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Revision as of 12:29, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 451339930 of page Testosterone_undecanoate for the Chem/Drugbox validation project (updated: 'CAS_number').  Latest revision as of 15:32, 15 August 2024 edit Danski14 (talk | contribs)Autopatrolled, Extended confirmed users16,432 edits more on half life etc 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Use dmy dates|date=May 2024}}
{{Drugbox
{{cs1 config|name-list-style=vanc|display-authors=6}}
| verifiedrevid = 451338374
{{Infobox drug
| IUPAC_name = phenanthren-17-yl] undecanoate
| Verifiedfields = verified
| image = Testosterone_undecanoate.png
| Watchedfields = verified
| verifiedrevid = 470603074
| image = Testosterone undecanoate.svg
| width = 250
| alt =
| image2 = Testosterone undecanoate molecule ball.png
| width2 = 250
| alt2 = <!-- Clinical data -->
| pronounce = {{IPAc-en|t|ɛ|ˈ|s|t|ɒ|s|t|ə|r|oʊ|n|_|ə|n|ˈ|d|ɛ|k|ə|n|oʊ|eɪ|t}} {{respell|teh|STOS|tə|rohn|_|ən|DEK|ə|noh|ayt}}
| tradename = Oral: Kyzatrex, Andriol, Jatenzo, Testoheal, others<br />IM: Aveed, Nebido, others
| Drugs.com = {{drugs.com|monograph|testosterone}}
| MedlinePlus = a614041
| DailyMedID = Testosterone_undecanoate
| pregnancy_AU = D
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Testosterone Use During Pregnancy | website=Drugs.com | date=20 August 2019 | url=https://www.drugs.com/pregnancy/testosterone.html | access-date=18 March 2020 | archive-date=1 February 2014 | archive-url=https://web.archive.org/web/20140201201902/http://www.drugs.com/pregnancy/testosterone.html | url-status=live }}</ref>
| pregnancy_category =
| addiction_liability = Moderate <ref name="d982">{{cite web | title=Anabolic steroid misuse | website=nhs.uk | date=2022-11-04 | url=https://www.nhs.uk/conditions/anabolic-steroid-misuse/ | access-date=2024-07-12}}</ref>
| routes_of_administration = ], ]
| class = ]; ]; ]
| ATC_prefix = G03
| ATC_suffix = BA03


<!-- Legal status -->| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
<!--Clinical data-->
| tradename = | legal_AU_comment =
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| pregnancy_category = X (]), ]ic effects
| legal_BR_comment =
| legal_status = Schedule III (])<br />Schedule IV (])
| legal_CA = Schedule IV
| routes_of_administration = oral,I.V
| legal_CA_comment =
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_UK_comment =
| legal_US = Schedule III
| legal_US_comment = <ref name="Jatenzo FDA label" /><ref name="Tlando FDA label" /><ref name="Kyzatrex FDA label">{{cite web | title=Kyzatrex- testosterone undecanoate capsule, liquid filled | website=DailyMed | date=18 October 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7f7167a7-2a25-47e2-acf5-33f499fce971 | access-date=21 January 2023 | archive-date=21 January 2023 | archive-url=https://web.archive.org/web/20230121062449/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7f7167a7-2a25-47e2-acf5-33f499fce971 | url-status=live }}</ref>
| legal_EU =
| legal_EU_comment =
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| 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=2022-11-04 | url=https://www.nhs.uk/conditions/anabolic-steroid-misuse/ | access-date=2024-07-12}}</ref>
<!--Pharmacokinetic data-->
| bioavailability = ]: 3–7%{{Medical citation needed|date=November 2017}}<br />]: high
| bioavailability = 7%
| protein_bound = High (])
| metabolism = ], ] and ]
| metabolism = ]
| elimination_half-life = 1-12 days
| metabolites = ], ], ]s of testosterone
| excretion = ]
| elimination_half-life = {{Abbrlink|IM|Intramuscular injection}} (in ]): 20.9 days<ref name="NieschlagBehre2010">{{cite book| vauthors = Nieschlag E, Behre HM, Nieschlag S |title=Andrology: Male Reproductive Health and Dysfunction|url=https://books.google.com/books?id=mEgckDNkonUC&pg=PA441|date=13 January 2010|publisher=Springer Science & Business Media|isbn=978-3-540-78355-8|pages=441–446}}</ref><ref name="pmid10229906" /><br />{{Abbr|IM|Intramuscular injection}} (in ]): 33.9 days<ref name="NieschlagBehre2010" /><ref name="pmid10229906" />
| excretion = ~90% ], 6% ]


<!--Identifiers--> <!-- Identifiers -->| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 5949-44-0
| CASNo_Ref =
| PubChem = 65157
| CAS_number = <!-- blanked - oldvalue: 5949-44-0 -->
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| CAS_supplemental =
| DrugBank = DB13946
| ATC_prefix = G03
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ATC_suffix = BA03
| ChemSpiderID = 58664
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| UNII_Ref = {{fdacite|correct|FDA}}
| StdInChI = 1S/C29H46O3/c1-4-5-6-7-8-9-10-11-27(31)32-26-15-14-24-23-13-12-21-20-22(30)16-18-28(21,2)25(23)17-19-29(24,26)3/h20,23-26H,4-19H2,1-3H3/t23?,24?,25?,26-,28-,29-/m0/s1
| UNII = H16A5VCT9C
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| StdInChIKey = LBERVHLCXUMDOT-SSRQPSIZSA-N
| KEGG = D06087
| PubChem = 65157
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 135741
| ChemSpiderID = 23089522
| KEGG_Ref = {{keggcite|correct|kegg}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 2107067
| KEGG = D06087
| synonyms = TU; Testosterone undecylate; Testosterone 17β-undecanoate; ORG-538; CLR-610


