td> <td>1:3–1:16 </td></tr> <tr> <td><a href="/wiki/Ethylestrenol" title="Ethylestrenol">Ethylestrenol</a></td> <td>1:2–1:19 </td></tr> <tr> <td><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a></td> <td>1:1–1:20 </td></tr> <tr class="sortbottom"> <td colspan="2" style="width: 1px; background-color:#eaecf0; text-align: center;">Notes: In rodents. Footnotes: a = Ratio of androgenic to anabolic activity. Sources: See template. </td></tr></tbody></table> As their name suggests, AAS have two different, but overlapping, types of effects: anabolic, meaning that they promote anabolism (cell growth), and androgenic (or virilizing), meaning that they affect the development and maintenance of masculine characteristics. Some examples of the anabolic effects of these hormones are increased <a href="/wiki/Protein_synthesis" class="mw-redirect" title="Protein synthesis">protein synthesis</a> from <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a>, increased appetite, increased bone remodeling and growth, and stimulation of <a href="/wiki/Bone_marrow" title="Bone marrow">bone marrow</a>, which increases the production of <a href="/wiki/Red_blood_cell" title="Red blood cell">red blood cells</a>. Through a number of <a href="#Mechanism_of_action">mechanisms</a> AAS stimulate the formation of muscle cells and hence cause an increase in the size of <a href="/wiki/Skeletal_muscles" class="mw-redirect" title="Skeletal muscles">skeletal muscles</a>, leading to increased strength.<a href="#cite_note-pmid16424293-142">[139]</a><a href="#cite_note-pmid16540931-12">[12]</a><a href="#cite_note-pmid10710012-143">[140]</a> The androgenic effects of AAS are numerous. Depending on the length of use, the side effects of the steroid can be irreversible. Processes affected include pubertal growth, <a href="/wiki/Sebaceous_gland" title="Sebaceous gland">sebaceous gland</a> oil production, and sexuality (especially in fetal development). Some examples of virilizing effects are <a href="/wiki/Clitoral_hypertrophy" class="mw-redirect" title="Clitoral hypertrophy">growth of the clitoris</a> in females and the <a href="/wiki/Penis" title="Penis">penis</a> in male children (the adult penis size does not change due to steroids[<a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)">medical citation needed</a>]), increased <a href="/wiki/Vocal_cord" class="mw-redirect" title="Vocal cord">vocal cord</a> size, increased <a href="/wiki/Libido" title="Libido">libido</a>, suppression of <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">natural</a> <a href="/wiki/Sex_hormone" title="Sex hormone">sex hormones</a>, and impaired <a href="/wiki/Spermatogenesis" title="Spermatogenesis">production of sperm</a>.<a href="#cite_note-pmid12017555-144">[141]</a> Effects on women include deepening of the voice, facial hair growth, and possibly a decrease in breast size. Men may develop an enlargement of breast tissue, known as gynecomastia, testicular atrophy, and a reduced sperm count.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] The androgenic:anabolic ratio of an AAS is an important factor when determining the clinical application of these compounds. Compounds with a high ratio of androgenic to an anabolic effects are the drug of choice in androgen-replacement therapy (e.g., treating <a href="/wiki/Hypogonadism" title="Hypogonadism">hypogonadism</a> in males), whereas compounds with a reduced androgenic:anabolic ratio are preferred for anemia and osteoporosis, and to reverse protein loss following trauma, surgery, or prolonged immobilization. Determination of androgenic:anabolic ratio is typically performed in animal studies, which has led to the marketing of some compounds claimed to have anabolic activity with weak androgenic effects. This disassociation is less marked in humans, where all AAS have significant androgenic effects.<a href="#cite_note-Chrousos-2012-80">[77]</a> A commonly used protocol for determining the androgenic:anabolic ratio, dating back to the 1950s, uses the relative weights of ventral <a href="/wiki/Prostate" title="Prostate">prostate</a> (VP) and <a href="/wiki/Levator_ani" title="Levator ani">levator ani</a> muscle (LA) of male <a href="/wiki/Laboratory_rat" title="Laboratory rat">rats</a>. The VP weight is an indicator of the androgenic effect, while the LA weight is an indicator of the anabolic effect. Two or more batches of rats are <a href="/wiki/Castrated" class="mw-redirect" title="Castrated">castrated</a> and given no treatment and respectively some AAS of interest. The LA/VP ratio for an AAS is calculated as the ratio of LA/VP weight gains produced by the treatment with that compound using castrated but untreated rats as baseline: (LAc,t–LAc)/(VPc,t–VPc). The LA/VP weight gain ratio from rat experiments is not unitary for testosterone (typically 0.3–0.4), but it is normalized for presentation purposes, and used as basis of comparison for other AAS, which have their androgenic:anabolic ratios scaled accordingly (as shown in the table above).<a href="#cite_note-pmid9593936-145">[142]</a><a href="#cite_note-pmid13064212-146">[143]</a> In the early 2000s, this procedure was standardized and generalized throughout <a href="/wiki/OECD" title="OECD">OECD</a> in what is now known as the Hershberger assay. <div class="mw-heading mw-heading4"><h4 id="Body_composition_and_strength_improvements">Body composition and strength improvements</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=29" title="Edit section: Body composition and strength improvements">edit</a>]</div> Anabolic steroids notably influence muscle fiber characteristics, affecting both the size and type of muscle fibers. This alteration significantly contributes to enhanced muscle strength and endurance.<a href="#cite_note-147">[144]</a> Anabolic-androgenic steroids (AAS) cause these changes by directly impacting the muscle tissue's cellular components. Studies have shown that these changes are not merely superficial but represent a profound transformation in the muscle's structural and functional properties. This transformation is a key factor in the steroids' ability to enhance physical performance and endurance.<a href="#cite_note-148">[145]</a> Body weight in men may increase by 2 to 5 kg as a result of short-term (<10 weeks) AAS use, which may be attributed mainly to an increase of lean mass. Animal studies also found that fat mass was reduced, but most studies in humans failed to elucidate significant fat mass decrements. The effects on lean body mass have been shown to be dose-dependent. Both <a href="/wiki/Muscle_hypertrophy" title="Muscle hypertrophy">muscle hypertrophy</a> and the formation of new <a href="/wiki/Muscle_fibers" class="mw-redirect" title="Muscle fibers">muscle fibers</a> have been observed. The hydration of lean mass remains unaffected by AAS use, although small increments of blood volume cannot be ruled out.<a href="#cite_note-pmid15248788-7">[7]</a> The upper region of the body (thorax, neck, shoulders, and upper arm) seems to be more susceptible for AAS than other body regions because of predominance of ARs in the upper body.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] The largest difference in muscle fiber size between AAS users and non-users was observed in type I muscle fibers of the <a href="/wiki/Vastus_lateralis" class="mw-redirect" title="Vastus lateralis">vastus lateralis</a> and the <a href="/wiki/Trapezius_muscle" class="mw-redirect" title="Trapezius muscle">trapezius muscle</a> as a result of long-term AAS self-administration. After drug withdrawal, the effects fade away slowly, but may persist for more than 6–12 weeks after cessation of AAS use.<a href="#cite_note-pmid15248788-7">[7]</a> Strength improvements in the range of 5 to 20% of baseline strength, depending largely on the drugs and dose used as well as the administration period. Overall, the exercise where the most significant improvements were observed is the <a href="/wiki/Bench_press" title="Bench press">bench press</a>.<a href="#cite_note-pmid15248788-7">[7]</a> For almost two decades, it was assumed that AAS exerted significant effects only in experienced strength athletes.<a href="#cite_note-pmid61389-149">[146]</a><a href="#cite_note-pmid7018798-150">[147]</a> A randomized controlled trial demonstrated, however, that even in novice athletes a 10-week strength training program accompanied by <a href="/wiki/Testosterone_enanthate" title="Testosterone enanthate">testosterone enanthate</a> at 600 mg/week may improve strength more than training alone does.<a href="#cite_note-pmid15248788-7">[7]</a><a href="#cite_note-pmid8637535-151">[148]</a> This dose is sufficient to significantly improve lean muscle mass relative to placebo even in subjects that did not exercise at all.<a href="#cite_note-pmid8637535-151">[148]</a> The anabolic effects of testosterone enanthate were highly dose dependent.<a href="#cite_note-pmid15248788-7">[7]</a><a href="#cite_note-pmid11701431-152">[149]</a> <div class="mw-heading mw-heading3"><h3 id="Dissociation_of_effects">Dissociation of effects</h3>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=30" title="Edit section: Dissociation of effects">edit</a>]</div> Endogenous/natural AAS like testosterone and DHT and synthetic AAS mediate their effects by binding to and activating the AR.<a href="#cite_note-pmid18500378-78">[75]</a> On the basis of animal <a href="/wiki/Bioassay" title="Bioassay">bioassays</a>, the effects of these agents have been divided into two partially dissociable types: anabolic (myotrophic) and androgenic.<a href="#cite_note-pmid18500378-78">[75]</a> Dissociation between the ratios of these two types of effects relative to the ratio observed with testosterone is observed in rat bioassays with various AAS.<a href="#cite_note-pmid18500378-78">[75]</a> Theories for the dissociation include differences between AAS in terms of their <a href="/wiki/Intracellular" class="mw-redirect" title="Intracellular">intracellular</a> <a href="/wiki/Metabolism" title="Metabolism">metabolism</a>, <a href="/wiki/Functional_selectivity" title="Functional selectivity">functional selectivity</a> (differential recruitment of <a href="/wiki/Coactivator" class="mw-redirect" title="Coactivator">coactivators</a>), and <a href="/wiki/Nuclear_receptor#Non-genomic" title="Nuclear receptor">non-genomic</a> mechanisms (i.e., signaling through non-AR <a href="/wiki/Membrane_androgen_receptor" title="Membrane androgen receptor">membrane androgen receptors</a>, or mARs).<a href="#cite_note-pmid18500378-78">[75]</a> Support for the latter two theories is limited and more hypothetical, but there is a good deal of support for the intracellular metabolism theory.<a href="#cite_note-pmid18500378-78">[75]</a> The measurement of the dissociation between anabolic and androgenic effects among AAS is based largely on a simple but outdated and unsophisticated model using rat tissue bioassays.<a href="#cite_note-pmid18500378-78">[75]</a> It has been referred to as the "<a href="/wiki/Myotrophic%E2%80%93androgenic_index" class="mw-redirect" title="Myotrophic–androgenic index">myotrophic–androgenic index</a>".<a href="#cite_note-pmid18500378-78">[75]</a> In this model, myotrophic or anabolic activity is measured by change in the weight of the rat <a href="/wiki/Bulbospongiosus_muscle" title="Bulbospongiosus muscle">bulbocavernosus</a>/<a href="/wiki/Levator_ani" title="Levator ani">levator ani</a> muscle, and androgenic activity is measured by change in the weight of the rat <a href="/wiki/Ventral_prostate" class="mw-redirect" title="Ventral prostate">ventral prostate</a> (or, alternatively, the rat <a href="/wiki/Seminal_vesicles" title="Seminal vesicles">seminal vesicles</a>), in response to exposure to the AAS.<a href="#cite_note-pmid18500378-78">[75]</a> The measurements are then compared to form a ratio.<a href="#cite_note-pmid18500378-78">[75]</a> <div class="mw-heading mw-heading4"><h4 id="Intracellular_metabolism">Intracellular metabolism</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=31" title="Edit section: Intracellular metabolism">edit</a>]</div> Testosterone is <a href="/wiki/Metabolized" class="mw-redirect" title="Metabolized">metabolized</a> in various tissues by <a href="/wiki/5%CE%B1-reductase" class="mw-redirect" title="5α-reductase">5α-reductase</a> into DHT, which is 3- to 10-fold more potent as an AR agonist, and by <a href="/wiki/Aromatase" title="Aromatase">aromatase</a> into <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>, which is an <a href="/wiki/Estrogen" title="Estrogen">estrogen</a> and lacks significant AR affinity.<a href="#cite_note-pmid18500378-78">[75]</a> In addition, DHT is metabolized by <a href="/wiki/3%CE%B1-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3α-hydroxysteroid dehydrogenase">3α-hydroxysteroid dehydrogenase</a> (3α-HSD) and <a href="/wiki/3%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3β-hydroxysteroid dehydrogenase">3β-hydroxysteroid dehydrogenase</a> (3β-HSD) into <a href="/wiki/3%CE%B1-androstanediol" class="mw-redirect" title="3α-androstanediol">3α-androstanediol</a> and <a href="/wiki/3%CE%B2-androstanediol" class="mw-redirect" title="3β-androstanediol">3β-androstanediol</a>, respectively, which are <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> with little or no AR affinity.<a href="#cite_note-pmid18500378-78">[75]</a> 5α-reductase is widely distributed throughout the body, and is concentrated to various extents in skin (particularly the scalp, face, and genital areas), prostate, seminal vesicles, liver, and the brain.<a href="#cite_note-pmid18500378-78">[75]</a> In contrast, expression of 5α-reductase in <a href="/wiki/Skeletal_muscle" title="Skeletal muscle">skeletal muscle</a> is undetectable.<a href="#cite_note-pmid18500378-78">[75]</a> Aromatase is highly expressed in <a href="/wiki/Adipose_tissue" title="Adipose tissue">adipose tissue</a> and the brain, and is also expressed significantly in skeletal muscle.<a href="#cite_note-pmid18500378-78">[75]</a> 3α-HSD is highly expressed in skeletal muscle as well.<a href="#cite_note-Llewellyn2011-73">[70]</a> Natural AAS like testosterone and DHT and synthetic AAS are analogues and are very similar structurally.<a href="#cite_note-pmid18500378-78">[75]</a> For this reason, they have the capacity to bind to and be metabolized by the same <a href="/wiki/Steroidogenic_enzyme" title="Steroidogenic enzyme">steroid-metabolizing</a> <a href="/wiki/Enzyme" title="Enzyme">enzymes</a>.<a href="#cite_note-pmid18500378-78">[75]</a> According to the intracellular metabolism explanation, the androgenic-to-anabolic ratio of a given AR agonist is related to its capacity to be transformed by the aforementioned enzymes in conjunction with the AR activity of any resulting products.<a href="#cite_note-pmid18500378-78">[75]</a> For instance, whereas the AR activity of testosterone is greatly potentiated by local conversion via 5α-reductase into DHT in tissues where 5α-reductase is expressed, an AAS that is not metabolized by 5α-reductase or is already 5α-reduced, such as DHT itself or a derivative (like <a href="/wiki/Mesterolone" title="Mesterolone">mesterolone</a> or <a href="/wiki/Drostanolone" title="Drostanolone">drostanolone</a>), would not undergo such potentiation in said tissues.<a href="#cite_note-pmid18500378-78">[75]</a> Moreover, nandrolone is metabolized by 5α-reductase, but unlike the case of testosterone and DHT, the 5α-reduced metabolite of nandrolone has much lower affinity for the AR than does nandrolone itself, and this results in reduced AR activation in 5α-reductase-expressing tissues.<a href="#cite_note-pmid18500378-78">[75]</a> As so-called "androgenic" tissues such as skin/hair follicles and male reproductive tissues are very high in 5α-reductase expression, while skeletal muscle is virtually devoid of 5α-reductase, this may primarily explain the high myotrophic–androgenic ratio and dissociation seen with nandrolone, as well as with various other AAS.<a href="#cite_note-pmid18500378-78">[75]</a> Aside from 5α-reductase, aromatase may inactivate testosterone signaling in skeletal muscle and adipose tissue, so AAS that lack aromatase affinity, in addition to being free of the potential side effect of <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a>, might be expected to have a higher myotrophic–androgenic ratio in comparison.<a href="#cite_note-pmid18500378-78">[75]</a> In addition, DHT is inactivated by high activity of 3α-HSD in skeletal muscle (and cardiac tissue), and AAS that lack affinity for 3α-HSD could similarly be expected to have a higher myotrophic–androgenic ratio (although perhaps also increased long-term cardiovascular risks).<a href="#cite_note-pmid18500378-78">[75]</a> In accordance, DHT, <a href="/wiki/Mestanolone" title="Mestanolone">mestanolone</a> (17α-methyl-DHT), and <a href="/wiki/Mesterolone" title="Mesterolone">mesterolone</a> (1α-methyl-DHT) are all described as very poorly anabolic due to inactivation by 3α-HSD in skeletal muscle, whereas other DHT derivatives with other structural features like <a href="/wiki/Metenolone" title="Metenolone">metenolone</a>, <a href="/wiki/Oxandrolone" title="Oxandrolone">oxandrolone</a>, <a href="/wiki/Oxymetholone" title="Oxymetholone">oxymetholone</a>, <a href="/wiki/Drostanolone" title="Drostanolone">drostanolone</a>, and <a href="/wiki/Stanozolol" title="Stanozolol">stanozolol</a> are all poor substrates for 3α-HSD and are described as potent anabolics.<a href="#cite_note-Llewellyn2011-73">[70]</a> The intracellular metabolism theory explains how and why remarkable dissociation between anabolic and androgenic effects might occur despite the fact that these effects are mediated through the same signaling receptor, and why this dissociation is invariably incomplete.<a href="#cite_note-pmid18500378-78">[75]</a> In support of the model is the rare condition <a href="/wiki/Congenital_5%CE%B1-reductase_type_2_deficiency" class="mw-redirect" title="Congenital 5α-reductase type 2 deficiency">congenital 5α-reductase type 2 deficiency</a>, in which the <a href="/wiki/5%CE%B1-reductase_type_2" class="mw-redirect" title="5α-reductase type 2">5α-reductase type 2</a> enzyme is defective, production of DHT is impaired, and DHT levels are low while testosterone levels are normal.<a href="#cite_note-pmid431680-153">[150]</a><a href="#cite_note-pmid16985920-154">[151]</a> Males with this condition are born with <a href="/wiki/Ambiguous_genitalia" class="mw-redirect" title="Ambiguous genitalia">ambiguous genitalia</a> and a severely underdeveloped or even absent prostate gland.<a href="#cite_note-pmid431680-153">[150]</a><a href="#cite_note-pmid16985920-154">[151]</a> In addition, at the time of puberty, such males develop normal musculature, voice deepening, and libido, but have reduced facial hair, a female pattern of body hair (i.e., largely restricted to the pubic triangle and underarms), no incidence of <a href="/wiki/Male_pattern_hair_loss" class="mw-redirect" title="Male pattern hair loss">male pattern hair loss</a>, and no prostate enlargement or incidence of <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a>.<a href="#cite_note-pmid16985920-154">[151]</a><a href="#cite_note-Sloane-2002-155">[152]</a><a href="#cite_note-Hanno-2014-156">[153]</a><a href="#cite_note-Jain-2006-157">[154]</a><a href="#cite_note-Harper-2007-158">[155]</a> They also notably do not develop gynecomastia as a consequence of their condition.<a href="#cite_note-Hanno-2014-156">[153]</a> <table class="wikitable sortable mw-collapsible mw-collapsed" style="margin: 1em auto;"> <caption class="nowrap"><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:Relative_affinities_of_nandrolone_and_related_steroids_at_the_androgen_receptor" title="Template:Relative affinities of nandrolone and related steroids at the androgen receptor"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Relative_affinities_of_nandrolone_and_related_steroids_at_the_androgen_receptor" title="Template talk:Relative affinities of nandrolone and related steroids at the androgen receptor"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Relative_affinities_of_nandrolone_and_related_steroids_at_the_androgen_receptor" title="Special:EditPage/Template:Relative affinities of nandrolone and related steroids at the androgen receptor"><abbr title="Edit this template">e</abbr></a></li></ul></div> Relative affinities of nandrolone and related steroids at the androgen receptor </caption> <tbody><tr> <th>Compound</th> <th><abbr title="Rat prostate androgen receptor at 4°C">rAR</abbr> (%)</th> <th><abbr title="Intact human MCF-7-cell androgen receptor at 37°C">hAR</abbr> (%) </th></tr> <tr> <td><a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">Testosterone</a></td> <td>38</td> <td>38 </td></tr> <tr> <td><a href="/wiki/Androstanolone" title="Androstanolone">5α-Dihydrotestosterone</a></td> <td>77</td> <td>100 </td></tr> <tr> <td><a href="/wiki/Nandrolone" title="Nandrolone">Nandrolone</a></td> <td>75</td> <td>92 </td></tr> <tr> <td><a href="/wiki/5%CE%B1-Dihydronandrolone" title="5α-Dihydronandrolone">5α-Dihydronandrolone</a></td> <td>35</td> <td>50 </td></tr> <tr> <td><a href="/wiki/Ethylestrenol" title="Ethylestrenol">Ethylestrenol</a></td> <td><abbr title="No data">ND</abbr></td> <td>2 </td></tr> <tr> <td><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a></td> <td><abbr title="No data">ND</abbr></td> <td>22 </td></tr> <tr> <td><a href="/wiki/5%CE%B1-Dihydronorethandrolone" title="5α-Dihydronorethandrolone">5α-Dihydronorethandrolone</a></td> <td><abbr title="No data">ND</abbr></td> <td>14 </td></tr> <tr> <td><a href="/wiki/Metribolone" title="Metribolone">Metribolone</a></td> <td>100</td> <td>110 </td></tr> <tr class="sortbottom"> <td colspan="9" style="width: 1px; background-color:#eaecf0; text-align: center;">Sources: See template. </td></tr></tbody></table> <div class="mw-heading mw-heading4"><h4 id="Functional_selectivity">Functional selectivity</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=32" title="Edit section: Functional selectivity">edit</a>]</div> An animal study found that two different kinds of <a href="/wiki/Androgen_response_element" class="mw-redirect" title="Androgen response element">androgen response elements</a> could differentially respond to testosterone and DHT upon activation of the AR.<a href="#cite_note-pmid11701661-10">[10]</a><a href="#cite_note-pmid11343670-159">[156]</a> Whether this is involved in the differences in the ratios of anabolic-to-myotrophic effect of different AAS is unknown however.<a href="#cite_note-pmid11701661-10">[10]</a><a href="#cite_note-pmid11343670-159">[156]</a><a href="#cite_note-pmid18500378-78">[75]</a> <div class="mw-heading mw-heading4"><h4 id="Non-genomic_mechanisms">Non-genomic mechanisms</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=33" title="Edit section: Non-genomic mechanisms">edit</a>]</div> Testosterone signals not only through the nuclear AR, but also through mARs, including <a href="/wiki/ZIP9" class="mw-redirect" title="ZIP9">ZIP9</a> and <a href="/wiki/GPRC6A" title="GPRC6A">GPRC6A</a>.<a href="#cite_note-pmid25257522-160">[157]</a><a href="#cite_note-pmid28479083-161">[158]</a> It has been proposed that differential signaling through mARs may be involved in the dissociation of the anabolic and androgenic effects of AAS.<a href="#cite_note-pmid18500378-78">[75]</a> Indeed, DHT has less than 1% of the affinity of testosterone for ZIP9, and the synthetic AAS <a href="/wiki/Metribolone" title="Metribolone">metribolone</a> and <a href="/wiki/Mibolerone" title="Mibolerone">mibolerone</a> are ineffective competitors for the receptor similarly.<a href="#cite_note-pmid28479083-161">[158]</a> This indicates that AAS do show differential interactions with the AR and mARs.<a href="#cite_note-pmid28479083-161">[158]</a> However, women with <a href="/wiki/Complete_androgen_insensitivity_syndrome" title="Complete androgen insensitivity syndrome">complete androgen insensitivity syndrome</a> (CAIS), who have a 46,XY ("male") <a href="/wiki/Genotype" title="Genotype">genotype</a> and <a href="/wiki/Testes" class="mw-redirect" title="Testes">testes</a> but a defect in the AR such that it is non-functional, are a challenge to this notion.<a href="#cite_note-pmid26303084-162">[159]</a> They are completely insensitive to the AR-mediated effects of androgens like testosterone, and show a perfectly female <a href="/wiki/Phenotype" title="Phenotype">phenotype</a> despite having testosterone levels in the high end of the normal male range.<a href="#cite_note-pmid26303084-162">[159]</a> These women have little or no <a href="/wiki/Sebum" class="mw-redirect" title="Sebum">sebum</a> production, incidence of <a href="/wiki/Acne" title="Acne">acne</a>, or body hair growth (including in the pubic and axillary areas).<a href="#cite_note-pmid26303084-162">[159]</a> Moreover, CAIS women have <a href="/wiki/Lean_body_mass" title="Lean body mass">lean body mass</a> that is normal for females but is of course greatly reduced relative to males.<a href="#cite_note-Orwoll-2009-163">[160]</a> These observations suggest that the AR is mainly or exclusively responsible for masculinization and myotrophy caused by androgens.<a href="#cite_note-pmid26303084-162">[159]</a><a href="#cite_note-Orwoll-2009-163">[160]</a><a href="#cite_note-Rahwan1988-164">[161]</a> The mARs have however been found to be involved in some of the health-related effects of testosterone, like modulation of prostate cancer risk and progression.<a href="#cite_note-pmid28479083-161">[158]</a><a href="#cite_note-pmid21681779-165">[162]</a> <div class="mw-heading mw-heading4"><h4 id="Antigonadotropic_effects">Antigonadotropic effects</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=34" title="Edit section: Antigonadotropic effects">edit</a>]</div> Changes in endogenous testosterone levels may also contribute to differences in myotrophic–androgenic ratio between testosterone and synthetic AAS.<a href="#cite_note-Llewellyn2011-73">[70]</a> AR agonists are <a href="/wiki/Antigonadotropic" class="mw-redirect" title="Antigonadotropic">antigonadotropic</a> – that is, they dose-dependently suppress gonadal testosterone production and hence reduce systemic testosterone concentrations.<a href="#cite_note-Llewellyn2011-73">[70]</a> By suppressing endogenous testosterone levels and effectively replacing AR signaling in the body with that of the exogenous AAS, the myotrophic–androgenic ratio of a given AAS may be further, dose-dependently increased, and this hence may be an additional factor contributing to the differences in myotrophic–androgenic ratio among different AAS.<a href="#cite_note-Llewellyn2011-73">[70]</a> In addition, some AAS, such as 19-nortestosterone derivatives like nandrolone, are also potent <a href="/wiki/Progestogen" title="Progestogen">progestogens</a>, and activation of the <a href="/wiki/Progesterone_receptor" title="Progesterone receptor">progesterone receptor</a> (PR) is antigonadotropic similarly to activation of the AR.<a href="#cite_note-Llewellyn2011-73">[70]</a> The combination of sufficient AR and PR activation can suppress circulating testosterone levels into the <a href="/wiki/Castrate" class="mw-redirect" title="Castrate">castrate</a> range in men (i.e., complete suppression of gonadal testosterone production and circulating testosterone levels decreased by about 95%).<a href="#cite_note-pmid20933120-50">[50]</a><a href="#cite_note-pmid9920070-166">[163]</a> As such, combined progestogenic activity may serve to further increase the myotrophic–androgenic ratio for a given AAS.<a href="#cite_note-Llewellyn2011-73">[70]</a> <div class="mw-heading mw-heading3"><h3 id="GABAA_receptor_modulation">GABAA receptor modulation</h3>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=35" title="Edit section: GABAA receptor modulation">edit</a>]</div> Some AAS, such as testosterone, DHT, stanozolol, and methyltestosterone, have been found to modulate the <a href="/wiki/GABAA_receptor" title="GABAA receptor">GABAA receptor</a> similarly to endogenous <a href="/wiki/Neurosteroid" title="Neurosteroid">neurosteroids</a> like <a href="/wiki/Allopregnanolone" title="Allopregnanolone">allopregnanolone</a>, <a href="/wiki/3%CE%B1-androstanediol" class="mw-redirect" title="3α-androstanediol">3α-androstanediol</a>, <a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">dehydroepiandrosterone sulfate</a>, and <a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">pregnenolone sulfate</a>.<a href="#cite_note-pmid18500378-78">[75]</a> It has been suggested that this may contribute as an alternative or additional mechanism to the neurological and behavioral effects of AAS.<a href="#cite_note-pmid18500378-78">[75]</a><a href="#cite_note-pmid8294123-167">[164]</a><a href="#cite_note-pmid7603620-168">[165]</a><a href="#cite_note-pmid8858992-169">[166]</a><a href="#cite_note-pmid16814373-170">[167]</a><a href="#cite_note-pmid17433821-171">[168]</a><a href="#cite_note-pmid19376158-172">[169]</a> <div class="mw-heading mw-heading3"><h3 id="Comparison_of_AAS">Comparison of AAS</h3>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=36" title="Edit section: Comparison of AAS">edit</a>]</div> AAS differ in a variety of ways including in their capacities to be <a href="/wiki/Metabolized" class="mw-redirect" title="Metabolized">metabolized</a> by <a href="/wiki/Steroidogenic" class="mw-redirect" title="Steroidogenic">steroidogenic</a> <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> such as <a href="/wiki/5%CE%B1-reductase" class="mw-redirect" title="5α-reductase">5α-reductase</a>, <a href="/wiki/3-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3-hydroxysteroid dehydrogenase">3-hydroxysteroid dehydrogenases</a>, and <a href="/wiki/Aromatase" title="Aromatase">aromatase</a>, in whether their potency as AR agonists is potentiated or diminished by 5α-reduction, in their ratios of <a href="/wiki/Anabolic" class="mw-redirect" title="Anabolic">anabolic</a>/<a href="/wiki/Myotrophic" class="mw-redirect" title="Myotrophic">myotrophic</a> to <a href="/wiki/Androgen" title="Androgen">androgenic</a> effect, in their <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogenic</a>, <a href="/wiki/Progestogen" title="Progestogen">progestogenic</a>, and <a href="/wiki/Neurosteroid" title="Neurosteroid">neurosteroid</a> activities, in their <a href="/wiki/Oral_administration" title="Oral administration">oral</a> activity, and in their capacity to produce <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">hepatotoxicity</a>.<a href="#cite_note-Llewellyn2011-73">[70]</a><a href="#cite_note-pmid18500378-78">[75]</a><a href="#cite_note-pmid8674183-173">[170]</a> <table class="wikitable sortable mw-collapsible mw-collapsed" style="margin-left: auto; margin-right: auto; border: none;"> <caption class="nowrap"><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:Pharmacological_properties_of_major_anabolic_steroids" title="Template:Pharmacological properties of major anabolic steroids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Pharmacological_properties_of_major_anabolic_steroids" title="Template talk:Pharmacological properties of major anabolic steroids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Pharmacological_properties_of_major_anabolic_steroids" title="Special:EditPage/Template:Pharmacological properties of major anabolic steroids"><abbr title="Edit this template">e</abbr></a></li></ul></div> Pharmacological properties of major anabolic steroids </caption> <tbody><tr> <th>Compound</th> <th>Class</th> <th><a href="/wiki/5%CE%B1-Reductase" title="5α-Reductase"><abbr title="Metabolized by 5α-reductase">5α-R</abbr></a></th> <th><a href="/wiki/Aromatase" title="Aromatase"><abbr title="Metabolized by aromatase">AROM</abbr></a></th> <th><a href="/wiki/3-Hydroxysteroid_dehydrogenase" title="3-Hydroxysteroid dehydrogenase"><abbr title="Metabolized by 3α- and/or 3β-hydroxysteroid dehydrogenase">3-HSD</abbr></a></th> <th><a class="mw-selflink-fragment" href="#Anabolic_and_androgenic_effects"><abbr title="Anabolic:androgenic ratio (amount of anabolic (myotrophic) effect relative to androgenic effect)">AAR</abbr></a></th> <th><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)"><abbr title="Estrogenic activity">Estr</abbr></a></th> <th><a href="/wiki/Progestin" class="mw-redirect" title="Progestin"><abbr title="Progestogenic activity">Prog</abbr></a></th> <th><a href="/wiki/Oral_administration" title="Oral administration"><abbr title="Oral activity">Oral</abbr></a></th> <th><a href="/wiki/Hepatotoxicity" title="Hepatotoxicity"><abbr title="Hepatotoxicity">Hepat</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 Hepatotoxicity </th></tr> <tr> <td><a href="/wiki/Androstanolone" title="Androstanolone">Androstanolone</a></td> <td><abbr title="Dihydrotestosterone">DHT</abbr></td> <td><style data-mw-deduplicate="TemplateStyles:r1239334494">@media screen{html.skin-theme-clientpref-night .mw-parser-output div:not(.notheme)>.tmp-color,html.skin-theme-clientpref-night .mw-parser-output p>.tmp-color,html.skin-theme-clientpref-night .mw-parser-output table:not(.notheme) .tmp-color{color:inherit!important}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output div:not(.notheme)>.tmp-color,html.skin-theme-clientpref-os .mw-parser-output p>.tmp-color,html.skin-theme-clientpref-os .mw-parser-output table:not(.notheme) .tmp-color{color:inherit!important}}</style>–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">*</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">– </td></tr> <tr> <td><a href="/wiki/Boldenone" title="Boldenone">Boldenone</a></td> <td><abbr title="Testosterone">T</abbr></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">±</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">**</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">±</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">– </td></tr> <tr> <td><a href="/wiki/Drostanolone" title="Drostanolone">Drostanolone</a></td> <td><abbr title="Dihydrotestosterone">DHT</abbr></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">***</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">– </td></tr> <tr> <td><a href="/wiki/Ethylestrenol" title="Ethylestrenol">Ethylestrenol</a></td> <td><abbr title="19-Nortestosterone">19-NT</abbr>; <abbr title="17α-Alkylated">17α-A</abbr></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+ (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">↓)</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">±</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">***</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+ </td></tr> <tr> <td><a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">Fluoxymesterone</a></td> <td><abbr title="Testosterone">T</abbr>; <abbr title="17α-Alkylated">17α-A</abbr></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+ (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">↑)</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">*</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+ </td></tr> <tr> <td><a href="/wiki/Mestanolone" title="Mestanolone">Mestanolone</a></td> <td><abbr title="Dihydrotestosterone">DHT</abbr>; <abbr title="17α-Alkylated">17α-A</abbr></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">*</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+ </td></tr> <tr> <td><a href="/wiki/Mesterolone" title="Mesterolone">Mesterolone</a></td> <td><abbr title="Dihydrotestosterone">DHT</abbr></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">*</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">±</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">– </td></tr> <tr> <td><a href="/wiki/Metandienone" title="Metandienone">Metandienone</a></td> <td><abbr title="Testosterone">T</abbr>; <abbr title="17α-Alkylated">17α-A</abbr></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">±</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">**</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+ </td></tr> <tr> <td><a href="/wiki/Metenolone" title="Metenolone">Metenolone</a></td> <td><abbr title="Dihydrotestosterone">DHT</abbr></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">**</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">±</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">– </td></tr> <tr> <td><a href="/wiki/Methyltestosterone" title="Methyltestosterone">Methyltestosterone</a></td> <td><abbr title="Testosterone">T</abbr>; <abbr title="17α-Alkylated">17α-A</abbr></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+ (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">↑)</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">*</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+ </td></tr> <tr> <td><a href="/wiki/Nandrolone" title="Nandrolone">Nandrolone</a></td> <td><abbr title="19-Nortestosterone">19-NT</abbr></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+ (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">↓)</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">±</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">***</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">±</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">– </td></tr> <tr> <td><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a></td> <td><abbr title="19-Nortestosterone">19-NT</abbr>; <abbr title="17α-Alkylated">17α-A</abbr></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+ (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">↓)</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">±</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">***</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+ </td></tr> <tr> <td><a href="/wiki/Oxandrolone" title="Oxandrolone">Oxandrolone</a></td> <td><abbr title="Dihydrotestosterone">DHT</abbr>; <abbr title="17α-Alkylated">17α-A</abbr></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">***</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">± </td></tr> <tr> <td><a href="/wiki/Oxymetholone" title="Oxymetholone">Oxymetholone</a></td> <td><abbr title="Dihydrotestosterone">DHT</abbr>; <abbr title="17α-Alkylated">17α-A</abbr></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">***</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+ </td></tr> <tr> <td><a href="/wiki/Stanozolol" title="Stanozolol">Stanozolol</a></td> <td><abbr title="Dihydrotestosterone">DHT</abbr>; <abbr title="17α-Alkylated">17α-A</abbr></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">***</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+ </td></tr> <tr> <td><a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">Testosterone</a></td> <td><abbr title="Testosterone">T</abbr></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+ (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">↑)</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">*</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">±a</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">– </td></tr> <tr> <td><a href="/wiki/Trenbolone" title="Trenbolone">Trenbolone</a></td> <td><abbr title="19-Nortestosterone">19-NT</abbr></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">***</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">– </td></tr> <tr class="sortbottom"> <td colspan="10" style="width: 1px; background-color:#eaecf0; text-align: center;">Key: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">+ = Yes. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">± = Low. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">– = No. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">↑ = Potentiated. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">↓ = Inactivated. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">*** = High. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">** = Moderate. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494">* = Low. Abbreviations: 5α-R = Metabolized by <a href="/wiki/5%CE%B1-reductase" class="mw-redirect" title="5α-reductase">5α-reductase</a>. AROM = Metabolized by <a href="/wiki/Aromatase" title="Aromatase">aromatase</a>. 