Testosterone undecanoate

Testosterone undecanoate
Clinical data
Pronunciation /tɛˈstɒstəroʊn ənˈdɛkənoʊ.eɪt/ tess-TOSS-tə-rohn ən-DEK-ə-noh-ayt
Pregnancy
category
Routes of
administration		 Oral, intramuscular injection
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability Oral: 3–7%
Intramuscular ~100%
Metabolism Liver, testis and prostate
Biological half-life 1–12 days
Excretion Urine
Identifiers
Synonyms Aveed, Andriol, Undestor, Nebido, Pantestone, Restandol, Cernos Depot, Nebido-R, Reandron 1000
17β-[(1-Oxoundecyl)oxy]-androst-4-en-3-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard 100.025.193
Chemical and physical data
Formula C30H48O3
Molar mass 456.70032 g/mol
3D model (JSmol)
 NYesY (what is this?)  (verify)

Testosterone undecanoate (USAN, BAN) (brand names Aveed, Andriol, Androxon, Cernos Depot, Nebido, Panteston, Restandol, Nebido-R, Reandron 1000, Undestor), or testosterone undecylate, is an androgen and anabolic steroid and a testosterone ester.[1][2][3] 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.[4][5] Unlike other testosterone esters, testosterone undecanoate is available in both oral and intramuscular formulations.[6]

Testosterone undecanoate has a very long elimination half-life and mean residence time when given as a depot intramuscular injection.[7] The elimination half-life and mean residence time of testosterone undecanoate are 2.5-fold and 4-fold longer than those of testosterone enanthate (the values for testosterone enanthate being 4.5 days and 8.5 days, respectively).[7]

Testosterone undecanoate is available in Europe and Aveed brand testosterone undecanoate was approved for use in the United States by the FDA in 2014, after three previous rejections due to safety concerns.[8][9] It is administered at a dosage of 1,000 mg every 12 weeks via intramuscular injection.[10] In addition to parenteral, an oral formulation of testosterone undecanoate (brand name Andriol) is also available in Europe, but must be taken two or three times a day in combination with food.[10][11]

The Reandron 1000 formulation (Nebido in the United States) contains 1000 mg of testosterone undecanoate suspended in castor oil with benzyl benzoate for solubilisation 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.[12] 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.[13] 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.

See also

References

  1. ↑ 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.
  2. ↑ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. ISBN 978-3-88763-075-1.
  3. ↑ 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.
  4. ↑ 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. PMID 17635694. doi:10.1111/j.1743-6109.2007.00556.x.
  5. ↑ 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. PMID 19749027. doi:10.1530/EJE-09-0412.
  6. ↑ Köhn, Frank-Michael; Schill, Wolf-Bernhard (November 2003). "A new oral testosterone undecanoate formulation". World Journal of Urology. 21 (5): 311–315. PMID 14579074. doi:10.1007/s00345-003-0372-x.
  7. 1 2 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.
  8. ↑ Norman Lavin (28 March 2012). Manual of Endocrinology and Metabolism. Lippincott Williams & Wilkins. pp. 313–. ISBN 978-1-4511-4914-2.
  9. ↑ Miriam E. Tucker (March 7, 2014). "FDA Approves Aveed Testosterone Jab, with Restrictions". Medscape. Retrieved December 13, 2016.
  10. 1 2 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.
  11. ↑ 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.
  12. ↑ 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. PMC 3261473 Freely accessible. PMID 22272209. doi:10.1155/2012/384054. 384054.
  13. ↑ "Nebido Monograph – Information for Health Care Professionals". Bayer. 2016. Retrieved 19 October 2016.


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