<!-- Chemical data -->| IUPAC_name = phenanthren-17-yl] undecanoate
<!--Chemical data-->
| C=30 | H=48 | O=3 | C = 30
| H = 48
| molecular_weight = 456.70032
| O = 3
| SMILES = CCCCCCCCCCC(=O)O1CC21(CC32CCC4=CC(=O)CC34C)C
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C30H48O3/c1-4-5-6-7-8-9-10-11-12-28(32)33-27-16-15-25-24-14-13-22-21-23(31)17-19-29(22,2)26(24)18-20-30(25,27)3/h21,24-27H,4-20H2,1-3H3/t24-,25-,26-,27-,29-,30-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = UDSFVOAUHKGBEK-CNQKSJKFSA-N
}} }}

<!-- Definition and medical uses -->
'''Testosterone undecanoate''', sold under the brand name '''Nebido''' among others, is an ] and ] (AAS) ] that is used mainly in the treatment of ],<ref name="NieschlagBehre2012">{{cite book|vauthors=Nieschlag E, Behre HM, Nieschlag S|title=Testosterone: Action, Deficiency, Substitution|url=https://books.google.com/books?id=MkrAPaQ4wJkC&pg=PA315|date=26 July 2012|publisher=Cambridge University Press|isbn=978-1-107-01290-5|pages=313–315, 321–322|access-date=3 January 2018|archive-date=7 April 2022|archive-url=https://web.archive.org/web/20220407103354/https://books.google.com/books?id=MkrAPaQ4wJkC&pg=PA315|url-status=live}}</ref><ref name="NieschlagBehre2010"/><ref name="Becker2001">{{cite book|vauthors=Becker KL|title=Principles and Practice of Endocrinology and Metabolism|url=https://books.google.com/books?id=FVfzRvaucq8C&pg=PA1185|year=2001|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-1750-2|pages=1185–|access-date=3 January 2018|archive-date=17 May 2020|archive-url=https://web.archive.org/web/20200517043226/https://books.google.com/books?id=FVfzRvaucq8C&pg=PA1185|url-status=live}}</ref><ref name="Llewellyn2011">{{cite book|vauthors=Llewellyn W|title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT180|year=2011|publisher=Molecular Nutrition LLC|isbn=978-0-9828280-1-4|pages=180–182, 331–334|access-date=3 January 2018|archive-date=3 July 2022|archive-url=https://web.archive.org/web/20220703055937/https://books.google.com/books?id=afKLA-6wW0oC&pg=PT180|url-status=live}}</ref><ref name="pmid27084565">{{cite journal | vauthors = Irwig MS | title = Testosterone therapy for transgender men | journal = The Lancet. Diabetes & Endocrinology | volume = 5 | issue = 4 | pages = 301–311 | date = April 2017 | pmid = 27084565 | doi = 10.1016/S2213-8587(16)00036-X }}</ref><ref name="pmid17635694">{{cite journal | vauthors = Jacobeit JW, Gooren LJ, Schulte HM | title = Long-acting intramuscular testosterone undecanoate for treatment of female-to-male transgender individuals | journal = The Journal of Sexual Medicine | volume = 4 | issue = 5 | pages = 1479–1484 | date = September 2007 | pmid = 17635694 | doi = 10.1111/j.1743-6109.2007.00556.x }}</ref><ref name="pmid19749027">{{cite journal | vauthors = Jacobeit JW, Gooren LJ, Schulte HM | title = Safety aspects of 36 months of administration of long-acting intramuscular testosterone undecanoate for treatment of female-to-male transgender individuals | journal = European Journal of Endocrinology | volume = 161 | issue = 5 | pages = 795–798 | date = November 2009 | pmid = 19749027 | doi = 10.1530/EJE-09-0412 | doi-access = free }}</ref> It is taken ] or given by ].<ref name="Llewellyn2011" /><ref name="BertelloniHiort2010">{{cite book|vauthors=Bertelloni S, Hiort O|title=New Concepts for Human Disorders of Sexual Development|url=https://books.google.com/books?id=CQhaAgAAQBAJ&pg=PA256|date=28 September 2010|publisher=S. Karger AG|isbn=978-3-8055-9569-8|pages=256–|access-date=3 November 2016|archive-date=8 November 2020|archive-url=https://web.archive.org/web/20201108083958/https://books.google.com/books?id=CQhaAgAAQBAJ&pg=PA256|url-status=live}}</ref>