3-HSD = Metabolized by <a href="/wiki/3%CE%B1-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3α-hydroxysteroid dehydrogenase"><abbr title="3α-hydroxysteroid dehydrogenase">3α-</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 3α-hydroxysteroid dehydrogenase and/or <a href="/wiki/3%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3β-hydroxysteroid dehydrogenase"><abbr title="3β-hydroxysteroid dehydrogenase">3β-HSD</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 3β-hydroxysteroid dehydrogenase. AAR = <a class="mw-selflink-fragment" href="#Anabolic_and_androgenic_effects">Anabolic-to-androgenic ratio</a> (amount of <a href="/wiki/Anabolic" class="mw-redirect" title="Anabolic">anabolic</a> (<a href="/wiki/Myotrophic" class="mw-redirect" title="Myotrophic">myotrophic</a>) effect relative to <a href="/wiki/Androgen" title="Androgen">androgenic</a> effect). Estr = <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogenic</a>. Prog = <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">Progestogenic</a>. Oral = <a href="/wiki/Oral_administration" title="Oral administration">Oral</a> activity. Hepat = <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">Hepatotoxicity</a>. Footnotes: a = As <a href="/wiki/Testosterone_undecanoate" title="Testosterone undecanoate">testosterone undecanoate</a>. Sources: See template. </td></tr></tbody></table> <table class="wikitable sortable mw-collapsible mw-collapsed" style="font-size:small; width:850px; margin-left: auto; margin-right: auto; border: none;"> <caption class="nowrap"><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:Relative_affinities_of_anabolic_steroids_and_related_steroids" title="Template:Relative affinities of anabolic steroids and related steroids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Relative_affinities_of_anabolic_steroids_and_related_steroids" title="Template talk:Relative affinities of anabolic steroids and related steroids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Relative_affinities_of_anabolic_steroids_and_related_steroids" title="Special:EditPage/Template:Relative affinities of anabolic steroids and related steroids"><abbr title="Edit this template">e</abbr></a></li></ul></div> Relative affinities of anabolic steroids and related steroids </caption> <tbody><tr> <th rowspan="2"><a href="/wiki/Steroid" title="Steroid">Steroid</a></th> <th rowspan="2" class="unsortable">Chemical name</th> <th colspan="7"><a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity">Relative binding affinities</a> (%) </th></tr> <tr> <th data-sort-type="number"><a href="/wiki/Progesterone_receptor" title="Progesterone receptor"><abbr title="Progesterone receptor">PR</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 Progesterone receptor</th> <th data-sort-type="number"><a href="/wiki/Androgen_receptor" title="Androgen receptor"><abbr title="Androgen receptor">AR</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 Androgen receptor</th> <th data-sort-type="number"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</th> <th data-sort-type="number"><a href="/wiki/Glucocorticoid_receptor" title="Glucocorticoid receptor"><abbr title="Glucocorticoid receptor">GR</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 Glucocorticoid receptor</th> <th data-sort-type="number"><a href="/wiki/Mineralocorticoid_receptor" title="Mineralocorticoid receptor"><abbr title="Mineralocorticoid receptor">MR</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 Mineralocorticoid receptor</th> <th data-sort-type="number"><a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="Sex hormone-binding globulin">SHBG</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 Sex hormone-binding globulin</th> <th data-sort-type="number"><a href="/wiki/Corticosteroid-binding_globulin" class="mw-redirect" title="Corticosteroid-binding globulin"><abbr title="Corticosteroid-binding globulin">CBG</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 Corticosteroid-binding globulin </th></tr> <tr> <td><a href="/wiki/Androstanolone" title="Androstanolone">Androstanolone</a></td> <td><abbr title="5α-Dihydrotestosterone">DHT</abbr></td> <td>1.4–1.5</td> <td>60–120</td> <td><0.1</td> <td><0.1–0.3</td> <td>0.15</td> <td>100</td> <td>0.8 </td></tr> <tr> <td><a href="/wiki/Boldenone" title="Boldenone">Boldenone</a></td> <td><abbr title="Δ1-Testosterone">Δ1-T</abbr></td> <td><1</td> <td>50–75</td> <td>?</td> <td><1</td> <td>?</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Danazol" title="Danazol">Danazol</a></td> <td><abbr title="2,3-Isoxazol-17α-ethynyltestosterone">2,3-Isoxazol-17α-Ety-T</abbr></td> <td>9</td> <td>8</td> <td>?</td> <td><0.1a</td> <td>?</td> <td>8</td> <td>10 </td></tr> <tr> <td><a href="/wiki/Dienolone" title="Dienolone">Dienolone</a></td> <td><abbr title="Δ9-19-Nortestosterone">∆9-19-NT</abbr></td> <td>17</td> <td>134</td> <td><0.1</td> <td>1.6</td> <td>0.3</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Dimethyldienolone" title="Dimethyldienolone">Dimethyldienolone</a></td> <td><abbr title="Δ9-7α,17α-Dimethyl-19-nortestosterone">∆9-7α,17α-DiMe-19-NT</abbr></td> <td>198</td> <td>122</td> <td>0.1</td> <td>6.1</td> <td>1.7</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Dimethyltrienolone" title="Dimethyltrienolone">Dimethyltrienolone</a></td> <td><abbr title="∆9,11-7α,17α-Dimethyl-19-nortestosterone">∆9,11-7α,17α-DiMe-19-NT</abbr></td> <td>306</td> <td>180</td> <td>0.1</td> <td>22</td> <td>52</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Drostanolone" title="Drostanolone">Drostanolone</a></td> <td><abbr title="2α-Methyl-5α-dihydrotestosterone">2α-Me-DHT</abbr></td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>39</td> <td>? </td></tr> <tr> <td><a href="/wiki/Ethisterone" title="Ethisterone">Ethisterone</a></td> <td><abbr title="17α-Ethynyltestosterone">17α-Ety-T</abbr></td> <td>35</td> <td>0.1</td> <td><1.0</td> <td><1.0</td> <td><1.0</td> <td>25–92</td> <td>0.3 </td></tr> <tr> <td><a href="/wiki/Ethylestrenol" title="Ethylestrenol">Ethylestrenol</a></td> <td><abbr title="3-Deketo-17α-ethyl-19-nortestosterone">3-DeO-17α-Et-19-NT</abbr></td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td><1</td> <td>? </td></tr> <tr> <td><a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">Fluoxymesterone</a></td> <td><abbr title="9α-Fluoro-11β-hydroxy-17α-methyltestosterone">9α-F-11β-OH-17α-Me-T</abbr></td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>≤3</td> <td>? </td></tr> <tr> <td><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></td> <td><abbr title="∆9,11-17α-Ethynyl-18-methyl-19-nortestosterone">∆9,11-17α-Ety-18-Me-19-NT</abbr></td> <td>75–76</td> <td>83–85</td> <td><0.1–10</td> <td>77</td> <td>3.2</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Levonorgestrel" title="Levonorgestrel">Levonorgestrel</a></td> <td><abbr title="17α-Ethynyl-18-methyl-19-nortestosterone">17α-Ety-18-Me-19-NT</abbr></td> <td>170</td> <td>84–87</td> <td><0.1</td> <td>14</td> <td>0.6–0.9</td> <td>14–50</td> <td><0.1 </td></tr> <tr> <td><a href="/wiki/Mestanolone" title="Mestanolone">Mestanolone</a></td> <td><abbr title="17α-Methyl-5α-dihydrotestosterone">17α-Me-DHT</abbr></td> <td>5–10</td> <td>100–125</td> <td>?</td> <td><1</td> <td>?</td> <td>84</td> <td>? </td></tr> <tr> <td><a href="/wiki/Mesterolone" title="Mesterolone">Mesterolone</a></td> <td><abbr title="1α-Methyl-5α-dihydrotestosterone">1α-Me-DHT</abbr></td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>82–440</td> <td>? </td></tr> <tr> <td><a href="/wiki/Metandienone" title="Metandienone">Metandienone</a></td> <td><abbr title="∆1-17α-Methyltestosterone">∆1-17α-Me-T</abbr></td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>2</td> <td>? </td></tr> <tr> <td><a href="/wiki/Metenolone" title="Metenolone">Metenolone</a></td> <td><abbr title="∆1-1-Methyl-5α-dihydrotestosterone">∆1-1-Me-DHT</abbr></td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>3</td> <td>? </td></tr> <tr> <td><a href="/wiki/Methandriol" title="Methandriol">Methandriol</a></td> <td><abbr title="17α-Methyl-5-androstenediol">17α-Me-A5</abbr></td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>40</td> <td>? </td></tr> <tr> <td><a href="/wiki/Methasterone" title="Methasterone">Methasterone</a></td> <td><abbr title="2α,17α-Dimethyl-5α-dihydrotestosterone">2α,17α-DiMe-DHT</abbr></td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>58</td> <td>? </td></tr> <tr> <td><a href="/wiki/Methyldienolone" title="Methyldienolone">Methyldienolone</a></td> <td><abbr title="Δ9-17α-Methyl-19-nortestosterone">∆9-17α-Me-19-NT</abbr></td> <td>71</td> <td>64</td> <td><0.1</td> <td>6</td> <td>0.4</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Methyltestosterone" title="Methyltestosterone">Methyltestosterone</a></td> <td><abbr title="17α-Methyltestosterone">17α-Me-T</abbr></td> <td>3</td> <td data-sort-value="45">45–125</td> <td><0.1</td> <td>1–5</td> <td>?</td> <td>5–64</td> <td><0.1 </td></tr> <tr> <td data-sort-value="Methyltestosterone, 1-"><a href="/wiki/Methyl-1-testosterone" title="Methyl-1-testosterone">Methyl-1-testosterone</a></td> <td><abbr title="∆1-17α-Methyl-5α-dihydrotestosterone">∆1-17α-Me-DHT</abbr></td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>69</td> <td>? </td></tr> <tr> <td><a href="/wiki/Metribolone" title="Metribolone">Metribolone</a></td> <td><abbr title="∆9,11-17α-Methyl-19-nortestosterone">∆9,11-17α-Me-19-NT</abbr></td> <td>208–210</td> <td>199–210</td> <td><0.1</td> <td>10–26</td> <td>18</td> <td>0.2–0.8</td> <td>≤0.4 </td></tr> <tr> <td><a href="/wiki/Mibolerone" title="Mibolerone">Mibolerone</a></td> <td><abbr title="7α,17α-Dimethyl-19-nortestosterone">7α,17α-DiMe-19-NT</abbr></td> <td>214</td> <td>108</td> <td><0.1</td> <td>1.4</td> <td>2.1</td> <td>6</td> <td>? </td></tr> <tr> <td><a href="/wiki/Nandrolone" title="Nandrolone">Nandrolone</a></td> <td><abbr title="19-Nortestosterone">19-NT</abbr></td> <td>20</td> <td>154–155</td> <td><0.1</td> <td>0.5</td> <td>1.6</td> <td>1–16</td> <td>0.1 </td></tr> <tr> <td><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a></td> <td><abbr title="17α-Ethyl-19-nortestosterone">17α-Et-19-NT</abbr></td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>3</td> <td>? </td></tr> <tr> <td><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></td> <td><abbr title="17α-Ethynyl-19-nortestosterone">17α-Ety-19-NT</abbr></td> <td>155–156</td> <td>43–45</td> <td><0.1</td> <td>2.7–2.8</td> <td>0.2</td> <td>5–21</td> <td>0.3 </td></tr> <tr> <td><a href="/wiki/Norgestrienone" title="Norgestrienone">Norgestrienone</a></td> <td><abbr title="∆9,11-17α-Ethynyl-19-nortestosterone">∆9,11-17α-Ety-19-NT</abbr></td> <td>63–65</td> <td>70</td> <td><0.1</td> <td>11</td> <td>1.8</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone</a></td> <td><abbr title="17α-Methyl-19-nortestosterone">17α-Me-19-NT</abbr></td> <td>100</td> <td>146</td> <td><0.1</td> <td>1.5</td> <td>0.6</td> <td>7</td> <td>? </td></tr> <tr> <td><a href="/wiki/Oxandrolone" title="Oxandrolone">Oxandrolone</a></td> <td><abbr title="2-Oxa-17α-methyl-5α-dihydrotestosterone">2-Oxa-17α-Me-DHT</abbr></td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td><1</td> <td>? </td></tr> <tr> <td><a href="/wiki/Oxymetholone" title="Oxymetholone">Oxymetholone</a></td> <td><abbr title="2-Hydroxymethylene-17α-methyl-5α-dihydrotestosterone">2-OHMeEne-17α-Me-DHT</abbr></td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>≤3</td> <td>? </td></tr> <tr> <td><a href="/wiki/RU-2309" title="RU-2309">RU-2309</a> (<abbr title="17α-Methyltetrahydrogestrinone">17α-Me-THG</abbr>)</td> <td><abbr title="∆9,11-17α,18-Dimethyl-19-nortestosterone">∆9,11-17α,18-DiMe-19-NT</abbr></td> <td>230</td> <td>143</td> <td><0.1</td> <td>155</td> <td>36</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Stanozolol" title="Stanozolol">Stanozolol</a></td> <td><abbr title="2,3-Pyrazol-17α-methyl-5α-dihydrotestosterone">2,3-Pyrazol-17α-Me-DHT</abbr></td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>1–36</td> <td>? </td></tr> <tr> <td><a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">Testosterone</a></td> <td><abbr title="Testosterone">T</abbr></td> <td>1.0–1.2</td> <td>100</td> <td><0.1</td> <td>0.17</td> <td>0.9</td> <td>19–82</td> <td>3–8 </td></tr> <tr> <td data-sort-value="Testosterone, 1-"><a href="/wiki/1-Testosterone" title="1-Testosterone">1-Testosterone</a></td> <td><abbr title="∆1-5α-Dihydrotestosterone">∆1-DHT</abbr></td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>98</td> <td>? </td></tr> <tr> <td><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></td> <td><abbr title="7α-Methyl-17α-ethynyl-19-nor-5(10)-testosterone">7α-Me-17α-Ety-19-N-5(10)-T</abbr></td> <td>12</td> <td>12</td> <td>1</td> <td>?</td> <td>?</td> <td>?</td> <td>? </td></tr> <tr> <td data-sort-value="Tibolone, Δ4-"><a href="/wiki/%CE%944-Tibolone" title="Δ4-Tibolone">Δ4-Tibolone</a></td> <td><abbr title="7α-Methyl-17α-ethynyl-19-nortestosterone">7α-Me-17α-Ety-19-NT</abbr></td> <td>180</td> <td>70</td> <td>1</td> <td><1</td> <td>2</td> <td>1–8</td> <td><1 </td></tr> <tr> <td><a href="/wiki/Trenbolone" title="Trenbolone">Trenbolone</a></td> <td><abbr title="∆9,11-19-Nortestosterone">∆9,11-19-NT</abbr></td> <td>74–75</td> <td>190–197</td> <td><0.1</td> <td>2.9</td> <td>1.33</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Trestolone" title="Trestolone">Trestolone</a></td> <td><abbr title="7α-Methyl-19-nortestosterone">7α-Me-19-NT</abbr></td> <td>50–75</td> <td>100–125</td> <td>?</td> <td><1</td> <td>?</td> <td>12</td> <td>? </td></tr> <tr class="sortbottom"> <td colspan="9" style="width: 1px; background-color:#eaecf0; text-align: center;">Notes: Values are percentages (%). Reference <a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a> (100%) were <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> for the <a href="/wiki/Progesterone_receptor" title="Progesterone receptor"><abbr title="progesterone receptor">PR</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 progesterone receptor, <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a> for the <a href="/wiki/Androgen_receptor" title="Androgen receptor"><abbr title="androgen receptor">AR</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 androgen receptor, <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a> for the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip estrogen receptor, <a href="/wiki/Dexamethasone" title="Dexamethasone">dexamethasone</a> for the <a href="/wiki/Glucocorticoid_receptor" title="Glucocorticoid receptor"><abbr title="glucocorticoid receptor">GR</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 glucocorticoid receptor, <a href="/wiki/Aldosterone" title="Aldosterone">aldosterone</a> for the <a href="/wiki/Mineralocorticoid_receptor" title="Mineralocorticoid receptor"><abbr title="mineralocorticoid receptor">MR</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 mineralocorticoid receptor, <a href="/wiki/Androstanolone" title="Androstanolone">dihydrotestosterone</a> for <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="sex hormone-binding globulin">SHBG</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 sex hormone-binding globulin, and <a href="/wiki/Hydrocortisone" title="Hydrocortisone">cortisol</a> for <a href="/wiki/Corticosteroid-binding_globulin" class="mw-redirect" title="Corticosteroid-binding globulin"><abbr title="corticosteroid-binding globulin">CBG</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 corticosteroid-binding globulin. Footnotes: a = 1-hour incubation time (4 hours is standard for this assay; may affect affinity value). Sources: See template. </td></tr></tbody></table> <table class="wikitable sortable mw-collapsible mw-collapsed" style="margin: 1em auto;"> <caption class="nowrap"><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:Parenteral_durations_of_androgens/anabolic_steroids" title="Template:Parenteral durations of androgens/anabolic steroids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Parenteral_durations_of_androgens/anabolic_steroids" title="Template talk:Parenteral durations of androgens/anabolic steroids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Parenteral_durations_of_androgens/anabolic_steroids" title="Special:EditPage/Template:Parenteral durations of androgens/anabolic steroids"><abbr title="Edit this template">e</abbr></a></li></ul></div> Parenteral durations of androgens/anabolic steroids </caption> <tbody><tr> <th>Medication</th> <th>Form</th> <th>Major brand names</th> <th data-sort-type="number">Duration </th></tr> <tr> <td><a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">Testosterone</a></td> <td>Aqueous suspension</td> <td>Andronaq, Sterotate, Virosterone</td> <td>2–3 days </td></tr> <tr> <td><a href="/wiki/Testosterone_propionate" title="Testosterone propionate">Testosterone propionate</a></td> <td>Oil solution</td> <td style="white-space: nowrap;">Androteston, Perandren, Testoviron</td> <td>3–4 days </td></tr> <tr> <td><a href="/wiki/Testosterone_phenylpropionate" title="Testosterone phenylpropionate">Testosterone phenylpropionate</a></td> <td>Oil solution</td> <td>Testolent</td> <td>8 days </td></tr> <tr> <td><a href="/wiki/Testosterone_isobutyrate" title="Testosterone isobutyrate">Testosterone isobutyrate</a></td> <td>Aqueous suspension</td> <td>Agovirin Depot, Perandren M</td> <td>14 days </td></tr> <tr> <td><a href="/wiki/Testosterone_propionate/testosterone_valerate/testosterone_undecylenate" title="Testosterone propionate/testosterone valerate/testosterone undecylenate">Mixed testosterone esters</a>a</td> <td>Oil solution</td> <td>Triolandren</td> <td>10–20 days </td></tr> <tr> <td><a href="/wiki/Testosterone_propionate/testosterone_ketolaurate" title="Testosterone propionate/testosterone ketolaurate">Mixed testosterone esters</a>b</td> <td>Oil solution</td> <td>Testosid Depot</td> <td>14–20 days </td></tr> <tr> <td><a href="/wiki/Testosterone_enanthate" title="Testosterone enanthate">Testosterone enanthate</a></td> <td>Oil solution</td> <td>Delatestryl</td> <td>14–28 days </td></tr> <tr> <td><a href="/wiki/Testosterone_cypionate" title="Testosterone cypionate">Testosterone cypionate</a></td> <td>Oil solution</td> <td>Depovirin</td> <td>14–28 days </td></tr> <tr> <td><a href="/wiki/Testosterone_propionate/testosterone_phenylpropionate/testosterone_isocaproate/testosterone_decanoate" title="Testosterone propionate/testosterone phenylpropionate/testosterone isocaproate/testosterone decanoate">Mixed testosterone esters</a>c</td> <td>Oil solution</td> <td>Sustanon 250</td> <td>28 days </td></tr> <tr> <td><a href="/wiki/Testosterone_undecanoate" title="Testosterone undecanoate">Testosterone undecanoate</a></td> <td>Oil solution</td> <td>Aveed, Nebido</td> <td>100 days </td></tr> <tr> <td><a href="/wiki/Testosterone_buciclate" title="Testosterone buciclate">Testosterone buciclate</a>d</td> <td>Aqueous suspension</td> <td>20 Aet-1, CDB-1781e</td> <td style="white-space: nowrap;">90–120 days </td></tr> <tr> <td><a href="/wiki/Nandrolone_phenylpropionate" title="Nandrolone phenylpropionate">Nandrolone phenylpropionate</a></td> <td>Oil solution</td> <td>Durabolin</td> <td>10 days </td></tr> <tr> <td><a href="/wiki/Nandrolone_decanoate" title="Nandrolone decanoate">Nandrolone decanoate</a></td> <td>Oil solution</td> <td>Deca Durabolin</td> <td>21–28 days </td></tr> <tr> <td><a href="/wiki/Methandriol" title="Methandriol">Methandriol</a></td> <td>Aqueous suspension</td> <td>Notandron, Protandren</td> <td>8 days </td></tr> <tr> <td><a href="/wiki/Methandriol_bisenanthoyl_acetate" title="Methandriol bisenanthoyl acetate">Methandriol bisenanthoyl acetate</a></td> <td>Oil solution</td> <td>Notandron Depot</td> <td>16 days </td></tr> <tr> <td><a href="/wiki/Metenolone_acetate" title="Metenolone acetate">Metenolone acetate</a></td> <td>Oil solution</td> <td>Primobolan</td> <td>3 days </td></tr> <tr> <td><a href="/wiki/Metenolone_enanthate" title="Metenolone enanthate">Metenolone enanthate</a></td> <td>Oil solution</td> <td>Primobolan Depot</td> <td>14 days </td></tr> <tr class="sortbottom"> <td colspan="4" style="width: 1px; background-color:#eaecf0; text-align: center;">Note: All are via <a href="/wiki/Intramuscular_injection" title="Intramuscular injection"><abbr title="intramuscular">i.m.</abbr> injection</a>. Footnotes: a = <a href="/wiki/Testosterone_propionate" title="Testosterone propionate"><abbr title="Testosterone propionate">TP</abbr></a>, <a href="/wiki/Testosterone_valerate" title="Testosterone valerate"><abbr title="Testosterone valerate">TV</abbr></a>, and <a href="/wiki/Testosterone_undecylenate" title="Testosterone undecylenate"><abbr title="Testosterone undecylenate">TUe</abbr></a>. b = <a href="/wiki/Testosterone_propionate" title="Testosterone propionate"><abbr title="Testosterone propionate">TP</abbr></a> and <a href="/wiki/Testosterone_ketolaurate" title="Testosterone ketolaurate"><abbr title="Testosterone ketolaurate">TKL</abbr></a>. c = <a href="/wiki/Testosterone_propionate" title="Testosterone propionate"><abbr title="Testosterone propionate">TP</abbr></a>, <a href="/wiki/Testosterone_phenylpropionate" title="Testosterone phenylpropionate"><abbr title="Testosterone phenylpropionate">TPP</abbr></a>, <a href="/wiki/Testosterone_isocaproate" title="Testosterone isocaproate"><abbr title="Testosterone isocaproate">TiCa</abbr></a>, and <a href="/wiki/Testosterone_decanoate" title="Testosterone decanoate"><abbr title="Testosterone decanoate">TD</abbr></a>. d = Studied but never marketed. e = Developmental code names. Sources: See template. </td></tr></tbody></table> <table class="wikitable sortable mw-collapsible mw-collapsed" style="text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap"><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:Pharmacokinetics_of_testosterone_esters" title="Template:Pharmacokinetics of testosterone esters"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Pharmacokinetics_of_testosterone_esters" title="Template talk:Pharmacokinetics of testosterone esters"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Pharmacokinetics_of_testosterone_esters" title="Special:EditPage/Template:Pharmacokinetics of testosterone esters"><abbr title="Edit this template">e</abbr></a></li></ul></div> Pharmacokinetics of testosterone esters </caption> <tbody><tr> <th>Testosterone ester</th> <th>Form</th> <th>Route</th> <th><a href="/wiki/Time_to_peak_levels" class="mw-redirect" title="Time to peak levels"><abbr title="Time to peak levels">Tmax</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 Time to peak levels</th> <th><a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life"><abbr title="Elimination half-life">t1/2</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 Elimination half-life</th> <th><a href="/wiki/Mean_residence_time" class="mw-redirect" title="Mean residence time"><abbr title="Mean residence time">MRT</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 Mean residence time </th></tr> <tr> <td><a href="/wiki/Testosterone_undecanoate" title="Testosterone undecanoate">Testosterone undecanoate</a></td> <td>Oil-filled capsules</td> <td>Oral</td> <td>?</td> <td>1.6 hours</td> <td>3.7 hours </td></tr> <tr> <td><a href="/wiki/Testosterone_propionate" title="Testosterone propionate">Testosterone propionate</a></td> <td>Oil solution</td> <td>Intramuscular injection</td> <td>?</td> <td>0.8 days</td> <td>1.5 days </td></tr> <tr> <td><a href="/wiki/Testosterone_enanthate" title="Testosterone enanthate">Testosterone enanthate</a></td> <td>Castor oil solution</td> <td>Intramuscular injection</td> <td>10 days</td> <td>4.5 days</td> <td>8.5 days </td></tr> <tr> <td><a href="/wiki/Testosterone_undecanoate" title="Testosterone undecanoate">Testosterone undecanoate</a></td> <td>Tea seed oil solution</td> <td>Intramuscular injection</td> <td>13.0 days</td> <td>20.9 days</td> <td>34.9 days </td></tr> <tr> <td><a href="/wiki/Testosterone_undecanoate" title="Testosterone undecanoate">Testosterone undecanoate</a></td> <td>Castor oil solution</td> <td>Intramuscular injection</td> <td>11.4 days</td> <td>33.9 days</td> <td>36.0 days </td></tr> <tr> <td><a href="/wiki/Testosterone_buciclate" title="Testosterone buciclate">Testosterone buciclate</a>a</td> <td>Aqueous suspension</td> <td>Intramuscular injection</td> <td>25.8 days</td> <td>29.5 days</td> <td>60.0 days </td></tr> <tr class="sortbottom"> <td colspan="6" style="background-color:#eaecf0; text-align: center;">Notes: <a href="/wiki/Testosterone_cypionate" title="Testosterone cypionate">Testosterone cypionate</a> has similar pharmacokinetics to <abbr title="testosterone enanthate">Testosterone enanthate</abbr>. Footnotes: a = Never marketed. Sources: See template. </td></tr></tbody></table> <div class="mw-heading mw-heading4"><h4 id="5α-Reductase_and_androgenicity">5α-Reductase and androgenicity</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=37" title="Edit section: 5α-Reductase and androgenicity">edit</a>]</div> Testosterone can be robustly converted by <a href="/wiki/5%CE%B1-reductase" class="mw-redirect" title="5α-reductase">5α-reductase</a> into DHT in so-called androgenic tissues such as <a href="/wiki/Skin" title="Skin">skin</a>, <a href="/wiki/Scalp" title="Scalp">scalp</a>, <a href="/wiki/Prostate" title="Prostate">prostate</a>, and <a href="/wiki/Seminal_vesicles" title="Seminal vesicles">seminal vesicles</a>, but not in <a href="/wiki/Muscle" title="Muscle">muscle</a> or <a href="/wiki/Bone" title="Bone">bone</a>, where 5α-reductase either is not expressed or is only minimally expressed.<a href="#cite_note-pmid18500378-78">[75]</a> As DHT is 3- to 10-fold more potent as an agonist of the AR than is testosterone, the AR agonist activity of testosterone is thus markedly and selectively potentiated in such tissues.<a href="#cite_note-pmid18500378-78">[75]</a> In contrast to testosterone, DHT and other 4,5α-dihydrogenated AAS are already 5α-reduced, and for this reason, cannot be potentiated in androgenic tissues.<a href="#cite_note-pmid18500378-78">[75]</a> 19-Nortestosterone derivatives like <a href="/wiki/Nandrolone" title="Nandrolone">nandrolone</a> can be <a href="/wiki/Metabolized" class="mw-redirect" title="Metabolized">metabolized</a> by 5α-reductase similarly to testosterone, but 5α-reduced metabolites of 19-nortestosterone derivatives (e.g., <a href="/wiki/5%CE%B1-dihydronandrolone" class="mw-redirect" title="5α-dihydronandrolone">5α-dihydronandrolone</a>) tend to have reduced activity as AR agonists, resulting in reduced androgenic activity in tissues that express 5α-reductase.<a href="#cite_note-pmid18500378-78">[75]</a> In addition, some 19-nortestosterone derivatives, including <a href="/wiki/Trestolone" title="Trestolone">trestolone</a> (7α-methyl-19-nortestosterone (MENT)), <a href="/wiki/11%CE%B2-methyl-19-nortestosterone" class="mw-redirect" title="11β-methyl-19-nortestosterone">11β-methyl-19-nortestosterone</a> (11β-MNT), and <a href="/wiki/Dimethandrolone" title="Dimethandrolone">dimethandrolone</a> (7α,11β-dimethyl-19-nortestosterone), cannot be 5α-reduced.<a href="#cite_note-pmid20599615-174">[171]</a> Conversely, certain 17α-alkylated AAS like methyltestosterone are 5α-reduced and potentiated in androgenic tissues similarly to testosterone.<a href="#cite_note-pmid18500378-78">[75]</a><a href="#cite_note-Llewellyn2011-73">[70]</a> 17α-Alkylated DHT derivatives cannot be potentiated via 5α-reductase however, as they are already 4,5α-reduced.<a href="#cite_note-pmid18500378-78">[75]</a><a href="#cite_note-Llewellyn2011-73">[70]</a> The capacity to be metabolized by 5α-reductase and the AR activity of the resultant metabolites appears to be one of the major, if not the most important determinant of the <a href="/wiki/Androgenic-myotrophic_ratio" class="mw-redirect" title="Androgenic-myotrophic ratio">androgenic–myotrophic ratio</a> for a given AAS.<a href="#cite_note-pmid18500378-78">[75]</a> AAS that are not potentiated by 5α-reductase or that are weakened by 5α-reductase in androgenic tissues have a reduced risk of androgenic side effects such as <a href="/wiki/Acne" title="Acne">acne</a>, <a href="/wiki/Androgenic_alopecia" class="mw-redirect" title="Androgenic alopecia">androgenic alopecia</a> (male-pattern baldness), <a href="/wiki/Hirsutism" title="Hirsutism">hirsutism</a> (excessive male-pattern hair growth), <a href="/wiki/Benign_prostatic_hyperplasia" title="Benign prostatic hyperplasia">benign prostatic hyperplasia</a> (prostate enlargement), and <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a>, while incidence and magnitude of other effects such as <a href="/wiki/Muscle_hypertrophy" title="Muscle hypertrophy">muscle hypertrophy</a>, bone changes,<a href="#cite_note-Orwoll-2009-2-175">[172]</a> <a href="/wiki/Voice_deepening" class="mw-redirect" title="Voice deepening">voice deepening</a>, and changes in <a href="/wiki/Sex_drive" class="mw-redirect" title="Sex drive">sex drive</a> show no difference.<a href="#cite_note-pmid18500378-78">[75]</a><a href="#cite_note-Fillit-2010-176">[173]</a> <div class="mw-heading mw-heading4"><h4 id="Aromatase_and_estrogenicity">Aromatase and estrogenicity</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=38" title="Edit section: Aromatase and estrogenicity">edit</a>]</div> Testosterone can be <a href="/wiki/Metabolized" class="mw-redirect" title="Metabolized">metabolized</a> by <a href="/wiki/Aromatase" title="Aromatase">aromatase</a> into <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>, and many other AAS can be metabolized into their corresponding <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogenic</a> metabolites as well.<a href="#cite_note-pmid18500378-78">[75]</a> As an example, the 17α-alkylated AAS <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a> and <a href="/wiki/Metandienone" title="Metandienone">metandienone</a> are converted by aromatase into <a href="/wiki/Methylestradiol" title="Methylestradiol">methylestradiol</a>.<a href="#cite_note-Thieme-2009-177">[174]</a> 4,5α-Dihydrogenated derivatives of testosterone such as DHT cannot be aromatized, whereas 19-nortestosterone derivatives like nandrolone can be but to a greatly reduced extent.<a href="#cite_note-pmid18500378-78">[75]</a><a href="#cite_note-pmid18555683-178">[175]</a> Some 19-nortestosterone derivatives, such as dimethandrolone and 11β-MNT, cannot be aromatized due to <a href="/wiki/Steric_hindrance" class="mw-redirect" title="Steric hindrance">steric hindrance</a> provided by their 11β-methyl group, whereas the closely related AAS trestolone (7α-methyl-19-nortestosterone), in relation to its lack of an 11β-methyl group, can be aromatized.<a href="#cite_note-pmid18555683-178">[175]</a> AAS that are 17α-alkylated (and not also 4,5α-reduced or 19-demethylated) are also aromatized but to a lesser extent than is testosterone.<a href="#cite_note-pmid18500378-78">[75]</a><a href="#cite_note-Llewellyn2011c-179">[176]</a> However, it is notable that estrogens that are 17α-substituted (e.g., <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a> and methylestradiol) are of markedly increased estrogenic potency due to improved <a href="/wiki/Metabolic_stability" class="mw-redirect" title="Metabolic stability">metabolic stability</a>,<a href="#cite_note-Thieme-2009-177">[174]</a> and for this reason, 17α-alkylated AAS can actually have high estrogenicity and comparatively greater estrogenic effects than testosterone.<a href="#cite_note-Thieme-2009-177">[174]</a><a href="#cite_note-Llewellyn2011-73">[70]</a> The major effect of estrogenicity is <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a> (woman-like breasts).<a href="#cite_note-pmid18500378-78">[75]</a> AAS that have a high potential for aromatization like testosterone and particularly methyltestosterone show a high risk of gynecomastia at sufficiently high dosages, while AAS that have a reduced potential for aromatization like nandrolone show a much lower risk (though still potentially significant at high dosages).<a href="#cite_note-pmid18500378-78">[75]</a> In contrast, AAS that are 4,5α-reduced, and some other AAS (e.g., 11β-methylated 19-nortestosterone derivatives), have no risk of gynecomastia.<a href="#cite_note-pmid18500378-78">[75]</a> In addition to gynecomastia, AAS with high estrogenicity have increased antigonadotropic activity, which results in increased potency in suppression of the <a href="/wiki/Hypothalamic-pituitary-gonadal_axis" class="mw-redirect" title="Hypothalamic-pituitary-gonadal axis">hypothalamic-pituitary-gonadal axis</a> and <a href="/wiki/Gonad" title="Gonad">gonadal</a> testosterone production.<a href="#cite_note-Suvisaari-2000-180">[177]</a> <div class="mw-heading mw-heading4"><h4 id="Progestogenic_activity">Progestogenic activity</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=39" title="Edit section: Progestogenic activity">edit</a>]</div> Many 19-nortestosterone derivatives, including nandrolone, <a href="/wiki/Trenbolone" title="Trenbolone">trenbolone</a>, <a href="/wiki/Ethylestrenol" title="Ethylestrenol">ethylestrenol</a> (ethylnandrol), <a href="/wiki/Metribolone" title="Metribolone">metribolone</a> (R-1881), trestolone, 11β-MNT, dimethandrolone, and others, are potent agonists of the <a href="/wiki/Progesterone_receptor" title="Progesterone receptor">progesterone receptor</a> (PR) and hence are <a href="/wiki/Progestogen" title="Progestogen">progestogens</a> in addition to AAS.<a href="#cite_note-pmid18500378-78">[75]</a><a href="#cite_note-pmid16497801-181">[178]</a> Similarly to the case of estrogenic activity, the progestogenic activity of these drugs serves to augment their antigonadotropic activity.<a href="#cite_note-pmid16497801-181">[178]</a> This results in increased potency and effectiveness of these AAS as <a href="https://en.wiktionary.org/wiki/antispermatogenic" class="extiw" title="wikt:antispermatogenic">antispermatogenic agents</a> and <a href="/wiki/Male_contraceptive" title="Male contraceptive">male contraceptives</a> (or, put in another way, increased potency and effectiveness in producing <a href="/wiki/Azoospermia" title="Azoospermia">azoospermia</a> and reversible <a href="/wiki/Male_infertility" title="Male infertility">male infertility</a>).<a href="#cite_note-pmid16497801-181">[178]</a> <div class="mw-heading mw-heading4"><h4 id="Oral_activity_and_hepatotoxicity">Oral activity and hepatotoxicity</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=40" title="Edit section: Oral activity and hepatotoxicity">edit</a>]</div> Non-17α-alkylated testosterone derivatives such as testosterone itself, DHT, and nandrolone all have poor oral <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> due to extensive first-pass hepatic metabolism and hence are not orally active.<a href="#cite_note-pmid18500378-78">[75]</a> A notable exception to this are AAS that are androgen <a href="/wiki/Precursor_(biochemistry)" class="mw-redirect" title="Precursor (biochemistry)">precursors</a> or <a href="/wiki/Androgen_prohormone" title="Androgen prohormone">prohormones</a>, including <a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">dehydroepiandrosterone</a> (DHEA), <a href="/wiki/Androstenediol" title="Androstenediol">androstenediol</a>, <a href="/wiki/Androstenedione" title="Androstenedione">androstenedione</a>, <a href="/wiki/Boldione" title="Boldione">boldione</a> (androstadienedione), <a href="/wiki/Bolandiol" title="Bolandiol">bolandiol</a> (norandrostenediol), <a href="/wiki/Bolandione" title="Bolandione">bolandione</a> (norandrostenedione), <a href="/wiki/Dienedione" title="Dienedione">dienedione</a>, <a href="/wiki/Mentabolan" class="mw-redirect" title="Mentabolan">mentabolan</a> (MENT dione, trestione), and <a href="/wiki/Methoxydienone" title="Methoxydienone">methoxydienone</a> (methoxygonadiene) (although these are relatively weak AAS).<a href="#cite_note-Warren-2000-182">[179]</a><a href="#cite_note-Haff-2015-183">[180]</a> AAS that are not orally active are used almost exclusively in the form of <a href="/wiki/Androgen_ester" title="Androgen ester">esters</a> administered by <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a>, which act as <a href="/wiki/Depot_injection" title="Depot injection">depots</a> and function as long-acting <a href="/wiki/Prodrug" title="Prodrug">prodrugs</a>.<a href="#cite_note-pmid18500378-78">[75]</a> Examples include testosterone, as <a href="/wiki/Testosterone_cypionate" title="Testosterone cypionate">testosterone cypionate</a>, <a href="/wiki/Testosterone_enanthate" title="Testosterone enanthate">testosterone enanthate</a>, and <a href="/wiki/Testosterone_propionate" title="Testosterone propionate">testosterone propionate</a>, and nandrolone, as <a href="/wiki/Nandrolone_phenylpropionate" title="Nandrolone phenylpropionate">nandrolone phenylpropionate</a> and <a href="/wiki/Nandrolone_decanoate" title="Nandrolone decanoate">nandrolone decanoate</a>, among many others (see <a href="/wiki/Androgen_ester" title="Androgen ester">here</a> for a full list of testosterone and nandrolone esters).<a href="#cite_note-pmid18500378-78">[75]</a> An exception is the very long-chain ester <a href="/wiki/Testosterone_undecanoate" title="Testosterone undecanoate">testosterone undecanoate</a>, which is orally active, albeit with only very low oral bioavailability (approximately 3%).<a href="#cite_note-Lemke-2012-184">[181]</a> In contrast to most other AAS, 17α-alkylated testosterone derivatives show resistance to metabolism due to steric hindrance and are orally active, though they may be esterified and administered via intramuscular injection as well.<a href="#cite_note-pmid18500378-78">[75]</a> In addition to oral activity, 17α-alkylation also confers a high potential for <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">hepatotoxicity</a>, and all 17α-alkylated AAS have been associated, albeit uncommonly and only after prolonged use (different estimates between 1 and 17%),<a href="#cite_note-Karch-2001-185">[182]</a><a href="#cite_note-pmid20153798-186">[183]</a> with hepatotoxicity.<a href="#cite_note-pmid18500378-78">[75]</a><a href="#cite_note-pmid3042375-187">[184]</a><a href="#cite_note-Jameson-2015-188">[185]</a> In contrast, <a href="/wiki/Testosterone_ester" class="mw-redirect" title="Testosterone ester">testosterone esters</a> have only extremely rarely or never been associated with hepatotoxicity,<a href="#cite_note-pmid20153798-186">[183]</a> and other non-17α-alkylated AAS only rarely,[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] although long-term use may reportedly still increase the risk of hepatic changes (but at a much lower rate than 17α-alkylated AAS and reportedly not at replacement dosages).<a href="#cite_note-Karch-2001-185">[182]</a><a href="#cite_note-Nieschlag-2012-189">[186]</a><a href="#cite_note-Becker-2001-77">[74]</a>[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">additional citation(s) needed</a>] In accordance, D-ring <a href="/wiki/Glucuronide" title="Glucuronide">glucuronides</a> of testosterone and DHT have been found to be cholestatic.<a href="#cite_note-CameronFeuer2012-190">[187]</a> Aside from prohormones and testosterone undecanoate, almost all orally active AAS are 17α-alkylated.<a href="#cite_note-pmid11589254-191">[188]</a> A few AAS that are not 17α-alkylated are orally active.<a href="#cite_note-pmid18500378-78">[75]</a> Some examples include the testosterone 17-ethers <a href="/wiki/Cloxotestosterone" title="Cloxotestosterone">cloxotestosterone</a>, <a href="/wiki/Quinbolone" title="Quinbolone">quinbolone</a>, and <a href="/wiki/Silandrone" title="Silandrone">silandrone</a>,[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] which are prodrugs (to testosterone, <a href="/wiki/Boldenone" title="Boldenone">boldenone</a> (Δ1-testosterone), and testosterone, respectively), the DHT 17-ethers <a href="/wiki/Mepitiostane" title="Mepitiostane">mepitiostane</a>, <a href="/wiki/Mesabolone" title="Mesabolone">mesabolone</a>, and <a href="/wiki/Prostanozol" title="Prostanozol">prostanozol</a> (which are also prodrugs), the 1-methylated DHT derivatives <a href="/wiki/Mesterolone" title="Mesterolone">mesterolone</a> and <a href="/wiki/Metenolone" title="Metenolone">metenolone</a> (although these are relatively weak AAS),<a href="#cite_note-pmid18500378-78">[75]</a><a href="#cite_note-Becker-2001-77">[74]</a> and the 19-nortestosterone derivatives dimethandrolone and 11β-MNT, which have improved resistance to first-pass hepatic metabolism due to their 11β-methyl groups (in contrast to them, the related AAS trestolone (7α-methyl-19-nortestosterone) is not orally active).