Testosterone undecanoate

Testosterone undecanoate
Clinical data
Pronunciation/tɛˈstɒstəroʊn ənˈdɛkənoʊeɪt/ teh-STOS-tə-rohn ən-DEK-ə-noh-ayt
Trade namesOral: Kyzatrex, Andriol, Jatenzo, Testoheal, others
IM: Aveed, Nebido, others
Other namesTU; Testosterone undecylate; Testosterone 17β-undecanoate; ORG-538; CLR-610
AHFS/Drugs.comMonograph
MedlinePlusa614041
License data
Pregnancy
category
Dependence
liability		Moderate [2]
Addiction
liability		Moderate [2]
Routes of
administration		By mouth, intramuscular injection
Drug classAndrogen; Anabolic steroid; Androgen ester
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: 3–7%[medical citation needed]
Intramuscular: high
Protein bindingHigh (testosterone)
MetabolismLiver
MetabolitesTestosterone, undecanoic acid, metabolites of testosterone
Elimination half-lifeIMTooltip Intramuscular injection (in tea seed oil): 20.9 days[7][8]
IM (in castor oil): 33.9 days[7][8]
Excretion~90% Urine, 6% feces
Identifiers
  • [(8R,9S,10R,13S,14S,17S)-10,13-Dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] undecanoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.025.193 Edit this at Wikidata
Chemical and physical data
FormulaC30H48O3
Molar mass456.711 g·mol−1
3D model (JSmol)
  • CCCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
  • InChI=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 ☒N
  • Key:UDSFVOAUHKGBEK-CNQKSJKFSA-N ☒N
  (verify)

Testosterone undecanoate, sold under the brand name Nebido among others, is an androgen and anabolic steroid (AAS) medication that is used mainly in the treatment of low testosterone levels in men,[9][7][10][11][12][13][14] It is taken by mouth or given by injection into muscle.[11][15]

Side effects of testosterone undecanoate include symptoms of masculinization like acne, increased hair growth, voice changes, hypertension, elevated liver enzymes, hypertriglyceridemia, and increased sexual desire.[11] The drug is a prodrug of testosterone, the biological ligand of the androgen receptor (AR) and hence is an androgen and anabolic steroid.[16][11] It has strong androgenic effects and moderate anabolic effects, which make it useful for producing masculinization and suitable for androgen replacement therapy.[11] Testosterone undecanoate is a testosterone ester and a prodrug of testosterone in the body.[10][9][7] Because of this, it is considered to be a natural and bioidentical form of testosterone.[17]

Testosterone undecanoate was introduced in China for use by injection and in the European Union for use by mouth in the 1970s.[18][19] It became available for use by injection in the European Union in the early to mid 2000s and in the United States in 2014.[20][21] Formulations for use by mouth are approved in the United States.[4][5][22] Along with testosterone enanthate, testosterone cypionate, and testosterone propionate, testosterone undecanoate is one of the most widely used testosterone esters.[16][7][11] 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.[23][9][7][8][11] In addition to its medical use, testosterone undecanoate is used to improve physique and performance.[11] The drug is a controlled substance in many countries.[11]

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.[24]

