Editing Testosterone (section)

{{Short description|Primary male sex hormone}}
{{About|testosterone as a hormone|its use as a medication|Testosterone (medication)|other uses}}
{{Use mdy dates|date=February 2015}}
{{cs1 config |name-list-style=vanc|display-authors=6}}
{{Chembox
<!-- Images -->
|ImageFile1=Testosteron.svg
|ImageSize1=225px
|ImageClass1=skin-invert
|ImageAlt1=The chemical structure of testosterone.
|ImageFile2=Testosterone molecule ball.png
|ImageSize2=225px
|ImageAlt2=A ball-and-stick model of testosterone.
<!-- Names -->
|IUPACName=17β-Hydroxyandrost-4-en-3-one
|SystematicName=(1''S'',3a''S'',3b''R'',9a''R'',9b''S'',11a''S'')-1-Hydroxy-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7''H''-cyclopenta[''a'']phenanthren-7-one
|OtherNames=Androst-4-en-17β-ol-3-one
|Watchedfields=verified
|verifiedrevid=649778658
<!-- Sections -->
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 58-22-0
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17347
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 386630
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5791
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00624
| EINECS = 200-370-5
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00075
| PubChem = 6013
| SMILES = O=C1C=C2[C@](C)(CC1)[C@H]3CC[C@]4(C)[C@H](CC[C@H]4[C@@H]3CC2)O
| 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MUMGGOZAMZWBJJ-DYKIIFRCSA-N
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3XMK78S47O
  }}
|Section2={{Chembox Properties
| C=19 | H=28 | O=2
| Appearance =
| Density =
| MeltingPtC = 151.0
| MeltingPt_ref =<ref>{{cite book | veditors = Haynes WM | year = 2011 | title = CRC Handbook of Chemistry and Physics | edition = 92nd | publisher = [[CRC Press]]| isbn = 978-1-4398-5511-9|page=3.304| title-link = CRC Handbook of Chemistry and Physics }}</ref>
| BoilingPt =
| Solubility =
  }}
|Section5={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
  }}
|Section6={{Chembox Pharmacology
| ATCvet =
| ATCCode_prefix = G03
| ATCCode_suffix = BA03
| ATC_Supplemental =
| Licence_EU=yes
| AdminRoutes = [[Transdermal]] ([[gel]], [[cream (pharmaceutical)|cream]], [[Topical medication#Topical solution|solution]], [[transdermal patch|patch]]), [[oral administration|by mouth]] (as [[testosterone undecanoate]]), [[buccal administration|in the cheek]], [[intranasal]] (gel), [[intramuscular injection]] (as [[Testosterone esters|ester]]s), [[subdermal implant|subcutaneous pellet]]s
| Bioavail = Oral: very low (due to extensive [[first pass effect|first pass metabolism]])
| Excretion = [[Urine]] (90%), [[feces]] (6%)
| HalfLife = 30–60&nbsp;minutes<ref>{{cite journal | url=https://www.goldjournal.net/article/0090-4295(94)90145-7/abstract | doi=10.1016/0090-4295(94)90145-7 | title=The time for serum testosterone to reach castrate level after bilateral orchiectomy or oral estrogen in the management of metastatic prostatic cancer | date=1994 | journal=Urology | volume=43 | issue=6 | pages=834–837 | pmid=8197647 | vauthors = Lin BJ, Chen K, Chen M, Chang LS | url-access=subscription }}</ref>
| Metabolism = [[Liver]] (mainly [[redox|reduction]] and [[conjugation (biochemistry)|conjugation]])