<a href="#cite_note-pmid18500378-78">[75]</a><a href="#cite_note-pmid16497801-181">[178]</a> As these AAS are not 17α-alkylated, they show minimal potential for hepatotoxicity.<a href="#cite_note-pmid18500378-78">[75]</a> <div class="mw-heading mw-heading4"><h4 id="Neurosteroid_activity">Neurosteroid activity</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=41" title="Edit section: Neurosteroid activity">edit</a>]</div> DHT, via its metabolite <a href="/wiki/3%CE%B1-androstanediol" class="mw-redirect" title="3α-androstanediol">3α-androstanediol</a> (produced by <a href="/wiki/3%CE%B1-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3α-hydroxysteroid dehydrogenase">3α-hydroxysteroid dehydrogenase</a> (3α-HSD)), is a <a href="/wiki/Neurosteroid" title="Neurosteroid">neurosteroid</a> that acts via <a href="/wiki/Positive_allosteric_modulation" class="mw-redirect" title="Positive allosteric modulation">positive allosteric modulation</a> of the <a href="/wiki/GABAA_receptor" title="GABAA receptor">GABAA receptor</a>.<a href="#cite_note-pmid18500378-78">[75]</a> Testosterone, via conversion into DHT, also produces 3α-androstanediol as a metabolite and hence has similar activity.<a href="#cite_note-pmid18500378-78">[75]</a> Some AAS that are or can be 5α-reduced, including testosterone, DHT, <a href="/wiki/Stanozolol" title="Stanozolol">stanozolol</a>, and methyltestosterone, among many others, can or may modulate the GABAA receptor, and this may contribute as an alternative or additional mechanism to their <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> effects in terms of mood, anxiety, aggression, and sex drive.<a href="#cite_note-pmid18500378-78">[75]</a><a href="#cite_note-pmid8294123-167">[164]</a><a href="#cite_note-pmid7603620-168">[165]</a><a href="#cite_note-pmid8858992-169">[166]</a><a href="#cite_note-pmid16814373-170">[167]</a><a href="#cite_note-pmid17433821-171">[168]</a><a href="#cite_note-pmid19376158-172">[169]</a> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=42" title="Edit section: Chemistry">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/List_of_androgens/anabolic_steroids" class="mw-redirect" title="List of androgens/anabolic steroids">List of androgens/anabolic steroids</a>, <a href="/wiki/List_of_androgen_esters" title="List of androgen esters">List of androgen esters</a>, and <a href="/wiki/Structure%E2%80%93activity_relationships_of_anabolic_steroids" title="Structure–activity relationships of anabolic steroids">Structure–activity relationships of anabolic steroids</a></div> AAS are <a href="/wiki/Androstane" title="Androstane">androstane</a> or <a href="/wiki/Estrane" title="Estrane">estrane</a> <a href="/wiki/Steroid" title="Steroid">steroids</a>. They include testosterone (androst-4-en-17β-ol-3-one) and <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivatives</a> with various <a href="/wiki/Structural_modification" class="mw-redirect" title="Structural modification">structural modifications</a> such as:<a href="#cite_note-pmid18500378-78">[75]</a><a href="#cite_note-pmid20020376-192">[189]</a><a href="#cite_note-Llewellyn2011-73">[70]</a> <ul><li><a href="/wiki/17%CE%B1-Alkylated_anabolic_steroid" title="17α-Alkylated anabolic steroid">17α-Alkylation</a>: <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone</a>, <a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">fluoxymesterone</a>, <a href="/wiki/Oxandrolone" title="Oxandrolone">oxandrolone</a>, <a href="/wiki/Oxymetholone" title="Oxymetholone">oxymetholone</a>, <a href="/wiki/Stanozolol" title="Stanozolol">stanozolol</a>, <a href="/wiki/Norethandrolone" title="Norethandrolone">norethandrolone</a>, <a href="/wiki/Ethylestrenol" title="Ethylestrenol">ethylestrenol</a></li> <li><a href="/wiki/19-Nortestosterone" class="mw-redirect" title="19-Nortestosterone">19-Demethylation</a>: <a href="/wiki/Nandrolone" title="Nandrolone">nandrolone</a>, <a href="/wiki/Trenbolone" title="Trenbolone">trenbolone</a>, <a href="/wiki/Norethandrolone" title="Norethandrolone">norethandrolone</a>, <a href="/wiki/Ethylestrenol" title="Ethylestrenol">ethylestrenol</a>, <a href="/wiki/Trestolone" title="Trestolone">trestolone</a>, <a href="/wiki/Dimethandrolone" title="Dimethandrolone">dimethandrolone</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">5α-Reduction</a>: <a href="/wiki/Androstanolone" title="Androstanolone">androstanolone</a>, <a href="/wiki/Drostanolone" title="Drostanolone">drostanolone</a>, <a href="/wiki/Mestanolone" title="Mestanolone">mestanolone</a>, <a href="/wiki/Mesterolone" title="Mesterolone">mesterolone</a>, <a href="/wiki/Metenolone" title="Metenolone">metenolone</a>, <a href="/wiki/Oxandrolone" title="Oxandrolone">oxandrolone</a>, <a href="/wiki/Oxymetholone" title="Oxymetholone">oxymetholone</a>, <a href="/wiki/Stanozolol" title="Stanozolol">stanozolol</a></li> <li><a href="/wiki/Androgen_ester" title="Androgen ester">3β- and/or 17β-esterification</a>: <a href="/wiki/Testosterone_enanthate" title="Testosterone enanthate">testosterone enanthate</a>, <a href="/wiki/Nandrolone_decanoate" title="Nandrolone decanoate">nandrolone decanoate</a>, <a href="/wiki/Drostanolone_propionate" title="Drostanolone propionate">drostanolone propionate</a>, <a href="/wiki/Boldenone_undecylenate" title="Boldenone undecylenate">boldenone undecylenate</a>, <a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">trenbolone acetate</a></li></ul> As well as others such as <a href="/wiki/Boldenone" title="Boldenone">1-dehydrogenation</a> (e.g., <a href="/wiki/Metandienone" title="Metandienone">metandienone</a>, <a href="/wiki/Boldenone" title="Boldenone">boldenone</a>), <a href="/wiki/Mesterolone" title="Mesterolone">1-substitution</a> (e.g., <a href="/wiki/Mesterolone" title="Mesterolone">mesterolone</a>, <a href="/wiki/Metenolone" title="Metenolone">metenolone</a>), <a href="/wiki/Drostanolone" title="Drostanolone">2-substitution</a> (e.g., <a href="/wiki/Drostanolone" title="Drostanolone">drostanolone</a>, <a href="/wiki/Oxymetholone" title="Oxymetholone">oxymetholone</a>, <a href="/wiki/Stanozolol" title="Stanozolol">stanozolol</a>), <a href="/wiki/4-hydroxytestosterone" class="mw-redirect" title="4-hydroxytestosterone">4-substitution</a> (e.g., <a href="/wiki/Clostebol" title="Clostebol">clostebol</a>, <a href="/wiki/Oxabolone" title="Oxabolone">oxabolone</a>), and various other modifications.<a href="#cite_note-pmid18500378-78">[75]</a><a href="#cite_note-pmid20020376-192">[189]</a><a href="#cite_note-Llewellyn2011-73">[70]</a> <table class="wikitable sortable mw-collapsible mw-collapsed" style="font-size:small; text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap"><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:Structural_aspects_of_androgens_and_anabolic_steroids" title="Template:Structural aspects of androgens and anabolic steroids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Structural_aspects_of_androgens_and_anabolic_steroids" title="Template talk:Structural aspects of androgens and anabolic steroids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Structural_aspects_of_androgens_and_anabolic_steroids" title="Special:EditPage/Template:Structural aspects of androgens and anabolic steroids"><abbr title="Edit this template">e</abbr></a></li></ul></div> Structural aspects of androgens and anabolic steroids </caption> <tbody><tr> <th>Classes</th> <th>Androgen</th> <th class="unsortable">Structure</th> <th class="unsortable">Chemical name</th> <th>Features </th></tr> <tr> <td rowspan="11">Testosterone </td> <td><a href="/wiki/4-Hydroxytestosterone" title="4-Hydroxytestosterone">4-Hydroxytestosterone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:4-hydroxytestosterone.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/26/4-hydroxytestosterone.png/30px-4-hydroxytestosterone.png" decoding="async" width="30" height="23" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/26/4-hydroxytestosterone.png/45px-4-hydroxytestosterone.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/26/4-hydroxytestosterone.png/60px-4-hydroxytestosterone.png 2x" data-file-width="858" data-file-height="670" /></a><figcaption></figcaption></figure> </td> <td>4-Hydroxytestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Androstenediol" title="Androstenediol">Androstenediol</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Androstendiol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Androstendiol.svg/30px-Androstendiol.svg.png" decoding="async" width="30" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Androstendiol.svg/45px-Androstendiol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Androstendiol.svg/60px-Androstendiol.svg.png 2x" data-file-width="306" data-file-height="187" /></a><figcaption></figcaption></figure> </td> <td>5-Androstenediol (androst-5-ene-3β,17β-diol) </td> <td>Prohormone </td></tr> <tr> <td><a href="/wiki/Androstenedione" title="Androstenedione">Androstenedione</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Androstendion.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/50/Androstendion.svg/30px-Androstendion.svg.png" decoding="async" width="30" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/50/Androstendion.svg/45px-Androstendion.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/50/Androstendion.svg/60px-Androstendion.svg.png 2x" data-file-width="277" data-file-height="187" /></a><figcaption></figcaption></figure> </td> <td>4-Androstenedione (androst-4-ene-3,17-dione) </td> <td>Prohormone </td></tr> <tr> <td><a href="/wiki/Boldenone" title="Boldenone">Boldenone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Boldenone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Boldenone.svg/30px-Boldenone.svg.png" decoding="async" width="30" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Boldenone.svg/45px-Boldenone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Boldenone.svg/60px-Boldenone.svg.png 2x" data-file-width="545" data-file-height="370" /></a><figcaption></figcaption></figure> </td> <td>1-Dehydrotestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Boldione" title="Boldione">Boldione</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Boldione.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Boldione.png/30px-Boldione.png" decoding="async" width="30" height="21" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Boldione.png/45px-Boldione.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Boldione.png/60px-Boldione.png 2x" data-file-width="809" data-file-height="555" /></a><figcaption></figcaption></figure> </td> <td>1-Dehydro-4-androstenedione </td> <td>Prohormone </td></tr> <tr> <td><a href="/wiki/Clostebol" title="Clostebol">Clostebol</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Clostebol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/91/Clostebol.svg/30px-Clostebol.svg.png" decoding="async" width="30" height="25" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/91/Clostebol.svg/45px-Clostebol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/91/Clostebol.svg/60px-Clostebol.svg.png 2x" data-file-width="1125" data-file-height="920" /></a><figcaption></figcaption></figure> </td> <td>4-Chlorotestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Cloxotestosterone" title="Cloxotestosterone">Cloxotestosterone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Cloxotestosterone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Cloxotestosterone.svg/30px-Cloxotestosterone.svg.png" decoding="async" width="30" height="21" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Cloxotestosterone.svg/45px-Cloxotestosterone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Cloxotestosterone.svg/60px-Cloxotestosterone.svg.png 2x" data-file-width="1355" data-file-height="960" /></a><figcaption></figcaption></figure> </td> <td>Testosterone 17-chloral hemiacetal ether </td> <td>Ether </td></tr> <tr> <td><a href="/wiki/Prasterone" title="Prasterone">Prasterone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Dehydroepiandrosteron.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Dehydroepiandrosteron.svg/30px-Dehydroepiandrosteron.svg.png" decoding="async" width="30" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Dehydroepiandrosteron.svg/45px-Dehydroepiandrosteron.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/66/Dehydroepiandrosteron.svg/60px-Dehydroepiandrosteron.svg.png 2x" data-file-width="293" data-file-height="187" /></a><figcaption></figcaption></figure> </td> <td>5-Dehydroepiandrosterone (androst-5-en-3β-ol-17-one) </td> <td>Prohormone </td></tr> <tr> <td><a href="/wiki/Quinbolone" title="Quinbolone">Quinbolone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Quinbolone.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/26/Quinbolone.png/30px-Quinbolone.png" decoding="async" width="30" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/26/Quinbolone.png/45px-Quinbolone.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/26/Quinbolone.png/60px-Quinbolone.png 2x" data-file-width="1075" data-file-height="662" /></a><figcaption></figcaption></figure> </td> <td>1-Dehydrotestosterone 17β-cyclopentenyl enol ether </td> <td>Ether </td></tr> <tr> <td><a href="/wiki/Silandrone" title="Silandrone">Silandrone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Silandrone.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Silandrone.png/30px-Silandrone.png" decoding="async" width="30" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Silandrone.png/45px-Silandrone.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Silandrone.png/60px-Silandrone.png 2x" data-file-width="990" data-file-height="668" /></a><figcaption></figcaption></figure> </td> <td>Testosterone 17β-trimethylsilyl ether </td> <td>Ether </td></tr> <tr> <td><a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">Testosterone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Testosteron.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Testosteron.svg/30px-Testosteron.svg.png" decoding="async" width="30" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Testosteron.svg/45px-Testosteron.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Testosteron.svg/60px-Testosteron.svg.png 2x" data-file-width="512" data-file-height="341" /></a><figcaption></figcaption></figure> </td> <td>Androst-4-en-17β-ol-3-one </td> <td>– </td></tr> <tr> <td rowspan="18">17α-Alkylated testosterone </td> <td><a href="/wiki/Bolasterone" title="Bolasterone">Bolasterone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Bolasterone.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Bolasterone.png/30px-Bolasterone.png" decoding="async" width="30" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Bolasterone.png/45px-Bolasterone.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Bolasterone.png/60px-Bolasterone.png 2x" data-file-width="853" data-file-height="560" /></a><figcaption></figcaption></figure> </td> <td>7α,17α-Dimethyltestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Calusterone" title="Calusterone">Calusterone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Calusterone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f2/Calusterone.svg/30px-Calusterone.svg.png" decoding="async" width="30" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f2/Calusterone.svg/45px-Calusterone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f2/Calusterone.svg/60px-Calusterone.svg.png 2x" data-file-width="512" data-file-height="342" /></a><figcaption></figcaption></figure> </td> <td>7β,17α-Dimethyltestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Chlorodehydromethylandrostenediol" title="Chlorodehydromethylandrostenediol">Chlorodehydromethylandrostenediol</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Halodrol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Halodrol.svg/30px-Halodrol.svg.png" decoding="async" width="30" height="21" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Halodrol.svg/45px-Halodrol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Halodrol.svg/60px-Halodrol.svg.png 2x" data-file-width="1260" data-file-height="885" /></a><figcaption></figcaption></figure> </td> <td>1-Dehydro-4-chloro-17α-methyl-4-androstenediol </td> <td>Prohormone </td></tr> <tr> <td><a href="/wiki/Chlorodehydromethyltestosterone" title="Chlorodehydromethyltestosterone">Chlorodehydromethyltestosterone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:4-Chlorodehydromethyltestosterone.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e7/4-Chlorodehydromethyltestosterone.png/30px-4-Chlorodehydromethyltestosterone.png" decoding="async" width="30" height="22" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e7/4-Chlorodehydromethyltestosterone.png/45px-4-Chlorodehydromethyltestosterone.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e7/4-Chlorodehydromethyltestosterone.png/60px-4-Chlorodehydromethyltestosterone.png 2x" data-file-width="846" data-file-height="610" /></a><figcaption></figcaption></figure> </td> <td>1-Dehydro-4-chloro-17α-methyltestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Chloromethylandrostenediol" title="Chloromethylandrostenediol">Chloromethylandrostenediol</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Chloromethylandrostenediol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Chloromethylandrostenediol.svg/30px-Chloromethylandrostenediol.svg.png" decoding="async" width="30" height="21" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Chloromethylandrostenediol.svg/45px-Chloromethylandrostenediol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Chloromethylandrostenediol.svg/60px-Chloromethylandrostenediol.svg.png 2x" data-file-width="1260" data-file-height="885" /></a><figcaption></figcaption></figure> </td> <td>4-Chloro-17α-methyl-4-androstenediol </td> <td>– </td></tr> <tr> <td><a href="/wiki/Enestebol" title="Enestebol">Enestebol</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Enestebol.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/01/Enestebol.png/30px-Enestebol.png" decoding="async" width="30" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/01/Enestebol.png/45px-Enestebol.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/01/Enestebol.png/60px-Enestebol.png 2x" data-file-width="856" data-file-height="676" /></a><figcaption></figcaption></figure> </td> <td>1-Dehydro-4-hydroxy-17α-methyltestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Ethyltestosterone" title="Ethyltestosterone">Ethyltestosterone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Ethyltestosterone_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6a/Ethyltestosterone_structure.png/30px-Ethyltestosterone_structure.png" decoding="async" width="30" height="21" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6a/Ethyltestosterone_structure.png/45px-Ethyltestosterone_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6a/Ethyltestosterone_structure.png/60px-Ethyltestosterone_structure.png 2x" data-file-width="1000" data-file-height="688" /></a><figcaption></figcaption></figure> </td> <td>17α-Ethyltestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">Fluoxymesterone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Fluoxymesterone_structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Fluoxymesterone_structure.svg/30px-Fluoxymesterone_structure.svg.png" decoding="async" width="30" height="22" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Fluoxymesterone_structure.svg/45px-Fluoxymesterone_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Fluoxymesterone_structure.svg/60px-Fluoxymesterone_structure.svg.png 2x" data-file-width="1100" data-file-height="790" /></a><figcaption></figcaption></figure> </td> <td>9α-Fluoro-11β-hydroxy-17α-methyltestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Formebolone" title="Formebolone">Formebolone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Formebolone.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Formebolone.png/30px-Formebolone.png" decoding="async" width="30" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Formebolone.png/45px-Formebolone.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Formebolone.png/60px-Formebolone.png 2x" data-file-width="948" data-file-height="561" /></a><figcaption></figcaption></figure> </td> <td>1-Dehydro-2-formyl-11α-hydroxy-17α-methyltestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Hydroxystenozole" title="Hydroxystenozole">Hydroxystenozole</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Hydroxystenozole.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Hydroxystenozole.png/30px-Hydroxystenozole.png" decoding="async" width="30" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Hydroxystenozole.png/45px-Hydroxystenozole.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Hydroxystenozole.png/60px-Hydroxystenozole.png 2x" data-file-width="924" data-file-height="622" /></a><figcaption></figcaption></figure> </td> <td>17α-Methyl-2'H-androsta-2,4-dieno[3,2-c]pyrazol-17β-ol </td> <td>Ring-fused </td></tr> <tr> <td><a href="/wiki/Metandienone" title="Metandienone">Metandienone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Metandienone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/16/Metandienone.svg/30px-Metandienone.svg.png" decoding="async" width="30" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/16/Metandienone.svg/45px-Metandienone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/16/Metandienone.svg/60px-Metandienone.svg.png 2x" data-file-width="512" data-file-height="308" /></a><figcaption></figcaption></figure> </td> <td>1-Dehydro-17α-methyltestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Methandriol" title="Methandriol">Methandriol</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Methandriol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Methandriol.svg/30px-Methandriol.svg.png" decoding="async" width="30" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Methandriol.svg/45px-Methandriol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Methandriol.svg/60px-Methandriol.svg.png 2x" data-file-width="1255" data-file-height="745" /></a><figcaption></figcaption></figure> </td> <td>17α-Methyl-5-androstenediol </td> <td>Prohormone </td></tr> <tr> <td><a href="/wiki/Methylclostebol" title="Methylclostebol">Methylclostebol</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Methylclostebol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Methylclostebol.svg/30px-Methylclostebol.svg.png" decoding="async" width="30" height="25" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Methylclostebol.svg/45px-Methylclostebol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Methylclostebol.svg/60px-Methylclostebol.svg.png 2x" data-file-width="1125" data-file-height="930" /></a><figcaption></figcaption></figure> </td> <td>4-Chloro-17α-methyltestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Methyltestosterone" title="Methyltestosterone">Methyltestosterone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Methyltestosterone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/14/Methyltestosterone.svg/30px-Methyltestosterone.svg.png" decoding="async" width="30" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/14/Methyltestosterone.svg/45px-Methyltestosterone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/14/Methyltestosterone.svg/60px-Methyltestosterone.svg.png 2x" data-file-width="512" data-file-height="299" /></a><figcaption></figcaption></figure> </td> <td>17α-Methyltestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Methyltestosterone_hexyl_ether" class="mw-redirect" title="Methyltestosterone hexyl ether">Methyltestosterone hexyl ether</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Methyltestosterone_3-hexyl_ether.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/28/Methyltestosterone_3-hexyl_ether.svg/30px-Methyltestosterone_3-hexyl_ether.svg.png" decoding="async" width="30" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/28/Methyltestosterone_3-hexyl_ether.svg/45px-Methyltestosterone_3-hexyl_ether.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/28/Methyltestosterone_3-hexyl_ether.svg/60px-Methyltestosterone_3-hexyl_ether.svg.png 2x" data-file-width="1900" data-file-height="745" /></a><figcaption></figcaption></figure> </td> <td>17α-Methyltestosterone 3-hexyl enol ether </td> <td>Ether </td></tr> <tr> <td><a href="/wiki/Oxymesterone" title="Oxymesterone">Oxymesterone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Oxymesterone.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/Oxymesterone.png/30px-Oxymesterone.png" decoding="async" width="30" height="22" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/Oxymesterone.png/45px-Oxymesterone.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/74/Oxymesterone.png/60px-Oxymesterone.png 2x" data-file-width="1000" data-file-height="727" /></a><figcaption></figcaption></figure> </td> <td>4-Hydroxy-17α-methyltestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Penmesterol" title="Penmesterol">Penmesterol</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Penmesterol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/Penmesterol.svg/30px-Penmesterol.svg.png" decoding="async" width="30" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/Penmesterol.svg/45px-Penmesterol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/25/Penmesterol.svg/60px-Penmesterol.svg.png 2x" data-file-width="512" data-file-height="244" /></a><figcaption></figcaption></figure> </td> <td>17α-Methyltestosterone 3-cyclopentyl enol ether </td> <td>Ether </td></tr> <tr> <td><a href="/wiki/Tiomesterone" title="Tiomesterone">Tiomesterone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Tiomesterone_structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Tiomesterone_structure.svg/30px-Tiomesterone_structure.svg.png" decoding="async" width="30" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Tiomesterone_structure.svg/45px-Tiomesterone_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Tiomesterone_structure.svg/60px-Tiomesterone_structure.svg.png 2x" data-file-width="466" data-file-height="374" /></a><figcaption></figcaption></figure> </td> <td>1α,7α-Diacetylthio-17α-methyltestosterone </td> <td>– </td></tr> <tr> <td rowspan="1">Other 17α-substituted testosterone </td> <td><a href="/wiki/Danazol" title="Danazol">Danazol</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Danazol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/Danazol.svg/30px-Danazol.svg.png" decoding="async" width="30" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/Danazol.svg/45px-Danazol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/30/Danazol.svg/60px-Danazol.svg.png 2x" data-file-width="512" data-file-height="335" /></a><figcaption></figcaption></figure> </td> <td>2,3-Isoxazol-17α-ethynyltestosterone </td> <td>Ring-fused </td></tr> <tr> <td rowspan="11">Dihydrotestosterone </td> <td><a href="/wiki/1-Testosterone" title="1-Testosterone">1-Testosterone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:1-testosterone.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/1-testosterone.png/30px-1-testosterone.png" decoding="async" width="30" height="21" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/1-testosterone.png/45px-1-testosterone.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b7/1-testosterone.png/60px-1-testosterone.png 2x" data-file-width="914" data-file-height="640" /></a><figcaption></figcaption></figure> </td> <td>1-Dehydro-4,5α-dihydrotestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Androstanolone" title="Androstanolone">Androstanolone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Androstanolone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Androstanolone.svg/30px-Androstanolone.svg.png" decoding="async" width="30" height="22" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Androstanolone.svg/45px-Androstanolone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Androstanolone.svg/60px-Androstanolone.svg.png 2x" data-file-width="550" data-file-height="405" /></a><figcaption></figcaption></figure> </td> <td>4,5α-Dihydrotestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Bolazine" title="Bolazine">Bolazine</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Bolazine.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Bolazine.png/30px-Bolazine.png" decoding="async" width="30" height="17" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Bolazine.png/45px-Bolazine.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Bolazine.png/60px-Bolazine.png 2x" data-file-width="1761" data-file-height="988" /></a><figcaption></figcaption></figure> </td> <td>C3 azine dimer of drostanolone </td> <td>Dimer </td></tr> <tr> <td><a href="/wiki/Drostanolone" title="Drostanolone">Drostanolone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Drostanolone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Drostanolone.svg/30px-Drostanolone.svg.png" decoding="async" width="30" height="22" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Drostanolone.svg/45px-Drostanolone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Drostanolone.svg/60px-Drostanolone.svg.png 2x" data-file-width="1241" data-file-height="894" /></a><figcaption></figcaption></figure> </td> <td>2α-Methyl-4,5α-dihydrotestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Epitiostanol.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Epitiostanol.png/30px-Epitiostanol.png" decoding="async" width="30" height="21" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Epitiostanol.png/45px-Epitiostanol.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Epitiostanol.png/60px-Epitiostanol.png 2x" data-file-width="854" data-file-height="612" /></a><figcaption></figcaption></figure> </td> <td>2α,3α-Epithio-3-deketo-4,5α-dihydrotestosterone </td> <td>Ring-fused </td></tr> <tr> <td><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Mepitiostane.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Mepitiostane.svg/30px-Mepitiostane.svg.png" decoding="async" width="30" height="23" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Mepitiostane.svg/45px-Mepitiostane.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Mepitiostane.svg/60px-Mepitiostane.svg.png 2x" data-file-width="512" data-file-height="397" /></a><figcaption></figcaption></figure> </td> <td>2α,3α-Epithio-3-deketo-4,5α-dihydrotestosterone 17β-(1-methoxycyclopentane) ether </td> <td>Ring-fused; Ether </td></tr> <tr> <td><a href="/wiki/Mesabolone" title="Mesabolone">Mesabolone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Mesabolone.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Mesabolone.png/30px-Mesabolone.png" decoding="async" width="30" height="22" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Mesabolone.png/45px-Mesabolone.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/95/Mesabolone.png/60px-Mesabolone.png 2x" data-file-width="1083" data-file-height="806" /></a><figcaption></figcaption></figure> </td> <td>1-Dehydro-4,5α-Dihydrotestosterone 17β-(1-methoxycyclohexane) ether </td> <td>Ether </td></tr> <tr> <td><a href="/wiki/Mesterolone" title="Mesterolone">Mesterolone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Mesterolone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/38/Mesterolone.svg/30px-Mesterolone.svg.png" decoding="async" width="30" height="22" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/38/Mesterolone.svg/45px-Mesterolone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/38/Mesterolone.svg/60px-Mesterolone.svg.png 2x" data-file-width="550" data-file-height="405" /></a><figcaption></figcaption></figure> </td> <td>1α-Methyl-4,5α-dihydrotestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Metenolone" title="Metenolone">Metenolone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Metenolone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/de/Metenolone.svg/30px-Metenolone.svg.png" decoding="async" width="30" height="22" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/de/Metenolone.svg/45px-Metenolone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/de/Metenolone.svg/60px-Metenolone.svg.png 2x" data-file-width="1140" data-file-height="840" /></a><figcaption></figcaption></figure> </td> <td>1-Dehydro-1-methyl-4,5α-dihydrotestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Prostanozol" title="Prostanozol">Prostanozol</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Prostanozol.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Prostanozol.png/30px-Prostanozol.png" decoding="async" width="30" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Prostanozol.png/45px-Prostanozol.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Prostanozol.png/60px-Prostanozol.png 2x" data-file-width="1000" data-file-height="612" /></a><figcaption></figcaption></figure> </td> <td>2'H-5α-Androst-2-eno[3,2-c]pyrazol-17β-ol 17β-tetrahydropyran ether </td> <td>Ether </td></tr> <tr> <td><a href="/wiki/Stenbolone" title="Stenbolone">Stenbolone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Stenbolone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/Stenbolone.svg/30px-Stenbolone.svg.png" decoding="async" width="30" height="22" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/Stenbolone.svg/45px-Stenbolone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/dc/Stenbolone.svg/60px-Stenbolone.svg.png 2x" data-file-width="1140" data-file-height="840" /></a><figcaption></figcaption></figure> </td> <td>1-Dehydro-2-methyl-4,5α-dihydrotestosterone </td> <td>– </td></tr> <tr> <td rowspan="13">17α-Alkylated dihydrotestosterone </td> <td><a href="/wiki/Androisoxazole" title="Androisoxazole">Androisoxazole</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Androisoxazole.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Androisoxazole.png/30px-Androisoxazole.png" decoding="async" width="30" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Androisoxazole.png/45px-Androisoxazole.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/Androisoxazole.png/60px-Androisoxazole.png 2x" data-file-width="1000" data-file-height="617" /></a><figcaption></figcaption></figure> </td> <td>17α-Methyl-5α-androstano[3,2-c]isoxazol-17β-ol </td> <td>Ring-fused </td></tr> <tr> <td><a href="/wiki/Desoxymethyltestosterone" title="Desoxymethyltestosterone">Desoxymethyltestosterone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Desoxymethyltestosterone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/Desoxymethyltestosterone.svg/30px-Desoxymethyltestosterone.svg.png" decoding="async" width="30" height="23" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/Desoxymethyltestosterone.svg/45px-Desoxymethyltestosterone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2b/Desoxymethyltestosterone.svg/60px-Desoxymethyltestosterone.svg.png 2x" data-file-width="510" data-file-height="385" /></a><figcaption></figcaption></figure> </td> <td>2-Dehydro-3-deketo-4,5α-dihydro-17α-methyltestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Furazabol" title="Furazabol">Furazabol</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Furazabol.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Furazabol.png/30px-Furazabol.png" decoding="async" width="30" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Furazabol.png/45px-Furazabol.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Furazabol.png/60px-Furazabol.png 2x" data-file-width="625" data-file-height="374" /></a><figcaption></figcaption></figure> </td> <td>17α-Methyl-5α-androstano[2,3-c][1,2,5]oxadiazol-17β-ol </td> <td>Ring-fused </td></tr> <tr> <td><a href="/wiki/Mebolazine" title="Mebolazine">Mebolazine</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Mebolazine.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/17/Mebolazine.png/30px-Mebolazine.png" decoding="async" width="30" height="17" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/17/Mebolazine.png/45px-Mebolazine.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/17/Mebolazine.png/60px-Mebolazine.png 2x" data-file-width="1754" data-file-height="999" /></a><figcaption></figcaption></figure> </td> <td>C3 azine dimer of methasterone </td> <td>Dimer </td></tr> <tr> <td><a href="/wiki/Mestanolone" title="Mestanolone">Mestanolone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Mestanolone.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Mestanolone.png/30px-Mestanolone.png" decoding="async" width="30" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Mestanolone.png/45px-Mestanolone.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Mestanolone.png/60px-Mestanolone.png 2x" data-file-width="566" data-file-height="374" /></a><figcaption></figcaption></figure> </td> <td>4,5α-Dihydro-17α-methyltestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Methasterone" title="Methasterone">Methasterone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Methasterone.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3d/Methasterone.png/30px-Methasterone.png" decoding="async" width="30" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3d/Methasterone.png/45px-Methasterone.