<!-- Side effects and mechanism of action -->
]s of testosterone undecanoate include ]s of ] like ], ], ], ], elevated liver enzymes, hypertriglyceridemia, and increased ].<ref name="Llewellyn2011" /> The drug is a ] of testosterone, the ] of the ] (AR) and hence is an androgen and anabolic steroid.<ref name="pmid18500378">{{cite journal | vauthors = Kicman AT | title = Pharmacology of anabolic steroids | journal = British Journal of Pharmacology | volume = 154 | issue = 3 | pages = 502–521 | date = June 2008 | pmid = 18500378 | pmc = 2439524 | doi = 10.1038/bjp.2008.165 }}</ref><ref name="Llewellyn2011" /> It has strong ]ic effects and moderate ] effects, which make it useful for producing masculinization and suitable for ].<ref name="Llewellyn2011" /> Testosterone undecanoate is a ] and a ] of ] in the body.<ref name="Becker2001" /><ref name="NieschlagBehre2012" /><ref name="NieschlagBehre2010" /> Because of this, it is considered to be a natural and bioidentical form of testosterone.<ref name="pmid27032319">{{cite journal | vauthors = Santoro N, Braunstein GD, Butts CL, Martin KA, McDermott M, Pinkerton JV | title = Compounded Bioidentical Hormones in Endocrinology Practice: An Endocrine Society Scientific Statement | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 101 | issue = 4 | pages = 1318–1343 | date = April 2016 | pmid = 27032319 | doi = 10.1210/jc.2016-1271 | doi-access = free }}</ref>

<!-- History, society, and culture -->
Testosterone undecanoate was introduced in China for use by injection and in the European Union for use by mouth in the 1970s.<ref name="Hoberman2005" /><ref name="MundyFitzpatrick2010" /> It became available for use by injection in the European Union in the early to mid 2000s and in the United States in 2014.<ref name="MelmedPolonsky2015" /><ref name="Schering2004" /> Formulations for use by mouth are approved in the United States.<ref name="Jatenzo FDA label">{{cite web | title=Jatenzo- testosterone undecanoate capsule, liquid filled | website=DailyMed | date=11 January 2021 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=ed7b5d41-7475-4c10-99b9-b62b3434ae60 | access-date=27 May 2022 | archive-date=5 January 2022 | archive-url=https://web.archive.org/web/20220105204904/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=ed7b5d41-7475-4c10-99b9-b62b3434ae60 | url-status=live }}</ref><ref name="Tlando FDA label" /><ref name="FDA-approves-Jatenzo">{{cite press release |vauthors=Meyer L |title=FDA approves new oral testosterone capsule for treatment of men with certain forms of hypogonadism |url=https://www.fda.gov/news-events/press-announcements/fda-approves-new-oral-testosterone-capsule-treatment-men-certain-forms-hypogonadism |publisher=U.S. ] (FDA) |access-date=27 August 2020 |date=27 March 2019 |ref=45 |archive-date=7 September 2020 |archive-url=https://web.archive.org/web/20200907133655/https://www.fda.gov/news-events/press-announcements/fda-approves-new-oral-testosterone-capsule-treatment-men-certain-forms-hypogonadism |url-status=live }}</ref> Along with ], ], and ], testosterone undecanoate is one of the most widely used testosterone esters.<ref name="pmid18500378" /><ref name="NieschlagBehre2010" /><ref name="Llewellyn2011" /> However, it has advantages over other testosterone esters in that it can be taken by mouth and in that it has a far longer duration when given by injection.<ref name="Köhn-2003">{{cite journal | vauthors = Köhn FM, Schill WB | title = A new oral testosterone undecanoate formulation | journal = World Journal of Urology | volume = 21 | issue = 5 | pages = 311–315 | date = November 2003 | pmid = 14579074 | doi = 10.1007/s00345-003-0372-x | s2cid = 23627346 }}</ref><ref name="NieschlagBehre2012" /><ref name="NieschlagBehre2010" /><ref name="pmid10229906" /><ref name="Llewellyn2011" /> In addition to its medical use, testosterone undecanoate is used to ].<ref name="Llewellyn2011" /> The drug is a ] in many countries.<ref name="Llewellyn2011" />

Oral administration of testosterone undecanoate is an effective method to achieve therapeutic physiological levels of serum testosterone in patients with hypogonadism. In addition, oral therapy has been found to have a positive impact in these patients on quality of life factors such as sexual function, mood, and mental status, as documented in various studies.<ref>{{cite journal | vauthors = Ahmad SW, Molfetto G, Montoya D, Camero A | title = Is Oral Testosterone the New Frontier of Testosterone Replacement Therapy? | journal = Cureus | volume = 14 | issue = 8 | pages = e27796 | date = August 2022 | pmid = 36106278 | pmc = 9452423 | doi = 10.7759/cureus.27796 | doi-access = free }}</ref>

== Medical uses ==
Testosterone undecanoate is ] for testosterone replacement therapy in adult males for conditions associated with a deficiency or absence of endogenous testosterone.<ref name="Jatenzo FDA label" /><ref name="Tlando FDA label" /><ref name="Kyzatrex FDA label" />

==Side effects==
{{See also|Anabolic steroid#Adverse effects|Androgen replacement therapy#Adverse effects}}
]s of testosterone undecanoate include ] among others.<ref name="Llewellyn2011" />

