Testosterone undecanoate

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Testosterone undecanoate
Clinical data
Pronunciation/tɛˈstɒstəroʊn ənˈdɛkənoʊ.eɪt/ tess-TOSS-tə-rohn ən-DEK-ə-noh-ayt
Trade namesNebido, Aveed, Andriol, others
Other namesTestosterone undecylate; Testosterone 17β-undecanoate; ORG-538; CLR-610
Routes of
administration		By mouth, intramuscular injection
Drug classAndrogen; Anabolic steroid; Androgen ester
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: 3–7%[citation needed]
Intramuscular: ~100%[citation needed]
MetabolismLiver
Elimination half-lifeTea seed oil: 20.9 days (i.m.Tooltip intramuscular injection)[2][3]
Castor oil: 33.9 days (i.m.)[2][3]
ExcretionUrine
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
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.025.193 Edit this at Wikidata
Chemical and physical data
FormulaC30H48O3
Molar mass456.711 g/mol 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
 ☒NcheckY (what is this?)  (verify)

Testosterone undecanoate, sold under the brand names Nebido, Aveed, and Andriol among others, is an androgen and anabolic steroid.[4][5][6][7][8] It is used in androgen replacement therapy primarily for the treatment of male hypogonadism, and has also been investigated for use as a male contraceptive or as hormone replacement therapy in transgender men.[9][10] It is a synthetic androgen ester which acts as a prodrug of testosterone, and hence is considered to be a natural and bioidentical form of testosterone. Unlike other testosterone esters, testosterone undecanoate is available in both oral and intramuscular formulations.[11] As an intramuscular injection, it is much longer-acting than most other testosterone esters.[2][3] Along with testosterone cypionate, testosterone enanthate, and testosterone propionate, testosterone undecanoate is one of the most widely used testosterone esters.[12]

Medical uses

See also: Androgen replacement therapy § Medical uses, and Anabolic steroid § Medical

Testosterone undecanoate is used in androgen replacement therapy. It is specifically approved only for the treatment of hypogonadism.[13][14][15] As an intramuscular injection, it is administered at a dosage of 1,000 mg once every 12 weeks.[16] Conversely, oral testosterone undecanoate must be taken two or three times a day with food.[16][17]

Side effects

See also: Anabolic steroid § Adverse effects, and Androgen replacement therapy § Adverse effects

Anaphylaxis

The Reandron 1000 formulation (Nebido in the United States) contains 1000 mg of testosterone undecanoate suspended in castor oil with benzyl benzoate for solubilization and as a preservative, and is administered by intramuscular injection. As an excipient, benzyl benzoate has been reported as a cause of anaphylaxis in a case in Australia.[18] Bayer 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.[19] In Australia, reports to ADRAC, which evaluates reports of adverse drug reactions for the Therapeutic Goods Administration, show several reports of allergic issues since the anaphylaxis case from 2011.[citation needed]

Pharmacology

Pharmacodynamics

See also: Testosterone § Mechanism of action, and Anabolic steroid § Pharmacology

Testosterone undecanoate is a prodrug of testosterone and is an androgen and anabolic–androgenic steroid (AAS). That is, it is an agonist of the androgen receptor (AR).

Pharmacokinetics

Testosterone undecanoate has a very long elimination half-life and mean residence time when given as a depot intramuscular injection.[20][2][3] Its elimination half-life is 20.9 days and its mean residence time is 34.9 days in tea seed oil, while its elimination half-life is 33.9 days and its mean residence time is 36.0 days in castor oil.[2][3] These values are substantially longer than those of testosterone enanthate (which, in castor oil, has values of 4.5 days and 8.5 days, respectively).[20] Testosterone undecanoate is administered via intramuscular injection once every three months or so.[16][21]

Chemistry

See also: Androgen ester and List of androgen esters

Testosterone undecanoate, or testosterone 17β-undecanoate, is a synthetic androstane steroid and a derivative of testosterone.[4][5] It is an androgen ester; specifically, it is the C17β undecylate (undecanoate) ester of testosterone.[4][5]