| ProteinBound = 97.0–99.5% (to {{abbrlink|SHBG|sex hormone-binding globulin}} and [[human serum albumin|albumin]])<ref name="MelmedPolonsky2015" />}}
}}
'''Testosterone''' is the primary male [[sex hormone]] and [[androgen]] in [[Male|males]].<ref>{{cite web |title=Understanding the risks of performance-enhancing drugs |url=https://www.mayoclinic.org/healthy-lifestyle/fitness/in-depth/performance-enhancing-drugs/art-20046134 |website=Mayo Clinic |access-date=30 December 2019 |language=en |archive-date=April 21, 2020 |archive-url=https://web.archive.org/web/20200421045948/https://www.mayoclinic.org/healthy-lifestyle/fitness/in-depth/performance-enhancing-drugs/art-20046134 |url-status=live }}</ref> In humans, testosterone plays a key role in the development of [[Male reproductive system|male reproductive]] tissues such as [[testicle]]s and [[prostate]], as well as promoting [[secondary sexual characteristic]]s such as increased [[muscle]] and [[bone]] mass, and the growth of [[androgenic hair|body hair]]. It is associated with increased [[aggression]], [[sex drive]], [[Dominance hierarchy|dominance]], [[courtship display]], and a wide range of behavioral characteristics.<ref name="pmid3549275">{{cite journal | vauthors = Mooradian AD, Morley JE, Korenman SG | title = Biological actions of androgens | journal = Endocrine Reviews| volume = 8 | issue = 1 | pages = 1–28 | date = Feb 1987 | pmid = 3549275 | doi = 10.1210/edrv-8-1-1 }}</ref> In addition, testosterone in both sexes is involved in health and well-being, where it has a significant effect on overall mood, cognition, social and sexual behavior, metabolism and energy output, the cardiovascular system, and in the prevention of [[osteoporosis]].<ref name="pmid19707253">{{cite journal | vauthors = Bassil N, Alkaade S, Morley JE | title = The benefits and risks of testosterone replacement therapy: a review | journal = Therapeutics and Clinical Risk Management | volume = 5 | issue = 3 | pages = 427–48 | date = Jun 2009 | pmid = 19707253 | pmc = 2701485 | doi =  10.2147/tcrm.s3025 | doi-access = free }}</ref><ref name="pmid19011293">{{cite book | vauthors = Tuck SP, Francis RM | chapter = Testosterone, bone and osteoporosis | volume = 37 | pages = 123–32 | year = 2009 | pmid = 19011293 | doi = 10.1159/000176049 | isbn = 978-3-8055-8622-1 | series = Frontiers of Hormone Research | title = Advances in the Management of Testosterone Deficiency }}</ref> Insufficient levels of testosterone in men may lead to abnormalities including frailty, accumulation of adipose fat tissue within the body, anxiety and depression, sexual performance issues, and bone loss.

Excessive levels of testosterone in men may be associated with [[hyperandrogenism]], higher risk of [[heart failure]], increased [[Death|mortality]] in men with [[prostate cancer]],<ref>{{cite journal | vauthors = Gann PH, Hennekens CH, Ma J, Longcope C, Stampfer MJ | title = Prospective study of sex hormone levels and risk of prostate cancer | journal = Journal of the National Cancer Institute | volume = 88 | issue = 16 | pages = 1118–1126 | date = August 1996 | pmid = 8757191 | doi = 10.1093/jnci/88.16.1118 | doi-access = free | citeseerx = 10.1.1.524.1837 }}</ref> and [[male pattern baldness]].

