Testosterone enanthate

Testosterone enanthate
Clinical data
Trade namesDelatestryl, Xyosted, others
Other namesTE; Testosterone heptanoate; Testosterone 17β-heptanoate; NSC-17591
Routes of
administration		Intramuscular injection, subcutaneous injection
Drug classAndrogen; Anabolic steroid; Androgen ester
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: very low
Intramuscular: high
MetabolismLiver
Elimination half-lifeIntramuscular: 4–5 days[1]
ExcretionUrine
Identifiers
IUPAC name
  • [(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] heptanoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.686
Chemical and physical data
FormulaC26H40O3
Molar mass400.603 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
InChI
  • InChI=1S/C26H40O3/c1-4-5-6-7-8-24(28)29-23-12-11-21-20-10-9-18-17-19(27)13-15-25(18,2)22(20)14-16-26(21,23)3/h17,20-23H,4-16H2,1-3H3/t20-,21-,22-,23-,25-,26-/m0/s1
  • Key:VOCBWIIFXDYGNZ-IXKNJLPQSA-N

Testosterone enanthate is used in the treatment of low testosterone levels in men.[2][3][4] It is also used in hormone therapy for women[5] and transgender men. It is given by injection into muscle or subcutaneously usually once every one to four weeks.[4][6][1]

Side effects of testosterone enanthate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.[4] The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT).[7][4] Testosterone enanthate is a testosterone ester and a long-lasting prodrug of testosterone in the body.[6][2][3] Because of this, it is considered to be a natural and bioidentical form of testosterone,[8] which make it useful for producing masculinization and suitable for androgen replacement therapy.[4] Esterase enzymes break the ester bond in testosterone enantate, releasing free testosterone and enanthic acid through hydrolysis.[9] [10] [11] This process ensures a sustained release of testosterone in the body.[12]

Testosterone enanthate was introduced for medical use in 1954.[13][3] Along with testosterone cypionate, testosterone undecanoate, and testosterone propionate, it is one of the most widely used testosterone esters.[7][3][4] In addition to its medical use, testosterone enanthate is used to improve physique and performance.[4] The drug is a controlled substance in many countries and so non-medical use is generally illicit.[4]

  1. ^ a b Luetjens CM, Wistuba J, Weinbauer G, Nieschlag E (2007). "The Leydig Cell as a Target for Male Contraception". The Leydig Cell in Health and Disease. Contemporary Endocrinology. Humana Press. pp. 415–442. doi:10.1007/978-1-59745-453-7_29. ISBN 978-1-58829-754-9.
  2. ^ a b Nieschlag E, Behre HM, Nieschlag S (26 July 2012). Testosterone: Action, Deficiency, Substitution. Cambridge University Press. pp. 315–. ISBN 978-1-107-01290-5. Archived from the original on 7 April 2024. Retrieved 3 January 2018.
  3. ^ a b c d Nieschlag E, Behre HM, Nieschlag S (13 January 2010). Andrology: Male Reproductive Health and Dysfunction. Springer Science & Business Media. pp. 442–. ISBN 978-3-540-78355-8. Archived from the original on 14 January 2023. Retrieved 19 November 2016.
  4. ^ a b c d e f g h Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 208–211. ISBN 978-0-9828280-1-4. Archived from the original on 2024-04-07. Retrieved 2018-01-03.
  5. ^ Irwig MS (April 2017). "Testosterone therapy for women". The Lancet. Diabetes & Endocrinology. 5 (4): 301–311. doi:10.1016/S2213-8587(16)00036-X. PMID 27084565.
  6. ^ a b Becker KL (2001). Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. pp. 1185, 1187. ISBN 978-0-7817-1750-2. Archived from the original on 2024-04-07. Retrieved 2018-01-03.
  7. ^ 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.
  8. ^ 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.
  9. ^ Figueiredo MG, Gagliano-Jucá T, Basaria S (2022). "Testosterone Therapy with Subcutaneous Injections: A Safe, Practical, and Reasonable Option". The Journal of Clinical Endocrinology & Metabolism. 107 (3): 614–626. doi:10.1210/clinem/dgab772. PMC 9006970. PMID 34698352.
  10. ^ "Testosterone enantate - Knowledge and References".
  11. ^ Nieschlag E, Behre H, Bouchard P, Corrales J, Jones T, Stalla G, et al. (2004). "Testosterone replacement therapy: Current trends and future directions". Human Reproduction Update. 10 (5): 409–419. doi:10.1093/humupd/dmh035. PMID 15297434.
  12. ^ Barzkar N, Sohail M, Tamadoni Jahromi S, Gozari M, Poormozaffar S, Nahavandi R, et al. (2021). "Marine Bacterial Esterases: Emerging Biocatalysts for Industrial Applications". Applied Biochemistry and Biotechnology. 193 (4): 1187–1214. doi:10.1007/s12010-020-03483-8. PMID 33411134. Archived from the original on 2023-09-07. Retrieved 2024-11-06.
  13. ^ Cite error: The named reference Publishing2013 was invoked but never defined (see the help page).
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.