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3d/Methasterone.png/60px-Methasterone.png 2x" data-file-width="1000" data-file-height="667" /></a><figcaption></figcaption></figure> </td> <td>2α,17α-Dimethyl-4,5α-dihydrotestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Methyl-1-testosterone" title="Methyl-1-testosterone">Methyl-1-testosterone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Methyl-1-testosterone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/Methyl-1-testosterone.svg/30px-Methyl-1-testosterone.svg.png" decoding="async" width="30" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/Methyl-1-testosterone.svg/45px-Methyl-1-testosterone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/30/Methyl-1-testosterone.svg/60px-Methyl-1-testosterone.svg.png 2x" data-file-width="512" data-file-height="330" /></a><figcaption></figcaption></figure> </td> <td>1-Dehydro-4,5α-dihydro-17α-methyltestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Methyldiazinol" title="Methyldiazinol">Methyldiazinol</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Methyldiazirinol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Methyldiazirinol.svg/30px-Methyldiazirinol.svg.png" decoding="async" width="30" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Methyldiazirinol.svg/45px-Methyldiazirinol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/41/Methyldiazirinol.svg/60px-Methyldiazirinol.svg.png 2x" data-file-width="1120" data-file-height="728" /></a><figcaption></figcaption></figure> </td> <td>3-Deketo-3-azi-4,5α-dihydro-17α-methyltestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Methylepitiostanol" title="Methylepitiostanol">Methylepitiostanol</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Methylepitiostanol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Methylepitiostanol.svg/30px-Methylepitiostanol.svg.png" decoding="async" width="30" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Methylepitiostanol.svg/45px-Methylepitiostanol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Methylepitiostanol.svg/60px-Methylepitiostanol.svg.png 2x" data-file-width="512" data-file-height="343" /></a><figcaption></figcaption></figure> </td> <td>2α,3α-Epithio-3-deketo-4,5α-dihydro-17α-methyltestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Methylstenbolone" title="Methylstenbolone">Methylstenbolone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Methylstenbolone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8f/Methylstenbolone.svg/30px-Methylstenbolone.svg.png" decoding="async" width="30" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8f/Methylstenbolone.svg/45px-Methylstenbolone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8f/Methylstenbolone.svg/60px-Methylstenbolone.svg.png 2x" data-file-width="1100" data-file-height="730" /></a><figcaption></figcaption></figure> </td> <td>1-Dehydro-2,17α-dimethyl-4,5α-dihydrotestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Oxandrolone" title="Oxandrolone">Oxandrolone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Oxandrolone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Oxandrolone.svg/30px-Oxandrolone.svg.png" decoding="async" width="30" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Oxandrolone.svg/45px-Oxandrolone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Oxandrolone.svg/60px-Oxandrolone.svg.png 2x" data-file-width="512" data-file-height="338" /></a><figcaption></figcaption></figure> </td> <td>2-Oxa-4,5α-dihydro-17α-methyltestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Oxymetholone" title="Oxymetholone">Oxymetholone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Oxymetholone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Oxymetholone.svg/30px-Oxymetholone.svg.png" decoding="async" width="30" height="17" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Oxymetholone.svg/45px-Oxymetholone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Oxymetholone.svg/60px-Oxymetholone.svg.png 2x" data-file-width="512" data-file-height="292" /></a><figcaption></figcaption></figure> </td> <td>2-Hydroxymethylene-4,5α-dihydro-17α-methyltestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Stanozolol" title="Stanozolol">Stanozolol</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Stanozolol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Stanozolol.svg/30px-Stanozolol.svg.png" decoding="async" width="30" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Stanozolol.svg/45px-Stanozolol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Stanozolol.svg/60px-Stanozolol.svg.png 2x" data-file-width="512" data-file-height="299" /></a><figcaption></figcaption></figure> </td> <td>17α-Methyl-2'H-5α-androst-2-eno[3,2-c]pyrazol-17β-ol </td> <td>Ring-fused </td></tr> <tr> <td rowspan="17">19-Nortestosterone </td> <td><a href="/wiki/11%CE%B2-Methyl-19-nortestosterone" title="11β-Methyl-19-nortestosterone">11β-Methyl-19-nortestosterone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:11%CE%B2-Methyl-19-nortestosterone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/11%CE%B2-Methyl-19-nortestosterone.svg/30px-11%CE%B2-Methyl-19-nortestosterone.svg.png" decoding="async" width="30" height="21" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/11%CE%B2-Methyl-19-nortestosterone.svg/45px-11%CE%B2-Methyl-19-nortestosterone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6c/11%CE%B2-Methyl-19-nortestosterone.svg/60px-11%CE%B2-Methyl-19-nortestosterone.svg.png 2x" data-file-width="1125" data-file-height="780" /></a><figcaption></figcaption></figure> </td> <td>11β-Methyl-19-nortestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/19-Nor-5-androstenediol" title="19-Nor-5-androstenediol">19-Nor-5-androstenediol</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:19-Nor-5-androstenediol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/42/19-Nor-5-androstenediol.svg/30px-19-Nor-5-androstenediol.svg.png" decoding="async" width="30" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/42/19-Nor-5-androstenediol.svg/45px-19-Nor-5-androstenediol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/42/19-Nor-5-androstenediol.svg/60px-19-Nor-5-androstenediol.svg.png 2x" data-file-width="1175" data-file-height="780" /></a><figcaption></figcaption></figure> </td> <td>19-Nor-5-androstenediol </td> <td>Prohormone </td></tr> <tr> <td><a href="/wiki/19-Nordehydroepiandrosterone" title="19-Nordehydroepiandrosterone">19-Nordehydroepiandrosterone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:19-Nordehydroepiandrosterone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/19-Nordehydroepiandrosterone.svg/30px-19-Nordehydroepiandrosterone.svg.png" decoding="async" width="30" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/19-Nordehydroepiandrosterone.svg/45px-19-Nordehydroepiandrosterone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/53/19-Nordehydroepiandrosterone.svg/60px-19-Nordehydroepiandrosterone.svg.png 2x" data-file-width="203" data-file-height="123" /></a><figcaption></figcaption></figure> </td> <td>19-Nor-5-dehydroepiandrosterone </td> <td>Prohormone </td></tr> <tr> <td><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Bolandiol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Bolandiol.svg/30px-Bolandiol.svg.png" decoding="async" width="30" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Bolandiol.svg/45px-Bolandiol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Bolandiol.svg/60px-Bolandiol.svg.png 2x" data-file-width="512" data-file-height="311" /></a><figcaption></figcaption></figure> </td> <td>19-Nor-4-androstenediol </td> <td>Prohormone </td></tr> <tr> <td><a href="/wiki/Bolandione" title="Bolandione">Bolandione</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:19-norandrostenedione.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/19-norandrostenedione.png/30px-19-norandrostenedione.png" decoding="async" width="30" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/19-norandrostenedione.png/45px-19-norandrostenedione.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0d/19-norandrostenedione.png/60px-19-norandrostenedione.png 2x" data-file-width="1020" data-file-height="693" /></a><figcaption></figcaption></figure> </td> <td>19-Nor-4-androstenedione </td> <td>Prohormone </td></tr> <tr> <td><a href="/wiki/Bolmantalate" title="Bolmantalate">Bolmantalate</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Bolmantalate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Bolmantalate.svg/30px-Bolmantalate.svg.png" decoding="async" width="30" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Bolmantalate.svg/45px-Bolmantalate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Bolmantalate.svg/60px-Bolmantalate.svg.png 2x" data-file-width="1475" data-file-height="950" /></a><figcaption></figcaption></figure> </td> <td>19-Nortestosterone 17β-adamantoate </td> <td>Ester </td></tr> <tr> <td><a href="/wiki/Dienedione" title="Dienedione">Dienedione</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Dienedione.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/51/Dienedione.svg/30px-Dienedione.svg.png" decoding="async" width="30" height="21" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/51/Dienedione.svg/45px-Dienedione.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/51/Dienedione.svg/60px-Dienedione.svg.png 2x" data-file-width="512" data-file-height="360" /></a><figcaption></figcaption></figure> </td> <td>9-Dehydro-19-nor-4-androstenedione </td> <td>Prohormone </td></tr> <tr> <td><a href="/wiki/Dienolone" title="Dienolone">Dienolone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Dienolone_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Dienolone_structure.png/30px-Dienolone_structure.png" decoding="async" width="30" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Dienolone_structure.png/45px-Dienolone_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/96/Dienolone_structure.png/60px-Dienolone_structure.png 2x" data-file-width="1000" data-file-height="666" /></a><figcaption></figcaption></figure> </td> <td>9-Dehydro-19-nortestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Dimethandrolone" title="Dimethandrolone">Dimethandrolone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Dimethandrolone_structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Dimethandrolone_structure.svg/30px-Dimethandrolone_structure.svg.png" decoding="async" width="30" height="21" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Dimethandrolone_structure.svg/45px-Dimethandrolone_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/19/Dimethandrolone_structure.svg/60px-Dimethandrolone_structure.svg.png 2x" data-file-width="1125" data-file-height="780" /></a><figcaption></figcaption></figure> </td> <td>7α,11β-Dimethyl-19-nortestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Methoxydienone" title="Methoxydienone">Methoxydienone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Methoxydienone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Methoxydienone.svg/30px-Methoxydienone.svg.png" decoding="async" width="30" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Methoxydienone.svg/45px-Methoxydienone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Methoxydienone.svg/60px-Methoxydienone.svg.png 2x" data-file-width="1165" data-file-height="775" /></a><figcaption></figcaption></figure> </td> <td>2,5(10)-Didehydro-18-methyl-19-norepiandrosterone 3-methyl ether </td> <td>Prohormone; Ether </td></tr> <tr> <td><a href="/wiki/Nandrolone" title="Nandrolone">Nandrolone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Nandrolone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/48/Nandrolone.svg/30px-Nandrolone.svg.png" decoding="async" width="30" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/48/Nandrolone.svg/45px-Nandrolone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/48/Nandrolone.svg/60px-Nandrolone.svg.png 2x" data-file-width="512" data-file-height="342" /></a><figcaption></figcaption></figure> </td> <td>19-Nortestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Norclostebol" title="Norclostebol">Norclostebol</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Norclostebol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Norclostebol.svg/30px-Norclostebol.svg.png" decoding="async" width="30" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Norclostebol.svg/45px-Norclostebol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/71/Norclostebol.svg/60px-Norclostebol.svg.png 2x" data-file-width="1037" data-file-height="830" /></a><figcaption></figcaption></figure> </td> <td>4-Chloro-19-nortestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Oxabolone" title="Oxabolone">Oxabolone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Oxabolone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Oxabolone.svg/30px-Oxabolone.svg.png" decoding="async" width="30" height="23" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Oxabolone.svg/45px-Oxabolone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Oxabolone.svg/60px-Oxabolone.svg.png 2x" data-file-width="512" data-file-height="399" /></a><figcaption></figcaption></figure> </td> <td>4-Hydroxy-19-nortestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Trestolone" title="Trestolone">Trestolone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Trestolone_structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/91/Trestolone_structure.svg/30px-Trestolone_structure.svg.png" decoding="async" width="30" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/91/Trestolone_structure.svg/45px-Trestolone_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/91/Trestolone_structure.svg/60px-Trestolone_structure.svg.png 2x" data-file-width="512" data-file-height="331" /></a><figcaption></figcaption></figure> </td> <td>7α-Methyl-19-nortestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Trenbolone" title="Trenbolone">Trenbolone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Trenbolone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Trenbolone.svg/30px-Trenbolone.svg.png" decoding="async" width="30" height="21" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Trenbolone.svg/45px-Trenbolone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/db/Trenbolone.svg/60px-Trenbolone.svg.png 2x" data-file-width="1125" data-file-height="780" /></a><figcaption></figcaption></figure> </td> <td>9,11-Didehydro-19-nortestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Trendione" title="Trendione">Trendione</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Trendione.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Trendione.svg/30px-Trendione.svg.png" decoding="async" width="30" height="21" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Trendione.svg/45px-Trendione.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Trendione.svg/60px-Trendione.svg.png 2x" data-file-width="990" data-file-height="695" /></a><figcaption></figcaption></figure> </td> <td>9,11-Didehydro-19-nor-4-androstenedione </td> <td>Prohormone </td></tr> <tr> <td><a href="/wiki/Trestione" class="mw-redirect" title="Trestione">Trestione</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:7%CE%B1-Methyl-19-norandrostenedione.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/7%CE%B1-Methyl-19-norandrostenedione.svg/30px-7%CE%B1-Methyl-19-norandrostenedione.svg.png" decoding="async" width="30" height="22" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/7%CE%B1-Methyl-19-norandrostenedione.svg/45px-7%CE%B1-Methyl-19-norandrostenedione.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fb/7%CE%B1-Methyl-19-norandrostenedione.svg/60px-7%CE%B1-Methyl-19-norandrostenedione.svg.png 2x" data-file-width="1075" data-file-height="780" /></a><figcaption></figcaption></figure> </td> <td>7α-Methyl-19-nor-4-androstenedione </td> <td>Prohormone </td></tr> <tr> <td rowspan="14">17α-Alkylated 19-nortestosterone </td> <td><a href="/wiki/Dimethyltrienolone" title="Dimethyltrienolone">Dimethyltrienolone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:7a17a-dimethyltrenbolone.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/7a17a-dimethyltrenbolone.png/30px-7a17a-dimethyltrenbolone.png" decoding="async" width="30" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/7a17a-dimethyltrenbolone.png/45px-7a17a-dimethyltrenbolone.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/96/7a17a-dimethyltrenbolone.png/60px-7a17a-dimethyltrenbolone.png 2x" data-file-width="1000" data-file-height="606" /></a><figcaption></figcaption></figure> </td> <td>7α,17α-Dimethyl-9,11-didehydro-19-nortestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Dimethyldienolone" title="Dimethyldienolone">Dimethyldienolone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Dimethyldienolone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Dimethyldienolone.svg/30px-Dimethyldienolone.svg.png" decoding="async" width="30" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Dimethyldienolone.svg/45px-Dimethyldienolone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Dimethyldienolone.svg/60px-Dimethyldienolone.svg.png 2x" data-file-width="1125" data-file-height="660" /></a><figcaption></figcaption></figure> </td> <td>7α,17α-Dimethyl-9-dehydro-19-nortestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Ethyldienolone" title="Ethyldienolone">Ethyldienolone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Ethyldienolone.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/34/Ethyldienolone.png/30px-Ethyldienolone.png" decoding="async" width="30" height="21" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/34/Ethyldienolone.png/45px-Ethyldienolone.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/34/Ethyldienolone.png/60px-Ethyldienolone.png 2x" data-file-width="1000" data-file-height="688" /></a><figcaption></figcaption></figure> </td> <td>9-Dehydro-17α-ethyl-19-nortestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Ethylestrenol" title="Ethylestrenol">Ethylestrenol</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Ethylestrenol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Ethylestrenol.svg/30px-Ethylestrenol.svg.png" decoding="async" width="30" height="23" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Ethylestrenol.svg/45px-Ethylestrenol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Ethylestrenol.svg/60px-Ethylestrenol.svg.png 2x" data-file-width="512" data-file-height="390" /></a><figcaption></figcaption></figure> </td> <td>17α-Ethyl-3-deketo-19-nortestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Methyldienolone" title="Methyldienolone">Methyldienolone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Methyldienolone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Methyldienolone.svg/30px-Methyldienolone.svg.png" decoding="async" width="30" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Methyldienolone.svg/45px-Methyldienolone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Methyldienolone.svg/60px-Methyldienolone.svg.png 2x" data-file-width="512" data-file-height="299" /></a><figcaption></figcaption></figure> </td> <td>9-Dehydro-17α-methyl-19-nortestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Methylhydroxynandrolone" title="Methylhydroxynandrolone">Methylhydroxynandrolone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Methylhydroxynandrolone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Methylhydroxynandrolone.svg/30px-Methylhydroxynandrolone.svg.png" decoding="async" width="30" height="22" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Methylhydroxynandrolone.svg/45px-Methylhydroxynandrolone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Methylhydroxynandrolone.svg/60px-Methylhydroxynandrolone.svg.png 2x" data-file-width="1205" data-file-height="885" /></a><figcaption></figcaption></figure> </td> <td>4-Hydroxy-17α-methyl-19-nortestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Metribolone" title="Metribolone">Metribolone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Methyltrienolone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f2/Methyltrienolone.svg/30px-Methyltrienolone.svg.png" decoding="async" width="30" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f2/Methyltrienolone.svg/45px-Methyltrienolone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f2/Methyltrienolone.svg/60px-Methyltrienolone.svg.png 2x" data-file-width="585" data-file-height="350" /></a><figcaption></figcaption></figure> </td> <td>9,11-Didehydro-17α-methyl-19-nortestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Mibolerone" title="Mibolerone">Mibolerone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Mibolerone_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Mibolerone_structure.png/30px-Mibolerone_structure.png" decoding="async" width="30" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Mibolerone_structure.png/45px-Mibolerone_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Mibolerone_structure.png/60px-Mibolerone_structure.png 2x" data-file-width="904" data-file-height="538" /></a><figcaption></figcaption></figure> </td> <td>7α,17α-Dimethyl-19-nortestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Norboletone" title="Norboletone">Norboletone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Norboletone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Norboletone.svg/30px-Norboletone.svg.png" decoding="async" width="30" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Norboletone.svg/45px-Norboletone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Norboletone.svg/60px-Norboletone.svg.png 2x" data-file-width="512" data-file-height="341" /></a><figcaption></figcaption></figure> </td> <td>17α-Ethyl-18-methyl-19-nortestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Norethandrolone_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Norethandrolone_structure.png/30px-Norethandrolone_structure.png" decoding="async" width="30" height="21" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Norethandrolone_structure.png/45px-Norethandrolone_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/64/Norethandrolone_structure.png/60px-Norethandrolone_structure.png 2x" data-file-width="904" data-file-height="638" /></a><figcaption></figcaption></figure> </td> <td>17α-Ethyl-19-nortestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Methylestrenolone.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c5/Methylestrenolone.png/30px-Methylestrenolone.png" decoding="async" width="30" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c5/Methylestrenolone.png/45px-Methylestrenolone.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c5/Methylestrenolone.png/60px-Methylestrenolone.png 2x" data-file-width="841" data-file-height="561" /></a><figcaption></figcaption></figure> </td> <td>17α-Methyl-19-nortestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Propetandrol" title="Propetandrol">Propetandrol</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Propetandrol.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Propetandrol.png/30px-Propetandrol.png" decoding="async" width="30" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Propetandrol.png/45px-Propetandrol.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Propetandrol.png/60px-Propetandrol.png 2x" data-file-width="1222" data-file-height="561" /></a><figcaption></figcaption></figure> </td> <td>17α-Ethyl-19-nortestosterone 3-propionate </td> <td>Ester </td></tr> <tr> <td><a href="/wiki/RU-2309" title="RU-2309">RU-2309</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:RU-2309.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/RU-2309.svg/30px-RU-2309.svg.png" decoding="async" width="30" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/RU-2309.svg/45px-RU-2309.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/80/RU-2309.svg/60px-RU-2309.svg.png 2x" data-file-width="1125" data-file-height="690" /></a><figcaption></figcaption></figure> </td> <td>9,11-Didehydro-17α,18-dimethyl-19-nortestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Tetrahydrogestrinone" title="Tetrahydrogestrinone">Tetrahydrogestrinone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Tetrahydrogestrinone_Structural_Formula_V1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Tetrahydrogestrinone_Structural_Formula_V1.svg/30px-Tetrahydrogestrinone_Structural_Formula_V1.svg.png" decoding="async" width="30" height="21" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Tetrahydrogestrinone_Structural_Formula_V1.svg/45px-Tetrahydrogestrinone_Structural_Formula_V1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Tetrahydrogestrinone_Structural_Formula_V1.svg/60px-Tetrahydrogestrinone_Structural_Formula_V1.svg.png 2x" data-file-width="512" data-file-height="352" /></a><figcaption></figcaption></figure> </td> <td>9,11-Didehydro-17α-ethyl-18-methyl-19-nortestosterone </td> <td>– </td></tr> <tr> <td rowspan="3">Other 17α-substituted 19-nortestosterone </td> <td><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Gestrinone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/df/Gestrinone.svg/30px-Gestrinone.svg.png" decoding="async" width="30" height="22" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/df/Gestrinone.svg/45px-Gestrinone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/df/Gestrinone.svg/60px-Gestrinone.svg.png 2x" data-file-width="512" data-file-height="373" /></a><figcaption></figcaption></figure> </td> <td>9,11-Didehydro-17α-ethynyl-18-methyl-19-nortestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Tibolone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/15/Tibolone.svg/30px-Tibolone.svg.png" decoding="async" width="30" height="22" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/15/Tibolone.svg/45px-Tibolone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/15/Tibolone.svg/60px-Tibolone.svg.png 2x" data-file-width="512" data-file-height="373" /></a><figcaption></figcaption></figure> </td> <td>5(10)-Dehydro-7α-methyl-17α-ethynyl-19-nortestosterone </td> <td>– </td></tr> <tr> <td><a href="/wiki/Vinyltestosterone" title="Vinyltestosterone">Vinyltestosterone</a>a </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Norvinisterone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/40/Norvinisterone.svg/30px-Norvinisterone.svg.png" decoding="async" width="30" height="21" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/40/Norvinisterone.svg/45px-Norvinisterone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/40/Norvinisterone.svg/60px-Norvinisterone.svg.png 2x" data-file-width="512" data-file-height="352" /></a><figcaption></figcaption></figure> </td> <td>17α-Ethenyltestosterone </td> <td>– </td></tr> <tr class="sortbottom"> <td colspan="5" style="width: 1px; background-color:#eaecf0; text-align: center;">Notes: Esters of androgens and anabolic steroids are mostly not included in this table; see <a href="/wiki/List_of_androgen_esters" title="List of androgen esters">here</a> instead. Weakly androgenic progestins are mostly not included in this table; see <a href="/wiki/Template:Structural_aspects_of_marketed_progestogens" class="mw-redirect" title="Template:Structural aspects of marketed progestogens">here</a> instead. Footnotes: a = Never marketed. </td></tr></tbody></table> <table class="wikitable sortable mw-collapsible mw-collapsed" style="font-size:small; text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap"><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:Structural_properties_of_major_testosterone_esters" title="Template:Structural properties of major testosterone esters"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Structural_properties_of_major_testosterone_esters" title="Template talk:Structural properties of major testosterone esters"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Structural_properties_of_major_testosterone_esters" title="Special:EditPage/Template:Structural properties of major testosterone esters"><abbr title="Edit this template">e</abbr></a></li></ul></div> Structural properties of major testosterone esters </caption> <tbody><tr> <th rowspan="2">Androgen</th> <th rowspan="2" class="unsortable">Structure</th> <th colspan="4">Ester</th> <th rowspan="2">Relative <abbr title="molecular weight">mol. weight</abbr></th> <th rowspan="2">Relative <abbr title="testosterone">T</abbr> contentb</th> <th rowspan="2">logPc </th></tr> <tr> <th>Position(s)</th> <th>Moiet(ies)</th> <th>Type</th> <th>Lengtha </th></tr> <tr> <td><a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">Testosterone</a></td> <td style="text-align:center;"><a href="/wiki/File:Testosteron.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Testosteron.svg/35px-Testosteron.svg.png" decoding="async" width="35" height="23" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Testosteron.svg/53px-Testosteron.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Testosteron.svg/70px-Testosteron.svg.png 2x" data-file-width="512" data-file-height="341" /></a></td> <td>–</td> <td>–</td> <td>–</td> <td>–</td> <td>1.00</td> <td>1.00</td> <td>3.0–3.4 </td></tr> <tr> <td><a href="/wiki/Testosterone_propionate" title="Testosterone propionate">Testosterone propionate</a></td> <td style="text-align:center;"><a href="/wiki/File:Testosterone_propionate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Testosterone_propionate.svg/35px-Testosterone_propionate.svg.png" decoding="async" width="35" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Testosterone_propionate.svg/53px-Testosterone_propionate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/93/Testosterone_propionate.svg/70px-Testosterone_propionate.svg.png 2x" data-file-width="1310" data-file-height="900" /></a></td> <td>C17β</td> <td><a href="/wiki/Propanoic_acid" class="mw-redirect" title="Propanoic acid">Propanoic acid</a></td> <td>Straight-chain fatty acid</td> <td>3</td> <td>1.19</td> <td>0.84</td> <td>3.7–4.9 </td></tr> <tr> <td><a href="/wiki/Testosterone_isobutyrate" title="Testosterone isobutyrate">Testosterone isobutyrate</a></td> <td style="text-align:center;"><a href="/wiki/File:Testosterone_isobutyrate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Testosterone_isobutyrate.svg/35px-Testosterone_isobutyrate.svg.png" decoding="async" width="35" height="23" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Testosterone_isobutyrate.svg/53px-Testosterone_isobutyrate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Testosterone_isobutyrate.svg/70px-Testosterone_isobutyrate.svg.png 2x" data-file-width="685" data-file-height="450" /></a></td> <td>C17β</td> <td><a href="/wiki/Isobutyric_acid" title="Isobutyric acid">Isobutyric acid</a></td> <td>Branched-chain fatty acid</td> <td>– (~3)</td> <td>1.24</td> <td>0.80</td> <td>4.9–5.3 </td></tr> <tr> <td><a href="/wiki/Testosterone_isocaproate" title="Testosterone isocaproate">Testosterone isocaproate</a></td> <td style="text-align:center;"><a href="/wiki/File:Testosterone_isocaproate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Testosterone_isocaproate.svg/35px-Testosterone_isocaproate.svg.png" decoding="async" width="35" height="22" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Testosterone_isocaproate.svg/53px-Testosterone_isocaproate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Testosterone_isocaproate.svg/70px-Testosterone_isocaproate.svg.png 2x" data-file-width="1585" data-file-height="995" /></a></td> <td>C17β</td> <td><a href="/wiki/Isohexanoic_acid" class="mw-redirect" title="Isohexanoic acid">Isohexanoic acid</a></td> <td>Branched-chain fatty acid</td> <td>– (~5)</td> <td>1.34</td> <td>0.75</td> <td>4.4–6.3 </td></tr> <tr> <td><a href="/wiki/Testosterone_caproate" title="Testosterone caproate">Testosterone caproate</a></td> <td style="text-align:center;"><a href="/wiki/File:Testosterone_caproate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Testosterone_caproate.svg/35px-Testosterone_caproate.svg.png" decoding="async" width="35" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Testosterone_caproate.svg/53px-Testosterone_caproate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/70/Testosterone_caproate.svg/70px-Testosterone_caproate.svg.png 2x" data-file-width="870" data-file-height="475" /></a></td> <td>C17β</td> <td><a href="/wiki/Hexanoic_acid" class="mw-redirect" title="Hexanoic acid">Hexanoic acid</a></td> <td>Straight-chain fatty acid</td> <td>6</td> <td>1.35</td> <td>0.75</td> <td>5.8–6.5 </td></tr> <tr> <td><a href="/wiki/Testosterone_phenylpropionate" title="Testosterone phenylpropionate">Testosterone phenylpropionate</a></td> <td style="text-align:center;"><a href="/wiki/File:Testosterone_phenpropionate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/08/Testosterone_phenpropionate.svg/35px-Testosterone_phenpropionate.svg.png" decoding="async" width="35" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/08/Testosterone_phenpropionate.svg/53px-Testosterone_phenpropionate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/08/Testosterone_phenpropionate.svg/70px-Testosterone_phenpropionate.svg.png 2x" data-file-width="870" data-file-height="475" /></a></td> <td>C17β</td> <td><a href="/wiki/Phenylpropanoic_acid" title="Phenylpropanoic acid">Phenylpropanoic acid</a></td> <td>Aromatic fatty acid</td> <td>– (~6)</td> <td>1.46</td> <td>0.69</td> <td>5.8–6.5 </td></tr> <tr> <td><a href="/wiki/Testosterone_cypionate" title="Testosterone cypionate">Testosterone cypionate</a></td> <td style="text-align:center;"><a href="/wiki/File:Testosterone_cypionate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Testosterone_cypionate.svg/35px-Testosterone_cypionate.svg.png" decoding="async" width="35" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Testosterone_cypionate.svg/53px-Testosterone_cypionate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Testosterone_cypionate.svg/70px-Testosterone_cypionate.svg.png 2x" data-file-width="1650" data-file-height="900" /></a></td> <td>C17β</td> <td><a href="/wiki/Cyclopentylpropanoic_acid" class="mw-redirect" title="Cyclopentylpropanoic acid">Cyclopentylpropanoic acid</a></td> <td>Cyclic carboxylic acid</td> <td>– (~6)</td> <td>1.43</td> <td>0.70</td> <td>5.1–7.0 </td></tr> <tr> <td><a href="/wiki/Testosterone_enanthate" title="Testosterone enanthate">Testosterone enanthate</a></td> <td style="text-align:center;"><a href="/wiki/File:Testosterone_enanthate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Testosterone_enanthate.svg/35px-Testosterone_enanthate.svg.png" decoding="async" width="35" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Testosterone_enanthate.svg/53px-Testosterone_enanthate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Testosterone_enanthate.svg/70px-Testosterone_enanthate.svg.png 2x" data-file-width="930" data-file-height="475" /></a></td> <td>C17β</td> <td><a href="/wiki/Heptanoic_acid" class="mw-redirect" title="Heptanoic acid">Heptanoic acid</a></td> <td>Straight-chain fatty acid</td> <td>7</td> <td>1.39</td> <td>0.72</td> <td>3.6–7.0 </td></tr> <tr> <td><a href="/wiki/Testosterone_decanoate" title="Testosterone decanoate">Testosterone decanoate</a></td> <td style="text-align:center;"><a href="/wiki/File:Testosterone_decanoate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c0/Testosterone_decanoate.svg/35px-Testosterone_decanoate.svg.png" decoding="async" width="35" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c0/Testosterone_decanoate.svg/53px-Testosterone_decanoate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c0/Testosterone_decanoate.svg/70px-Testosterone_decanoate.svg.png 2x" data-file-width="1115" data-file-height="475" /></a></td> <td>C17β</td> <td><a href="/wiki/Decanoic_acid" class="mw-redirect" title="Decanoic acid">Decanoic acid</a></td> <td>Straight-chain fatty acid</td> <td>10</td> <td>1.53</td> <td>0.65</td> <td>6.3–8.6 </td></tr> <tr> <td><a href="/wiki/Testosterone_undecanoate" title="Testosterone undecanoate">Testosterone undecanoate</a></td> <td style="text-align:center;"><a href="/wiki/File:Testosterone_undecanoate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/86/Testosterone_undecanoate.svg/35px-Testosterone_undecanoate.svg.png" decoding="async" width="35" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/86/Testosterone_undecanoate.svg/53px-Testosterone_undecanoate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/86/Testosterone_undecanoate.svg/70px-Testosterone_undecanoate.svg.png 2x" data-file-width="1170" data-file-height="465" /></a></td> <td>C17β</td> <td><a href="/wiki/Undecanoic_acid" class="mw-redirect" title="Undecanoic acid">Undecanoic acid</a></td> <td>Straight-chain fatty acid</td> <td>11</td> <td>1.58</td> <td>0.63</td> <td>6.7–9.2 </td></tr> <tr> <td><a href="/wiki/Testosterone_buciclate" title="Testosterone buciclate">Testosterone buciclate</a>d</td> <td style="text-align:center;"><a href="/wiki/File:Testosterone_buciclate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Testosterone_buciclate.svg/25px-Testosterone_buciclate.svg.png" decoding="async" width="25" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Testosterone_buciclate.svg/38px-Testosterone_buciclate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Testosterone_buciclate.svg/50px-Testosterone_buciclate.svg.png 2x" data-file-width="945" data-file-height="450" /></a></td> <td>C17β</td> <td><a href="/wiki/Bucyclic_acid" class="mw-redirect" title="Bucyclic acid">Bucyclic acid</a>e</td> <td>Cyclic carboxylic acid</td> <td>– (~9)</td> <td>1.58</td> <td>0.63</td> <td>7.9–8.5 </td></tr> <tr class="sortbottom"> <td colspan="10" style="width: 1px; background-color:#eaecf0; text-align: center;">Footnotes: a = Length of <a href="/wiki/Ester" title="Ester">ester</a> in <a href="/wiki/Carbon" title="Carbon">carbon</a> <a href="/wiki/Atom" title="Atom">atoms</a> for <a href="/wiki/Straight-chain_fatty_acid" class="mw-redirect" title="Straight-chain fatty acid">straight-chain fatty acids</a> or approximate length of ester in carbon atoms for <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> or <a href="/wiki/Cyclic_compound" title="Cyclic compound">cyclic</a> fatty acids. b = Relative testosterone content by weight (i.e., relative <a href="/wiki/Androgen" title="Androgen">androgenic</a>/<a class="mw-selflink selflink">anabolic</a> <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potency</a>). c = Experimental or predicted <a href="/wiki/Partition_coefficient" title="Partition coefficient">octanol/water partition coefficient</a> (i.e., <a href="/wiki/Lipophilicity" title="Lipophilicity">lipophilicity</a>/<a href="/wiki/Hydrophobicity" class="mw-redirect" title="Hydrophobicity">hydrophobicity</a>). Retrieved from <a href="/wiki/PubChem" title="PubChem">PubChem</a>, <a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a>, and <a href="/wiki/DrugBank" title="DrugBank">DrugBank</a>. d = Never marketed. e = <a href="/wiki/Bucyclic_acid" class="mw-redirect" title="Bucyclic acid">Bucyclic acid</a> = trans-4-Butylcyclohexane-1-carboxylic acid. Sources: See individual articles. </td></tr></tbody></table> <table class="wikitable sortable mw-collapsible mw-collapsed" style="font-size:small; text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap"><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:Structural_properties_of_major_anabolic_steroid_esters" title="Template:Structural properties of major anabolic steroid esters"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Structural_properties_of_major_anabolic_steroid_esters" title="Template talk:Structural properties of major anabolic steroid esters"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Structural_properties_of_major_anabolic_steroid_esters" title="Special:EditPage/Template:Structural properties of major anabolic steroid esters"><abbr title="Edit this template">e</abbr></a></li></ul></div> Structural properties of major anabolic steroid esters </caption> <tbody><tr> <th rowspan="2">Anabolic steroid</th> <th rowspan="2" class="unsortable">Structure</th> <th colspan="4">Ester</th> <th rowspan="2">Relative <abbr title="molecular weight">mol. weight</abbr></th> <th rowspan="2">Relative <abbr title="androgen/anabolic steroid">AAS</abbr> contentb</th> <th rowspan="2">Durationc </th></tr> <tr> <th>Position</th> <th>Moiety</th> <th>Type</th> <th>Lengtha </th></tr> <tr> <td><a href="/wiki/Boldenone_undecylenate" title="Boldenone undecylenate">Boldenone undecylenate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Boldenone_undecylenate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3d/Boldenone_undecylenate.svg/35px-Boldenone_undecylenate.svg.png" decoding="async" width="35" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3d/Boldenone_undecylenate.svg/53px-Boldenone_undecylenate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3d/Boldenone_undecylenate.svg/70px-Boldenone_undecylenate.svg.png 2x" data-file-width="1170" data-file-height="465" /></a><figcaption></figcaption></figure></td> <td>C17β</td> <td><a href="/wiki/Undecylenic_acid" title="Undecylenic acid">Undecylenic acid</a></td> <td>Straight-chain fatty acid</td> <td>11</td> <td>1.58</td> <td>0.63</td> <td>Long </td></tr> <tr> <td><a href="/wiki/Drostanolone_propionate" title="Drostanolone propionate">Drostanolone propionate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Drostanolone_propionate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/68/Drostanolone_propionate.svg/35px-Drostanolone_propionate.svg.png" decoding="async" width="35" height="25" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/68/Drostanolone_propionate.svg/53px-Drostanolone_propionate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/68/Drostanolone_propionate.svg/70px-Drostanolone_propionate.svg.png 2x" data-file-width="1567" data-file-height="1132" /></a><figcaption></figcaption></figure></td> <td>C17β</td> <td><a href="/wiki/Propanoic_acid" class="mw-redirect" title="Propanoic acid">Propanoic acid</a></td> <td>Straight-chain fatty acid</td> <td>3</td> <td>1.18</td> <td>0.84</td> <td>Short </td></tr> <tr> <td><a href="/wiki/Metenolone_acetate" title="Metenolone acetate">Metenolone acetate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Metenolone_acetate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/Metenolone_acetate.svg/35px-Metenolone_acetate.svg.png" decoding="async" width="35" height="27" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/Metenolone_acetate.svg/53px-Metenolone_acetate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/80/Metenolone_acetate.svg/70px-Metenolone_acetate.svg.png 2x" data-file-width="1270" data-file-height="980" /></a><figcaption></figcaption></figure></td> <td>C17β</td> <td><a href="/wiki/Ethanoic_acid" class="mw-redirect" title="Ethanoic acid">Ethanoic acid</a></td> <td>Straight-chain fatty acid</td> <td>2</td> <td>1.14</td> <td>0.88</td> <td>Short </td></tr> <tr> <td><a href="/wiki/Metenolone_enanthate" title="Metenolone enanthate">Metenolone enanthate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Metenolone_enanthate.