Back إنانثات التستوستيرون Arabic تستوسترون انانتات Persian Testosteron enantat ID Enantato de testosterona Portuguese Тестостерона энантат Russian Testosterone enanthate Vietnamese 庚酸睾酮 Chinese

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
  • [(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 Edit this at Wikidata
Chemical and physical data
FormulaC26H40O3
Molar mass400.603 g·mol−1
3D model (JSmol)
  • 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=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[medical citation needed]. 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).

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