Testosterone (medication)のソースを表示

{{Short description|Medication and naturally occurring steroid hormone}}
{{About|testosterone as a medication|the natural hormone|Testosterone}}
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{{Use mdy dates|date=March 2025}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 649778658
| drug_name = Testosterone
| image = Testosteron.svg
| image_class = skin-invert-image
| width = 225
| alt = 
| image2 = Testosterone molecule ball.png
| width2 = 225
| alt2 = 
| caption = <!-- Clinical data -->
| pronounce = {{IPAc-en|t|ɛ|ˈ|s|t|ɒ|s|t|ə|r|oʊ|n}} {{respell|teh|STOS|tə|rohn}}<ref>[https://web.archive.org/web/20171201080834/https://en.oxforddictionaries.com/definition/testosterone Testosterone]. [[Oxford Dictionaries (website)|Oxford Dictionaries]].</ref>
| tradename = AndroGel, Testim, TestoGel, [[#Brand names|others]]
| Drugs.com = {{drugs.com|monograph|testosterone}}
| MedlinePlus = a619028
| DailyMedID = Testosterone
| pregnancy_AU = D
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Testosterone Use During Pregnancy | website=Drugs.com | date=August 20, 2019 | url=https://www.drugs.com/pregnancy/testosterone.html | access-date=January 8, 2020 | archive-date=February 1, 2014 | archive-url=https://web.archive.org/web/20140201201902/http://www.drugs.com/pregnancy/testosterone.html | url-status=live }}</ref>
| pregnancy_category = [[Contraindication|Contraindicated]] due to [[teratogen]]ic effects
| addiction_liability = Moderate <ref name="d982">{{cite web | title=Anabolic steroid misuse | website=nhs.uk | date=November 4, 2022 | url=https://www.nhs.uk/conditions/anabolic-steroid-misuse/ | access-date=July 12, 2024}}</ref>
| routes_of_administration = [[buccal administration|buccal]], [[intranasal administration|intranasal]], [[subcutaneous implant]], [[transdermal administration|transdermal]] ([[gel]], [[cream]], [[transdermal patch|patch]]).
| class = [[Androgen]], [[anabolic steroid]]
| ATC_prefix = G03
| ATC_suffix = BA03
| ATC_supplemental = <!-- Legal status -->
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->{{Citation needed|date=August 2023}}
| legal_AU_comment = 
| legal_BR = C5
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=March 31, 2023 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=August 3, 2023 |access-date=August 15, 2023 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=April 4, 2023}}</ref>
| legal_CA = Schedule IV{{citation needed|date=August 2023}}
| legal_CA_comment = 
| legal_DE = <!-- Anlage I, II, III or Unscheduled-->{{citation needed|date=August 2023}}
| legal_DE_comment = 
| legal_NZ = <!-- Class A, B, C -->{{citation needed|date=August 2023}}
| legal_NZ_comment = 
| legal_UK = Class C{{citation needed|date=August 2023}}
| legal_UK_comment = 
| legal_US = Schedule III{{citation needed|date=August 2023}}
| legal_US_comment = 
| legal_EU = Rx-only
| legal_EU_comment = <ref>{{cite web | author = Human Medicines Evaluation Division | title = Active substance: testosterone (all formulations apart from topical use) | url = https://www.ema.europa.eu/documents/psusa/testosterone-all-formulations-apart-topical-use-list-nationally-authorised-medicinal-products-psusa/00010631/202112_en.pdf | work= List of nationally authorised medicinal products | publisher = European Medicines Agency | date = September 1, 2022 | access-date = September 6, 2022 | archive-date = September 6, 2022 | archive-url = https://web.archive.org/web/20220906054434/https://www.ema.europa.eu/en/documents/psusa/testosterone-all-formulations-apart-topical-use-list-nationally-authorised-medicinal-products-psusa/00010631/202112_en.pdf | url-status = live }}</ref><ref>{{cite web | author = Human Medicines Evaluation Division | title = Active substance: testosterone (topical use) | url = https://www.ema.europa.eu/documents/psusa/testosterone-topical-use-list-nationally-authorised-medicinal-products-psusa/00002908/202112_en.pdf | work= List of nationally authorised medicinal products | publisher = European Medicines Agency | date = September 1, 2022 | access-date = September 6, 2022 | archive-date = September 6, 2022 | archive-url = https://web.archive.org/web/20220906054434/https://www.ema.europa.eu/en/documents/psusa/testosterone-topical-use-list-nationally-authorised-medicinal-products-psusa/00002908/202112_en.pdf | url-status = live }}</ref>
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV-->{{citation needed|date=August 2023}}
| legal_UN_comment = 
| legal_status = Rx-only