===Anaphylaxis===
The Reandron 1000 formulation (Aveed in the United States) contains 1,000&nbsp;mg of testosterone undecanoate ] in 4 ml ] with ] for ] and as a ], and is administered by ]. As an ] in Reandron 1000, benzyl benzoate has been reported as a cause of ] (a serious life-threatening ]) in a case in ].<ref>{{cite journal | vauthors = Ong GS, Somerville CP, Jones TW, Walsh JP | title = Anaphylaxis triggered by benzyl benzoate in a preparation of depot testosterone undecanoate | journal = Case Reports in Medicine | volume = 2012 | pages = 384054 | year = 2012 | pmid = 22272209 | pmc = 3261473 | doi = 10.1155/2012/384054 | id = 384054 | doi-access = free }}</ref> ] includes this report in information for health professionals and recommends that physicians "should be aware of the potential for serious allergic reactions" to preparations of this type.<ref name = Nebido>{{cite web|title = Nebido Monograph &ndash; Information for Health Care Professionals|url = http://www.nebido.com/en/hcp/product-information/nebido-monograph/index.php|year = 2016|access-date = 19 October 2016|publisher = ]|archive-date = 19 October 2016|archive-url = https://web.archive.org/web/20161019155919/http://www.nebido.com/en/hcp/product-information/nebido-monograph/index.php|url-status = live}}</ref> In Australia, reports to the ] (ADRAC), which evaluates reports of ] for the ] (TGA), show several reports of allergic reactions since the anaphylaxis case from 2011.{{Medical citation needed|date=October 2017}}

==Pharmacology==

===Pharmacodynamics===
{{See also|Testosterone#Mechanism of action|Anabolic steroid#Pharmacology}}

{{Relative androgenic to anabolic activity in animals}}

Testosterone undecanoate is a ] of testosterone and is an androgen and ] (AAS). That is, it is an ] of the ] (AR).

===Pharmacokinetics===
Testosterone undecanoate has a very long ] and ] when given as a ] ].<ref name="PayneHardy2007">{{cite book|vauthors=Payne AH, Hardy MP|title=The Leydig Cell in Health and Disease|url=https://books.google.com/books?id=x4ttqKIAOg0C&pg=PA423|date=28 October 2007|publisher=Springer Science & Business Media|isbn=978-1-59745-453-7|pages=423–|access-date=6 October 2016|archive-date=10 November 2020|archive-url=https://web.archive.org/web/20201110065252/https://books.google.com/books?id=x4ttqKIAOg0C&pg=PA423|url-status=live}}</ref><ref name="NieschlagBehre2010" /><ref name="pmid10229906">{{cite journal | vauthors = Behre HM, Abshagen K, Oettel M, Hübler D, Nieschlag E | title = Intramuscular injection of testosterone undecanoate for the treatment of male hypogonadism: phase I studies | journal = European Journal of Endocrinology | volume = 140 | issue = 5 | pages = 414–419 | date = May 1999 | pmid = 10229906 | doi = 10.1530/eje.0.1400414 | citeseerx = 10.1.1.503.1752 | s2cid = 22597244 }}</ref> Its elimination half-life is 20.9&nbsp;days and its ] is 34.9&nbsp;days in ], while its elimination half-life is 33.9&nbsp;days and its mean residence time is 36.0&nbsp;days in ].<ref name="NieschlagBehre2010" /><ref name="pmid10229906" /> These values are substantially longer than those of ] (which, in castor oil, has values of 4.5&nbsp;days and 8.5&nbsp;days, respectively).<ref name="PayneHardy2007" />