History

In the late 1970s, testosterone undecanoate was introduced for oral use in Europe,[22] although intramuscular testosterone undecanoate had already been in use in China for several years.[23] Intramuscular testosterone undecanoate was not introduced in Europe and the United States until much later, in the early to mid 2000s and 2014, respectively.[24][25] Testosterone undecanoate was approved in the United States after three previous rejections due to safety concerns.[26]

Society and culture

Generic names

Testosterone undecanoate is the generic name of the drug and its USANTooltip United States Adopted Name and BANTooltip British Approved Name.[4][5][6][7] It is also referred to as testosterone undecylate.[4][5][6][7]

Brand names

Testosterone undecanoate is or has been marketed under a variety of brand names including Aveed, Andriol, Androxon, Cernos Depot, Nebido, Panteston, Restandol, Nebido-R, Reandron 1000, and Undestor.[4][5][6][7]

Availability

See also: List of androgens/anabolic steroids available in the United States

Intramuscular testosterone undecanoate is available in the United States, Canada, Europe, and elsewhere in the world.[8][27][28] It is approved in over 100 countries worldwide.[27][8] Oral testosterone undecanoate is available in Canada, Europe, Mexico, Asia, and elsewhere but not in the United States.[27][29] Intramuscular testosterone undecanoate is marketed most commonly as Nebido in Canada and Europe and as Aveed in the United States while oral testosterone undecanoate is marketed most commonly as Andriol.[8][27][28]

Legal status

Testosterone undecanoate, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act and a schedule IV controlled substance in Canada under the Controlled Drugs and Substances Act.[30][31]

Research

As of June 2017, an oral formulation of testosterone undecanoate is in preregistration for the treatment of hypogonadism in the United States.[32]

As of January 2017, intramuscular testosterone undecanoate is in phase II clinical trials for the treatment of non-alcoholic steatohepatitis in the United Kingdom.[13]