<!-- Pharmacokinetic data -->| dependency_liability = Moderate <ref name="d982">{{cite web | title=Anabolic steroid misuse | website=nhs.uk | date=November 4, 2022 | url=https://www.nhs.uk/conditions/anabolic-steroid-misuse/ | access-date=July 12, 2024}}</ref>
| bioavailability = Oral: very low (due to extensive [[first pass effect|first pass metabolism]])
| protein_bound = 97.0–99.5% (to {{abbrlink|SHBG|sex hormone-binding globulin}} and [[human serum albumin|albumin]])<ref name="MelmedPolonsky2015">{{cite book|vauthors=Melmed S, Polonsky KS, Larsen PR|title=Williams Textbook of Endocrinology|url=https://books.google.com/books?id=iPIACwAAQBAJ&pg=PA709|date=November 11, 2015|publisher=Elsevier Health Sciences|isbn=978-0-323-34157-8|pages=709, 711, 765|access-date=November 18, 2016|archive-date=April 14, 2019|archive-url=https://web.archive.org/web/20190414214954/https://books.google.com/books?id=iPIACwAAQBAJ&pg=PA709|url-status=live}}</ref>
| metabolism = [[Liver]] (mainly [[redox|reduction]] and [[conjugation (biochemistry)|conjugation]])
| metabolites = 
| onset = 
| elimination_half-life = 2–4&nbsp;hours{{Citation needed|date=October 2016}}
| duration_of_action = 
| excretion = [[Urine]] (90%), [[feces]] (6%)

<!-- Identifiers -->| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 58-22-0
| CAS_supplemental = <br />{{CAS|57-85-2}} ([[propionate]])<!-- Also CAS verified --><br />{{CAS|315-37-7}} ([[enanthate]])<br />{{CAS|58-20-8}} ([[cypionate]])<br />{{CAS|5949-44-0}} ([[undecanoate]])
| PubChem = 6013
| IUPHAR_ligand = 2858
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00624
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5791
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3XMK78S47O
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00075
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17347
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 386630
| NIAID_ChemDB = 
| PDB_ligand = 
| synonyms = Androst-4-en-17β-ol-3-one

<!-- Chemical and physical data -->| IUPAC_name = (8''R'',9''S'',10''R'',13''S'',14''S'',17''S'')-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[''a'']phenanthren-3-one
| C = 19
| H = 28
| O = 2
| SMILES = O=C4\C=C2/[C@]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)(C)CC4
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1
| StdInChI_comment = 
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MUMGGOZAMZWBJJ-DYKIIFRCSA-N
| density = 
| density_notes = 
| melting_point = 155
| melting_high = 
| melting_notes = 
| boiling_point = 
| boiling_notes = 
| solubility = 
| sol_units = 
| specific_rotation = +110.2°
}}