Testosterone undecaondate has very low bioavailability when taken orally, only about 3-7% in men and 4-10% in women.<ref name="TäuberSchröder1986">{{cite journal | vauthors = Täuber U, Schröder K, Düsterberg B, Matthes H | title = Absolute bioavailability of testosterone after oral administration of testosterone-undecanoate and testosterone | journal = European Journal of Drug Metabolism and Pharmacokinetics | volume = 11 | issue = 2 | pages = 145–149 | year = 1986 | pmid = 3770015 | doi = 10.1007/BF03189840 | s2cid = 32305408 }}</ref><ref name="LemkeWilliams2012">{{cite book | vauthors = Lemke TL, Williams DA | title = Foye's Principles of Medicinal Chemistry | url = https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA1360 | date = 24 January 2012 | publisher = Lippincott Williams & Wilkins | isbn = 978-1-60913-345-0 | pages = 1360– }}</ref><ref>{{cite journal | vauthors = Täuber U, Schröder K, Düsterberg B, Matthes H | title = Absolute bioavailability of testosterone after oral administration of testosterone-undecanoate and testosterone | journal = European Journal of Drug Metabolism and Pharmacokinetics | volume = 11 | issue = 2 | pages = 145–149 | date = April 1986 | pmid = 3770015 | doi = 10.1007/BF03189840 }}</ref> This bioavailability is increased with food, especially foods containing fat, thus it is typically recommended to be taken with a meal.<ref name="BehreNieschlag2012">{{cite book| vauthors = Behre HM, Nieschlag E, Nieschlag S |chapter=Testosterone preparations for clinical use in males| veditors = Nieschlag E, Behre HM, Nieschlag S |pages=309–335|doi=10.1017/CBO9781139003353.016|title=Testosterone: Action, Deficiency, Substitution|date=26 July 2012|publisher=Cambridge University Press|isbn=978-1-107-01290-5}}</ref><ref name="Hohl2017">{{cite book|vauthors = Hohl A |title=Testosterone: From Basic to Clinical Aspects|url=https://books.google.com/books?id=Et6TDgAAQBAJ&pg=PA13|date=30 March 2017|publisher=Springer|isbn=978-3-319-46086-4|pages=13–}}</ref><ref name="pmid12627930">{{cite journal | vauthors = Bagchus WM, Hust R, Maris F, Schnabel PG, Houwing NS | title = Important effect of food on the bioavailability of oral testosterone undecanoate | journal = Pharmacotherapy | volume = 23 | issue = 3 | pages = 319–325 | date = March 2003 | pmid = 12627930 | doi = 10.1592/phco.23.3.319.32104 | s2cid = 24440953 }}</ref><ref name="pmid17371478">{{cite journal | vauthors = Schnabel PG, Bagchus W, Lass H, Thomsen T, Geurts TB | title = The effect of food composition on serum testosterone levels after oral administration of Andriol Testocaps | journal = Clinical Endocrinology | volume = 66 | issue = 4 | pages = 579–585 | date = April 2007 | pmid = 17371478 | pmc = 1859980 | doi = 10.1111/j.1365-2265.2007.02781.x }}</ref> It is absorbed through the lymphatic system (90-100%) and peak serum levels are reached after about 3-5 hours.<ref name="LemkeWilliams2012" /><ref name="newpharmk">{{cite journal | vauthors = Roth MY, Dudley RE, Hull L, Leung A, Christenson P, Wang C, Swerdloff R, Amory JK | title = Steady-state pharmacokinetics of oral testosterone undecanoate with concomitant inhibition of 5α-reductase by finasteride | journal = International Journal of Andrology | volume = 34 | issue = 6 Pt 1 | pages = 541–547 | date = December 2011 | pmid = 20969601 | doi = 10.1111/j.1365-2605.2010.01120.x | pmc = 4269219 }}</ref><ref>{{cite journal | vauthors = Yin AY, Htun M, Swerdloff RS, Diaz-Arjonilla M, Dudley RE, Faulkner S, Bross R, Leung A, Baravarian S, Hull L, Longstreth JA, Kulback S, Flippo G, Wang C | title = Reexamination of pharmacokinetics of oral testosterone undecanoate in hypogonadal men with a new self-emulsifying formulation | journal = Journal of Andrology | volume = 33 | issue = 2 | pages = 190–201 | date = 4 March 2012 | pmid = 21474786 | doi = 10.2164/jandrol.111.013169 | pmc = 4168025 }}</ref> From there, plasma levels decline, typically reaching pre-dose levels after 6-12 hours. The elimination half-life via the oral route has been stated to be 1.6&nbsp;hours, with a ] of 3.7&nbsp;hours.<ref name="NieschlagBehre2010"/> However, there is a large amount of individual variability in its duration of action.<ref name="pharmk2">{{cite journal | vauthors = Behre HM, Wang C, Handelsman DJ, Nieschlag E |title=Pharmacology of testosterone preparations |journal=Testosterone |date=1 January 2001 |pages=405–444 |doi=10.1017/CBO9780511545221.015}}</ref> For this reason it is often dosed twice or even three times a day.<ref name="pharmk2"/><ref name="newpharmk"/>

Testosterone undecanoate is metabolized partially in the intestinal wall into 5-alpha-dihydrotestosterone undecanoate (DHTU).<ref name="dhtu">{{cite journal | vauthors = Lachance S, Dhingra O, Bernstein J, Gagnon S, Savard C, Pelletier N, Boudreau N, Lévesque A | title = Importance of measuring testosterone in enzyme-inhibited plasma for oral testosterone undecanoate androgen replacement therapy clinical trials | journal = Future Science OA | volume = 1 | issue = 4 | pages = FSO55 | date = November 2015 | pmid = 28031910 | doi = 10.4155/fso.15.55 }}</ref> In the blood, non-specific esterases metabolize testosterone undecanoate into testosterone and DHTU into ] (DHT).<ref name="dhtu"/> Thus, testosterone undecanoate increases plasma levels of both testerone and DHT. The fact the conversion happens in the blood complicates the accurate measurement of blood levels of testosterone induced by the drug, as the conversion continues to occur while blood samples are being prepared for assay. Ideally, enzyme inhibitors should be used to properly assay the blood testosterone levels induced by testosterone undecanoate.<ref name="dhtu"/>

==Chemistry==
{{See also|Androgen ester|List of androgen esters}}

Testosterone undecanoate, or testosterone 17β-undecanoate, is a ] ] ] and a ] of ].<ref name="Elks2014">{{cite book|vauthors=Elks J|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA641|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=641–642|access-date=6 October 2016|archive-date=22 October 2020|archive-url=https://web.archive.org/web/20201022172120/https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA641|url-status=live}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA1002|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=1002–1004|access-date=13 December 2017|archive-date=25 January 2020|archive-url=https://web.archive.org/web/20200125043731/https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA1002|url-status=live}}</ref> It is an ]; specifically, it is the C17β ] (undecanoate) ] of testosterone.<ref name="Elks2014" /><ref name="IndexNominum2000" /> A related testosterone ester with a similarly very long duration is ].<ref name="NieschlagBehre2012" /><ref name="Becker2001" />

The first commercialized preparation of oral testosterone undecanoate had it dissolved in oleic acid.<ref name="pharmk2"/> This formulation had to be refrigerated in the pharmacy for reasons of stability and would only last about three months at room temperature.<ref name="pharmk2"/> A newer more stable pharmaceutical formulation with ] and ] has since been developed.<ref name="pharmk2"/> This new formulation can be stored at room temperature for three years.<ref name="pharmk2"/> A novel ] formulation of oral testosterone undecanoate in 300-mg capsules for use once per day has been under development.<<ref name="ByrneNieschlag2017">{{cite book| vauthors = Byrne MM, Nieschlag E |title=Reference Module in Neuroscience and Biobehavioral Psychology|chapter=Androgens: Pharmacological Use and Abuse ☆|year=2017|publisher=Elsevier |doi=10.1016/B978-0-12-809324-5.03356-3|isbn=9780128093245}}</ref>