Testosterone is a [[steroid hormone]] from the [[androstane]] class containing a [[ketone]] and a [[hydroxyl]] group at positions three and seventeen respectively. It is [[Biosynthesis|biosynthesized]] in several steps from cholesterol and is converted in the liver to inactive metabolites.<ref name = "Luetjens_2012" />  It exerts its action through binding to and activation of the [[androgen receptor]].<ref name = "Luetjens_2012">{{cite book | veditors = Nieschlag E, Behre HM, Nieschlag S | title = Testosterone: Action, Deficiency, Substitution | vauthors = Luetjens CM, Weinbauer GF | pages = 15–32 | chapter = Chapter 2: Testosterone: Biosynthesis, transport, metabolism and (non-genomic) actions | chapter-url = https://books.google.com/books?id=MkrAPaQ4wJkC&pg=PA15 | date = 2012 | publisher = Cambridge University Press | location = Cambridge | isbn = 978-1-107-01290-5 | edition = 4th }}</ref> In humans and most other [[vertebrate]]s, testosterone is secreted primarily by the [[testicles]] of males and, to a lesser extent, the [[ovaries]] of [[female]]s. On average, in adult males, levels of testosterone are about seven to eight times as great as in adult females.<ref name="pmid14981046">{{cite journal | vauthors = Torjesen PA, Sandnes L | title = Serum testosterone in women as measured by an automated immunoassay and a RIA | journal = Clinical Chemistry | volume = 50 | issue = 3 | pages = 678; author reply 678–9 | date = Mar 2004 | pmid = 14981046 | doi = 10.1373/clinchem.2003.027565 | doi-access = free }}</ref> As the metabolism of testosterone in males is more pronounced, the daily production is about 20 times greater in men.<ref name="pmid6025472">{{cite journal | vauthors = Southren AL, Gordon GG, Tochimoto S, Pinzon G, Lane DR, Stypulkowski W | title = Mean plasma concentration, metabolic clearance and basal plasma production rates of testosterone in normal young men and women using a constant infusion procedure: effect of time of day and plasma concentration on the metabolic clearance rate of testosterone | journal = The Journal of Clinical Endocrinology & Metabolism| volume = 27 | issue = 5 | pages = 686–94 | date = May 1967 | pmid = 6025472 | doi = 10.1210/jcem-27-5-686 }}</ref><ref name="pmid5843701">{{cite journal | vauthors = Southren AL, Tochimoto S, Carmody NC, Isurugi K | title = Plasma production rates of testosterone in normal adult men and women and in patients with the syndrome of feminizing testes | journal = The Journal of Clinical Endocrinology & Metabolism| volume = 25 | issue = 11 | pages = 1441–50 | date = Nov 1965 | pmid = 5843701 | doi = 10.1210/jcem-25-11-1441 }}</ref> Females are also more sensitive to the hormone.<ref name="isbn0-07-135739-4">{{cite book | vauthors = Dabbs M, Dabbs JM | title = Heroes, rogues, and lovers: testosterone and behavior | url = https://archive.org/details/heroesrogueslove00jame | url-access = registration | publisher = McGraw-Hill | location = New York | year = 2000 | isbn = 978-0-07-135739-5 }}</ref>{{Page needed|date=June 2023}}

In addition to its role as a natural hormone, testosterone is used as a [[medication]] to treat [[hypogonadism]] and [[breast cancer]].<ref name="AHFS2016">{{cite web |date=December 4, 2015 |title=Testosterone |url=https://www.drugs.com/monograph/testosterone.html |url-status=live |archive-url=https://web.archive.org/web/20160820173417/https://www.drugs.com/monograph/testosterone.html |archive-date=August 20, 2016 |access-date=3 September 2016 |website=Drugs.com |publisher=American Society of Health-System Pharmacists}}</ref> Since [[andropause|testosterone levels decrease as men age]], testosterone is sometimes used in older men to counteract this deficiency. It is also used illicitly to [[performance-enhancing substance|enhance physique and performance]], for instance in [[athlete]]s.<ref>{{cite report |collaboration=Institute of Medicine (US) Committee on Assessing the Need for Clinical Trials of Testosterone Replacement Therapy |vauthors=Liverman CT, Blazer DG |chapter=Introduction |title=Testosterone and Aging: Clinical Research Directions |date=2004 |publisher=National Academies Press (US) |chapter-url=https://www.ncbi.nlm.nih.gov/books/NBK216164/ |language=en |access-date=September 26, 2016 |archive-date=January 10, 2016 |archive-url=https://web.archive.org/web/20160110170928/http://www.ncbi.nlm.nih.gov/books/NBK216164/ |url-status=live }}</ref> The [[World Anti-Doping Agency]] lists it as S1 Anabolic agent substance "prohibited at all times".<ref>{{Cite web|title=What is Prohibited|url=https://www.wada-ama.org/en/content/what-is-prohibited/prohibited-at-all-times/anabolic-agents|access-date=2021-07-18|website=World Anti-Doping Agency|language=en|archive-date=November 12, 2020|archive-url=https://web.archive.org/web/20201112011132/https://www.wada-ama.org/en/content/what-is-prohibited/prohibited-at-all-times/anabolic-agents|url-status=dead}}</ref>