<!-- Definition and medical uses -->
'''Testosterone''' is a [[medication]] and naturally occurring [[testosterone|steroid hormone]].<ref name=AHFS2016/> It is used to treat [[male hypogonadism]], [[gender dysphoria]], and certain types of [[breast cancer]].<ref name=AHFS2016/><ref>{{cite web |title=List of Gender Dysphoria Medications (6 Compared) |url=https://www.drugs.com/condition/gender-dysphoria.html |website=Drugs.com |access-date=May 6, 2020 |language=en |archive-date=April 26, 2020 |archive-url=https://web.archive.org/web/20200426180544/https://www.drugs.com/condition/gender-dysphoria.html |url-status=live }}</ref> It may also be used to increase [[athletic ability]] in the form of [[doping in sport|doping]].<ref name=AHFS2016/> It is unclear if the use of testosterone for [[andropause|low levels due to aging]] is beneficial or harmful.<ref name=FDA2015>{{cite web |author=Staff |title=Testosterone Products: Drug Safety Communication – FDA Cautions About Using Testosterone Products for Low Testosterone Due to Aging; Requires Labeling Change to Inform of Possible Increased Risk of Heart Attack And Stroke |url=https://www.fda.gov/Safety/MedWatch/SafetyInformation/SafetyAlertsforHumanMedicalProducts/ucm436280.htm |date=March 3, 2015 |work=[[FDA]] |access-date=March 5, 2015 |url-status=live |archive-url=https://web.archive.org/web/20150305015556/https://www.fda.gov/Safety/MedWatch/SafetyInformation/SafetyAlertsforHumanMedicalProducts/ucm436280.htm |archive-date=March 5, 2015}}</ref> Testosterone can be administered through several different routes, including [[Topical medication|topical]] [[gel|gels]] or [[transdermal patch|patches]], [[Nasal spray|nasal sprays]], subdermal implants, or [[Buccal administration|tablets dissolved inside the mouth]].<ref name=AHFS2016/> 

<!-- Side effects -->
Common [[side effect]]s of testosterone include [[acne]], [[swelling (medical)|swelling]], and [[gynecomastia|breast enlargement in men]].<ref name=AHFS2016/> Serious side effects may include [[liver toxicity]], [[heart disease]], and behavioral changes.<ref name=AHFS2016/> Women and children who are exposed may develop [[virilization|masculinization]].<ref name=AHFS2016/> It is recommended that individuals with [[prostate cancer]] should not use the medication.<ref name=AHFS2016/> It can cause harm to the baby if used during [[pregnancy]] or [[breastfeeding]].<ref name=AHFS2016/> Testosterone is in the [[androgen]] family of medications.<ref name=AHFS2016/>

<!-- History, society and culture -->
Testosterone was first isolated in 1935, and approved for medical use in 1939.<ref>{{cite book | vauthors = Taylor WN | title = Anabolic Steroids and the Athlete | date = 2002 | publisher = McFarland | isbn = 978-0-7864-1128-3 | page = 180 | edition = 2nd | url = https://books.google.com/books?id=OGcQ0Tp2AFcC&pg=PA180 | url-status = live | archive-url = https://web.archive.org/web/20160914142007/https://books.google.com/books?id=OGcQ0Tp2AFcC&pg=PA180 | archive-date = September 14, 2016}}</ref><ref name=Fis2006>{{cite book |vauthors=Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=481 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA481 |language=en |access-date=August 18, 2020 |archive-date=August 23, 2022 |archive-url=https://web.archive.org/web/20220823114136/https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA481 |url-status=live }}</ref> Rates of use have increased three times in the United States between 2001 and 2011.<ref name=Des2016>{{cite journal | vauthors = Desroches B, Kohn TP, Welliver C, Pastuszak AW | title = Testosterone therapy in the new era of Food and Drug Administration oversight | journal = Translational Andrology and Urology | volume = 5 | issue = 2 | pages = 207–12 | date = April 2016 | pmid = 27141448 | pmc = 4837303 | doi = 10.21037/tau.2016.03.13 | doi-access = free }}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO23rd">{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) | year = 2023 | hdl = 10665/371090 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2023.02 | hdl-access=free }}</ref> It is available as a [[generic medication]].<ref name=AHFS2016>{{cite web |title=Testosterone|url=https://www.drugs.com/monograph/testosterone.html|website=Drugs.com |publisher=American Society of Health-System Pharmacists|access-date=September 3, 2016|date=December 4, 2015 |archive-url=https://web.archive.org/web/20160820173417/https://www.drugs.com/monograph/testosterone.html |archive-date=August 20, 2016|url-status=live}}</ref> In 2022, it was the 118th most commonly prescribed medication in the United States, with more than 5{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=August 30, 2024 | archive-date=August 30, 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Testosterone Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Testosterone | access-date = August 30, 2024 }}</ref>
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