==History==
In the late 1970s, testosterone undecanoate was introduced for oral use in ],<ref name="Hoberman2005">{{cite book | vauthors = Hoberman J | title = Testosterone Dreams: Rejuvenation, Aphrodisia, Doping | url = https://archive.org/details/testosteronedrea00hobe | url-access = registration | date = 21 February 2005 |publisher=University of California Press|isbn=978-0-520-93978-3|pages=–}}</ref> although intramuscular testosterone undecanoate had already been in use in ] for several years.<ref name="MundyFitzpatrick2010">{{cite book|vauthors=Mundy AR, Fitzpatrick J, Neal DE, George NJ|title=The Scientific Basis of Urology|url=https://books.google.com/books?id=h6HSBQAAQBAJ&pg=PA294|date=26 July 2010|publisher=CRC Press|isbn=978-1-84184-749-8|pages=294–|access-date=27 October 2017|archive-date=14 April 2019|archive-url=https://web.archive.org/web/20190414215011/https://books.google.com/books?id=h6HSBQAAQBAJ&pg=PA294|url-status=live}}</ref> Intramuscular testosterone undecanoate was not introduced in Europe and the ] until much later, in the early to mid 2000s and 2014, respectively.<ref name="MelmedPolonsky2015">{{cite book|vauthors=Melmed S, Polonsky KS, Larsen PR, Kronenberg MH|title=Williams Textbook of Endocrinology|url=https://books.google.com/books?id=iPIACwAAQBAJ&pg=PA709|date=11 November 2015|publisher=Elsevier Health Sciences|isbn=978-0-323-34157-8|pages=709, 711, 765|access-date=27 October 2017|archive-date=14 April 2019|archive-url=https://web.archive.org/web/20190414214954/https://books.google.com/books?id=iPIACwAAQBAJ&pg=PA709|url-status=live}}</ref><ref name="Schering2004">{{cite journal | vauthors = | title = Testosterone Undecanoate-Schering AG | journal = Drugs in R&D | volume = 5 | issue = 6 | pages = 368–369 | year = 2004 | pmid = 15563244 | doi = 10.2165/00126839-200405060-00012 | s2cid = 43349541 }}</ref> Testosterone undecanoate was approved in the United States only in 2014 after three previous rejections due to safety concerns.<ref name="Medscape2014">{{cite web|vauthors=Tucker ME|title=FDA Approves Aveed Testosterone Jab, with Restrictions|url=http://www.medscape.com/viewarticle/821632|website=]|access-date=13 December 2016|date=7 March 2014|archive-date=1 February 2017|archive-url=https://web.archive.org/web/20170201230413/http://www.medscape.com/viewarticle/821632|url-status=live}}</ref>

==Society and culture==

===Generic names===
''Testosterone undecanoate'' is the ] of the drug and its {{abbrlink|USAN|United States Adopted Name}} and {{abbrlink|BAN|British Approved Name}}.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012">{{cite book|vauthors=Morton IK, Hall JM|title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA270|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|access-date=6 October 2016|archive-date=19 August 2020|archive-url=https://web.archive.org/web/20200819233400/https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA270|url-status=live}}</ref><ref name="Drugs.com">{{Cite web | url=https://www.drugs.com/international/testosterone.html | title=Testosterone | website=Drugs.com | access-date=27 October 2017 | archive-date=13 November 2016 | archive-url=https://web.archive.org/web/20161113175707/https://www.drugs.com/international/testosterone.html | url-status=live }}</ref> It is also referred to as ''testosterone undecylate''.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" />

===Brand names===
Testosterone undecanoate is or has been marketed under a variety of brand names, including Andriol, Androxon, Aveed, Cernos Depot, Jatenzo, Kyzatrex,<ref name="Kyzatrex FDA label" /> Nebido, Nebido-R, Panteston, Reandron 1000, Restandol, Sustanon 250, Undecanoate 250, and Undestor.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref>{{Cite web|title=Testosterone undecanoate profile and most popular brands in USA|url=http://downsizefitness.com/rankings/testosterone-undecanoate/|access-date=6 September 2020|website=Downsizefitness.com|archive-date=3 July 2022|archive-url=https://web.archive.org/web/20220703055939/http://downsizefitness.com/rankings/testosterone-undecanoate/|url-status=live}}</ref><ref name="Drugs.com" />

===Availability===
{{See also|List of androgens/anabolic steroids available in the United States}}
Oral testosterone undecanoate is available in Europe, Mexico, Asia, and the United States.<ref name="NieschlagNieschlag2017" /><ref name="ArnoldPfaff2002">{{cite book|vauthors=Arnold AP, Pfaff DW, Etgen AM, Fahrbach SE, Rubin RT|title=Hormones, Brain and Behavior, Five-Volume Set|url=https://books.google.com/books?id=cGbE2nC__Q0C&pg=PA20|date=10 June 2002|publisher=Academic Press|isbn=978-0-12-532104-4|pages=20–|access-date=27 October 2017|archive-date=22 November 2020|archive-url=https://web.archive.org/web/20201122130644/https://books.google.com/books?id=cGbE2nC__Q0C&pg=PA20|url-status=live}}</ref>