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/Metenolone_enanthate.png/35px-Metenolone_enanthate.png" decoding="async" width="35" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/Metenolone_enanthate.png/53px-Metenolone_enanthate.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/36/Metenolone_enanthate.png/70px-Metenolone_enanthate.png 2x" data-file-width="1368" data-file-height="699" /></a><figcaption></figcaption></figure></td> <td>C17β</td> <td><a href="/wiki/Heptanoic_acid" class="mw-redirect" title="Heptanoic acid">Heptanoic acid</a></td> <td>Straight-chain fatty acid</td> <td>7</td> <td>1.37</td> <td>0.73</td> <td>Long </td></tr> <tr> <td><a href="/wiki/Nandrolone_decanoate" title="Nandrolone decanoate">Nandrolone decanoate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Nandrolone_decanoate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Nandrolone_decanoate.svg/35px-Nandrolone_decanoate.svg.png" decoding="async" width="35" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Nandrolone_decanoate.svg/53px-Nandrolone_decanoate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Nandrolone_decanoate.svg/70px-Nandrolone_decanoate.svg.png 2x" data-file-width="2240" data-file-height="990" /></a><figcaption></figcaption></figure></td> <td>C17β</td> <td><a href="/wiki/Decanoic_acid" class="mw-redirect" title="Decanoic acid">Decanoic acid</a></td> <td>Straight-chain fatty acid</td> <td>10</td> <td>1.56</td> <td>0.64</td> <td>Long </td></tr> <tr> <td><a href="/wiki/Nandrolone_phenylpropionate" title="Nandrolone phenylpropionate">Nandrolone phenylpropionate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Nandrolone_phenylpropionate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Nandrolone_phenylpropionate.svg/35px-Nandrolone_phenylpropionate.svg.png" decoding="async" width="35" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Nandrolone_phenylpropionate.svg/53px-Nandrolone_phenylpropionate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Nandrolone_phenylpropionate.svg/70px-Nandrolone_phenylpropionate.svg.png 2x" data-file-width="1755" data-file-height="990" /></a><figcaption></figcaption></figure></td> <td>C17β</td> <td><a href="/wiki/Phenylpropanoic_acid" title="Phenylpropanoic acid">Phenylpropanoic acid</a></td> <td>Aromatic fatty acid</td> <td>– (~6–7)</td> <td>1.48</td> <td>0.67</td> <td>Long </td></tr> <tr> <td><a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">Trenbolone acetate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Trenbolone_acetate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6b/Trenbolone_acetate.svg/35px-Trenbolone_acetate.svg.png" decoding="async" width="35" height="26" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6b/Trenbolone_acetate.svg/53px-Trenbolone_acetate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6b/Trenbolone_acetate.svg/70px-Trenbolone_acetate.svg.png 2x" data-file-width="615" data-file-height="465" /></a><figcaption></figcaption></figure></td> <td>C17β</td> <td><a href="/wiki/Ethanoic_acid" class="mw-redirect" title="Ethanoic acid">Ethanoic acid</a></td> <td>Straight-chain fatty acid</td> <td>2</td> <td>1.16</td> <td>0.87</td> <td>Short </td></tr> <tr> <td><a href="/wiki/Trenbolone_enanthate" title="Trenbolone enanthate">Trenbolone enanthate</a>d</td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Trenbolone_enanthate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Trenbolone_enanthate.svg/35px-Trenbolone_enanthate.svg.png" decoding="async" width="35" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Trenbolone_enanthate.svg/53px-Trenbolone_enanthate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Trenbolone_enanthate.svg/70px-Trenbolone_enanthate.svg.png 2x" data-file-width="925" data-file-height="465" /></a><figcaption></figcaption></figure></td> <td>C17β</td> <td><a href="/wiki/Heptanoic_acid" class="mw-redirect" title="Heptanoic acid">Heptanoic acid</a></td> <td>Straight-chain fatty acid</td> <td>7</td> <td>1.41</td> <td>0.71</td> <td>Long </td></tr> <tr class="sortbottom"> <td colspan="10" style="width: 1px; background-color:#eaecf0; text-align: center;">Footnotes: a = Length of <a href="/wiki/Ester" title="Ester">ester</a> in <a href="/wiki/Carbon" title="Carbon">carbon</a> <a href="/wiki/Atom" title="Atom">atoms</a> for <a href="/wiki/Straight-chain_fatty_acid" class="mw-redirect" title="Straight-chain fatty acid">straight-chain fatty acids</a> or approximate length of ester in carbon atoms for <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> fatty acids. b = Relative androgen/anabolic steroid content by weight (i.e., relative <a href="/wiki/Androgen" title="Androgen">androgenic</a>/<a class="mw-selflink selflink">anabolic</a> <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potency</a>). c = <a href="/wiki/Duration_of_action" class="mw-redirect" title="Duration of action">Duration</a> by <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular</a> or <a href="/wiki/Subcutaneous_injection" class="mw-redirect" title="Subcutaneous injection">subcutaneous injection</a> in <a href="/wiki/Oil_solution" class="mw-redirect" title="Oil solution">oil solution</a>. d = Never marketed. Sources: See individual articles. </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Structural_conversions_of_anabolic_steroids">Structural conversions of anabolic steroids</h3>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=43" title="Edit section: Structural conversions of anabolic steroids">edit</a>]</div> <div class="mw-heading mw-heading4"><h4 id="Testosterone_to_derivatives">Testosterone to derivatives</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=44" title="Edit section: Testosterone to derivatives">edit</a>]</div> Conversion to DHT,<a href="#cite_note-193">[190]</a> nandrolone,<a href="#cite_note-pmid18500378-78">[75]</a> metandienone (Dianabol),<a href="#cite_note-194">[191]</a> chlorodehydromethyltestosterone (Turinabol),<a href="#cite_note-195">[192]</a> fluoxymesterone (Halotestin),<a href="#cite_note-196">[193]</a> and boldenone (Equipoise):<a href="#cite_note-197">[194]</a> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Testosterone_Derivatives.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/Testosterone_Derivatives.jpg/400px-Testosterone_Derivatives.jpg" decoding="async" width="400" height="288" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/Testosterone_Derivatives.jpg/600px-Testosterone_Derivatives.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/89/Testosterone_Derivatives.jpg/800px-Testosterone_Derivatives.jpg 2x" data-file-width="990" data-file-height="712" /></a><figcaption>Red arrows show molecular differences from testosterone structural conversion to six different anabolic steroids.</figcaption></figure> <div class="mw-heading mw-heading4"><h4 id="DHT_to_derivatives">DHT to derivatives</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=45" title="Edit section: DHT to derivatives">edit</a>]</div> DHT to stanozolol (Winstrol),<a href="#cite_note-198">[195]</a> metenolone acetate (Primobolan),<a href="#cite_note-199">[196]</a> oxymetholone (Anadrol),<a href="#cite_note-200">[197]</a> and methasterone (Superdrol):<a href="#cite_note-201">[198]</a> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:DHT_Derivatives.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/DHT_Derivatives.jpg/400px-DHT_Derivatives.jpg" decoding="async" width="400" height="284" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/DHT_Derivatives.jpg/600px-DHT_Derivatives.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c6/DHT_Derivatives.jpg/800px-DHT_Derivatives.jpg 2x" data-file-width="940" data-file-height="668" /></a><figcaption>Red arrows show molecular differences from DHT structural conversion to four different anabolic steroids.</figcaption></figure> <div class="mw-heading mw-heading4"><h4 id="Nandrolone_to_derivatives">Nandrolone to derivatives</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=46" title="Edit section: Nandrolone to derivatives">edit</a>]</div> Nandrolone to trestolone,<a href="#cite_note-202">[199]</a> trenbolone,<a href="#cite_note-203">[200]</a> norboletone,<a href="#cite_note-204">[201]</a> and ethylestrenol:<a href="#cite_note-205">[202]</a> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Nandrolone_Derivatives.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Nandrolone_Derivatives.jpg/400px-Nandrolone_Derivatives.jpg" decoding="async" width="400" height="272" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Nandrolone_Derivatives.jpg/600px-Nandrolone_Derivatives.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Nandrolone_Derivatives.jpg/800px-Nandrolone_Derivatives.jpg 2x" data-file-width="966" data-file-height="658" /></a><figcaption>Red arrows show molecular differences from nandrolone structural conversion to four different anabolic steroids.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Detection_in_body_fluids">Detection in body fluids</h3>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=47" title="Edit section: Detection in body fluids">edit</a>]</div> The most commonly employed human physiological specimen for detecting AAS usage is urine, although both blood and hair have been investigated for this purpose. The AAS, whether of endogenous or exogenous origin, are subject to extensive hepatic biotransformation by a variety of enzymatic pathways. The primary urinary metabolites may be detectable for up to 30 days after the last use, depending on the specific agent, dose and route of administration. A number of the drugs have common metabolic pathways, and their excretion profiles may overlap those of the endogenous steroids, making interpretation of testing results a very significant challenge to the analytical chemist. Methods for detection of the substances or their excretion products in urine specimens usually involve <a href="/wiki/Gas_chromatography%E2%80%93mass_spectrometry" title="Gas chromatography–mass spectrometry">gas chromatography–mass spectrometry</a> or liquid chromatography-mass spectrometry.<a href="#cite_note-pmid18570179-206">[203]</a><a href="#cite_note-pmid19429460-207">[204]</a><a href="#cite_note-pmid19465014-208">[205]</a><a href="#cite_note-Baselt-2008-209">[206]</a> <div class="mw-heading mw-heading2"><h2 id="History">History</h2>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=48" title="Edit section: History">edit</a>]</div> <table class="wikitable plainrowheaders floatright"> <caption class="nowrap">Introduction of various anabolic steroids </caption> <tbody><tr> <th scope="col" style="width: 150px;">Generic name </th> <th scope="col" style="width: 75px;">Class<a href="#cite_note-210">[a]</a> </th> <th scope="col" style="width: 75px;">Brand name </th> <th scope="col" style="width: 30px;">Route<a href="#cite_note-211">[b]</a> </th> <th scope="col" style="width: 30px;"><abbr title="Introduced in">Intr.</abbr> </th></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Androstanolone" title="Androstanolone">Androstanolone</a><a href="#cite_note-212">[c]</a><a href="#cite_note-limited-213">[d]</a> </th> <td>DHT</td> <td>Andractim</td> <td>PO,<a href="#cite_note-dc-214">[e]</a> IM, TD</td> <td>1953 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Boldenone_undecylenate" title="Boldenone undecylenate">Boldenone undecylenate</a><a href="#cite_note-vet-215">[f]</a> </th> <td>Ester</td> <td>Equipoise<a href="#cite_note-others-216">[g]</a></td> <td>IM</td> <td>1960s </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Danazol" title="Danazol">Danazol</a> </th> <td>Alkyl</td> <td>Danocrine</td> <td>PO</td> <td>1971 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Drostanolone_propionate" title="Drostanolone propionate">Drostanolone propionate</a><a href="#cite_note-dc-214">[e]</a> </th> <td>DHT Ester</td> <td>Masteron</td> <td>IM</td> <td>1961 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Ethylestrenol" title="Ethylestrenol">Ethylestrenol</a><a href="#cite_note-limited-213">[d]</a> </th> <td>19-NT Alkyl</td> <td>Maxibolin<a href="#cite_note-others-216">[g]</a></td> <td>PO</td> <td>1961 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">Fluoxymesterone</a><a href="#cite_note-limited-213">[d]</a> </th> <td>Alkyl</td> <td>Halotestin<a href="#cite_note-others-216">[g]</a></td> <td>PO</td> <td>1957 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Mestanolone" title="Mestanolone">Mestanolone</a><a href="#cite_note-dc-214">[e]</a> </th> <td>DHT Alkyl</td> <td>Androstalone<a href="#cite_note-others-216">[g]</a></td> <td>PO</td> <td>1950s </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Mesterolone" title="Mesterolone">Mesterolone</a> </th> <td>DHT</td> <td>Proviron</td> <td>PO</td> <td>1967 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Metandienone" title="Metandienone">Metandienone</a><a href="#cite_note-limited-213">[d]</a> </th> <td>Alkyl</td> <td>Dianabol</td> <td>PO, IM</td> <td>1958 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Metenolone_acetate" title="Metenolone acetate">Metenolone acetate</a><a href="#cite_note-limited-213">[d]</a> </th> <td>DHT Ester</td> <td>Primobolan</td> <td>PO</td> <td>1961 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Metenolone_enanthate" title="Metenolone enanthate">Metenolone enanthate</a><a href="#cite_note-limited-213">[d]</a> </th> <td>DHT Ester</td> <td>Primobolan Depot</td> <td>IM</td> <td>1962 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Methyltestosterone" title="Methyltestosterone">Methyltestosterone</a><a href="#cite_note-limited-213">[d]</a> </th> <td>Alkyl</td> <td>Metandren</td> <td>PO</td> <td>1936 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Nandrolone_decanoate" title="Nandrolone decanoate">Nandrolone decanoate</a> </th> <td>19-NT Ester</td> <td>Deca-Durabolin</td> <td>IM</td> <td>1962 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Nandrolone_phenylpropionate" title="Nandrolone phenylpropionate">Nandrolone phenylpropionate</a><a href="#cite_note-limited-213">[d]</a> </th> <td>19-NT Ester</td> <td>Durabolin</td> <td>IM</td> <td>1959 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a><a href="#cite_note-limited-213">[d]</a> </th> <td>19-NT Alkyl</td> <td>Nilevar<a href="#cite_note-others-216">[g]</a></td> <td>PO</td> <td>1956 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Oxandrolone" title="Oxandrolone">Oxandrolone</a><a href="#cite_note-limited-213">[d]</a> </th> <td>DHT Alkyl</td> <td>Oxandrin<a href="#cite_note-others-216">[g]</a></td> <td>PO</td> <td>1964 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Oxymetholone" title="Oxymetholone">Oxymetholone</a><a href="#cite_note-limited-213">[d]</a> </th> <td>DHT Alkyl</td> <td>Anadrol<a href="#cite_note-others-216">[g]</a></td> <td>PO</td> <td>1961 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Prasterone" title="Prasterone">Prasterone</a><a href="#cite_note-217">[h]</a> </th> <td>Prohormone</td> <td>Intrarosa<a href="#cite_note-others-216">[g]</a></td> <td>PO, IM, vaginal</td> <td>1970s </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Stanozolol" title="Stanozolol">Stanozolol</a><a href="#cite_note-dc-214">[e]</a> </th> <td>DHT Alkyl</td> <td>Winstrol<a href="#cite_note-others-216">[g]</a></td> <td>PO, IM</td> <td>1962 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Testosterone_cypionate" title="Testosterone cypionate">Testosterone cypionate</a> </th> <td>Ester</td> <td>Depo-Testosterone</td> <td>IM</td> <td>1951 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Testosterone_enanthate" title="Testosterone enanthate">Testosterone enanthate</a> </th> <td>Ester</td> <td>Delatestryl</td> <td>IM</td> <td>1954 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Testosterone_propionate" title="Testosterone propionate">Testosterone propionate</a> </th> <td>Ester</td> <td>Testoviron</td> <td>IM</td> <td>1937 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Testosterone_undecanoate" title="Testosterone undecanoate">Testosterone undecanoate</a> </th> <td>Ester</td> <td>Andriol<a href="#cite_note-others-216">[g]</a></td> <td>PO, IM</td> <td>1970s </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">Trenbolone acetate</a><a href="#cite_note-vet-215">[f]</a> </th> <td>19-NT Ester</td> <td>Finajet<a href="#cite_note-others-216">[g]</a></td> <td>IM</td> <td>1970s </td></tr> <tr class="sortbottom"> <td colspan="7" style="width:1px; background:#eaecf0; text-align:center;"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist reflist-lower-alpha"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-210"><a href="#cite_ref-210">^</a> DHT = dihydrotestosterone; 19-NT = 19-nortestosterone </li> <li id="cite_note-211"><a href="#cite_ref-211">^</a> IM = <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">Intramuscular injection</a>; PO = Oral (by mouth); TD = Transdermal </li> <li id="cite_note-212"><a href="#cite_ref-212">^</a> Also known as dihydrotestosterone </li> <li id="cite_note-limited-213">^ <a href="#cite_ref-limited_213-0">a</a> <a href="#cite_ref-limited_213-1">b</a> <a href="#cite_ref-limited_213-2">c</a> <a href="#cite_ref-limited_213-3">d</a> <a href="#cite_ref-limited_213-4">e</a> <a href="#cite_ref-limited_213-5">f</a> <a href="#cite_ref-limited_213-6">g</a> <a href="#cite_ref-limited_213-7">h</a> <a href="#cite_ref-limited_213-8">i</a> <a href="#cite_ref-limited_213-9">j</a> <a href="#cite_ref-limited_213-10">k</a> Availability limited </li> <li id="cite_note-dc-214">^ <a href="#cite_ref-dc_214-0">a</a> <a href="#cite_ref-dc_214-1">b</a> <a href="#cite_ref-dc_214-2">c</a> <a href="#cite_ref-dc_214-3">d</a> No longer marketed </li> <li id="cite_note-vet-215">^ <a href="#cite_ref-vet_215-0">a</a> <a href="#cite_ref-vet_215-1">b</a> Available for veterinary use only </li> <li id="cite_note-others-216">^ <a href="#cite_ref-others_216-0">a</a> <a href="#cite_ref-others_216-1">b</a> <a href="#cite_ref-others_216-2">c</a> <a href="#cite_ref-others_216-3">d</a> <a href="#cite_ref-others_216-4">e</a> <a href="#cite_ref-others_216-5">f</a> <a href="#cite_ref-others_216-6">g</a> <a href="#cite_ref-others_216-7">h</a> <a href="#cite_ref-others_216-8">i</a> <a href="#cite_ref-others_216-9">j</a> <a href="#cite_ref-others_216-10">k</a> Also marketed under other brand names </li> <li id="cite_note-217"><a href="#cite_ref-217">^</a> Also known as dehydroepiandrosterone </li> </ol></div></div> </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Discovery_of_androgens">Discovery of androgens</h3>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=49" title="Edit section: Discovery of androgens">edit</a>]</div> The use of <a href="/wiki/Gonadal" class="mw-redirect" title="Gonadal">gonadal</a> <a href="/wiki/Steroid" title="Steroid">steroids</a> pre-dates their identification and isolation. Use of cow urine for treatment of ascites, heart failure, renal failure and vitiligo has been elaborately described in <a href="/wiki/Sushruta_Samhita" title="Sushruta Samhita">Sushruta Samhita</a>, suggesting that ancient Indians had some understanding of steroidal properties of cow urine around 6th century BCE.<a href="#cite_note-Randhawa-2015-218">[207]</a> Extraction of hormones from urines began in China around 100 BCE.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] Medical use of <a href="/wiki/Testicle" title="Testicle">testicle</a> extract began in the late 19th century while its effects on strength were still being studied.<a href="#cite_note-pmid12017555-144">[141]</a> The isolation of gonadal steroids can be traced back to 1931, when <a href="/wiki/Adolf_Butenandt" title="Adolf Butenandt">Adolf Butenandt</a>, a chemist in <a href="/wiki/Marburg" title="Marburg">Marburg</a>, purified 15 milligrams of the male hormone <a href="/wiki/Androstenone" title="Androstenone">androstenone</a> from tens of thousands of litres of urine. This steroid was subsequently <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">synthesized</a> in 1934 by <a href="/wiki/Leopold_Ru%C5%BEi%C4%8Dka" title="Leopold Ružička">Leopold Ružička</a>, a chemist in <a href="/wiki/Zurich" title="Zurich">Zurich</a>.<a href="#cite_note-pmid7817189-219">[208]</a> In the 1930s, it was already known that the <a href="/wiki/Testes" class="mw-redirect" title="Testes">testes</a> contain a more powerful androgen than <a href="/wiki/Androstenone" title="Androstenone">androstenone</a>, and three groups of scientists, funded by competing <a href="/wiki/Pharmaceutical_companies" class="mw-redirect" title="Pharmaceutical companies">pharmaceutical companies</a> in the Netherlands, Germany, and Switzerland, raced to isolate it.<a href="#cite_note-pmid7817189-219">[208]</a><a href="#cite_note-pmid11176375-220">[209]</a> This hormone was first identified by Karoly Gyula David, E. Dingemanse, J. Freud and Ernst Laqueur in a May 1935 paper "On Crystalline Male Hormone from Testicles (Testosterone)."<a href="#cite_note-David-1935-221">[210]</a> They named the hormone <a href="/wiki/Testosterone" title="Testosterone">testosterone</a>, from the <a href="/wiki/Stem_(linguistics)" class="mw-redirect" title="Stem (linguistics)">stems</a> of testicle and <a href="/wiki/Sterol" title="Sterol">sterol</a>, and the suffix of <a href="/wiki/Ketone" title="Ketone">ketone</a>. The <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">chemical synthesis</a> of testosterone was achieved in August that year, when Butenandt and G. Hanisch published a paper describing "A Method for Preparing Testosterone from Cholesterol."<a href="#cite_note-Butenandt-1935-222">[211]</a> Only a week later, the third group, Ruzicka and A. Wettstein, announced a patent application in a paper "On the Artificial Preparation of the Testicular Hormone Testosterone (Androsten-3-one-17-ol)."<a href="#cite_note-Ruzicka-1935-223">[212]</a> Ruzicka and Butenandt were offered the 1939 <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize in Chemistry</a> for their work, but the <a href="/wiki/Nazi_Germany" title="Nazi Germany">Nazi</a> government forced Butenandt to decline the honor, although he accepted the prize after the end of World War II.<a href="#cite_note-pmid7817189-219">[208]</a><a href="#cite_note-pmid11176375-220">[209]</a> Clinical trials on humans, involving either PO doses of <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a> or injections of <a href="/wiki/Testosterone_propionate" title="Testosterone propionate">testosterone propionate</a>, began as early as 1937.<a href="#cite_note-pmid7817189-219">[208]</a> There are often reported rumors that German soldiers were administered AAS during the Second World War, the aim being to increase their aggression and stamina, but these are, as yet, unproven.<a href="#cite_note-Lenahan-2003-125">[122]</a>: 6  <a href="/wiki/Adolf_Hitler" title="Adolf Hitler">Adolf Hitler</a> himself, according to his physician, was injected with testosterone derivatives to treat various ailments.<a href="#cite_note-Taylor-2009-224">[213]</a> AAS were used in experiments conducted by the Nazis on concentration camp inmates,<a href="#cite_note-Taylor-2009-224">[213]</a> and later by the allies attempting to treat the malnourished victims that survived Nazi camps.<a href="#cite_note-Lenahan-2003-125">[122]</a>: 6  President <a href="/wiki/John_F._Kennedy" title="John F. Kennedy">John F. Kennedy</a> was administered steroids both before and during his presidency.<a href="#cite_note-Suarez-2002-225">[214]</a> <div class="mw-heading mw-heading3"><h3 id="Development_of_synthetic_AAS">Development of synthetic AAS</h3>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=50" title="Edit section: Development of synthetic AAS">edit</a>]</div> The development of muscle-building properties of testosterone was pursued in the 1940s, in the Soviet Union and in <a href="/wiki/Eastern_Bloc" title="Eastern Bloc">Eastern Bloc</a> countries such as East Germany, where steroid programs were used to enhance the performance of <a href="/wiki/Olympic_Games" title="Olympic Games">Olympic</a> and other <a href="/wiki/Amateur_sports" title="Amateur sports">amateur</a> <a href="/wiki/Olympic_weightlifting" title="Olympic weightlifting">weight lifters</a>. In response to the success of Russian weightlifters, the U.S. Olympic Team physician <a href="/wiki/John_Bosley_Ziegler" title="John Bosley Ziegler">John Ziegler</a> worked with synthetic chemists to develop an AAS with reduced androgenic effects.<a href="#cite_note-pmid16510635-226">[215]</a> Ziegler's work resulted in the production of <a href="/wiki/Methandrostenolone" class="mw-redirect" title="Methandrostenolone">methandrostenolone</a>, which Ciba Pharmaceuticals marketed as Dianabol. The new steroid was approved for use in the U.S. by the <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) in 1958. It was most commonly administered to burn victims and the elderly. The drug's <a href="/wiki/Off-label_use" title="Off-label use">off-label users</a> were mostly bodybuilders and weight lifters. Although Ziegler prescribed only small doses to athletes, he soon discovered that those having used Dianabol developed enlarged prostates and atrophied testes.<a href="#cite_note-www.slate.com-227">[216]</a> AAS were placed on the list of banned substances of the <a href="/wiki/International_Olympic_Committee" title="International Olympic Committee">International Olympic Committee</a> (IOC) in 1976, and a decade later, the committee introduced "out-of-competition" doping tests because many athletes used AAS in their training period rather than during competition.<a href="#cite_note-pmid15248788-7">[7]</a> Three major ideas governed modifications of testosterone into a multitude of AAS: <a href="/wiki/Alkylation" title="Alkylation">Alkylation</a> at C17α position with <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a> or <a href="/wiki/Ethyl_group" title="Ethyl group">ethyl group</a> created POly active compounds because it slows the degradation of the drug by the liver; <a href="/wiki/Esterification" class="mw-redirect" title="Esterification">esterification</a> of testosterone and <a href="/wiki/Nortestosterone" class="mw-redirect" title="Nortestosterone">nortestosterone</a> at the C17β position allows the substance to be administered parenterally and increases the duration of effectiveness because agents soluble in oily liquids may be present in the body for several months; and alterations of the ring structure were applied for both PO and parenteral agents to seeking to obtain different anabolic-to-androgenic effect ratios.<a href="#cite_note-pmid15248788-7">[7]</a> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=51" title="Edit section: Society and culture">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Etymology">Etymology</h3>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=52" title="Edit section: Etymology">edit</a>]</div> Androgens were discovered in the 1930s and were characterized as having effects described as androgenic (i.e., virilizing) and anabolic (e.g., myotrophic, renotrophic).<a href="#cite_note-Llewellyn2011-73">[70]</a><a href="#cite_note-pmid18500378-78">[75]</a> The term anabolic steroid can be dated as far back as at least the mid-1940s, when it was used to describe the at-the-time hypothetical concept of a testosterone-derived steroid with anabolic effects but with minimal or no androgenic effects.<a href="#cite_note-Kochakian-1946-228">[217]</a> This concept was formulated based on the observation that steroids had ratios of renotrophic to androgenic potency that differed significantly, which suggested that anabolic and androgenic effects might be dissociable.<a href="#cite_note-Kochakian-1946-228">[217]</a> In 1953, a testosterone-derived steroid known as <a href="/wiki/Norethandrolone" title="Norethandrolone">norethandrolone</a> (17α-ethyl-19-nortestosterone) was synthesized at <a href="/wiki/G._D._Searle_%26_Company" class="mw-redirect" title="G. D. Searle & Company">G. D. Searle & Company</a> and was studied as a <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestin</a>, but was not marketed.<a href="#cite_note-Kochakian2012-229">[218]</a> Subsequently, in 1955, it was re-examined for testosterone-like activity in animals and was found to have similar anabolic activity to testosterone, but only one-sixteenth of its androgenic potency.<a href="#cite_note-Kochakian2012-229">[218]</a><a href="#cite_note-Sneader2005-230">[219]</a> It was the first steroid with a marked and favorable separation of anabolic and androgenic effect to be discovered, and has accordingly been described as the "first anabolic steroid".<a href="#cite_note-Wermuth2011-231">[220]</a><a href="#cite_note-Wright1994-232">[221]</a> Norethandrolone was introduced for medical use in 1956, and was quickly followed by numerous similar steroids, for instance <a href="/wiki/Nandrolone_phenylpropionate" title="Nandrolone phenylpropionate">nandrolone phenylpropionate</a> in 1959 and <a href="/wiki/Stanozolol" title="Stanozolol">stanozolol</a> in 1962.<a href="#cite_note-Wermuth2011-231">[220]</a><a href="#cite_note-Wright1994-232">[221]</a><a href="#cite_note-Office1957-233">[222]</a><a href="#cite_note-Mozayani-2011-234">[223]</a> With these developments, anabolic steroid became the preferred term to refer to such steroids (over "androgen"), and entered widespread use. Although anabolic steroid was originally intended to specifically describe testosterone-derived steroids with a marked dissociation of anabolic and androgenic effect, it is applied today indiscriminately to all steroids with AR agonism-based anabolic effects regardless of their androgenic potency, including even non-synthetic and non-preferentially-anabolic steroids like testosterone.<a href="#cite_note-Llewellyn2011-73">[70]</a><a href="#cite_note-pmid18500378-78">[75]</a><a href="#cite_note-Kochakian2012-229">[218]</a> While many anabolic steroids have diminished androgenic potency in comparison to anabolic potency, there is no anabolic steroid that is exclusively anabolic, and hence all anabolic steroids retain at least some degree of androgenicity.<a href="#cite_note-Llewellyn2011-73">[70]</a><a href="#cite_note-pmid18500378-78">[75]</a><a href="#cite_note-Kochakian2012-229">[218]</a> (Likewise, all "androgens" are inherently anabolic.)<a href="#cite_note-Llewellyn2011-73">[70]</a><a href="#cite_note-pmid18500378-78">[75]</a><a href="#cite_note-Kochakian2012-229">[218]</a> Indeed, it is probably not possible to fully dissociate anabolic effects from androgenic effects, as both types of effects are mediated by the same signaling receptor, the AR.<a href="#cite_note-pmid18500378-78">[75]</a> As such, the distinction between the terms anabolic steroid and androgen is questionable, and this is the basis for the revised and more recent term anabolic–androgenic steroid (AAS).<a href="#cite_note-Llewellyn2011-73">[70]</a><a href="#cite_note-pmid18500378-78">[75]</a><a href="#cite_note-Kochakian2012-229">[218]</a> <a href="/wiki/David_Handelsman" title="David Handelsman">David Handelsman</a> has criticized terminology and understanding surrounding AAS in many publications.<a href="#cite_note-pmid21511988-235">[224]</a><a href="#cite_note-pmid33484556-236">[225]</a><a href="#cite_note-pmid35277356-237">[226]</a><a href="#cite_note-pmid24024843-238">[227]</a><a href="#cite_note-IyerHandelsman2017-239">[228]</a><a href="#cite_note-IyerHandelsman2016-240">[229]</a><a href="#cite_note-Handelsman2012-241">[230]</a><a href="#cite_note-pmid25905231-242">[231]</a> According to Handelsman, the pharmaceutical industry attempted to dissociate the so-called "androgenic" and "anabolic" effects of AAS in the mid-20th-century in order to create non-masculinizing anabolic agents that would be more suitable for use in women and children.<a href="#cite_note-pmid21511988-235">[224]</a> However, this effort failed comprehensively and was abandoned by the 1970s.<a href="#cite_note-pmid21511988-235">[224]</a><a href="#cite_note-pmid33484556-236">[225]</a> This failure was due to the subsequent discovery of a singular androgen receptor (AR) mediating the effects of AAS in both muscle and reproductive tissue, along with misinterpretation of flawed animal androgen bioassays employed to distinguish between androgenic or virilizing effects and anabolic or myotrophic effects (i.e., the Hershberger assay involving the unrepresentative levator ani muscle).<a href="#cite_note-pmid21511988-235">[224]</a><a href="#cite_note-pmid33484556-236">[225]</a> In reality, all AAS have essentially similar AR-mediated effects,<a href="#cite_note-pmid25905231-242">[231]</a> even if some may differ in potency to a degree in certain tissues (e.g., skin, hair follicles, prostate gland) based on susceptibility to 5α-reduction and associated metabolic amplification or inactivation or lack thereof.<a href="#cite_note-pmid25905231-242">[231]</a><a href="#cite_note-pmid12880534-8">[8]</a> Per Handelsman, the terms "anabolic steroid" and "anabolic–androgenic steroid" are obsolete, meaningless, and falsely distinguish these agents from androgens when there is no physiological basis for such distinction.<a href="#cite_note-pmid21511988-235">[224]</a><a href="#cite_note-pmid33484556-236">[225]</a> In fact, it has been noted that the use and distinction of the concepts "anabolic" and "androgenic" as well as the term "anabolic–androgenic steroid" are oxymoronic, as anabolic refers to muscle-building while androgenic refers to induction and maintenance of male secondary sexual characteristics (which in principle would include anabolic or muscle-building effects).<a href="#cite_note-pmid21511988-235">[224]</a><a href="#cite_note-pmid33484556-236">[225]</a><a href="#cite_note-pmid36644692-243">[232]</a> Handelsman has argued that these terms should be discarded and instead, AAS should all simply be referred to as "androgens", with him using this term exclusively to refer to these agents in his publications.<a href="#cite_note-pmid21511988-235">[224]</a><a href="#cite_note-pmid33484556-236">[225]</a> Although the term "anabolic–androgenic steroid" is technically valid in describing two types of actions of these agents, Handelsman considers the term unnecessary and redundant and likens it to hypothetical never-used terms like "luteal–gestational progestins" or "mammary–uterine estrogens".<a href="#cite_note-pmid21511988-235">[224]</a> Handelsman also notes that "anabolic steroid" is easily and unnecessarily confusable with <a href="/wiki/Corticosteroid" title="Corticosteroid">corticosteroids</a>.<a href="#cite_note-pmid21511988-235">[224]</a> Aside from AAS, Handelsman has criticized the term "<a href="/wiki/Selective_androgen_receptor_modulator" title="Selective androgen receptor modulator">selective androgen receptor modulator</a> (SARM)" and claims about these agents as well.<a href="#cite_note-pmid35277356-237">[226]</a><a href="#cite_note-pmid21511988-235">[224]</a><a href="#cite_note-pmid33484556-236">[225]</a><a href="#cite_note-Handelsman2012-241">[230]</a> <div class="mw-heading mw-heading3"><h3 id="Legal_status">Legal status</h3>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=53" title="Edit section: Legal status">edit</a>]</div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Compounds_showing_anabolic_and_androgenic_effects.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/en/thumb/3/39/Compounds_showing_anabolic_and_androgenic_effects.png/220px-Compounds_showing_anabolic_and_androgenic_effects.png" decoding="async" width="220" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/3/39/Compounds_showing_anabolic_and_androgenic_effects.png/330px-Compounds_showing_anabolic_and_androgenic_effects.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/3/39/Compounds_showing_anabolic_and_androgenic_effects.png/440px-Compounds_showing_anabolic_and_androgenic_effects.png 2x" data-file-width="1016" data-file-height="555" /></a><figcaption>Various compounds with anabolic and androgenic effects, their relation with AAS</figcaption></figure> The legal status of AAS varies from country to country: some have stricter controls on their use or prescription than others though in many countries they are not illegal. In the U.S., AAS are currently listed as Schedule III <a href="/wiki/Controlled_substances" class="mw-redirect" title="Controlled substances">controlled substances</a> under the <a href="/wiki/Controlled_Substances_Act" title="Controlled Substances Act">Controlled Substances Act</a>, which makes simple possession of such substances without a prescription a federal crime punishable by up to one year in prison for the first offense. Unlawful distribution or possession with intent to distribute AAS as a first offense is punished by up to ten years in prison.<a href="#cite_note-US_Department_of_Justice-244">[233]</a> In Canada, AAS and their derivatives are part of the <a href="/wiki/Controlled_Drugs_and_Substances_Act" title="Controlled Drugs and Substances Act">Controlled Drugs and Substances Act</a> and are <a href="/wiki/Controlled_Drugs_and_Substances_Act#Schedule_IV" title="Controlled Drugs and Substances Act">Schedule IV</a> substances, meaning that it is illegal to obtain or sell them without a prescription; however, possession is not punishable, a consequence reserved for schedule I, II, or III substances. Those guilty of buying or selling AAS in Canada can be imprisoned for up to 18 months.<a href="#cite_note-laws-lois.justice.gc.ca-245">[234]</a> Import and export also carry similar penalties. In Canada, researchers have concluded that steroid use among student athletes is extremely widespread. A study conducted in 1993 by the Canadian Centre for Drug-Free Sport found that nearly 83,000 Canadians between the ages of 11 and 18 use steroids.<a href="#cite_note-Deacon-1994-246">[235]</a> AAS are also illegal without prescription in Australia,<a href="#cite_note-Australian_Institute_of_Criminology-2006-247">[236]</a> Argentina,[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] Brazil,[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] and Portugal,[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] and are listed as Class C <a href="/wiki/Controlled_Drug" class="mw-redirect" title="Controlled Drug">Controlled Drugs</a> in the United Kingdom. AAS are readily available without a prescription in some countries such as Mexico and Thailand. <table class="wikitable"> <caption>Legal status of anabolic substances in most western countries </caption> <tbody><tr> <th>Substance</th> <th>Example</th> <th>Classified as hormonal substances</th> <th>Anabolic and androgenic effects</th> <th>Legally sold OTC </th></tr> <tr> <th>Natural testosterone </th> <td>testosterone</td> <td>hormonal</td> <td>yes</td> <td>not legal </td></tr> <tr> <th>Artificially created anabolic steroids </th> <td>trenbolone, oxandrolone</td> <td>hormonal</td> <td>yes</td> <td>not legal </td></tr> <tr> <th>Prohormones </th> <td>4-androstenedione</td> <td>hormonal</td> <td>indirect only</td> <td>not legal </td></tr> <tr> <th>Phytoandrogens </th> <td>daidzein, gutta-percha triterpenoids</td> <td>no</td> <td>yes</td> <td>legal </td></tr> <tr> <th>Phytosteroids </th> <td>campesterol, beta-sitosterole, stigmasterol</td> <td>no</td> <td>indirect only</td> <td>legal </td></tr> <tr> <th>Xenoandrogens </th> <td>modified tocopherols, modified nicotinamide</td> <td>no</td> <td>yes</td> <td>legal </td></tr> <tr> <th>Phytoecdysteroids </th> <td>(25S)-20, 22-O-(R-ethylidene)inokosterone</td> <td>no</td> <td>yes</td> <td>legal </td></tr> <tr> <th><a href="/wiki/Selective_androgen_receptor_modulators" class="mw-redirect" title="Selective androgen receptor modulators">Selective androgen receptor modulators</a> </th> <td><a href="/wiki/Ostarine" class="mw-redirect" title="Ostarine">ostarine</a></td> <td></td> <td>anabolic<a href="#cite_note-pmid30503797-248">[237]</a></td> <td>not for human consumption<a href="#cite_note-pmid32852861-249">[238]</a><a href="#cite_note-Turnock-2023-250">[239]</a> </td></tr></tbody></table> <div class="mw-heading mw-heading4"><h4 id="United_States">United States</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=54" title="Edit section: United States">edit</a>]</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:SteroidpillsDEA.