See also

References

  1. ^ "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 Oct 2023.
  2. ^ a b c d e Nieschlag, Eberhart; Behre, Hermann M.; Nieschlag, Susan (January 13, 2010). Andrology: Male Reproductive Health and Dysfunction. Springer Science & Business Media. pp. 441–446. ISBN 978-3-540-78355-8. Archived from the original on June 23, 2016. {{cite book}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help); Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  3. ^ a b c d e Behre HM, Abshagen K, Oettel M, Hübler D, Nieschlag E (1999). "Intramuscular injection of testosterone undecanoate for the treatment of male hypogonadism: phase I studies". Eur. J. Endocrinol. 140 (5): 414–9. doi:10.1530/eje.0.1400414. PMID 10229906.
  4. ^ a b c d e f J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 641–642. ISBN 978-1-4757-2085-3.
  5. ^ a b c d e f Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1002–1004. ISBN 978-3-88763-075-1.
  6. ^ a b c d I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. ISBN 978-94-011-4439-1.
  7. ^ a b c d https://www.drugs.com/international/testosterone.html
  8. ^ a b c d William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 360, 574. ISBN 978-0-9828280-1-4.
  9. ^ JW Jacobeit; LJ Gooren; HM Schulte (2007). "Long-acting intramuscular testosterone undecanoate for treatment of female-to-male transgender individuals". The Journal of Sexual Medicine. 4 (5): 1479–84. doi:10.1111/j.1743-6109.2007.00556.x. PMID 17635694.
  10. ^ JW Jacobeit; LJ Gooren; HM Schulte (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): 795–8. doi:10.1530/EJE-09-0412. PMID 19749027.
  11. ^ Köhn, Frank-Michael; Schill, Wolf-Bernhard (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.
  12. ^ Kicman, A T (2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–521. doi:10.1038/bjp.2008.165. ISSN 0007-1188. PMC 2439524. PMID 18500378.
  13. ^ a b http://adisinsight.springer.com/drugs/800017041
  14. ^ http://adisinsight.springer.com/drugs/800011489
  15. ^ https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022219s000lbl.pdf
  16. ^ a b c S. Bertelloni; O. Hiort (28 September 2010). New Concepts for Human Disorders of Sexual Development. S. Karger AG. pp. 256–. ISBN 978-3-8055-9569-8.
  17. ^ Jean L. Fourcroy (27 October 2008). Pharmacology, Doping and Sports: A Scientific Guide for Athletes, Coaches, Physicians, Scientists and Administrators. Routledge. pp. 25–. ISBN 978-1-134-08880-5.
  18. ^ Ong, G. S. Y.; Somerville, C. P.; Jones, T. W.; Walsh, J. P. (2012). "Anaphylaxis Triggered by Benzyl Benzoate in a Preparation of Depot Testosterone Undecanoate". Case Rep Med. 2012. doi:10.1155/2012/384054. PMC 3261473. PMID 22272209. 384054.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  19. ^ "Nebido Monograph – Information for Health Care Professionals". Bayer. 2016. Retrieved 19 October 2016.
  20. ^ a b Anita H. Payne; Matthew P. Hardy (28 October 2007). The Leydig Cell in Health and Disease. Springer Science & Business Media. pp. 423–. ISBN 978-1-59745-453-7.
  21. ^ Yeung, Sai-Ching Jim; Escalante, Carmen P.; Gagel, Robert F. (2009). Medical Care of Cancer Patients. PMPH-USA. pp. 247–. ISBN 978-1-60795-008-0. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  22. ^ Hoberman, John (21 February 2005). Testosterone Dreams: Rejuvenation, Aphrodisia, Doping. University of California Press. pp. 134–. ISBN 978-0-520-93978-3. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  23. ^ Mundy, Anthony R.; Fitzpatrick, John; Neal, David E.; George, Nicholas J. R. (26 July 2010). The Scientific Basis of Urology. CRC Press. pp. 294–. ISBN 978-1-84184-749-8. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  24. ^ Melmed, Shlomo; Polonsky, Kenneth S.; Larsen, P. Reed; Kronenberg, Henry M. (11 November 2015). Williams Textbook of Endocrinology. Elsevier Health Sciences. pp. 709, 711, 765. ISBN 978-0-323-34157-8. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  25. ^ Adis R&D Profile (2004). "Testosterone Undecanoate—Schering AG". Drugs. 5 (6): 368–369. doi:10.2165/00126839-200405060-00012.
  26. ^ Miriam E. Tucker (March 7, 2014). "FDA Approves Aveed Testosterone Jab, with Restrictions". Medscape. Retrieved December 13, 2016.
  27. ^ a b c d Nieschlag, Eberhard; Nieschlag, Susan (2017). "The History of Testosterone and The Testes: From Antiquity to Modern Times": 1–19. doi:10.1007/978-3-319-46086-4_1. {{cite journal}}: Cite journal requires |journal= (help)
  28. ^ a b "Drug Product Database - Health Canada". Health Canada. Archived from the original on November 19, 2016. Retrieved November 13, 2016. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  29. ^ Arthur P. Arnold; Donald W. Pfaff; Anne M. Etgen; Susan E. Fahrbach, Robert T. Rubin (10 June 2002). Hormones, Brain and Behavior, Five-Volume Set. Academic Press. pp. 20–. ISBN 978-0-12-532104-4.
  30. ^ Steven B. Karch, MD, FFFLM (21 December 2006). Drug Abuse Handbook, Second Edition. CRC Press. pp. 30–. ISBN 978-1-4200-0346-8.{{cite book}}: CS1 maint: multiple names: authors list (link)
  31. ^ Linda Lane Lilley; Julie S. Snyder; Shelly Rainforth Collins (5 August 2016). Pharmacology for Canadian Health Care Practice. Elsevier Health Sciences. pp. 50–. ISBN 978-1-77172-066-3.
  32. ^ http://adisinsight.springer.com/drugs/800027560

External links


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