Intramuscular testosterone undecanoate has been approved worldwide,<ref name="NieschlagNieschlag2017" /><ref name="Llewellyn2011" /> including the European Union, Russia, and the United States.<ref name="Llewellyn2011" /><ref name="NieschlagNieschlag2017">{{cite book| vauthors = Nieschlag E, Nieschlag S |chapter=The History of Testosterone and the Testes: From Antiquity to Modern Times |title=Testosterone |year=2017 |pages=1–19 |publisher=Springer |doi=10.1007/978-3-319-46086-4_1 |isbn=978-3-319-46084-0}}</ref><ref name="DPD@HealthCanada">{{cite web |title=Drug Product Database |publisher=Health Canada |url=http://www.hc-sc.gc.ca/dhp-mps/prodpharma/databasdon/index-eng.php |access-date=13 November 2016 |url-status=live |archive-url=https://web.archive.org/web/20161119200516/http://www.hc-sc.gc.ca/dhp-mps/prodpharma/databasdon/index-eng.php |archive-date=19 November 2016 |date=18 March 2010 }}</ref> Intramuscular testosterone undecanoate is marketed as Nebido in Europe and as Aveed in the United States while oral testosterone undecanoate is marketed as Andriol.<ref name="Llewellyn2011" /><ref name="NieschlagNieschlag2017" /><ref name="DPD@HealthCanada" />

===Legal status===
Testosterone undecanoate, along with other AAS, is a ] ] in the ] under the ] and a ] controlled substance in ] under the ].<ref name="FFFLM2006">{{cite book|vauthors=Karch SB|title=Drug Abuse Handbook, Second Edition|url=https://books.google.com/books?id=ZjrMBQAAQBAJ&pg=PA30|date=21 December 2006|publisher=CRC Press|isbn=978-1-4200-0346-8|pages=30–|access-date=11 November 2017|archive-date=14 April 2019|archive-url=https://web.archive.org/web/20190414215105/https://books.google.com/books?id=ZjrMBQAAQBAJ&pg=PA30|url-status=live}}</ref><ref name="LilleySnyder2016">{{cite book|vauthors=Lilley LL, Snyder JS, Collins SR|title=Pharmacology for Canadian Health Care Practice|url=https://books.google.com/books?id=dNgoDwAAQBAJ&pg=PA50|date=5 August 2016|publisher=Elsevier Health Sciences|isbn=978-1-77172-066-3|page=50|access-date=11 November 2017|archive-date=14 April 2019|archive-url=https://web.archive.org/web/20190414214954/https://books.google.com/books?id=dNgoDwAAQBAJ&pg=PA50|url-status=live}}</ref>

In March 2019, the US ] approved testosterone undecanoate (Jatenzo), an oral testosterone capsule to treat men with certain forms of ]. These men have low testosterone levels due to specific medical conditions, such as genetic disorders like Klinefelter syndrome or tumors that have damaged the pituitary gland.<ref name="FDA-approves-Jatenzo" /> The FDA granted the approval of Jatenzo to Clarus Therapeutics.<ref name="FDA-approves-Jatenzo" /><ref>{{Cite web|url=http://clarustherapeutics.com/content/investors-and-media/releases/clarus-receives-fda-approval-of-jatenzo.htm|title=Clarus Therapeutics Receives U.S. FDA Approval of Jatenzo (Testosterone Undecanoate Capsules for Oral Use) (CIII) for Testosterone Replacement Therapy in Certain Adult Men|website=Clarustherapeutics.com|access-date=14 March 2022|archive-date=19 February 2020|archive-url=https://web.archive.org/web/20200219030921/http://www.clarustherapeutics.com/content/investors-and-media/releases/clarus-receives-fda-approval-of-jatenzo.htm|url-status=live}}</ref>

In March 2022, testosterone undecanoate (Tlando) was approved for medical use in the United States.<ref name="Tlando FDA label">{{cite web | title=Tlando- testosterone undecanoate capsule, liquid filled | website=DailyMed | date=28 March 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=479b55bd-2023-486a-8922-3b1de48b935c | access-date=27 May 2022 | archive-date=3 July 2022 | archive-url=https://web.archive.org/web/20220703055940/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=479b55bd-2023-486a-8922-3b1de48b935c | url-status=live }}</ref>

In July 2022, Kyzatrex, an oral testosterone undecanoate capsule, was approved for medical use in the United States.<ref name="Kyzatrex FDA label" /><ref name="Drug Approval Package: Kyzatrex Capsules" /> The FDA granted the approval of Kyzatrex to Marius Pharmaceuticals.<ref name="Drug Approval Package: Kyzatrex Capsules">{{cite web | title=Drug Approval Package: Kyzatrex Capsules | website=accessdata.fda.gov | date=21 December 2022 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2022/213953Orig1s000TOC.cfm | access-date=18 May 2024}}</ref><ref>{{Cite web |title=Kyzatrex (testosterone undecanoate) FDA Approval History |url=https://www.drugs.com/history/kyzatrex.html |access-date=6 April 2023 |website=Drugs.com |archive-date=6 April 2023 |archive-url=https://web.archive.org/web/20230406163529/https://www.drugs.com/history/kyzatrex.html |url-status=live }}</ref>