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/4/46/SteroidpillsDEA.jpg" decoding="async" width="200" height="170" class="mw-file-element" data-file-width="200" data-file-height="170" /></a><figcaption> Steroid pills intercepted by the US Drug Enforcement Administration during the Operation Raw Deal bust in September 2007</figcaption></figure> The history of the U.S. legislation on AAS goes back to the late 1980s, when the <a href="/wiki/U.S._Congress" class="mw-redirect" title="U.S. Congress">U.S. Congress</a> considered placing AAS under the Controlled Substances Act following the controversy over <a href="/wiki/Ben_Johnson_(Canadian_sprinter)" title="Ben Johnson (Canadian sprinter)">Ben Johnson's</a> victory at the <a href="/wiki/1988_Summer_Olympics" title="1988 Summer Olympics">1988 Summer Olympics</a> in <a href="/wiki/Seoul" title="Seoul">Seoul</a>. AAS were added to Schedule III of the Controlled Substances Act in the <a href="/wiki/Anabolic_Steroids_Control_Act_of_1990" class="mw-redirect" title="Anabolic Steroids Control Act of 1990">Anabolic Steroids Control Act of 1990</a>.<a href="#cite_note-congress-251">[240]</a> The same act also introduced more stringent controls with higher criminal penalties for offenses involving the illegal distribution of AAS and human growth hormone. By the early 1990s, after AAS were scheduled in the U.S., several pharmaceutical companies stopped manufacturing or marketing the products in the U.S., including <a href="/wiki/Ciba_Specialty_Chemicals" title="Ciba Specialty Chemicals">Ciba</a>, <a href="/wiki/G._D._Searle_%26_Company" class="mw-redirect" title="G. D. Searle & Company">Searle</a>, <a href="/wiki/Syntex" title="Syntex">Syntex</a>, and others. In the Controlled Substances Act, AAS are defined to be any drug or hormonal substance chemically and pharmacologically related to testosterone (other than <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogens</a>, <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestins</a>, and <a href="/wiki/Corticosteroid" title="Corticosteroid">corticosteroids</a>) that promote muscle growth. The act was amended by the Anabolic Steroid Control Act of 2004, which added <a href="/wiki/Prohormone" title="Prohormone">prohormones</a> to the list of <a href="/wiki/Controlled_substance" title="Controlled substance">controlled substances</a>, with effect from 20 January 2005.<a href="#cite_note-usdoj-252">[241]</a> Even though they can still be prescribed by a medical doctor in the U.S., the use of anabolic steroids for injury recovery purposes has been a taboo subject, even amongst the majority of sports medicine doctors and endocrinologists. <div class="mw-heading mw-heading4"><h4 id="United_Kingdom">United Kingdom</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=55" title="Edit section: United Kingdom">edit</a>]</div> In the United Kingdom, AAS are classified as class C drugs, which puts them in the same class as <a href="/wiki/Benzodiazepines" class="mw-redirect" title="Benzodiazepines">benzodiazepines</a>. AAS are in Schedule 4, which is divided in 2 parts; Part 1 contains most of the benzodiazepines and Part 2 contains the AAS. Part 1 drugs are subject to full import and export controls with possession being an offence without an appropriate prescription. There is no restriction on the possession when it is part of a medicinal product. Part 2 drugs require a Home Office licence for importation and export unless the substance is in the form of a medicinal product and is for self-administration by a person.<a href="#cite_note-Egton_Medical_Information_Systems_Limited-253">[242]</a> <div class="mw-heading mw-heading3"><h3 id="Status_in_sports">Status in sports</h3>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=56" title="Edit section: Status in sports">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Doping_in_sport" title="Doping in sport">Doping in sport</a></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Anabolic_substances_and_their_legal_status_in_most_Western_countries.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/en/thumb/f/f2/Anabolic_substances_and_their_legal_status_in_most_Western_countries.png/220px-Anabolic_substances_and_their_legal_status_in_most_Western_countries.png" decoding="async" width="220" height="174" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/f2/Anabolic_substances_and_their_legal_status_in_most_Western_countries.png/330px-Anabolic_substances_and_their_legal_status_in_most_Western_countries.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/f2/Anabolic_substances_and_their_legal_status_in_most_Western_countries.png/440px-Anabolic_substances_and_their_legal_status_in_most_Western_countries.png 2x" data-file-width="600" data-file-height="474" /></a><figcaption>Legal status of AAS and other drugs with anabolic effects in Western countries</figcaption></figure> AAS are banned by all major sports bodies including <a href="/wiki/Association_of_Tennis_Professionals" title="Association of Tennis Professionals">Association of Tennis Professionals</a>, <a href="/wiki/Major_League_Baseball" title="Major League Baseball">Major League Baseball</a>, <a href="/wiki/F%C3%A9d%C3%A9ration_Internationale_de_Football_Association" class="mw-redirect" title="Fédération Internationale de Football Association">Fédération Internationale de Football Association</a>,<a href="#cite_note-FIFA-254">[243]</a> the <a href="/wiki/Olympics" class="mw-redirect" title="Olympics">Olympics</a>,<a href="#cite_note-International_Olympic_Committee-1999-255">[244]</a> the <a href="/wiki/National_Basketball_Association" title="National Basketball Association">National Basketball Association</a>,<a href="#cite_note-NBA_Policy-1999-256">[245]</a> the <a href="/wiki/National_Hockey_League" title="National Hockey League">National Hockey League</a>,<a href="#cite_note-nhlpa.com-257">[246]</a> <a href="/wiki/World_Wrestling_Entertainment" class="mw-redirect" title="World Wrestling Entertainment">World Wrestling Entertainment</a> and the <a href="/wiki/National_Football_League" title="National Football League">National Football League</a>.<a href="#cite_note-nflpa.com-2006-258">[247]</a> The <a href="/wiki/World_Anti-Doping_Agency" title="World Anti-Doping Agency">World Anti-Doping Agency</a> (WADA) maintains the list of performance-enhancing substances used by many major sports bodies and includes all anabolic agents, which includes all AAS and precursors as well as all hormones and related substances.<a href="#cite_note-WADA-2003-259">[248]</a><a href="#cite_note-WADA-2005-260">[249]</a> <div class="mw-heading mw-heading3"><h3 id="Usage">Usage</h3>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=57" title="Edit section: Usage">edit</a>]</div> <div class="mw-heading mw-heading4"><h4 id="Law_enforcement">Law enforcement</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=58" title="Edit section: Law enforcement">edit</a>]</div> United States federal law enforcement officials have expressed concern about AAS use by police officers. "It's a big problem, and from the number of cases, it's something we shouldn't ignore. It's not that we set out to target cops, but when we're in the middle of an active investigation into <a href="/wiki/Steroid" title="Steroid">steroids</a>, there have been quite a few cases that have led back to police officers," says Lawrence Payne, a spokesman for the United States <a href="/wiki/Drug_Enforcement_Administration" title="Drug Enforcement Administration">Drug Enforcement Administration</a>.<a href="#cite_note-Keeping-2010-261">[250]</a> The FBI Law Enforcement Bulletin stated that "Anabolic steroid abuse by police officers is a serious problem that merits greater awareness by departments across the country".<a href="#cite_note-The_Police_Chief-2008-262">[251]</a> It is also believed that police officers across the United Kingdom "are using criminals to buy steroids" which he claims to be a top risk factor for <a href="/wiki/Police_corruption" title="Police corruption">police corruption</a>. <div class="mw-heading mw-heading4"><h4 id="Professional_wrestling">Professional wrestling</h4>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=59" title="Edit section: Professional wrestling">edit</a>]</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/WWE#Wellness_Program" title="WWE">WWE § Wellness Program</a></div> Following the <a href="/wiki/Chris_Benoit_double-murder_and_suicide" title="Chris Benoit double-murder and suicide">Chris Benoit double-murder and suicide</a> in 2007, the <a href="/wiki/Oversight_and_Government_Reform_Committee" class="mw-redirect" title="Oversight and Government Reform Committee">Oversight and Government Reform Committee</a> investigated steroid usage in the wrestling industry.<a href="#cite_note-Lockhart-2010-263">[252]</a> The Committee investigated <a href="/wiki/WWE" title="WWE">WWE</a> and <a href="/wiki/Total_Nonstop_Action_Wrestling" title="Total Nonstop Action Wrestling">Total Nonstop Action Wrestling</a>, asking for documentation of their companies' drug policies. WWE CEO and chairman, <a href="/wiki/Linda_McMahon" title="Linda McMahon">Linda</a> and <a href="/wiki/Vince_McMahon" title="Vince McMahon">Vince McMahon</a> respectively, both testified. The documents stated that 75 wrestlers—roughly 40 percent—had tested positive for drug use since 2006, most commonly for steroids.<a href="#cite_note-oversight.house.gov-264">[253]</a><a href="#cite_note-The_Day-2007-265">[254]</a> <div class="mw-heading mw-heading3"><h3 id="Economics">Economics</h3>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=60" title="Edit section: Economics">edit</a>]</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/Illegal_trade_in_anabolic_steroids" class="mw-redirect" title="Illegal trade in anabolic steroids">Illegal trade in anabolic steroids</a></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Rd17.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/34/Rd17.jpg/220px-Rd17.jpg" decoding="async" width="220" height="112" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/34/Rd17.jpg/330px-Rd17.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/34/Rd17.jpg/440px-Rd17.jpg 2x" data-file-width="1280" data-file-height="652" /></a><figcaption>Several large buckets containing tens of thousands of AAS vials confiscated by the <a href="/wiki/DEA" class="mw-redirect" title="DEA">DEA</a> during Operation Raw Deal in 2007</figcaption></figure> AAS are frequently produced in pharmaceutical laboratories, but, in nations where stricter laws are present, they are also produced in small home-made underground laboratories, usually from raw substances imported from abroad.<a href="#cite_note-Assael-2007-266">[255]</a> In these countries, the majority of steroids are obtained illegally through <a href="/wiki/Black_market" title="Black market">black market</a> trade.<a href="#cite_note-Yesalis-2000-267">[256]</a><a href="#cite_note-Black-1996-268">[257]</a> These steroids are usually manufactured in other countries, and therefore must be <a href="/wiki/Smuggled" class="mw-redirect" title="Smuggled">smuggled</a> across international borders. As with most significant smuggling operations, <a href="/wiki/Organized_crime" title="Organized crime">organized crime</a> is involved.<a href="#cite_note-Pound-2006-269">[258]</a> In the late 2000s, the worldwide trade in illicit AAS increased significantly, and authorities announced record captures on three continents. In 2006, Finnish authorities announced a record seizure of 11.8 million AAS tablets. A year later, the <a href="/wiki/DEA" class="mw-redirect" title="DEA">DEA</a> seized 11.4 million units of AAS in the largest U.S. seizure ever. In the first three months of 2008, Australian customs reported a record 300 seizures of AAS shipments.<a href="#cite_note-pmid18599224-117">[114]</a> In the U.S., Canada, and Europe, illegal steroids are sometimes purchased just as any other illegal drug, through dealers who are able to obtain the drugs from a number of sources. Illegal AAS are sometimes sold at gyms and competitions, and through the mail, but may also be obtained through pharmacists, veterinarians, and physicians.<a href="#cite_note-National_Institute_on_Drug_Abuse-270">[259]</a> In addition, a significant number of counterfeit products are sold as AAS, in particular via mail order from websites posing as overseas pharmacies. In the U.S., black-market importation continues from Mexico, Thailand, and other countries where steroids are more easily available, as they are legal.<a href="#cite_note-Office_of_the_Inspector_General-2007-271">[260]</a> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=61" title="Edit section: Research">edit</a>]</div> AAS, alone and in combination with <a href="/wiki/Progestogen" title="Progestogen">progestogens</a>, have been studied as potential <a href="/wiki/Male_hormonal_contraceptive" class="mw-redirect" title="Male hormonal contraceptive">male hormonal contraceptives</a>.<a href="#cite_note-pmid20933120-50">[50]</a> Dual AAS and <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestins</a> such as <a href="/wiki/Trestolone" title="Trestolone">trestolone</a> and <a href="/wiki/Dimethandrolone_undecanoate" title="Dimethandrolone undecanoate">dimethandrolone undecanoate</a> have also been studied as male contraceptives, with the latter under active investigation as of 2018.<a href="#cite_note-pmid23063338-272">[261]</a><a href="#cite_note-pmid16497801-181">[178]</a><a href="#cite_note-EndocrineSociety2018-273">[262]</a> Topical androgens have been used and studied in the treatment of <a href="/wiki/Cellulite" title="Cellulite">cellulite</a> in women.<a href="#cite_note-pmid12626029-274">[263]</a> Topical androstanolone on the abdomen has been found to significantly decrease subcutaneous abdominal fat in women, and hence may be useful for improving body silhouette.<a href="#cite_note-pmid12626029-274">[263]</a> However, men and <a href="/wiki/Hyperandrogenic" class="mw-redirect" title="Hyperandrogenic">hyperandrogenic</a> women have higher amounts of abdominal fat than healthy women, and androgens have been found to increase abdominal fat in <a href="/wiki/Postmenopausal" class="mw-redirect" title="Postmenopausal">postmenopausal</a> women and <a href="/wiki/Transgender_men" class="mw-redirect" title="Transgender men">transgender men</a> as well.<a href="#cite_note-pmid25781555-275">[264]</a> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=62" title="Edit section: See also">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1184024115">.mw-parser-output .div-col{margin-top:0.3em;column-width:30em}.mw-parser-output .div-col-small{font-size:90%}.mw-parser-output .div-col-rules{column-rule:1px solid #aaa}.mw-parser-output .div-col dl,.mw-parser-output .div-col ol,.mw-parser-output .div-col ul{margin-top:0}.mw-parser-output .div-col li,.mw-parser-output .div-col dd{page-break-inside:avoid;break-inside:avoid-column}</style><div class="div-col" style="column-width: 30em;"> <ul><li><a href="/wiki/Selective_androgen_receptor_modulator" title="Selective androgen receptor modulator">Selective androgen receptor modulator</a></li> <li><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogen</a></li> <li><a href="/wiki/Mossman-Pacey_paradox" class="mw-redirect" title="Mossman-Pacey paradox">Mossman-Pacey paradox</a></li> <li><a href="/wiki/Steroid_rosacea" title="Steroid rosacea">Steroid rosacea</a></li> <li><a href="/wiki/Steroid_use_in_Bollywood" title="Steroid use in Bollywood">Steroid use in Bollywood</a></li> <li><a href="/wiki/List_of_androgens/anabolic_steroids_available_in_the_United_States" title="List of androgens/anabolic steroids available in the United States">List of androgens/anabolic steroids available in the United States</a></li> <li><a href="/wiki/Juiced_(book)" title="Juiced (book)">Juiced</a>, 2005 book</li> <li><a href="/wiki/Bigger,_Stronger,_Faster*" title="Bigger, Stronger, Faster*">Bigger, Stronger, Faster*</a>, 2008 documentary film</li></ul> </div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=63" title="Edit section: References">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-pmid29494025-1"><a href="#cite_ref-pmid29494025_1-0">^</a> <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="CITEREFGanesanRahmanZito2023" class="citation book cs1">Ganesan K, Rahman S, Zito PM (2023). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/books/NBK482418/">"Anabolic Steroids"</a>. StatPearls. 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Lippincott Williams & Wilkins. pp. 1358–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-60913-345-0" title="Special:BookSources/978-1-60913-345-0"><bdi>978-1-60913-345-0</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210414135448/https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA1358">Archived</a> from the original on 14 April 2021. 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Springer Science & Business Media. pp. 176–177. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-68223-0" title="Special:BookSources/978-3-642-68223-0"><bdi>978-3-642-68223-0</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210213223558/https://books.google.com/books?id=W1cGCAAAQBAJ&pg=PT176">Archived</a> from the original on 13 February 2021. 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In Fillit HM, Rockwood K, Woodhouse K (eds.). Brocklehurst's Textbook of Geriatric Medicine and Gerontology. Elsevier Health Sciences. pp. 166–167. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4377-2075-4" title="Special:BookSources/978-1-4377-2075-4"><bdi>978-1-4377-2075-4</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200109183401/https://books.google.com/books?id=DPcUtY0kP7oC&pg=PA166">Archived</a> from the original on 9 January 2020. 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In Thieme D, Hemmersbach P (eds.). Doping in Sports. Springer Science & Business Media. pp. 470–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-540-79088-4" title="Special:BookSources/978-3-540-79088-4"><bdi>978-3-540-79088-4</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200109183423/https://books.google.com/books?id=R-hIC-caIn8C&pg=PA470">Archived</a> from the original on 9 January 2020. 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The Journal of Steroid Biochemistry and Molecular Biology. 110 (3–5): 214–222. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.jsbmb.2007.11.009">10.1016/j.jsbmb.2007.11.009</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2575079">2575079</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/18555683">18555683</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Steroid+Biochemistry+and+Molecular+Biology&rft.atitle=Dimethandrolone+%287alpha%2C11beta-dimethyl-19-nortestosterone%29+and+11beta-methyl-19-nortestosterone+are+not+converted+to+aromatic+A-ring+products+in+the+presence+of+recombinant+human+aromatase&rft.volume=110&rft.issue=3%E2%80%935&rft.pages=214-222&rft.date=2008-06&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2575079%23id-name%3DPMC&rft_id=info%3Apmid%2F18555683&rft_id=info%3Adoi%2F10.1016%2Fj.jsbmb.2007.11.009&rft.aulast=Attardi&rft.aufirst=BJ&rft.au=Pham%2C+TC&rft.au=Radler%2C+LC&rft.au=Burgenson%2C+J&rft.au=Hild%2C+SA&rft.au=Reel%2C+JR&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2575079&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-Llewellyn2011c-179"><a href="#cite_ref-Llewellyn2011c_179-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLlewellyn,_William2011" class="citation book cs1">Llewellyn, William (2011). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=afKLA-6wW0oC&pg=PT533">Anabolics</a>. Molecular Nutrition Llc. pp. 533–, 402–412, 460–467. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-9828280-1-4" title="Special:BookSources/978-0-9828280-1-4"><bdi>978-0-9828280-1-4</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200517071827/https://books.google.com/books?id=afKLA-6wW0oC&pg=PT533">Archived</a> from the original on 17 May 2020. 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Helsinki: University of Helsinki. p. 14. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/952-91-2950-5" title="Special:BookSources/952-91-2950-5"><bdi>952-91-2950-5</bdi></a>. Archived from <a rel="nofollow" class="external text" href="http://ethesis.helsinki.fi/julkaisut/laa/biola/vk/suvisaari/7alphame.pdf">the original</a> (PDF) on 11 August 2017. Retrieved 2 December 2016. <q>Androgens, estrogens and progestins exert a negative feedback effect on the secretion of GnRH and LH by their actions on the pituitary and the hypothalamus. Most of the negative feedback effect of androgens is caused by their estrogenic metabolites produced by aromatization. 5α-Reduction does not seem to be necessary for the negative feedback effect of testosterone. (Rittmaster et al, 1992; Kumar et al, 1995a; Hayes et al, 2000).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adissertation&rft.title=7%CE%B1-Methyl-19-nortestosterone+%28MENT%29+Pharmacokinetics+and+Antigonadotropic+Effects+in+Men&rft.degree=Ph.D.&rft.inst=University+of+Helsinki&rft.date=2000&rft.isbn=952-91-2950-5&rft.aulast=Suvisaari&rft.aufirst=J&rft_id=http%3A%2F%2Fethesis.helsinki.fi%2Fjulkaisut%2Flaa%2Fbiola%2Fvk%2Fsuvisaari%2F7alphame.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-pmid16497801-181">^ <a href="#cite_ref-pmid16497801_181-0">a</a> <a href="#cite_ref-pmid16497801_181-1">b</a> <a href="#cite_ref-pmid16497801_181-2">c</a> <a href="#cite_ref-pmid16497801_181-3">d</a> <a href="#cite_ref-pmid16497801_181-4">e</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAttardiHildReel2006" class="citation journal cs1">Attardi BJ, Hild SA, Reel JR (June 2006). <a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fen.2005-1524">"Dimethandrolone undecanoate: a new potent orally active androgen with progestational activity"</a>. Endocrinology. 147 (6): 3016–3026. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fen.2005-1524">10.1210/en.2005-1524</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16497801">16497801</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Endocrinology&rft.atitle=Dimethandrolone+undecanoate%3A+a+new+potent+orally+active+androgen+with+progestational+activity&rft.volume=147&rft.issue=6&rft.pages=3016-3026&rft.date=2006-06&rft_id=info%3Adoi%2F10.1210%2Fen.2005-1524&rft_id=info%3Apmid%2F16497801&rft.aulast=Attardi&rft.aufirst=BJ&rft.au=Hild%2C+SA&rft.au=Reel%2C+JR&rft_id=https%3A%2F%2Fdoi.org%2F10.1210%252Fen.2005-1524&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-Warren-2000-182"><a href="#cite_ref-Warren-2000_182-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMyhalLamb2000" class="citation book cs1">Myhal M, Lamb DR (1 May 2000). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=HNJ9BwAAQBAJ&pg=PA458">"Hormones as Performance-Enhancing Drugs"</a>. In Warren MP, Constantini NW (eds.). Sports Endocrinology. Springer Science & Business Media. pp. 458–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-59259-016-2" title="Special:BookSources/978-1-59259-016-2"><bdi>978-1-59259-016-2</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170928135842/https://books.google.com/books?id=HNJ9BwAAQBAJ&pg=PA458">Archived</a> from the original on 28 September 2017. Retrieved 2 December 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Hormones+as+Performance-Enhancing+Drugs&rft.btitle=Sports+Endocrinology&rft.pages=458-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2000-05-01&rft.isbn=978-1-59259-016-2&rft.aulast=Myhal&rft.aufirst=M&rft.au=Lamb%2C+DR&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DHNJ9BwAAQBAJ%26pg%3DPA458&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-Haff-2015-183"><a href="#cite_ref-Haff-2015_183-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCampbell2015" class="citation book cs1">Campbell B (23 September 2015). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=bfuXCgAAQBAJ&pg=PA233">"Performance-Enhancing Substances and Methods"</a>. In Haff GG, Triplett NT (eds.). Essentials of Strength Training and Conditioning (4th ed.). Human Kinetics. pp. 233–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4925-0162-6" title="Special:BookSources/978-1-4925-0162-6"><bdi>978-1-4925-0162-6</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180217202709/https://books.google.com/books?id=bfuXCgAAQBAJ&pg=PA233">Archived</a> from the original on 17 February 2018. 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Lippincott Williams & Wilkins. pp. 1360–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-60913-345-0" title="Special:BookSources/978-1-60913-345-0"><bdi>978-1-60913-345-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Men%27s+Health&rft.btitle=Foye%27s+Principles+of+Medicinal+Chemistry&rft.pages=1360-&rft.edition=7th&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2012-01-24&rft.isbn=978-1-60913-345-0&rft.aulast=Lemke&rft.aufirst=TL&rft.au=Williams%2C+DA&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DSd6ot9ul-bUC%26pg%3DPA1360&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-Karch-2001-185">^ <a href="#cite_ref-Karch-2001_185-0">a</a> <a href="#cite_ref-Karch-2001_185-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKarchDrummer2001" class="citation book cs1">Karch SB, Drummer O (26 December 2001). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=AUTWJwn8uOwC&pg=PA489">"Anabolic Steroids"</a>. Karch's Pathology of Drug Abuse (Third ed.). CRC Press. pp. 489–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4200-4211-5" title="Special:BookSources/978-1-4200-4211-5"><bdi>978-1-4200-4211-5</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200109183415/https://books.google.com/books?id=AUTWJwn8uOwC&pg=PA489">Archived</a> from the original on 9 January 2020. 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"Uber krystallinisches mannliches Hormon aus Hoden (Testosteron) wirksamer als aus harn oder aus Cholesterin bereitetes Androsteron". 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"Über die Umwandlung des Dehydro-androsterons in Δ4-Androsten-ol-(17)-0n-(3) (Testosteron); ein Weg zur Darstellung des Testosterons aus Cholesterin (Vorläuf. Mitteil.)" [On the conversion of dehydro-Δ4-androstene androsterons in-ol (17) 0n (3) (testosterone), a way to represent the testosterone from cholesterol (Vorläuf. msgs.)]. 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"Sexualhormone VII. Uber die kunstliche Herstellung des Testikelhormons. Testosteron (Androsten-3-one-17-ol.)" [Sex hormones VII About the artificial production of testosterone Testikelhormons (androstene-3-one-17-ol)]. Helvetica Chimica Acta (in German). 18: 1264–75. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fhlca.193501801176">10.1002/hlca.193501801176</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Helvetica+Chimica+Acta&rft.atitle=Sexualhormone+VII.+Uber+die+kunstliche+Herstellung+des+Testikelhormons.+Testosteron+%28Androsten-3-one-17-ol.%29&rft.volume=18&rft.pages=1264-75&rft.date=1935&rft_id=info%3Adoi%2F10.1002%2Fhlca.193501801176&rft.aulast=Ruzicka&rft.aufirst=L&rft.au=Wettstein%2C+A&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-Taylor-2009-224">^ <a href="#cite_ref-Taylor-2009_224-0">a</a> <a href="#cite_ref-Taylor-2009_224-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTaylor2009" class="citation book cs1">Taylor WN (1 January 2009). 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McFarland & Company. p. 181. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7864-1128-3" title="Special:BookSources/978-0-7864-1128-3"><bdi>978-0-7864-1128-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Anabolic+Steroids+and+the+Athlete&rft.pages=181&rft.pub=McFarland+%26+Company&rft.date=2009-01-01&rft.isbn=978-0-7864-1128-3&rft.aulast=Taylor&rft.aufirst=WN&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-Suarez-2002-225"><a href="#cite_ref-Suarez-2002_225-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSuarezSenior_CorrespondentKelmanphysician2002" class="citation web cs1">Suarez R, Senior Correspondent, Kelman J, physician (18 November 2002). <a rel="nofollow" class="external text" href="https://www.pbs.org/newshour/bb/health/july-dec02/jfk_11-18.html">"President Kennedy's Health Secrets"</a>. PBS NewsHour. Public Broadcasting System. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20140122095434/http://www.pbs.org/newshour/bb/health/july-dec02/jfk_11-18.html">Archived</a> from the original on 22 January 2014. Retrieved 24 August 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=PBS+NewsHour&rft.atitle=President+Kennedy%27s+Health+Secrets&rft.date=2002-11-18&rft.aulast=Suarez&rft.aufirst=R&rft.au=Senior+Correspondent&rft.au=Kelman%2C+J&rft.au=physician&rft_id=https%3A%2F%2Fwww.pbs.org%2Fnewshour%2Fbb%2Fhealth%2Fjuly-dec02%2Fjfk_11-18.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-pmid16510635-226"><a href="#cite_ref-pmid16510635_226-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCalfeeFadale2006" class="citation journal cs1">Calfee R, Fadale P (March 2006). <a rel="nofollow" class="external text" href="https://doi.org/10.1542%2Fpeds.2005-1429">"Popular ergogenic drugs and supplements in young athletes"</a>. Pediatrics. 117 (3): e577–e589. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1542%2Fpeds.2005-1429">10.1542/peds.2005-1429</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16510635">16510635</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:6559714">6559714</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pediatrics&rft.atitle=Popular+ergogenic+drugs+and+supplements+in+young+athletes&rft.volume=117&rft.issue=3&rft.pages=e577-e589&rft.date=2006-03&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A6559714%23id-name%3DS2CID&rft_id=info%3Apmid%2F16510635&rft_id=info%3Adoi%2F10.1542%2Fpeds.2005-1429&rft.aulast=Calfee&rft.aufirst=R&rft.au=Fadale%2C+P&rft_id=https%3A%2F%2Fdoi.org%2F10.1542%252Fpeds.2005-1429&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-www.slate.com-227"><a href="#cite_ref-www.slate.com_227-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPeters2005" class="citation web cs1">Peters J (18 February 2005). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20110907192748/http://www.slate.com/id/2113752">"The Man Behind the Juice"</a>. Slate. Archived from <a rel="nofollow" class="external text" href="http://www.slate.com/id/2113752/">the original</a> on 7 September 2011. Retrieved 29 April 2008.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Slate&rft.atitle=The+Man+Behind+the+Juice&rft.date=2005-02-18&rft.aulast=Peters&rft.aufirst=J&rft_id=http%3A%2F%2Fwww.slate.com%2Fid%2F2113752%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-Kochakian-1946-228">^ <a href="#cite_ref-Kochakian-1946_228-0">a</a> <a href="#cite_ref-Kochakian-1946_228-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKochakian1946" class="citation book cs1">Kochakian CD (1946). "The Protein Anabolic Effects of Steroid Hormones". In Harris RS, Thimann KV (eds.). Vitamins and Hormones. Vol. 4. Academic Press. pp. 255–310. <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%2FS0083-6729%2808%2961085-7">10.1016/S0083-6729(08)61085-7</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-709804-3" title="Special:BookSources/978-0-12-709804-3"><bdi>978-0-12-709804-3</bdi></a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0083-6729">0083-6729</a>. <q>In recent years several laboratories (Kochakian, Albright, Wilkins) have entertained the hope of finding a protein anabolic steroid without any, or with only minor, sexual effects. These studies have received special impetus and encouragement from the observation of Kochakian that certain steroids have greater renotrophic (anabolic?) than androgenic effects.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=The+Protein+Anabolic+Effects+of+Steroid+Hormones&rft.btitle=Vitamins+and+Hormones&rft.pages=255-310&rft.pub=Academic+Press&rft.date=1946&rft.issn=0083-6729&rft_id=info%3Adoi%2F10.1016%2FS0083-6729%2808%2961085-7&rft.isbn=978-0-12-709804-3&rft.aulast=Kochakian&rft.aufirst=CD&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-Kochakian2012-229">^ <a href="#cite_ref-Kochakian2012_229-0">a</a> <a href="#cite_ref-Kochakian2012_229-1">b</a> <a href="#cite_ref-Kochakian2012_229-2">c</a> <a href="#cite_ref-Kochakian2012_229-3">d</a> <a href="#cite_ref-Kochakian2012_229-4">e</a> <a href="#cite_ref-Kochakian2012_229-5">f</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPottsArnoldBeyler2012" class="citation book cs1">Potts GO, Arnold A, Beyler AL (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=3-LrCAAAQBAJ&pg=PA361">"Dissociation of the Androgenic and Other Hormonal Activities from the Protein Anabolic Effects of Steroids"</a>. In Kochakian CD (ed.). Anabolic-Androgenic Steroids. Springer Science & Business Media. pp. 370–373, 380. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-66353-6" title="Special:BookSources/978-3-642-66353-6"><bdi>978-3-642-66353-6</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210414135445/https://books.google.com/books?id=3-LrCAAAQBAJ&pg=PA361">Archived</a> from the original on 14 April 2021. Retrieved 1 April 2019.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Dissociation+of+the+Androgenic+and+Other+Hormonal+Activities+from+the+Protein+Anabolic+Effects+of+Steroids&rft.btitle=Anabolic-Androgenic+Steroids&rft.pages=370-373%2C+380&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-3-642-66353-6&rft.aulast=Potts&rft.aufirst=GO&rft.au=Arnold%2C+A&rft.au=Beyler%2C+AL&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D3-LrCAAAQBAJ%26pg%3DPA361&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-Sneader2005-230"><a href="#cite_ref-Sneader2005_230-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSneader2005" class="citation book cs1">Sneader W (23 June 2005). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Cb6BOkj9fK4C&pg=PA206">"Hormone Analogs"</a>. Drug Discovery: A History. John Wiley & Sons. pp. 206–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-89979-2" title="Special:BookSources/978-0-471-89979-2"><bdi>978-0-471-89979-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Hormone+Analogs&rft.btitle=Drug+Discovery%3A+A+History&rft.pages=206-&rft.pub=John+Wiley+%26+Sons&rft.date=2005-06-23&rft.isbn=978-0-471-89979-2&rft.aulast=Sneader&rft.aufirst=W&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DCb6BOkj9fK4C%26pg%3DPA206&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-Wermuth2011-231">^ <a href="#cite_ref-Wermuth2011_231-0">a</a> <a href="#cite_ref-Wermuth2011_231-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChast2011" class="citation book cs1">Chast F (2 May 2011). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Qmt1_DQkCpEC&pg=PA34">"A History of Drug Discovery"</a>. In Wermuth CG (ed.). The Practice of Medicinal Chemistry. Academic Press. pp. 34–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-056877-5" title="Special:BookSources/978-0-08-056877-5"><bdi>978-0-08-056877-5</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210414083232/https://books.google.com/books?id=Qmt1_DQkCpEC&pg=PA34">Archived</a> from the original on 14 April 2021. Retrieved 28 June 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=A+History+of+Drug+Discovery&rft.btitle=The+Practice+of+Medicinal+Chemistry&rft.pages=34-&rft.pub=Academic+Press&rft.date=2011-05-02&rft.isbn=978-0-08-056877-5&rft.aulast=Chast&rft.aufirst=F&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DQmt1_DQkCpEC%26pg%3DPA34&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-Wright1994-232">^ <a href="#cite_ref-Wright1994_232-0">a</a> <a href="#cite_ref-Wright1994_232-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWright1994" class="citation book cs1">Wright JE (1994). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=GnbZAAAAMAAJ">Altered States: The Use and Abuse of Anabolic Steroids</a>. Masters Press. p. 33. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-57028-013-9" title="Special:BookSources/978-1-57028-013-9"><bdi>978-1-57028-013-9</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210414083330/https://books.google.com/books?id=GnbZAAAAMAAJ">Archived</a> from the original on 14 April 2021. Retrieved 28 June 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Altered+States%3A+The+Use+and+Abuse+of+Anabolic+Steroids&rft.pages=33&rft.pub=Masters+Press&rft.date=1994&rft.isbn=978-1-57028-013-9&rft.aulast=Wright&rft.aufirst=JE&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DGnbZAAAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-Office1957-233"><a href="#cite_ref-Office1957_233-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFUnited_States._Patent_Office1957" class="citation book cs1">United States. Patent Office (1957). <a rel="nofollow" class="external text" href="https://archive.org/details/officialgazette722unit">Official Gazette of the United States Patent Office</a>. U.S. Patent Office.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Official+Gazette+of+the+United+States+Patent+Office&rft.pub=U.S.+Patent+Office.&rft.date=1957&rft.au=United+States.+Patent+Office&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fofficialgazette722unit&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-Mozayani-2011-234"><a href="#cite_ref-Mozayani-2011_234-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFvon_DeutschAbukhalafSocci2011" class="citation book cs1">von Deutsch DA, Abukhalaf IK, Socci RR (18 September 2011). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=NhBJ6kg_uP0C&pg=PA651">"Anabolic doping agents"</a>. In Mozayani A, Raymon L (eds.). Handbook of Drug Interactions: A Clinical and Forensic Guide. Springer Science & Business Media. pp. 651–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-61779-222-9" title="Special:BookSources/978-1-61779-222-9"><bdi>978-1-61779-222-9</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210414135237/https://books.google.com/books?id=NhBJ6kg_uP0C&pg=PA651">Archived</a> from the original on 14 April 2021. Retrieved 28 June 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Anabolic+doping+agents&rft.btitle=Handbook+of+Drug+Interactions%3A+A+Clinical+and+Forensic+Guide&rft.pages=651-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2011-09-18&rft.isbn=978-1-61779-222-9&rft.aulast=von+Deutsch&rft.aufirst=DA&rft.au=Abukhalaf%2C+IK&rft.au=Socci%2C+RR&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DNhBJ6kg_uP0C%26pg%3DPA651&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-pmid21511988-235">^ <a href="#cite_ref-pmid21511988_235-0">a</a> <a href="#cite_ref-pmid21511988_235-1">b</a> <a href="#cite_ref-pmid21511988_235-2">c</a> <a href="#cite_ref-pmid21511988_235-3">d</a> <a href="#cite_ref-pmid21511988_235-4">e</a> <a href="#cite_ref-pmid21511988_235-5">f</a> <a href="#cite_ref-pmid21511988_235-6">g</a> <a href="#cite_ref-pmid21511988_235-7">h</a> <a href="#cite_ref-pmid21511988_235-8">i</a> <a href="#cite_ref-pmid21511988_235-9">j</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHandelsman2011" class="citation journal cs1">Handelsman DJ (May 2011). "Commentary: androgens and "anabolic steroids": the one-headed janus". Endocrinology. 152 (5): 1752–4. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fen.2010-1501">10.1210/en.2010-1501</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21511988">21511988</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Endocrinology&rft.atitle=Commentary%3A+androgens+and+%22anabolic+steroids%22%3A+the+one-headed+janus&rft.volume=152&rft.issue=5&rft.pages=1752-4&rft.date=2011-05&rft_id=info%3Adoi%2F10.1210%2Fen.2010-1501&rft_id=info%3Apmid%2F21511988&rft.aulast=Handelsman&rft.aufirst=DJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-pmid33484556-236">^ <a href="#cite_ref-pmid33484556_236-0">a</a> <a href="#cite_ref-pmid33484556_236-1">b</a> <a href="#cite_ref-pmid33484556_236-2">c</a> <a href="#cite_ref-pmid33484556_236-3">d</a> <a href="#cite_ref-pmid33484556_236-4">e</a> <a href="#cite_ref-pmid33484556_236-5">f</a> <a href="#cite_ref-pmid33484556_236-6">g</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHandelsman2021" class="citation journal cs1">Handelsman DJ (July 2021). "Androgen Misuse and Abuse". Endocr Rev. 42 (4): 457–501. