Chemical compound
Testosterone enanthate Trade names Delatestryl, Xyosted, others Other names TE; Testosterone heptanoate; Testosterone 17β-heptanoate; NSC-17591 Routes of administration Intramuscular injection , subcutaneous injection Drug class Androgen ; Anabolic steroid ; Androgen ester Legal status
Bioavailability Oral : very lowIntramuscular : highMetabolism Liver Elimination half-life Intramuscular : 4–5 days[ 2] Excretion Urine
[(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 InfoCard 100.005.686 Formula C 26 H 40 O 3 Molar mass 400.603 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 an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men .[ 3] [ 4] [ 5] It is also used in hormone therapy for women [ 6] and transgender men [medical citation needed ] . It is given by injection into muscle or subcutaneously usually once every one to four weeks.[ 5] [ 7] [ 2]
Side effects of testosterone enanthate include symptoms of masculinization like acne , increased hair growth , voice changes , and increased sexual desire .[ 5] 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).[ 8] [ 5] Testosterone enanthate is a testosterone ester and a long-lasting prodrug of testosterone in the body.[ 7] [ 3] [ 4] Because of this, it is considered to be a natural and bioidentical form of testosterone,[ 9] which make it useful for producing masculinization and suitable for androgen replacement therapy .[ 5] Esterase enzymes break the ester bond in testosterone enantate, releasing free testosterone and enanthic acid through hydrolysis .[ 10]
[ 11]
[ 12] This process ensures a sustained release of testosterone in the body.[ 13]
Testosterone enanthate was introduced for medical use in 1954.[ 14] [ 4] Along with testosterone cypionate , testosterone undecanoate , and testosterone propionate , it is one of the most widely used testosterone esters .[ 8] [ 4] [ 5] In addition to its medical use, testosterone enanthate is used to improve physique and performance .[ 5] The drug is a controlled substance in many countries and so non-medical use is generally illicit.[ 5]
^ "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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ https://academic.oup.com/jcem/article/107/3/614/6410585
^ "Testosterone enantate - Knowledge and References" .
^ https://academic.oup.com/humupd/article/10/5/409/769303
^ 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 .
^ Cite error: The named reference Publishing2013
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