==Research==
===Non-alcoholic steatohepatitis===
In 2013, a ] ] testing intramuscular testosterone undecanoate for the treatment of ] (NASH) was initiated in the ].<ref>{{Cite journal|url=https://clinicaltrials.gov/ct2/show/NCT01919294|title=Pilot Open Study of Testosterone Replacement in Non-alcoholic Steatohepatitis|date=25 April 2017|access-date=14 March 2022|website=Clinicaltrials.gov|archive-date=9 April 2021|archive-url=https://web.archive.org/web/20210409174402/https://clinicaltrials.gov/ct2/show/NCT01919294|url-status=live}}</ref> In the United States in 2018, Lipocine Inc. began investigating the potential of using an oral testosterone undecanoate formulation, known as LPCN-1144, in patients with NASH.<ref>{{Cite web|url=https://www.lipocine.com/pipeline/lpcn-1144/clinical-trials.htm|title=Lipocine Inc. - Clinical Trials|website=Lipocine.com|access-date=14 March 2022|archive-date=24 May 2019|archive-url=https://web.archive.org/web/20190524084410/https://www.lipocine.com/pipeline/lpcn-1144/clinical-trials.htm|url-status=live}}</ref>

=== Osteoporosis ===
In 2013, a study aimed to evaluate the efficacy of testosterone undecanoate therapy on bone mineral density (BMD) and biochemical markers of bone turnover in elderly males with ] and low serum testosterone levels.

They study found that administering low-dose testosterone undecanoate (TU) at a rate of 20&nbsp;mg per day to elderly men with low serum testosterone and osteoporosis effectively increases bone mineral density in the lumbar spine and femoral neck, and improves bone turnover, similar to the standard-dose TU (40&nbsp;mg, per day) treatment. The treatment did not exhibit any adverse side effects on the prostate gland, including ]. Therefore, low-dose TU appears to be a safe and cost-effective protocol for treating elderly male osteoporosis.<ref name="pmid23533404">{{cite journal | vauthors = Wang YJ, Zhan JK, Huang W, Wang Y, Liu Y, Wang S, Tan P, Tang ZY, Liu YS | title = Effects of low-dose testosterone undecanoate treatment on bone mineral density and bone turnover markers in elderly male osteoporosis with low serum testosterone | journal = International Journal of Endocrinology | volume = 2013 | issue = | pages = 570413 | date = 2013 | pmid = 23533404 | pmc = 3603196 | doi = 10.1155/2013/570413 | doi-access = free }}</ref> However, further clinical trials with larger sample sizes, multiple centers, and long-term follow-ups are required to determine the efficacy and safety of low-dose testosterone undecanoate treatment in elderly male osteoporosis with low serum testosterone.

== Health implications ==
=== Risks associated with treatment of late-onset hypogonadism ===
There is a potential concern in the medical community that the administration of testosterone therapy for the treatment of ] may escalate the risks associated with ], ] and heart diseases.<ref name="pmid35266057">{{cite journal |vauthors=Snyder P |title=Testosterone treatment of late-onset hypogonadism - benefits and risks |journal=Rev Endocr Metab Disord |volume=23 |issue=6 |pages=1151–1157 |date=December 2022 |pmid=35266057 |doi=10.1007/s11154-022-09712-1}}</ref>

=== Body composition ===
In 2020, a study that evaluated the effects of testosterone therapy in men with testosterone deficiency and varying degrees of weight (normal weight, overweight, and obesity) on anthropometric and metabolic parameters found that long-term testosterone undecanoate therapy in hypogonadal men, regardless of their weight at the start of the study, led to improvements in several body composition parameters, including body weight, waist circumference, and body mass index. Additionally, testosterone undecanoate therapy was found to lower fasting blood glucose and HbA1c levels and improve lipid profiles in this population.<ref name="pmid32060355">{{cite journal | vauthors = Saad F, Doros G, Haider KS, Haider A | title = Differential effects of 11 years of long-term injectable testosterone undecanoate therapy on anthropometric and metabolic parameters in hypogonadal men with normal weight, overweight and obesity in comparison with untreated controls: real-world data from a controlled registry study | journal = International Journal of Obesity | volume = 44 | issue = 6 | pages = 1264–1278 | date = June 2020 | pmid = 32060355 | doi = 10.1038/s41366-019-0517-7 | s2cid = 211102413 | pmc = 7260126 }}</ref>

=== Bone density ===
There have been several studies that evaluate the effect of testosterone therapy on bone density or ] One study concluded that long-term testosterone replacement therapy (TRT) in middle-aged men with ] (LOH) and ] led to a significant increase in both vertebral and femoral bone mineral density (BMD) after 36 months of treatment, as measured by dual-energy x-ray absorptiometry. The TRT treatment was shown to induce a 5% per year increase in BMD without changes in body mass index (BMI). The study suggests that long-term TRT could be beneficial for improving bone health in middle-aged men with LOH and MS, even in the absence of osteoporosis.<ref>{{cite journal | vauthors = Aversa A, Bruzziches R, Francomano D, Greco EA, Fornari R, Di Luigi L, Lenzi A, Migliaccio S | title = Effects of long-acting testosterone undecanoate on bone mineral density in middle-aged men with late-onset hypogonadism and metabolic syndrome: results from a 36 months controlled study | journal = The Aging Male | volume = 15 | issue = 2 | pages = 96–102 | date = June 2012 | pmid = 22439807 | doi = 10.3109/13685538.2011.631230 | s2cid = 6594250 | doi-access = free }}</ref>

== References ==
{{Reflist}}

{{Testosterone}}
{{Androgens and antiandrogens}}
{{Androgen receptor modulators}}
{{Estrogen receptor modulators}}
{{Portal bar | Medicine}}
{{Authority control}}

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