  1. ^ "Testosterone Use During Pregnancy". Drugs.com. 20 August 2019. Archived from the original on 1 February 2014. Retrieved 18 March 2020.
  2. ^ a b "Anabolic steroid misuse". nhs.uk. 4 November 2022. Retrieved 12 July 2024.
  3. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  4. ^ a b "Jatenzo- testosterone undecanoate capsule, liquid filled". DailyMed. 11 January 2021. Archived from the original on 5 January 2022. Retrieved 27 May 2022.
  5. ^ a b Cite error: The named reference Tlando FDA label was invoked but never defined (see the help page).
  6. ^ "Kyzatrex- testosterone undecanoate capsule, liquid filled". DailyMed. 18 October 2022. Archived from the original on 21 January 2023. Retrieved 21 January 2023.
  7. ^ a b c d e f Nieschlag E, Behre HM, Nieschlag S (13 January 2010). Andrology: Male Reproductive Health and Dysfunction. Springer Science & Business Media. pp. 441–446. ISBN 978-3-540-78355-8.
  8. ^ a b c Cite error: The named reference pmid10229906 was invoked but never defined (see the help page).
  9. ^ a b c Nieschlag E, Behre HM, Nieschlag S (26 July 2012). Testosterone: Action, Deficiency, Substitution. Cambridge University Press. pp. 313–315, 321–322. ISBN 978-1-107-01290-5. Archived from the original on 7 April 2022. Retrieved 3 January 2018.
  10. ^ a b Becker KL (2001). Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. pp. 1185–. ISBN 978-0-7817-1750-2. Archived from the original on 17 May 2020. Retrieved 3 January 2018.
  11. ^ a b c d e f g h i Llewellyn W (2011). Anabolics. Molecular Nutrition LLC. pp. 180–182, 331–334. ISBN 978-0-9828280-1-4. Archived from the original on 3 July 2022. Retrieved 3 January 2018.
  12. ^ Irwig MS (April 2017). "Testosterone therapy for transgender men". The Lancet. Diabetes & Endocrinology. 5 (4): 301–311. doi:10.1016/S2213-8587(16)00036-X. PMID 27084565.
  13. ^ Jacobeit JW, Gooren LJ, Schulte HM (September 2007). "Long-acting intramuscular testosterone undecanoate for treatment of female-to-male transgender individuals". The Journal of Sexual Medicine. 4 (5): 1479–1484. doi:10.1111/j.1743-6109.2007.00556.x. PMID 17635694.
  14. ^ Jacobeit JW, Gooren LJ, Schulte HM (November 2009). "Safety aspects of 36 months of administration of long-acting intramuscular testosterone undecanoate for treatment of female-to-male transgender individuals". European Journal of Endocrinology. 161 (5): 795–798. doi:10.1530/EJE-09-0412. PMID 19749027.
  15. ^ Bertelloni S, Hiort O (28 September 2010). New Concepts for Human Disorders of Sexual Development. S. Karger AG. pp. 256–. ISBN 978-3-8055-9569-8. Archived from the original on 8 November 2020. Retrieved 3 November 2016.
  16. ^ a b Kicman AT (June 2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–521. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.
  17. ^ Santoro N, Braunstein GD, Butts CL, Martin KA, McDermott M, Pinkerton JV (April 2016). "Compounded Bioidentical Hormones in Endocrinology Practice: An Endocrine Society Scientific Statement". The Journal of Clinical Endocrinology and Metabolism. 101 (4): 1318–1343. doi:10.1210/jc.2016-1271. PMID 27032319.
  18. ^ Cite error: The named reference Hoberman2005 was invoked but never defined (see the help page).
  19. ^ Cite error: The named reference MundyFitzpatrick2010 was invoked but never defined (see the help page).
  20. ^ Cite error: The named reference MelmedPolonsky2015 was invoked but never defined (see the help page).
  21. ^ Cite error: The named reference Schering2004 was invoked but never defined (see the help page).
  22. ^ Meyer L (27 March 2019). "FDA approves new oral testosterone capsule for treatment of men with certain forms of hypogonadism" (Press release). U.S. Food and Drug Administration (FDA). Archived from the original on 7 September 2020. Retrieved 27 August 2020.
  23. ^ Köhn FM, Schill WB (November 2003). "A new oral testosterone undecanoate formulation". World Journal of Urology. 21 (5): 311–315. doi:10.1007/s00345-003-0372-x. PMID 14579074. S2CID 23627346.
  24. ^ Ahmad SW, Molfetto G, Montoya D, Camero A (August 2022). "Is Oral Testosterone the New Frontier of Testosterone Replacement Therapy?". Cureus. 14 (8): e27796. doi:10.7759/cureus.27796. PMC 9452423. PMID 36106278.