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fendrev%2Fbnab001">10.1210/endrev/bnab001</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/33484556">33484556</a>. <q>However, a third major quest, for the development of a nonvirilizing androgen ("anabolic steroid") suitable for use in women and children, based on dissociating the virilizing from the anabolic effects of androgens failed comprehensively (36). This failure is now understood as being due to the discovery of a singular androgen receptor (AR) together with the misinterpretation of nonspecific whole animal androgen bioassays employed to distinguish between anabolic and virilizing effects (37). The term "androgen" is used herein for both endogenous and synthetic androgens including references to chemicals named elsewhere as "anabolic steroids," "anabolic-androgenic steroids," or "specific AR modulators" (SARM), which continue to make an obsolete and oxymoronic distinction between virilizing and anabolic effects of androgens where there is no difference (36).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Endocr+Rev&rft.atitle=Androgen+Misuse+and+Abuse&rft.volume=42&rft.issue=4&rft.pages=457-501&rft.date=2021-07&rft_id=info%3Adoi%2F10.1210%2Fendrev%2Fbnab001&rft_id=info%3Apmid%2F33484556&rft.aulast=Handelsman&rft.aufirst=DJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-pmid35277356-237">^ <a href="#cite_ref-pmid35277356_237-0">a</a> <a href="#cite_ref-pmid35277356_237-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHandelsman2022" class="citation journal cs1">Handelsman DJ (July 2022). "History of androgens and androgen action". Best Pract Res Clin Endocrinol Metab. 36 (4): 101629. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.beem.2022.101629">10.1016/j.beem.2022.101629</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/35277356">35277356</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Best+Pract+Res+Clin+Endocrinol+Metab&rft.atitle=History+of+androgens+and+androgen+action&rft.volume=36&rft.issue=4&rft.pages=101629&rft.date=2022-07&rft_id=info%3Adoi%2F10.1016%2Fj.beem.2022.101629&rft_id=info%3Apmid%2F35277356&rft.aulast=Handelsman&rft.aufirst=DJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-pmid24024843-238"><a href="#cite_ref-pmid24024843_238-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHandelsman2013" class="citation journal cs1">Handelsman DJ (September 2013). "Mechanisms of action of testosterone--unraveling a Gordian knot". N Engl J Med. 369 (11): 1058–9. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1056%2FNEJMe1305307">10.1056/NEJMe1305307</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/24024843">24024843</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:44485330">44485330</a>. <q>These findings also highlight how obsolete is the term "anabolic steroid," when falsely distinguishing from "androgen," a dichotomy devoid of physiological meaning and lingering mainly as a media piñata.10</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=N+Engl+J+Med&rft.atitle=Mechanisms+of+action+of+testosterone--unraveling+a+Gordian+knot&rft.volume=369&rft.issue=11&rft.pages=1058-9&rft.date=2013-09&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A44485330%23id-name%3DS2CID&rft_id=info%3Apmid%2F24024843&rft_id=info%3Adoi%2F10.1056%2FNEJMe1305307&rft.aulast=Handelsman&rft.aufirst=DJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-IyerHandelsman2017-239"><a href="#cite_ref-IyerHandelsman2017_239-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFIyerHandelsman2017" class="citation book cs1">Iyer R, Handelsman DJ (2017). "Testosterone Misuse and Abuse". Testosterone. Cham: Springer International Publishing. pp. 375–402. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-319-46086-4_19">10.1007/978-3-319-46086-4_19</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-319-46084-0" title="Special:BookSources/978-3-319-46084-0"><bdi>978-3-319-46084-0</bdi></a>. <q>By definition, all androgens combine intrinsic anabolic and androgenic properties, which have never been meaningfully separated [67], manifest via the androgen receptor, a protein encoded by a single copy gene. Hence the singularity of androgen action means that the terms "anabolic steroid" or "androgenic-anabolic steroids" remain an obsolete terminology making a distinction between androgenic and anabolic effects where there is no real difference [67]. This obsolete yet widely used terminology represent a vestige of the unsuccessful quest by the pharmaceutical industry to dissociate the virilizing from anabolic properties and remains in the public mind mainly as a media piñata. Androgen abuse, a more appropriate term which encompasses illicit use of all available androgens, will be used in this chapter.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Testosterone+Misuse+and+Abuse&rft.btitle=Testosterone&rft.place=Cham&rft.pages=375-402&rft.pub=Springer+International+Publishing&rft.date=2017&rft_id=info%3Adoi%2F10.1007%2F978-3-319-46086-4_19&rft.isbn=978-3-319-46084-0&rft.aulast=Iyer&rft.aufirst=Rakesh&rft.au=Handelsman%2C+David+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-IyerHandelsman2016-240"><a href="#cite_ref-IyerHandelsman2016_240-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFIyerHandelsman2016" class="citation book cs1">Iyer R, Handelsman DJ (2016). "Androgens". Frontiers of Hormone Research. Vol. 47. S. Karger AG. pp. 82–100. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1159%2F000445159">10.1159/000445159</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-318-05868-0" title="Special:BookSources/978-3-318-05868-0"><bdi>978-3-318-05868-0</bdi></a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27347677">27347677</a>. <q>Following the hiatus of World War II, the pharmaceutical industry development of synthetic steroids included pursuing the goal of a nonvirilizing androgen ('anabolic steroid') potentially suitable for use to obtain pharmacological androgen effects in women and children. [...] the industrial quest for an 'anabolic steroid' based on dissociating the virilizing from the anabolic effects of androgens failed. This is now understood in the light of the later discovery of the singular AR together with the flawed interpretations of relatively nonspecific whole animal bioassays then used to screen synthetic steroids for supposedly distinct anabolic and virilizing effects. Yet, despite the industry's abandonment of this fruitless endeavor by 1980, and its recent reincarnation under the guise of developing a 'selective AR modulator' (SARM) [6], the empty concept of an 'anabolic steroid' persists as an ill-defined and misleading scientific terminology [7, 8] . In this paper, the more accurate and clearer term 'androgen' is used exclusively for both endogenous and synthetic androgens, but includes references to chemicals loosely defined elsewhere as 'anabolic steroids' or 'anabolicandrogenic steroids', which confuse by making an obsolete distinction where there is no difference.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Androgens&rft.btitle=Frontiers+of+Hormone+Research&rft.pages=82-100&rft.pub=S.+Karger+AG&rft.date=2016&rft_id=info%3Apmid%2F27347677&rft_id=info%3Adoi%2F10.1159%2F000445159&rft.isbn=978-3-318-05868-0&rft.aulast=Iyer&rft.aufirst=Rakesh&rft.au=Handelsman%2C+David+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-Handelsman2012-241">^ <a href="#cite_ref-Handelsman2012_241-0">a</a> <a href="#cite_ref-Handelsman2012_241-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHandelsman2012" class="citation book cs1">Handelsman DJ (26 July 2012). "Androgen therapy in non-gonadal disease". Testosterone. Cambridge University Press. pp. 372–407. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1017%2Fcbo9781139003353.018">10.1017/cbo9781139003353.018</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-139-00335-3" title="Special:BookSources/978-1-139-00335-3"><bdi>978-1-139-00335-3</bdi></a>. <q>The development of nonsteroidal androgens, marketed as "selective androgen receptor modulators" (SARMs), offers new possibilities for adjuvant pharmacological androgen therapy. In contrast to the full spectrum of androgen effects of testosterone, such SARMs would be pure androgens not subject to tissue-specific activation by aromatization to a corresponding estrogen or to amplification of androgenic potency by 5a-reduction. In this context the endogenous pure androgens nandrolone and DHT can be considered prototype SARMs. SARMs are not the modern embodiment of so-called "anabolic steroids," an outdated term referring to hypothetical but nonexistent non-virilizing androgens targeted exclusively to muscle, a failed concept lacking biological proof of principle (Handelsman 2011).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Androgen+therapy+in+non-gonadal+disease&rft.btitle=Testosterone&rft.pages=372-407&rft.pub=Cambridge+University+Press&rft.date=2012-07-26&rft_id=info%3Adoi%2F10.1017%2Fcbo9781139003353.018&rft.isbn=978-1-139-00335-3&rft.aulast=Handelsman&rft.aufirst=David+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-pmid25905231-242">^ <a href="#cite_ref-pmid25905231_242-0">a</a> <a href="#cite_ref-pmid25905231_242-1">b</a> <a href="#cite_ref-pmid25905231_242-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFeingoldAnawaltBlackmanBoyce2020" class="citation journal cs1">Feingold KR, Anawalt B, Blackman MR, Boyce A, Chrousos G, Corpas E, de Herder WW, Dhatariya K, Dungan K, Hofland J, Kalra S, Kaltsas G, Kapoor N, Koch C, Kopp P, Korbonits M, Kovacs CS, Kuohung W, Laferrère B, Levy M, McGee EA, McLachlan R, New M, Purnell J, Sahay R, Shah AS, Singer F, Sperling MA, Stratakis CA, Trence DL, Wilson DP, Handelsman DJ (5 October 2020). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/sites/books/NBK279000/">"Androgen Physiology, Pharmacology, Use and Misuse"</a>. Endotext. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/25905231">25905231</a>. <q>The identification of a single gene and protein for the androgen receptor in 1988 (584-586) explains the physiologic observation that, at equivalent doses, all androgens have essentially similar effects (587). The term "anabolic steroid" was invented during the post-WWII golden age of steroid pharmacology to define an idealized androgen lacking virilizing features but maintaining myotrophic properties so that it could be used safely in children and women. Although this quest proved illusory and was abandoned after all industry efforts failed to identify such a hypothetical synthetic androgen, the obsolete term "anabolic steroid" persists mainly as a lurid descriptor in popular media despite continuing to make a false distinction where there is no difference. Better understanding of the metabolic activation of androgens via 5α-reduction and aromatization in target tissues and the tissue-specific partial agonist/antagonist properties of some synthetic androgens may lead to more physiological concepts of tissue-specific androgen action ("specific androgen receptor modulator") governed by the physiological processes of pre-receptor androgen activation as well as post-receptor interaction with co-regulator proteins analogous to the development of synthetic estrogen partial agonists with tissue specificity ("specific estrogen receptor modulator") (588). The potential for new clinical therapeutic indications of novel tissue-selective androgens in clinical development remain to be fully evaluated (589).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Endotext&rft.atitle=Androgen+Physiology%2C+Pharmacology%2C+Use+and+Misuse&rft.date=2020-10-05&rft_id=info%3Apmid%2F25905231&rft.aulast=Feingold&rft.aufirst=KR&rft.au=Anawalt%2C+B&rft.au=Blackman%2C+MR&rft.au=Boyce%2C+A&rft.au=Chrousos%2C+G&rft.au=Corpas%2C+E&rft.au=de+Herder%2C+WW&rft.au=Dhatariya%2C+K&rft.au=Dungan%2C+K&rft.au=Hofland%2C+J&rft.au=Kalra%2C+S&rft.au=Kaltsas%2C+G&rft.au=Kapoor%2C+N&rft.au=Koch%2C+C&rft.au=Kopp%2C+P&rft.au=Korbonits%2C+M&rft.au=Kovacs%2C+CS&rft.au=Kuohung%2C+W&rft.au=Laferr%C3%A8re%2C+B&rft.au=Levy%2C+M&rft.au=McGee%2C+EA&rft.au=McLachlan%2C+R&rft.au=New%2C+M&rft.au=Purnell%2C+J&rft.au=Sahay%2C+R&rft.au=Shah%2C+AS&rft.au=Singer%2C+F&rft.au=Sperling%2C+MA&rft.au=Stratakis%2C+CA&rft.au=Trence%2C+DL&rft.au=Wilson%2C+DP&rft.au=Handelsman%2C+DJ&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fsites%2Fbooks%2FNBK279000%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-pmid36644692-243"><a href="#cite_ref-pmid36644692_243-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBondSmitde_Ronde2022" class="citation journal cs1">Bond P, Smit DL, de Ronde W (2022). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9837614">"Anabolic-androgenic steroids: How do they work and what are the risks?"</a>. Front Endocrinol (Lausanne). 13: 1059473. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3389%2Ffendo.2022.1059473">10.3389/fendo.2022.1059473</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9837614">9837614</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/36644692">36644692</a>. <q>Anabolic–androgenic steroids (AAS) are a class of natural and synthetic hormones that owe their name to their chemical structure (the steroid nucleus, see Figure 1) and the biological effects (anabolic and androgenic) they induce. 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Contraception. 87 (3): 288–295. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.contraception.2012.08.036">10.1016/j.contraception.2012.08.036</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23063338">23063338</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=7%CE%B1-methyl-19-nortestosterone+%28MENTR%29%3A+the+population+council%27s+contribution+to+research+on+male+contraception+and+treatment+of+hypogonadism&rft.volume=87&rft.issue=3&rft.pages=288-295&rft.date=2013-03&rft_id=info%3Adoi%2F10.1016%2Fj.contraception.2012.08.036&rft_id=info%3Apmid%2F23063338&rft.aulast=Nieschlag&rft.aufirst=E&rft.au=Kumar%2C+N&rft.au=Sitruk-Ware%2C+R&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-EndocrineSociety2018-273"><a href="#cite_ref-EndocrineSociety2018_273-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.endocrine.org/news-room/2018/dimethandrolone-undecanoate-shows-promise-as-a-male-birth-control-pill">"Dimethandrolone undecanoate shows promise as a male birth control pill"</a>. 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Retrieved 20 March 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Endocrine+Society&rft.atitle=Dimethandrolone+undecanoate+shows+promise+as+a+male+birth+control+pill&rft_id=https%3A%2F%2Fwww.endocrine.org%2Fnews-room%2F2018%2Fdimethandrolone-undecanoate-shows-promise-as-a-male-birth-control-pill&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-pmid12626029-274">^ <a href="#cite_ref-pmid12626029_274-0">a</a> <a href="#cite_ref-pmid12626029_274-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGruberWieserGruberFerlitsch2002" class="citation journal cs1">Gruber CJ, Wieser F, Gruber IM, Ferlitsch K, Gruber DM, Huber JC (December 2002). "Current concepts in aesthetic endocrinology". Gynecological Endocrinology. 16 (6): 431–441. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2Fgye.16.6.431.441">10.1080/gye.16.6.431.441</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12626029">12626029</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:37424524">37424524</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Gynecological+Endocrinology&rft.atitle=Current+concepts+in+aesthetic+endocrinology&rft.volume=16&rft.issue=6&rft.pages=431-441&rft.date=2002-12&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A37424524%23id-name%3DS2CID&rft_id=info%3Apmid%2F12626029&rft_id=info%3Adoi%2F10.1080%2Fgye.16.6.431.441&rft.aulast=Gruber&rft.aufirst=CJ&rft.au=Wieser%2C+F&rft.au=Gruber%2C+IM&rft.au=Ferlitsch%2C+K&rft.au=Gruber%2C+DM&rft.au=Huber%2C+JC&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> <li id="cite_note-pmid25781555-275"><a href="#cite_ref-pmid25781555_275-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSam2015" class="citation journal cs1">Sam S (February 2015). "Adiposity and metabolic dysfunction in polycystic ovary syndrome". Hormone Molecular Biology and Clinical Investigation. 21 (2): 107–116. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1515%2Fhmbci-2015-0008">10.1515/hmbci-2015-0008</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/25781555">25781555</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:23592351">23592351</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Hormone+Molecular+Biology+and+Clinical+Investigation&rft.atitle=Adiposity+and+metabolic+dysfunction+in+polycystic+ovary+syndrome&rft.volume=21&rft.issue=2&rft.pages=107-116&rft.date=2015-02&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A23592351%23id-name%3DS2CID&rft_id=info%3Apmid%2F25781555&rft_id=info%3Adoi%2F10.1515%2Fhmbci-2015-0008&rft.aulast=Sam&rft.aufirst=S&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=64" title="Edit section: Further reading">edit</a>]</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="CITEREFDaniels2003" class="citation book cs1">Daniels RC (1 February 2003). The Anabolic Steroid Handbook. RCD Books. p. 80. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-9548227-0-6" title="Special:BookSources/0-9548227-0-6"><bdi>0-9548227-0-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Anabolic+Steroid+Handbook&rft.pages=80&rft.pub=RCD+Books&rft.date=2003-02-01&rft.isbn=0-9548227-0-6&rft.aulast=Daniels&rft.aufirst=RC&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGallaway1997" class="citation book cs1">Gallaway S (15 January 1997). The Steroid Bible (3rd Sprl ed.). Belle Intl. p. 125. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/1-890342-00-9" title="Special:BookSources/1-890342-00-9"><bdi>1-890342-00-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Steroid+Bible&rft.pages=125&rft.edition=3rd+Sprl&rft.pub=Belle+Intl&rft.date=1997-01-15&rft.isbn=1-890342-00-9&rft.aulast=Gallaway&rft.aufirst=S&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLlewellyn2007" class="citation book cs1">Llewellyn W (28 January 2007). Anabolics 2007: Anabolic Steroid Reference Manual (6th ed.). Body of Science. p. 988. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-9679304-6-6" title="Special:BookSources/978-0-9679304-6-6"><bdi>978-0-9679304-6-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Anabolics+2007%3A+Anabolic+Steroid+Reference+Manual&rft.pages=988&rft.edition=6th&rft.pub=Body+of+Science&rft.date=2007-01-28&rft.isbn=978-0-9679304-6-6&rft.aulast=Llewellyn&rft.aufirst=W&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRobertsClapp2006" class="citation book cs1">Roberts A, Clapp B (January 2006). Anabolic Steroids: Ultimate Research Guide. Anabolic Books, LLC. p. 394. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/1-59975-100-3" title="Special:BookSources/1-59975-100-3"><bdi>1-59975-100-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Anabolic+Steroids%3A+Ultimate+Research+Guide&rft.pages=394&rft.pub=Anabolic+Books%2C+LLC&rft.date=2006-01&rft.isbn=1-59975-100-3&rft.aulast=Roberts&rft.aufirst=A&rft.au=Clapp%2C+B&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFYesalis2000" class="citation book cs1">Yesalis CE (2000). Anabolic Steroids in Sport and Exercise. Human Kinetics. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-88011-786-9" title="Special:BookSources/0-88011-786-9"><bdi>0-88011-786-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Anabolic+Steroids+in+Sport+and+Exercise&rft.pub=Human+Kinetics&rft.date=2000&rft.isbn=0-88011-786-9&rft.aulast=Yesalis&rft.aufirst=CE&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFragkakiAngelisKoupparisTsantili-Kakoulidou2009" class="citation journal cs1">Fragkaki AG, Angelis YS, Koupparis M, Tsantili-Kakoulidou A, Kokotos G, Georgakopoulos C (February 2009). "Structural characteristics of anabolic androgenic steroids contributing to binding to the androgen receptor and to their anabolic and androgenic activities. 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Steroids. 74 (2): 172–197. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.steroids.2008.10.016">10.1016/j.steroids.2008.10.016</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19028512">19028512</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:41356223">41356223</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Steroids&rft.atitle=Structural+characteristics+of+anabolic+androgenic+steroids+contributing+to+binding+to+the+androgen+receptor+and+to+their+anabolic+and+androgenic+activities.+Applied+modifications+in+the+steroidal+structure&rft.volume=74&rft.issue=2&rft.pages=172-197&rft.date=2009-02&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A41356223%23id-name%3DS2CID&rft_id=info%3Apmid%2F19028512&rft_id=info%3Adoi%2F10.1016%2Fj.steroids.2008.10.016&rft.aulast=Fragkaki&rft.aufirst=AG&rft.au=Angelis%2C+YS&rft.au=Koupparis%2C+M&rft.au=Tsantili-Kakoulidou%2C+A&rft.au=Kokotos%2C+G&rft.au=Georgakopoulos%2C+C&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMcRobbHandelsmanKazlauskasWilkinson2008" class="citation journal cs1">McRobb L, Handelsman DJ, Kazlauskas R, Wilkinson S, McLeod MD, Heather AK (May 2008). "Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay". The Journal of Steroid Biochemistry and Molecular Biology. 110 (1–2): 39–47. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.jsbmb.2007.10.008">10.1016/j.jsbmb.2007.10.008</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/18395441">18395441</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:5612000">5612000</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Steroid+Biochemistry+and+Molecular+Biology&rft.atitle=Structure-activity+relationships+of+synthetic+progestins+in+a+yeast-based+in+vitro+androgen+bioassay&rft.volume=110&rft.issue=1%E2%80%932&rft.pages=39-47&rft.date=2008-05&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A5612000%23id-name%3DS2CID&rft_id=info%3Apmid%2F18395441&rft_id=info%3Adoi%2F10.1016%2Fj.jsbmb.2007.10.008&rft.aulast=McRobb&rft.aufirst=L&rft.au=Handelsman%2C+DJ&rft.au=Kazlauskas%2C+R&rft.au=Wilkinson%2C+S&rft.au=McLeod%2C+MD&rft.au=Heather%2C+AK&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSchänzer1996" class="citation journal cs1">Schänzer W (July 1996). <a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fclinchem%2F42.7.1001">"Metabolism of anabolic androgenic steroids"</a>. Clinical Chemistry. 42 (7): 1001–1020. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fclinchem%2F42.7.1001">10.1093/clinchem/42.7.1001</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/8674183">8674183</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinical+Chemistry&rft.atitle=Metabolism+of+anabolic+androgenic+steroids&rft.volume=42&rft.issue=7&rft.pages=1001-1020&rft.date=1996-07&rft_id=info%3Adoi%2F10.1093%2Fclinchem%2F42.7.1001&rft_id=info%3Apmid%2F8674183&rft.aulast=Sch%C3%A4nzer&rft.aufirst=W&rft_id=https%3A%2F%2Fdoi.org%2F10.1093%252Fclinchem%252F42.7.1001&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTygart2009" class="citation journal cs1">Tygart TT (December 2009). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20141129012954/http://www.tpronline.org/download-free-article.cfm?id=548">"Steroids, the Media, and Youth"</a>. Prevention Researcher Integrated Research Services, Inc. 16 (7–9). SIRS Researcher. Archived from <a rel="nofollow" class="external text" href="http://www.tpronline.org/download-free-article.cfm?id=548">the original</a> on 29 November 2014. Retrieved 24 November 2013.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Prevention+Researcher+Integrated+Research+Services%2C+Inc.&rft.atitle=Steroids%2C+the+Media%2C+and+Youth&rft.volume=16&rft.issue=7%E2%80%939&rft.date=2009-12&rft.aulast=Tygart&rft.aufirst=TT&rft_id=http%3A%2F%2Fwww.tpronline.org%2Fdownload-free-article.cfm%3Fid%3D548&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFEisenhauer2005" class="citation web cs1">Eisenhauer L (7 November 2005). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20131202223132/http://business.highbeam.com/435553/article-1G1-138418723/do-look-ok-question-many-teens-struggle-every-day-and">"Do I Look OK?"</a>. St. Louis, MO: St. Louis Post-Dispatch. Archived from <a rel="nofollow" class="external text" href="http://business.highbeam.com/435553/article-1G1-138418723/do-look-ok-question-many-teens-struggle-every-day-and">the original</a> on 2 December 2013. Retrieved 25 October 2010.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Do+I+Look+OK%3F&rft.place=St.+Louis%2C+MO&rft.pub=St.+Louis+Post-Dispatch&rft.date=2005-11-07&rft.aulast=Eisenhauer&rft.aufirst=L&rft_id=http%3A%2F%2Fbusiness.highbeam.com%2F435553%2Farticle-1G1-138418723%2Fdo-look-ok-question-many-teens-struggle-every-day-and&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnabolic+steroid" class="Z3988"></li></ul> </div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2>[<a href="/w/index.php?title=Anabolic_steroid&action=edit&section=65" title="Edit section: External links">edit</a>]</div> <ul><li><a href="/wiki/File:Commons-logo.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/12px-Commons-logo.svg.png" decoding="async" width="12" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/18px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/24px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></a> Media related to <a href="https://commons.wikimedia.org/wiki/Category:Anabolic-androgenic_steroids" class="extiw" title="commons:Category:Anabolic-androgenic steroids">Anabolic-androgenic steroids</a> at Wikimedia Commons</li></ul> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output .navbox-subgroup{width:100%}.mw-parser-output .navbox-group,.mw-parser-output .navbox-title,.mw-parser-output .navbox-abovebelow{padding:0.25em 1em;line-height:1.5em;text-align:center}.mw-parser-output .navbox-group{white-space:nowrap;text-align:right}.mw-parser-output .navbox,.mw-parser-output .navbox-subgroup{background-color:#fdfdfd}.mw-parser-output .navbox-list{line-height:1.5em;border-color:#fdfdfd}.mw-parser-output .navbox-list-with-group{text-align:left;border-left-width:2px;border-left-style:solid}.mw-parser-output tr+tr>.navbox-abovebelow,.mw-parser-output tr+tr>.navbox-group,.mw-parser-output tr+tr>.navbox-image,.mw-parser-output tr+tr>.navbox-list{border-top:2px solid #fdfdfd}.mw-parser-output .navbox-title{background-color:#ccf}.mw-parser-output .navbox-abovebelow,.mw-parser-output .navbox-group,.mw-parser-output .navbox-subgroup .navbox-title{background-color:#ddf}.mw-parser-output .navbox-subgroup .navbox-group,.mw-parser-output .navbox-subgroup .navbox-abovebelow{background-color:#e6e6ff}.mw-parser-output .navbox-even{background-color:#f7f7f7}.mw-parser-output .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><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Androgens_and_antiandrogens" 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"><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:Androgens_and_antiandrogens" title="Template:Androgens and antiandrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Androgens_and_antiandrogens" title="Template talk:Androgens and antiandrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Androgens_and_antiandrogens" title="Special:EditPage/Template:Androgens and antiandrogens"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Androgens_and_antiandrogens" style="font-size:114%;margin:0 4em"><a href="/wiki/Androgen" title="Androgen">Androgens</a> and <a href="/wiki/Antiandrogen" title="Antiandrogen">antiandrogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Androgen" title="Androgen">Androgens</a> (incl. <a href="/wiki/Anabolic%E2%80%93androgenic_steroid" class="mw-redirect" title="Anabolic–androgenic steroid"><abbr title="anabolic–androgenic steroid">AAS</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 anabolic–androgenic steroid)</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:9em;;text-align:center;"><a href="/wiki/Androgen_receptor" title="Androgen receptor"><abbr title="Androgen receptor">AR</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 Androgen receptor <a href="/wiki/Agonist" title="Agonist">agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Testosterone derivatives: <a href="/wiki/Androstenediol_dipropionate" title="Androstenediol dipropionate">Androstenediol dipropionate</a></li> <li><a href="/wiki/Boldenone_undecylenate" title="Boldenone undecylenate">Boldenone undecylenate</a></li> <li><a href="/wiki/Clostebol" title="Clostebol">Clostebol</a></li> <li><a href="/wiki/Clostebol_acetate" title="Clostebol acetate">Clostebol acetate</a></li> <li><a href="/wiki/Clostebol_caproate" title="Clostebol caproate">Clostebol caproate</a></li> <li><a href="/wiki/Clostebol_propionate" title="Clostebol propionate">Clostebol propionate</a></li> <li><a href="/wiki/Cloxotestosterone_acetate" title="Cloxotestosterone acetate">Cloxotestosterone acetate</a></li> <li><a href="/wiki/Prasterone" title="Prasterone">Prasterone (dehydroepiandrosterone, DHEA)</a></li> <li><a href="/wiki/Prasterone_enanthate" title="Prasterone enanthate">Prasterone enanthate (DHEA enanthate)</a></li> <li><a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">Prasterone sulfate (DHEA sulfate)</a></li> <li><a href="/wiki/Quinbolone" title="Quinbolone">Quinbolone</a></li> <li><a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">Testosterone</a>#</li> <li><a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">Testosterone esters</a> (e.g., <a href="/wiki/Testosterone_cypionate" title="Testosterone cypionate">testosterone cypionate</a>, <a href="/wiki/Testosterone_enanthate" title="Testosterone enanthate">testosterone enanthate</a>, <a href="/wiki/Testosterone_propionate" title="Testosterone propionate">testosterone propionate</a>, <a href="/wiki/Testosterone_undecanoate" title="Testosterone undecanoate">testosterone undecanoate</a>, <a href="/wiki/Testosterone_ester_mixture" class="mw-redirect" title="Testosterone ester mixture">testosterone ester mixtures</a> (<a href="/wiki/Deposterona" class="mw-redirect" title="Deposterona">Deposterona</a>, <a href="/wiki/Omnadren" class="mw-redirect" title="Omnadren">Omnadren</a>, <a href="/wiki/Testosterone_propionate/testosterone_phenylpropionate/testosterone_isocaproate/testosterone_decanoate" title="Testosterone propionate/testosterone phenylpropionate/testosterone isocaproate/testosterone decanoate">Sustanon</a>, <a href="/wiki/Testoviron_depot" class="mw-redirect" title="Testoviron depot">Testoviron Depot</a>))</li></ul> <ul><li>Dihydrotestosterone derivatives: <a href="/wiki/Androstanolone" title="Androstanolone">Androstanolone (stanolone, dihydrotestosterone, DHT)</a></li> <li><a href="/wiki/List_of_androgen_esters#Dihydrotestosterone_esters" title="List of androgen esters">Androstanolone esters</a></li> <li><a href="/wiki/Bolazine_capronate" title="Bolazine capronate">Bolazine capronate</a></li> <li><a href="/wiki/Drostanolone_propionate" title="Drostanolone propionate">Drostanolone propionate (dromostanolone propionate)</a></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Mesterolone" title="Mesterolone">Mesterolone</a></li> <li><a href="/wiki/Metenolone_acetate" title="Metenolone acetate">Metenolone acetate (methenolone acetate)</a></li> <li><a href="/wiki/Metenolone_enanthate" title="Metenolone enanthate">Metenolone enanthate (methenolone enanthate)</a></li> <li><a href="/wiki/Stenbolone_acetate" title="Stenbolone acetate">Stenbolone acetate</a></li></ul> <ul><li>19-Nortestosterone derivatives: <a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li> <li><a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">Nandrolone esters</a> (e.g., <a href="/wiki/Nandrolone_decanoate" title="Nandrolone decanoate">nandrolone decanoate</a>, <a href="/wiki/Nandrolone_phenylpropionate" title="Nandrolone phenylpropionate">nandrolone phenylpropionate</a>)</li> <li><a href="/wiki/Norclostebol" title="Norclostebol">Norclostebol</a></li> <li><a href="/wiki/Norclostebol_acetate" title="Norclostebol acetate">Norclostebol acetate</a></li> <li><a href="/wiki/Oxabolone_cipionate" title="Oxabolone cipionate">Oxabolone cipionate (oxabolone cypionate)</a></li> <li><a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">Trenbolone acetate</a></li> <li><a href="/wiki/Trenbolone_hexahydrobenzylcarbonate" title="Trenbolone hexahydrobenzylcarbonate">Trenbolone hexahydrobenzylcarbonate (trenbolone cyclohexylmethylcarbonate)</a></li></ul> <ul><li>17α-Alkylated testosterone derivatives: <a href="/wiki/Bolasterone" title="Bolasterone">Bolasterone</a></li> <li><a href="/wiki/Calusterone" title="Calusterone">Calusterone</a></li> <li><a href="/wiki/Chlorodehydromethyltestosterone" title="Chlorodehydromethyltestosterone">Chlorodehydromethyltestosterone (CDMT)</a></li> <li><a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">Fluoxymesterone</a></li> <li><a href="/wiki/Formebolone" title="Formebolone">Formebolone</a></li> <li><a href="/wiki/Metandienone" title="Metandienone">Metandienone (methandienone, methandrostenolone)</a></li> <li><a href="/wiki/Methandriol" title="Methandriol">Methandriol (methylandrostenediol)</a></li> <li><a href="/wiki/Methandriol_bisenanthoyl_acetate" title="Methandriol bisenanthoyl acetate">Methandriol bisenanthoyl acetate</a></li> <li><a href="/wiki/Methandriol_dipropionate" title="Methandriol dipropionate">Methandriol dipropionate</a></li> <li><a href="/wiki/Methandriol_propionate" title="Methandriol propionate">Methandriol propionate</a></li> <li><a href="/wiki/Methyltestosterone" title="Methyltestosterone">Methyltestosterone</a></li> <li><a href="/wiki/Methyltestosterone_3-hexyl_ether" title="Methyltestosterone 3-hexyl ether">Methyltestosterone 3-hexyl ether</a></li> <li><a href="/wiki/Oxymesterone" title="Oxymesterone">Oxymesterone</a></li> <li><a href="/wiki/Penmesterol" title="Penmesterol">Penmesterol</a></li> <li><a href="/wiki/Tiomesterone" title="Tiomesterone">Tiomesterone (thiomesterone)</a></li></ul> <ul><li>17α-Alkylated dihydrotestosterone derivatives: <a href="/wiki/Androisoxazole" title="Androisoxazole">Androisoxazole</a></li> <li><a href="/wiki/Furazabol" title="Furazabol">Furazabol</a></li> <li><a href="/wiki/Mebolazine" title="Mebolazine">Mebolazine (dimethazine)</a></li> <li><a href="/wiki/Mestanolone" title="Mestanolone">Mestanolone</a></li> <li><a href="/wiki/Oxandrolone" title="Oxandrolone">Oxandrolone</a></li> <li><a href="/wiki/Oxymetholone" title="Oxymetholone">Oxymetholone</a></li> <li><a href="/wiki/Stanozolol" title="Stanozolol">Stanozolol</a></li></ul> <ul><li>17α-Alkylated 19-nortestosterone derivatives: <a href="/wiki/Ethylestrenol" title="Ethylestrenol">Ethylestrenol</a></li> <li><a href="/wiki/Mibolerone" title="Mibolerone">Mibolerone</a></li> <li><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a></li> <li><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone (methylestrenolone, normethisterone)</a></li> <li><a href="/wiki/Propetandrol" title="Propetandrol">Propetandrol (propethandrol)</a></li></ul> <ul><li>17α-Vinyltestosterone derivatives: <a href="/wiki/Norvinisterone" title="Norvinisterone">Norvinisterone (vinylnortestosterone)</a></li></ul> <ul><li>17α-Ethynyltestosterone derivatives: <a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li> <li><a href="/wiki/Progestin" class="mw-redirect" title="Progestin">Progestins</a> (e.g., <a href="/wiki/Ethisterone" title="Ethisterone">ethisterone (ethynyltestosterone)</a>, <a href="/wiki/Levonorgestrel" title="Levonorgestrel">levonorgestrel</a>, <a href="/wiki/Norgestrel" title="Norgestrel">norgestrel</a>, <a href="/wiki/Norethisterone" title="Norethisterone">norethisterone (norethindrone)</a>, <a href="/wiki/Lynestrenol" title="Lynestrenol">lynestrenol</a>, <a href="/wiki/Norgestrienone" title="Norgestrienone">norgestrienone</a>)</li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li>Progesterone derivatives: <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:9em;;text-align:center;"><a href="/wiki/Progonadotropin" title="Progonadotropin">Progonadotropins</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Antiestrogen" title="Antiestrogen">Antiestrogens</a> (e.g., <a href="/wiki/Tamoxifen" title="Tamoxifen">tamoxifen</a>, <a href="/wiki/Clomifene" title="Clomifene">clomifene</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist">GnRH agonists</a> (e.g., <a href="/wiki/Gonadotropin-releasing_hormone" title="Gonadotropin-releasing hormone">GnRH (gonadorelin)</a>, <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>)</li> <li><a href="/wiki/Gonadotropin" title="Gonadotropin">Gonadotropins</a> (e.g., <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone"><abbr title="luteinizing hormone">LH</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 luteinizing hormone, <a href="/wiki/Human_chorionic_gonadotropin" title="Human chorionic gonadotropin"><abbr title="human chorionic gonadotropin">hCG</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 human chorionic gonadotropin)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogens</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:9em;;text-align:center;"><a href="/wiki/Androgen_receptor" title="Androgen receptor"><abbr title="Androgen receptor">AR</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 Androgen receptor <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a> <a href="/wiki/Niraparib/abiraterone_acetate" title="Niraparib/abiraterone acetate">+niraparib</a></li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a></li> <li><a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone acetate</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a href="/wiki/Dienogest" title="Dienogest">Dienogest</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">Nomegestrol acetate</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a href="/wiki/Oxendolone" title="Oxendolone">Oxendolone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Potassium canrenoate</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/Apalutamide" title="Apalutamide">Apalutamide</a></li> <li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></li> <li><a href="/wiki/Cimetidine" title="Cimetidine">Cimetidine</a></li> <li><a href="/wiki/Darolutamide" title="Darolutamide">Darolutamide</a></li> <li><a href="/wiki/Enzalutamide" title="Enzalutamide">Enzalutamide</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Nilutamide" title="Nilutamide">Nilutamide</a></li> <li><a href="/wiki/Seviteronel" title="Seviteronel">Seviteronel</a>†</li> <li><a href="/wiki/Topilutamide" title="Topilutamide">Topilutamide (fluridil)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:9em;;text-align:center;"><a href="/wiki/Steroidogenesis_inhibitor" title="Steroidogenesis inhibitor">Steroidogenesis inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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%;text-align:center;"><a href="/wiki/5%CE%B1-Reductase_inhibitor" title="5α-Reductase inhibitor">5α-Reductase</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/Alfatradiol" title="Alfatradiol">Alfatradiol</a></li> <li><a href="/wiki/Dutasteride" title="Dutasteride">Dutasteride</a></li> <li><a href="/wiki/Epristeride" title="Epristeride">Epristeride</a></li> <li><a href="/wiki/Finasteride" title="Finasteride">Finasteride</a></li> <li><a href="/wiki/Saw_palmetto_extract" title="Saw palmetto extract">Saw palmetto extract</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a> <a href="/wiki/Niraparib/abiraterone_acetate" title="Niraparib/abiraterone acetate">+niraparib</a></li> <li><a href="/wiki/Aminoglutethimide" title="Aminoglutethimide">Aminoglutethimide</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Nilutamide" title="Nilutamide">Nilutamide</a></li> <li><a href="/wiki/Seviteronel" title="Seviteronel">Seviteronel</a>†</li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:9em;;text-align:center;"><a href="/wiki/Antigonadotropin" title="Antigonadotropin">Antigonadotropins</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/D2_receptor" class="mw-redirect" title="D2 receptor">D2 receptor</a> <a href="/wiki/Dopamine_antagonist" title="Dopamine antagonist">antagonists</a> (<a href="/wiki/Prolactin_releaser" class="mw-redirect" title="Prolactin releaser">prolactin releasers</a>) (e.g., <a href="/wiki/Domperidone" title="Domperidone">domperidone</a>, <a href="/wiki/Metoclopramide" title="Metoclopramide">metoclopramide</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Haloperidol" title="Haloperidol">haloperidol</a>, <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Sulpiride" title="Sulpiride">sulpiride</a>)</li> <li><a href="/wiki/Estrogen" title="Estrogen">Estrogens</a> (e.g., <a href="/wiki/Bifluranol" title="Bifluranol">bifluranol</a>, <a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">diethylstilbestrol</a>, <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>, <a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">estradiol esters</a>, <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a>, <a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">ethinylestradiol sulfonate</a>, <a href="/wiki/Paroxypropione" title="Paroxypropione">paroxypropione</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist">GnRH agonists</a> (e.g., <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>)</li> <li><a href="/wiki/GnRH_antagonist" class="mw-redirect" title="GnRH antagonist">GnRH antagonists</a> (e.g., <a href="/wiki/Cetrorelix" title="Cetrorelix">cetrorelix</a>)</li> <li><a href="/wiki/Progestogen" title="Progestogen">Progestogens</a> (incl., <a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">chlormadinone acetate</a>, <a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">cyproterone acetate</a>, <a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">hydroxyprogesterone caproate</a>, <a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">gestonorone caproate</a>, <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a>, <a href="/wiki/Megestrol_acetate" title="Megestrol acetate">megestrol acetate</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:9em;;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Androstenedione immunogens: <a href="/wiki/Androvax" title="Androvax">Androvax (androstenedione albumin)</a></li> <li><a href="/wiki/Ovandrotone_albumin" title="Ovandrotone albumin">Ovandrotone albumin (Fecundin)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li>#<a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li>‡<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>†<a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li>§Never to phase III</li></ul></li></ul> </div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators">Androgen receptor modulators</a></dd> <dd><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens">Estrogens and antiestrogens</a></dd> <dd><a href="/wiki/Template:Progestogens_and_antiprogestogens" title="Template:Progestogens and antiprogestogens">Progestogens and antiprogestogens</a></dd> <dd><a href="/wiki/List_of_androgens/anabolic_steroids" class="mw-redirect" title="List of androgens/anabolic steroids">List of androgens/anabolic steroids</a></dd></dl></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Androgen_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist 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"><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:Androgen_receptor_modulators" title="Template:Androgen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Androgen_receptor_modulators" title="Template talk:Androgen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Androgen_receptor_modulators" title="Special:EditPage/Template:Androgen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Androgen_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Androgen_receptor" title="Androgen receptor">Androgen receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Androgen_receptor" title="Androgen receptor"><abbr title="Androgen receptor">AR</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 Androgen receptor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Testosterone derivatives: <a href="/wiki/4-Androstenediol" title="4-Androstenediol">4-Androstenediol</a></li> <li><a href="/wiki/4-Dehydroepiandrosterone" title="4-Dehydroepiandrosterone">4-Dehydroepiandrosterone (4-DHEA)</a></li> <li><a href="/wiki/4-Hydroxytestosterone" title="4-Hydroxytestosterone">4-Hydroxytestosterone</a></li> <li><a href="/w/index.php?title=4,17%CE%B1-Dimethyltestosterone&action=edit&redlink=1" class="new" title="4,17α-Dimethyltestosterone (page does not exist)">4,17α-Dimethyltestosterone</a></li> <li><a href="/wiki/5-Androstenedione" title="5-Androstenedione">5-Androstenedione</a></li> <li><a href="/wiki/11-Ketotestosterone" title="11-Ketotestosterone">11-Ketotestosterone</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, 11-oxoandrostenedione)</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">Androstenediol (5-androstenediol)</a> <ul><li><a href="/wiki/Androstenediol_3%CE%B2-acetate" title="Androstenediol 3β-acetate">Androstenediol 3β-acetate</a></li> <li><a href="/wiki/Androstenediol_17%CE%B2-acetate" title="Androstenediol 17β-acetate">Androstenediol 17β-acetate</a></li> <li><a href="/wiki/Androstenediol_diacetate" title="Androstenediol diacetate">Androstenediol diacetate</a></li> <li><a href="/wiki/Androstenediol_dipropionate" title="Androstenediol dipropionate">Androstenediol dipropionate</a></li></ul></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">Androstenedione (4-androstenedione)</a></li> <li><a href="/wiki/Atamestane" title="Atamestane">Atamestane</a></li> <li><a href="/wiki/Boldenone" title="Boldenone">Boldenone</a> <ul><li><a href="/wiki/Boldenone_undecylenate" title="Boldenone undecylenate">Boldenone undecylenate</a></li></ul></li> <li><a href="/wiki/Boldione" title="Boldione">Boldione (1,4-androstadienedione)</a></li> <li><a href="/wiki/Clostebol" title="Clostebol">Clostebol</a> <ul><li><a href="/wiki/Clostebol_acetate" title="Clostebol acetate">Clostebol acetate</a></li> <li><a href="/wiki/Clostebol_caproate" title="Clostebol caproate">Clostebol caproate</a></li> <li><a href="/wiki/Clostebol_propionate" title="Clostebol propionate">Clostebol propionate</a></li></ul></li> <li><a href="/wiki/Cloxotestosterone" title="Cloxotestosterone">Cloxotestosterone</a> <ul><li><a href="/wiki/Cloxotestosterone_acetate" title="Cloxotestosterone acetate">Cloxotestosterone acetate</a></li></ul></li> <li><a href="/wiki/Dehydroandrosterone" title="Dehydroandrosterone">Dehydroandrosterone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA (androstenolone, prasterone; 5-DHEA)</a> <ul><li><a href="/wiki/Prasterone_enanthate" title="Prasterone enanthate">DHEA enanthate (prasterone enanthate)</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA sulfate</a></li></ul></li> <li><a href="/wiki/Exemestane" title="Exemestane">Exemestane</a></li> <li><a href="/wiki/Formestane" title="Formestane">Formestane</a></li> <li><a href="/wiki/Plomestane" title="Plomestane">Plomestane</a></li> <li><a href="/wiki/Quinbolone" title="Quinbolone">Quinbolone</a></li> <li><a href="/wiki/Silandrone" title="Silandrone">Silandrone</a></li> <li><a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">Testosterone</a># (<a href="/wiki/Testosterone/dutasteride" title="Testosterone/dutasteride">+dutasteride</a>) <ul><li><a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">Testosterone esters</a></li> <li><a href="/wiki/Polytestosterone_phloretin_phosphate" title="Polytestosterone phloretin phosphate">Polytestosterone phloretin phosphate</a></li></ul></li></ul> <ul><li>5α-Dihydrotestosterone derivatives: <a href="/wiki/1-Androstenediol" title="1-Androstenediol">1-Androstenediol</a></li> <li><a href="/wiki/1-Androstenedione" title="1-Androstenedione">1-Androstenedione</a></li> <li><a href="/wiki/1-Androsterone" title="1-Androsterone">1-Androsterone (1-andro, 1-DHEA)</a></li> <li><a href="/wiki/1-Testosterone" title="1-Testosterone">1-Testosterone</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/5%CE%B1-Androst-2-en-17-one" class="mw-redirect" title="5α-Androst-2-en-17-one">5α-Androst-2-en-17-one</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/11-Ketodihydrotestosterone" title="11-Ketodihydrotestosterone">11-Ketodihydrotestosterone</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li><a href="/wiki/Bolazine" title="Bolazine">Bolazine</a> <ul><li><a href="/wiki/Bolazine_capronate" title="Bolazine capronate">Bolazine capronate</a></li></ul></li> <li><a href="/w/index.php?title=Dihydroethyltestosterone&action=edit&redlink=1" class="new" title="Dihydroethyltestosterone (page does not exist)">Dihydroethyltestosterone</a></li> <li><a href="/wiki/Dihydrofluoxymesterone" title="Dihydrofluoxymesterone">Dihydrofluoxymesterone</a></li> <li><a href="/w/index.php?title=Dihydromethylandrostenediol&action=edit&redlink=1" class="new" title="Dihydromethylandrostenediol (page does not exist)">Dihydromethylandrostenediol</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">Dihydrotestosterone (DHT)</a> (<a href="/wiki/Androstanolone" title="Androstanolone">androstanolone, stanolone</a>) <ul><li><a href="/wiki/List_of_androgen_esters#Dihydrotestosterone_esters" title="List of androgen esters">Dihydrotestosterone esters</a></li></ul></li> <li><a href="/wiki/Drostanolone" title="Drostanolone">Drostanolone</a> <ul><li><a href="/wiki/Drostanolone_propionate" title="Drostanolone propionate">Drostanolone propionate</a></li></ul></li> <li><a href="/wiki/Epiandrosterone" title="Epiandrosterone">Epiandrosterone</a></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Mesabolone" title="Mesabolone">Mesabolone</a></li> <li><a href="/wiki/Mesterolone" title="Mesterolone">Mesterolone</a> <ul><li><a href="/wiki/Mesterolone_cipionate" title="Mesterolone cipionate">Mesterolone cipionate</a></li></ul></li> <li><a href="/wiki/Methyldiazinol" title="Methyldiazinol">Methyldiazinol</a></li> <li><a href="/wiki/Nisterime" title="Nisterime">Nisterime</a> <ul><li><a href="/wiki/Nisterime_acetate" title="Nisterime acetate">Nisterime acetate</a></li></ul></li> <li><a href="/wiki/Prostanozol" title="Prostanozol">Prostanozol</a></li> <li><a href="/wiki/Stenbolone" title="Stenbolone">Stenbolone</a> <ul><li><a href="/wiki/Stenbolone_acetate" title="Stenbolone acetate">Stenbolone acetate</a></li></ul></li> <li><a href="/wiki/Testifenon" title="Testifenon">Testifenon (testiphenon, testiphenone)</a></li></ul> <ul><li>19-Nortestosterone derivatives: <a href="/wiki/7%CE%B1-Methyl-19-norandrostenedione" title="7α-Methyl-19-norandrostenedione">7α-Methyl-19-norandrostenedione (MENT dione, trestione)</a></li> <li><a href="/wiki/11%CE%B2-Methyl-19-nortestosterone" title="11β-Methyl-19-nortestosterone">11β-Methyl-19-nortestosterone</a> <ul><li><a href="/wiki/11%CE%B2-Methyl-19-nortestosterone_dodecylcarbonate" title="11β-Methyl-19-nortestosterone dodecylcarbonate">11β-Methyl-19-nortestosterone dodecylcarbonate</a></li></ul></li> <li><a href="/wiki/19-Nor-5-androstenediol" title="19-Nor-5-androstenediol">19-Nor-5-androstenediol</a></li> <li><a href="/wiki/19-Nor-5-androstenedione" title="19-Nor-5-androstenedione">19-Nor-5-androstenedione</a></li> <li><a href="/wiki/19-Nordehydroepiandrosterone" title="19-Nordehydroepiandrosterone">19-Nordehydroepiandrosterone</a></li> <li><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a> <ul><li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li></ul></li> <li><a href="/wiki/Bolandione" title="Bolandione">Bolandione (19-nor-4-androstenedione)</a></li> <li><a href="/wiki/Bolmantalate" title="Bolmantalate">Bolmantalate (nandrolone adamantoate)</a></li> <li><a href="/wiki/Dienedione" title="Dienedione">Dienedione</a></li> <li><a href="/wiki/Dienolone" title="Dienolone">Dienolone</a></li> <li><a href="/wiki/Dimethandrolone" title="Dimethandrolone">Dimethandrolone</a> <ul><li><a href="/wiki/Dimethandrolone_buciclate" title="Dimethandrolone buciclate">Dimethandrolone buciclate</a></li> <li><a href="/wiki/Dimethandrolone_dodecylcarbonate" title="Dimethandrolone dodecylcarbonate">Dimethandrolone dodecylcarbonate</a></li> <li><a href="/wiki/Dimethandrolone_undecanoate" title="Dimethandrolone undecanoate">Dimethandrolone undecanoate</a></li></ul></li> <li><a href="/wiki/LS-1727" title="LS-1727">LS-1727 (nandrolone 17β-N-(2-chloroethyl)-N-nitrosocarbamate)</a></li> <li><a href="/wiki/Methoxydienone" title="Methoxydienone">Methoxydienone (methoxygonadiene)</a></li> <li><a href="/wiki/Nandrolone" title="Nandrolone">Nandrolone</a> <ul><li><a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">Nandrolone esters</a></li></ul></li> <li><a href="/wiki/Norclostebol" title="Norclostebol">Norclostebol</a> <ul><li><a href="/wiki/Norclostebol_acetate" title="Norclostebol acetate">Norclostebol acetate</a></li></ul></li> <li><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone (methylestrenolone, normethisterone)</a></li> <li><a href="/wiki/Oxabolone" title="Oxabolone">Oxabolone</a> <ul><li><a href="/wiki/Oxabolone_cipionate" title="Oxabolone cipionate">Oxabolone cipionate (oxabolone cypionate)</a></li></ul></li> <li><a href="/wiki/Trenbolone" title="Trenbolone">Trenbolone</a> <ul><li><a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">Trenbolone acetate</a></li> <li><a href="/wiki/Trenbolone_enanthate" title="Trenbolone enanthate">Trenbolone enanthate</a></li> <li><a href="/wiki/Trenbolone_hexahydrobenzylcarbonate" title="Trenbolone hexahydrobenzylcarbonate">Trenbolone hexahydrobenzylcarbonate</a></li> <li><a href="/wiki/Trenbolone_undecanoate" title="Trenbolone undecanoate">Trenbolone undecanoate</a></li></ul></li> <li><a href="/wiki/Trendione" title="Trendione">Trendione</a></li> <li><a href="/wiki/Trestolone" title="Trestolone">Trestolone (MENT)</a> <ul><li><a href="/wiki/Trestolone_acetate" title="Trestolone acetate">Trestolone acetate</a></li> <li><a href="/wiki/Trestolone_enanthate" title="Trestolone enanthate">Trestolone enanthate</a></li></ul></li></ul> <ul><li>5α-Dihydro-19-nortestosterone derivatives: <a href="/wiki/5%CE%B1-Dihydronandrolone" title="5α-Dihydronandrolone">5α-Dihydronandrolone</a></li> <li><a href="/w/index.php?title=5%CE%B1-Dihydrotrestolone&action=edit&redlink=1" class="new" title="5α-Dihydrotrestolone (page does not exist)">5α-Dihydrotrestolone</a></li> <li><a href="/wiki/19-Norandrosterone" title="19-Norandrosterone">19-Norandrosterone</a></li></ul> <ul><li>17α-Alkylated testosterone derivatives: <a href="/wiki/Bolasterone" title="Bolasterone">Bolasterone</a></li> <li><a href="/wiki/Calusterone" title="Calusterone">Calusterone</a></li> <li><a href="/wiki/Chlorodehydromethylandrostenediol" title="Chlorodehydromethylandrostenediol">Chlorodehydromethylandrostenediol (CDMA)</a></li> <li><a href="/wiki/Chlorodehydromethyltestosterone" title="Chlorodehydromethyltestosterone">Chlorodehydromethyltestosterone (CDMT)</a></li> <li><a href="/wiki/Chloromethylandrostenediol" title="Chloromethylandrostenediol">Chloromethylandrostenediol (CMA)</a></li> <li><a href="/wiki/Enestebol" title="Enestebol">Enestebol</a></li> <li><a href="/wiki/Ethyltestosterone" title="Ethyltestosterone">Ethyltestosterone</a></li> <li><a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">Fluoxymesterone</a></li> <li><a href="/wiki/Formebolone" title="Formebolone">Formebolone</a></li> <li><a href="/wiki/Hydroxystenozole" title="Hydroxystenozole">Hydroxystenozole</a></li> <li><a href="/wiki/Metandienone" title="Metandienone">Metandienone (methandrostenolone)</a></li> <li><a href="/wiki/Methandriol" title="Methandriol">Methandriol (methylandrostenediol)</a> <ul><li><a href="/wiki/Methandriol_bisenanthoyl_acetate" title="Methandriol bisenanthoyl acetate">Methandriol bisenanthoyl acetate</a></li> <li><a href="/wiki/Methandriol_diacetate" title="Methandriol diacetate">Methandriol diacetate</a></li> <li><a href="/wiki/Methandriol_dipropionate" title="Methandriol dipropionate">Methandriol dipropionate</a></li> <li><a href="/wiki/Methandriol_propionate" title="Methandriol propionate">Methandriol propionate</a></li></ul></li> <li><a href="/wiki/Methylclostebol" title="Methylclostebol">Methylclostebol (chloromethyltestosterone)</a></li> <li><a href="/wiki/Methyltestosterone" title="Methyltestosterone">Methyltestosterone</a> (<a href="/wiki/Esterified_estrogens/methyltestosterone" title="Esterified estrogens/methyltestosterone">+esterified estrogens</a>) <ul><li><a href="/wiki/Methyltestosterone_3-hexyl_ether" title="Methyltestosterone 3-hexyl ether">Methyltestosterone 3-hexyl ether</a></li></ul></li> <li><a href="/wiki/Oxymesterone" title="Oxymesterone">Oxymesterone</a></li> <li><a href="/wiki/Penmesterol" title="Penmesterol">Penmesterol</a></li> <li><a href="/wiki/Tiomesterone" title="Tiomesterone">Tiomesterone</a></li></ul> <ul><li>17α-Alkylated 5α-dihydrotestosterone derivatives: <a href="/wiki/Androisoxazole" title="Androisoxazole">Androisoxazole</a></li> <li><a href="/wiki/Desoxymethyltestosterone" title="Desoxymethyltestosterone">Desoxymethyltestosterone</a></li> <li><a href="/wiki/Furazabol" title="Furazabol">Furazabol</a></li> <li><a href="/wiki/Mebolazine" title="Mebolazine">Mebolazine (dimethazine)</a></li> <li><a href="/wiki/Mestanolone" title="Mestanolone">Mestanolone</a></li> <li><a href="/wiki/Metenolone" title="Metenolone">Metenolone</a> <ul><li><a href="/wiki/Metenolone_acetate" title="Metenolone acetate">Metenolone acetate</a></li> <li><a href="/wiki/Metenolone_enanthate" title="Metenolone enanthate">Metenolone enanthate</a></li></ul></li> <li><a href="/wiki/Methasterone" title="Methasterone">Methasterone</a></li> <li><a href="/wiki/Methyl-1-testosterone" title="Methyl-1-testosterone">Methyl-1-testosterone</a></li> <li><a href="/wiki/Methylepitiostanol" title="Methylepitiostanol">Methylepitiostanol</a></li> <li><a href="/wiki/Methylstenbolone" title="Methylstenbolone">Methylstenbolone</a></li> <li><a href="/wiki/Oxandrolone" title="Oxandrolone">Oxandrolone</a></li> <li><a href="/wiki/Oxymetholone" title="Oxymetholone">Oxymetholone</a></li> <li><a href="/wiki/Stanozolol" title="Stanozolol">Stanozolol</a></li></ul> <ul><li>17α-Alkylated 19-nortestosterone derivatives: <a href="/wiki/Bolenol" title="Bolenol">Bolenol</a></li> <li><a href="/wiki/Dimethyldienolone" title="Dimethyldienolone">Dimethyldienolone</a></li> <li><a href="/wiki/Dimethyltrienolone" title="Dimethyltrienolone">Dimethyltrienolone</a></li> <li><a href="/wiki/Ethyldienolone" title="Ethyldienolone">Ethyldienolone</a></li> <li><a href="/wiki/Ethylestrenol" title="Ethylestrenol">Ethylestrenol</a></li> <li><a href="/wiki/Methyldienolone" title="Methyldienolone">Methyldienolone</a></li> <li><a href="/wiki/Methylhydroxynandrolone" title="Methylhydroxynandrolone">Methylhydroxynandrolone (MOHN, MHN)</a></li> <li><a href="/wiki/Metribolone" title="Metribolone">Metribolone</a></li> <li><a href="/wiki/Mibolerone" title="Mibolerone">Mibolerone</a></li> <li><a href="/wiki/Norboletone" title="Norboletone">Norboletone</a></li> <li><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a></li> <li><a href="/wiki/Propetandrol" title="Propetandrol">Propetandrol</a></li> <li><a href="/wiki/RU-2309" title="RU-2309">RU-2309</a></li> <li><a href="/wiki/Tetrahydrogestrinone" title="Tetrahydrogestrinone">Tetrahydrogestrinone</a></li></ul> <ul><li>17α-Alkylated 5α-dihydro-19-nortestosterone derivatives: <a href="/wiki/5%CE%B1-Dihydronorethandrolone" title="5α-Dihydronorethandrolone">5α-Dihydronorethandrolone</a></li> <li><a href="/wiki/5%CE%B1-Dihydronormethandrone" title="5α-Dihydronormethandrone">5α-Dihydronormethandrone</a></li></ul> <ul><li>17α-Vinyltestosterone derivatives: <a href="/wiki/Norvinisterone" title="Norvinisterone">Norvinisterone (vinylnortestosterone)</a></li></ul> <ul><li>17α-Vinyl-19-nortestosterone derivatives: <a href="/wiki/Vinyltestosterone" title="Vinyltestosterone">Vinyltestosterone</a></li></ul> <ul><li>17α-Ethynyltestosterone derivatives: <a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Ethinylandrostenediol" title="Ethinylandrostenediol">Ethinylandrostenediol</a> <ul><li><a href="/wiki/Ethandrostate" title="Ethandrostate">Ethandrostate</a></li></ul></li> <li><a href="/wiki/Ethisterone" title="Ethisterone">Ethisterone (ethynyltestosterone)</a></li></ul> <ul><li>5α-Dihydro-17α-ethynyltestosterone derivatives: <a href="/wiki/17%CE%B1-Ethynyl-3%CE%B1-androstanediol" title="17α-Ethynyl-3α-androstanediol">17α-Ethynyl-3α-androstanediol</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B2-androstanediol" title="17α-Ethynyl-3β-androstanediol">17α-Ethynyl-3β-androstanediol</a></li> <li><a href="/wiki/Dihydroethisterone" class="mw-redirect" title="Dihydroethisterone">Dihydroethisterone</a></li></ul> <ul><li>17α-Ethynyl-19-nortestosterone derivatives: <a href="/wiki/%CE%944-Tibolone" title="Δ4-Tibolone">Δ4-Tibolone</a></li> <li><a href="/wiki/Desogestrel" title="Desogestrel">Desogestrel</a></li> <li><a href="/wiki/Etonogestrel" title="Etonogestrel">Etonogestrel</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a> <ul><li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li></ul></li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li> <li><a href="/wiki/Levonorgestrel" title="Levonorgestrel">Levonorgestrel</a></li> <li><a href="/wiki/Levonorgestrel_ester" class="mw-redirect" title="Levonorgestrel ester">Levonorgestrel esters</a> (e.g., <a href="/wiki/Levonorgestrel_butanoate" title="Levonorgestrel butanoate">levonorgestrel butanoate</a>)</li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a> <ul><li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li></ul></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></li> <li><a href="/wiki/Norethisterone_ester" class="mw-redirect" title="Norethisterone ester">Norethisterone esters</a> (e.g., <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a>, <a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">norethisterone enanthate</a>)</li> <li><a href="/wiki/Norgestrel" title="Norgestrel">Norgestrel</a></li> <li><a href="/wiki/Norgestrienone" title="Norgestrienone">Norgestrienone</a></li> <li><a href="/wiki/Quingestanol" title="Quingestanol">Quingestanol</a> <ul><li><a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">Quingestanol acetate</a></li></ul></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li>5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives: <a href="/wiki/5%CE%B1-Dihydrolevonorgestrel" title="5α-Dihydrolevonorgestrel">5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/5%CE%B1-Dihydronorethisterone" title="5α-Dihydronorethisterone">5α-Dihydronorethisterone</a></li></ul> <ul><li>Progesterone derivatives: <a href="/wiki/6%CE%B1-Methylprogesterone" title="6α-Methylprogesterone">6α-Methylprogesterone</a></li> <li><a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li></ul> <ul><li>Others/unsorted: <a href="/wiki/3-Keto-5%CE%B1-abiraterone" title="3-Keto-5α-abiraterone">3-Keto-5α-abiraterone</a></li> <li><a href="/wiki/5%CE%B1-Androstane" class="mw-redirect" title="5α-Androstane">5α-Androstane</a></li> <li><a href="/wiki/Alternariol" title="Alternariol">Alternariol</a></li> <li><a href="/wiki/Cl-4AS-1" title="Cl-4AS-1">Cl-4AS-1</a></li> <li><a href="/wiki/Drupanol" title="Drupanol">Drupanol</a></li> <li><a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li> <li><a href="/wiki/ZM-182345" title="ZM-182345">ZM-182345</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center"><a href="/wiki/Selective_androgen_receptor_modulator" title="Selective androgen receptor modulator"><abbr title="Selective androgen receptor modulator">SARMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective androgen receptor modulator</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Nonsteroidal: <a href="/w/index.php?title=198RL26&action=edit&redlink=1" class="new" title="198RL26 (page does not exist)">198RL26</a></li> <li><a href="/wiki/ACP-105" title="ACP-105">ACP-105</a></li> <li><a href="/wiki/AC-262,536" title="AC-262,536">AC-262,536</a></li> <li><a href="/wiki/Acetothiolutamide" title="Acetothiolutamide">Acetothiolutamide</a></li> <li><a href="/wiki/Acetoxolutamide" title="Acetoxolutamide">Acetoxolutamide</a></li> <li><a href="/wiki/Andarine" title="Andarine">Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)</a></li> <li><a href="/wiki/BMS-564,929" title="BMS-564,929">BMS-564,929</a></li> <li><a href="/w/index.php?title=DTIB&action=edit&redlink=1" class="new" title="DTIB (page does not exist)">DTIB</a></li> <li><a href="/wiki/Enobosarm" title="Enobosarm">Enobosarm (ostarine, MK-2866, GTx-024, S-22)</a></li> <li><a href="/w/index.php?title=FTBU-1&action=edit&redlink=1" class="new" title="FTBU-1 (page does not exist)">FTBU-1</a></li> <li><a href="/wiki/GLPG-0492" title="GLPG-0492">GLPG-0492</a></li> <li><a href="/wiki/GSK2881078" title="GSK2881078">GSK2881078</a></li> <li><a href="/wiki/GSK-4336A" title="GSK-4336A">GSK-4336A</a></li> <li><a href="/w/index.php?title=GSK-8698&action=edit&redlink=1" class="new" title="GSK-8698 (page does not exist)">GSK-8698</a></li> <li><a href="/wiki/LG121071" title="LG121071">LG121071 (LGD-121071)</a></li> <li><a href="/wiki/LGD-2226" title="LGD-2226">LGD-2226</a></li> <li><a href="/wiki/LGD-2941" title="LGD-2941">LGD-2941 (LGD-122941)</a></li> <li><a href="/wiki/LGD-3303" title="LGD-3303">LGD-3303</a></li> <li><a href="/wiki/LGD-4033" class="mw-redirect" title="LGD-4033">LGD-4033</a></li> <li><a href="/wiki/LY305" title="LY305">LY305</a></li> <li><a href="/wiki/JNJ-26146900" title="JNJ-26146900">JNJ-26146900</a></li> <li><a href="/wiki/JNJ-28330835" title="JNJ-28330835">JNJ-28330835</a></li> <li><a href="/wiki/JNJ-37654032" title="JNJ-37654032">JNJ-37654032</a></li> <li><a href="/wiki/OPK-88004" title="OPK-88004">OPK-88004 (LY-2452473, TT-701)</a></li> <li><a href="/w/index.php?title=ORM-11984&action=edit&redlink=1" class="new" title="ORM-11984 (page does not exist)">ORM-11984</a></li> <li><a href="/wiki/PF-06260414" title="PF-06260414">PF-06260414</a></li> <li><a href="/w/index.php?title=R-1_(drug)&action=edit&redlink=1" class="new" title="R-1 (drug) (page does not exist)">R-1</a></li> <li><a href="/wiki/RU-59063" title="RU-59063">RU-59063</a></li> <li><a href="/w/index.php?title=S-1_(drug)&action=edit&redlink=1" class="new" title="S-1 (drug) (page does not exist)">S-1</a></li> <li><a href="/wiki/S-23_(drug)" title="S-23 (drug)">S-23</a></li> <li><a href="/wiki/S-40503" title="S-40503">S-40503</a></li> <li><a href="/w/index.php?title=S-101479&action=edit&redlink=1" class="new" title="S-101479 (page does not exist)">S-101479</a></li> <li><a href="/wiki/Vosilasarm" title="Vosilasarm">Vosilasarm</a></li></ul> <ul><li>Steroidal: <a href="/w/index.php?title=EM-9017&action=edit&redlink=1" class="new" title="EM-9017 (page does not exist)">EM-9017</a></li> <li><a href="/wiki/MK-0773" title="MK-0773">MK-0773</a></li> <li><a href="/wiki/TFM-4AS-1" title="TFM-4AS-1">TFM-4AS-1</a></li> <li><a href="/wiki/YK-11" title="YK-11">YK-11</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/7%CE%B1-Thioprogesterone" title="7α-Thioprogesterone">7α-Thioprogesterone</a></li> <li><a href="/wiki/7%CE%B1-Thiospironolactone" title="7α-Thiospironolactone">7α-Thiospironolactone</a></li> <li><a href="/wiki/7%CE%B1-Thiomethylspironolactone" title="7α-Thiomethylspironolactone">7α-Thiomethylspironolactone</a></li> <li><a href="/wiki/11%CE%B1-Hydroxyprogesterone" title="11α-Hydroxyprogesterone">11α-Hydroxyprogesterone</a></li> <li><a href="/wiki/15%CE%B2-Hydroxycyproterone_acetate" title="15β-Hydroxycyproterone acetate">15β-Hydroxycyproterone acetate</a></li> <li><a href="/wiki/Abiraterone" class="mw-redirect" title="Abiraterone">Abiraterone</a></li> <li><a href="/wiki/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a></li> <li><a href="/wiki/Allyltestosterone" title="Allyltestosterone">Allyltestosterone</a></li> <li><a href="/wiki/Benorterone" title="Benorterone">Benorterone</a></li> <li><a href="/wiki/BOMT" title="BOMT">BOMT</a></li> <li><a href="/wiki/Canrenoic_acid" title="Canrenoic acid">Canrenoic acid</a></li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a></li> <li><a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone acetate</a></li> <li><a href="/wiki/Clascoterone" title="Clascoterone">Clascoterone</a></li> <li><a href="/wiki/Clometerone" title="Clometerone">Clometerone</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/Cyproterone" title="Cyproterone">Cyproterone</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Delanterone" title="Delanterone">Delanterone</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a href="/wiki/Dicirenone" title="Dicirenone">Dicirenone</a></li> <li><a href="/wiki/Dienogest" title="Dienogest">Dienogest</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/DU-41165" title="DU-41165">DU-41165</a></li> <li><a href="/wiki/Edogestrone" title="Edogestrone">Edogestrone</a></li> <li><a href="/w/index.php?title=EM-4350&action=edit&redlink=1" class="new" title="EM-4350 (page does not exist)">EM-4350</a></li> <li><a href="/wiki/EM-5854" title="EM-5854">EM-5854</a></li> <li><a href="/w/index.php?title=EM-5855&action=edit&redlink=1" class="new" title="EM-5855 (page does not exist)">EM-5855</a></li> <li><a href="/w/index.php?title=EM-6537&action=edit&redlink=1" class="new" title="EM-6537 (page does not exist)">EM-6537</a></li> <li><a href="/wiki/Epitestosterone" title="Epitestosterone">Epitestosterone</a></li> <li><a href="/wiki/Galeterone" title="Galeterone">Galeterone</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/w/index.php?title=Ludaterone&action=edit&redlink=1" class="new" title="Ludaterone (page does not exist)">Ludaterone</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Mespirenone" title="Mespirenone">Mespirenone</a></li> <li><a href="/wiki/Metogest" title="Metogest">Metogest</a></li> <li><a href="/wiki/Mexrenone" title="Mexrenone">Mexrenone</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">Nomegestrol acetate</a></li> <li><a href="/wiki/Nordinone" title="Nordinone">Nordinone</a></li> <li><a href="/wiki/Osaterone" title="Osaterone">Osaterone</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a href="/wiki/Oxendolone" title="Oxendolone">Oxendolone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Potassium canrenoate</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Prorenone" title="Prorenone">Prorenone</a></li> <li><a href="/wiki/Rosterolone" title="Rosterolone">Rosterolone</a></li> <li><a href="/w/index.php?title=RU-15328&action=edit&redlink=1" class="new" title="RU-15328 (page does not exist)">RU-15328</a></li> <li><a href="/wiki/SC-5233" title="SC-5233">SC-5233 (spirolactone)</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spirorenone" title="Spirorenone">Spirorenone</a></li> <li><a href="/wiki/Spiroxasone" title="Spiroxasone">Spiroxasone</a></li> <li><a href="/wiki/Topterone" title="Topterone">Topterone</a></li> <li><a href="/wiki/Trimegestone" title="Trimegestone">Trimegestone</a></li> <li><a href="/wiki/Trimethyltrienolone" title="Trimethyltrienolone">Trimethyltrienolone (R-2956)</a></li> <li><a href="/wiki/Zanoterone" title="Zanoterone">Zanoterone</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/5N-Bicalutamide" title="5N-Bicalutamide">5N-Bicalutamide</a></li> <li><a href="/wiki/AA560" title="AA560">AA560</a></li> <li><a href="/w/index.php?title=Antarlide&action=edit&redlink=1" class="new" title="Antarlide (page does not exist)">Antarlides</a></li> <li><a href="/w/index.php?title=Arabilin&action=edit&redlink=1" class="new" title="Arabilin (page does not exist)">Arabilin</a></li> <li><a href="/wiki/Apalutamide" title="Apalutamide">Apalutamide</a></li> <li><a href="/wiki/Atraric_acid" title="Atraric acid">Atraric acid</a></li> <li><a href="/w/index.php?title=AZD-3514&action=edit&redlink=1" class="new" title="AZD-3514 (page does not exist)">AZD-3514</a></li> <li><a href="/wiki/Bakuchiol" title="Bakuchiol">Bakuchiol</a></li> <li><a href="/wiki/Bavdegalutamide" title="Bavdegalutamide">Bavdegalutamide</a></li> <li><a href="/w/index.php?title=BAY-1024767&action=edit&redlink=1" class="new" title="BAY-1024767 (page does not exist)">BAY-1024767</a></li> <li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></li> <li><a href="/wiki/Bisphenol" title="Bisphenol">Bisphenols</a> (e.g., <a href="/wiki/Bisphenol_A_diglycidyl_ether" title="Bisphenol A diglycidyl ether">BADGE</a>, <a href="/w/index.php?title=Bisphenol_F_diglycidyl_ether&action=edit&redlink=1" class="new" title="Bisphenol F diglycidyl ether (page does not exist)">BFDGE</a>, <a href="/wiki/Bisphenol_A" title="Bisphenol A">bisphenol A</a>, <a href="/wiki/Bisphenol_F" title="Bisphenol F">bisphenol F</a>, <a href="/wiki/Bisphenol_S" title="Bisphenol S">bisphenol S</a>)</li> <li><a href="/w/index.php?title=BMS-501949&action=edit&redlink=1" class="new" title="BMS-501949 (page does not exist)">BMS-501949</a></li> <li><a href="/w/index.php?title=BMS-570511&action=edit&redlink=1" class="new" title="BMS-570511 (page does not exist)">BMS-570511</a></li> <li><a href="/wiki/BMS-641988" title="BMS-641988">BMS-641988</a></li> <li><a href="/w/index.php?title=CH5137291&action=edit&redlink=1" class="new" title="CH5137291 (page does not exist)">CH5137291</a></li> <li><a href="/wiki/Cimetidine" title="Cimetidine">Cimetidine</a></li> <li><a href="/wiki/Cioteronel" title="Cioteronel">Cioteronel</a></li> <li><a href="/wiki/Cyanonilutamide" title="Cyanonilutamide">Cyanonilutamide</a></li> <li><a href="/wiki/Darolutamide" title="Darolutamide">Darolutamide</a></li> <li><a href="/wiki/DDT" title="DDT">DDT</a> (via metabolite <a href="/wiki/Dichlorodiphenyldichloroethylene" title="Dichlorodiphenyldichloroethylene">p,p’-DDE</a>)</li> <li><a href="/wiki/Dieldrin" title="Dieldrin">Dieldrin</a></li> <li><a href="/wiki/DIMP_(antiandrogen)" title="DIMP (antiandrogen)">DIMP</a></li> <li><a href="/wiki/Endosulfan" title="Endosulfan">Endosulfan</a></li> <li><a href="/wiki/Enzalutamide" title="Enzalutamide">Enzalutamide</a></li> <li><a href="/wiki/EPI-001" title="EPI-001">EPI-001</a></li> <li><a href="/wiki/Fenarimol" title="Fenarimol">Fenarimol</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Hydroxyflutamide" title="Hydroxyflutamide">Hydroxyflutamide</a></li> <li><a href="/wiki/Inocoterone" title="Inocoterone">Inocoterone</a></li> <li><a href="/wiki/Inocoterone_acetate" title="Inocoterone acetate">Inocoterone acetate</a></li> <li><a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Ketodarolutamide" title="Ketodarolutamide">Ketodarolutamide</a></li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/w/index.php?title=LG-105&action=edit&redlink=1" class="new" title="LG-105 (page does not exist)">LG-105</a></li> <li><a href="/wiki/LG-120907" title="LG-120907">LG-120907</a></li> <li><a href="/w/index.php?title=LGD-1331&action=edit&redlink=1" class="new" title="LGD-1331 (page does not exist)">LGD-1331</a></li> <li><a href="/wiki/Linuron" title="Linuron">Linuron</a></li> <li><a href="/wiki/Masofaniten" title="Masofaniten">Masofaniten</a></li> <li><a href="/wiki/Methiocarb" title="Methiocarb">Methiocarb</a></li> <li><a href="/w/index.php?title=N-Butylbenzenesulfonamide&action=edit&redlink=1" class="new" title="N-Butylbenzenesulfonamide (page does not exist)">N-Butylbenzenesulfonamide</a></li> <li><a href="/wiki/N-Desmethylapalutamide" title="N-Desmethylapalutamide">N-Desmethylapalutamide</a></li> <li><a href="/wiki/N-Desmethylenzalutamide" title="N-Desmethylenzalutamide">N-Desmethylenzalutamide</a></li> <li><a href="/wiki/Nilutamide" title="Nilutamide">Nilutamide</a></li> <li><a href="/w/index.php?title=ONC1-13B&action=edit&redlink=1" class="new" title="ONC1-13B (page does not exist)">ONC1-13B</a></li> <li><a href="/wiki/Pentomone" title="Pentomone">Pentomone</a></li> <li><a href="/w/index.php?title=PF-998425&action=edit&redlink=1" class="new" title="PF-998425 (page does not exist)">PF-998425</a></li> <li><a href="/wiki/Phenothrin" title="Phenothrin">Phenothrin</a></li> <li><a href="/wiki/Prochloraz" title="Prochloraz">Prochloraz</a></li> <li><a href="/wiki/Procymidone" title="Procymidone">Procymidone</a></li> <li><a href="/wiki/Proxalutamide" title="Proxalutamide">Proxalutamide</a></li> <li><a href="/wiki/Pyrilutamide" title="Pyrilutamide">Pyrilutamide</a></li> <li><a href="/wiki/Ralaniten" title="Ralaniten">Ralaniten (EPI-002)</a></li> <li><a href="/wiki/Ralaniten_acetate" title="Ralaniten acetate">Ralaniten acetate (EPI-506)</a></li> <li><a href="/wiki/RD-162" title="RD-162">RD-162</a></li> <li><a href="/wiki/Rezvilutamide" title="Rezvilutamide">Rezvilutamide</a></li> <li><a href="/w/index.php?title=Ro_2-7239&action=edit&redlink=1" class="new" title="Ro 2-7239 (page does not exist)">Ro 2-7239</a></li> <li><a href="/w/index.php?title=Ro_5-2537&action=edit&redlink=1" class="new" title="Ro 5-2537 (page does not exist)">Ro 5-2537</a></li> <li><a href="/wiki/RU-22930" title="RU-22930">RU-22930</a></li> <li><a href="/wiki/RU-56187" title="RU-56187">RU-56187</a></li> <li><a href="/wiki/RU-57073" title="RU-57073">RU-57073</a></li> <li><a href="/wiki/RU-58642" title="RU-58642">RU-58642</a></li> <li><a href="/wiki/RU-58841" title="RU-58841">RU-58841</a></li> <li><a href="/wiki/Seviteronel" title="Seviteronel">Seviteronel</a></li> <li><a href="/wiki/Thalidomide" title="Thalidomide">Thalidomide</a></li> <li><a href="/wiki/Topilutamide" title="Topilutamide">Topilutamide (fluridil)</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li> <li><a href="/wiki/Vinclozolin" title="Vinclozolin">Vinclozolin</a></li> <li><a href="/w/index.php?title=YM-580&action=edit&redlink=1" class="new" title="YM-580 (page does not exist)">YM-580</a></li> <li><a href="/w/index.php?title=YM-92088&action=edit&redlink=1" class="new" title="YM-92088 (page does not exist)">YM-92088</a></li> <li><a href="/w/index.php?title=YM-175735&action=edit&redlink=1" class="new" title="YM-175735 (page does not exist)">YM-175735</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/GPRC6A" title="GPRC6A">GPRC6A</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cation" class="mw-redirect" title="Cation">Cations</a> (incl. <a href="/wiki/Aluminium" title="Aluminium">aluminium</a>, <a href="/wiki/Calcium" title="Calcium">calcium</a>, <a href="/wiki/Gadolinium" title="Gadolinium">gadolinium</a>, <a href="/wiki/Magnesium" title="Magnesium">magnesium</a>, <a href="/wiki/Strontium" title="Strontium">strontium</a>, <a href="/wiki/Zinc" title="Zinc">zinc</a>)</li> <li><a href="/wiki/Dehydroandrosterone" title="Dehydroandrosterone">Dehydroandrosterone</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">Dihydrotestosterone</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Amino_acid" title="Amino acid">L-α-Amino acids</a> (incl. <a href="/wiki/Arginine" title="Arginine">L-arginine</a>, <a href="/wiki/Lysine" title="Lysine">L-lysine</a>, <a href="/wiki/Ornithine" title="Ornithine">L-ornithine</a>)</li> <li><a href="/wiki/Osteocalcin" title="Osteocalcin">Osteocalcin</a></li> <li><a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="Sex hormone-binding globulin">SHBG</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 Sex hormone-binding globulin</li> <li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Androgens_and_antiandrogens" title="Template:Androgens and antiandrogens">Androgens and antiandrogens</a></dd> <dd><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators">Estrogen receptor modulators</a></dd> <dd><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators">Progesterone receptor modulators</a></dd> <dd><a href="/wiki/List_of_androgens_and_anabolic_steroids" title="List of androgens and anabolic steroids">List of androgens and anabolic steroids</a></dd></dl> </div></td></tr></tbody></table></div> <style 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