Chemistry:Testosterone enanthate

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Short description: Chemical compound
Testosterone enanthate
Testosterone enanthate.svg
Testosterone enanthate molecule ball.png
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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC26H40O3
Molar mass400.603 g·mol−1
3D model (JSmol)

Testosterone enanthate is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men.[2][3][4] It is also used in hormone therapy for transgender men.[5] 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] It has strong androgenic effects and moderate anabolic effects, which make it useful for producing masculinization and suitable for androgen replacement therapy.[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]

Testosterone enanthate was introduced for medical use in 1954.[9][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]

Medical uses

Testosterone enanthate is used primarily in androgen replacement therapy.[3][10] It is the most widely used form of testosterone in androgen replacement therapy.[3] The medication is specifically approved, in the United States , for the treatment of hypogonadism in men, delayed puberty in boys, and breast cancer in women.[11] It is also used in masculinizing hormone therapy for transgender men.[5]

Side effects

Side effects of testosterone enanthate include virilization among others.[4] Approximately 10 percent of testosterone enanthate will be converted to dihydrotestosterone in normal men.[12] Dihydrotestosterone (DHT) can promote masculine characteristics in both males and females. These masculine characteristics include: clitoral hypertrophy, androgenic alopecia, growth of body hair and deepening of the vocal cords. Dihydrotestosterone also plays an important role in male sexual function and may also be a contributing factor of ischemic priapism in males as shown in a study conducted on the use of finasteride to treat ischemic priapism in males. Testosterone enanthate can also lead to an increase in igf-1 and igf-bp.[13][14] Testosterone enanthate can also be converted to estradiol by aromatase,[15] which may lead to gynecomastia in males. Aromatase inhibitors can help to prevent the estrogenic activity of testosterone enanthate in the body.[15]

Pharmacology

Pharmacodynamics

v · d · e Androgenic vs. anabolic activity
of androgens/anabolic steroids
Medication Ratioa
Testosterone ~1:1
Androstanolone (DHT) ~1:1
Methyltestosterone ~1:1
Methandriol ~1:1
Fluoxymesterone 1:1–1:15
Metandienone 1:1–1:8
Drostanolone 1:3–1:4
Metenolone 1:2–1:30
Oxymetholone 1:2–1:9
Oxandrolone 1:3–1:13
Stanozolol 1:1–1:30
Nandrolone 1:3–1:16
Ethylestrenol 1:2–1:19
Norethandrolone 1:1–1:20
Notes: In rodents. Footnotes: a = Ratio of androgenic to anabolic activity. Sources: See template.

Testosterone enanthate 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 enanthate has an elimination half-life of 4.5 days and a mean residence time of 8.5 days when used as a depot intramuscular injection.[1] It requires frequent administration of approximately once per week, and large fluctuations in testosterone levels result with it, with levels initially being elevated and supraphysiological.[1]

Chemistry

Testosterone enanthate, or testosterone 17β-heptanoate, is a synthetic androstane steroid and a derivative of testosterone.[16][17] It is an androgen ester; specifically, it is the C17β enanthate (heptanoate) ester of testosterone.[16][17]

History

Testosterone enanthate was described as early as 1952[18] and was first introduced for medical use in the United States in 1954 under the brand name Delatestryl.[9][3]

Society and culture

Generic names

Testosterone enanthate is the generic name of the drug and its USAN and BAN.[16][17][19][20] It has also referred to as testosterone heptanoate.[16][17][19][20]

Brand names

Testosterone enanthate is marketed primarily under the brand name Delatestryl.[16][17][19][20]

It is or has been marketed under a variety of other brand names as well, including, among others:[16][17][19][20][21]

  • Andro LA
  • Andropository
  • Cypionat
  • Cypoprime
  • Depandro
  • Durathate
  • Everone
  • Testocyp
  • Testostroval
  • Testrin
  • Testro LA
  • Xyosted
  • pharmaqo labs

Availability

Testosterone enanthate is available in the United States and widely elsewhere throughout the world.[22][17][20] Testosterone enanthate (testosterone heptanoate) is often available in concentrations of 200 mg per milliliter of fluid.[23]

Legal status

Testosterone enanthate, 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.[24][25]

Research

As of October 2017, an auto-injection formulation of testosterone enanthate was in preregistration for the treatment of hypogonadism in the United States .[26]

Xyosted

On October 1, 2018, the U.S. Food and Drug Administration (FDA) announced the approval of Xyosted. Xyosted, a product of Antares Pharma, Inc., is a single-use disposable auto-injector that dispenses testosterone enanthate. Xyosted is the first FDA-approved subcutaneous testosterone enanthate product for testosterone replacement therapy in adult males.[27]

References

  1. ↑ 1.0 1.1 1.2 1.3 "The Leydig Cell as a Target for Male Contraception". The Leydig Cell in Health and Disease. Contemporary Endocrinology. Humana Press. 2007. pp. 415–442. doi:10.1007/978-1-59745-453-7_29. ISBN 978-1-58829-754-9. 
  2. ↑ 2.0 2.1 Testosterone: Action, Deficiency, Substitution. Cambridge University Press. 26 July 2012. pp. 315–. ISBN 978-1-107-01290-5. https://books.google.com/books?id=MkrAPaQ4wJkC&pg=PA315. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 3.6 Andrology: Male Reproductive Health and Dysfunction. Springer Science & Business Media. 13 January 2010. pp. 442–. ISBN 978-3-540-78355-8. https://books.google.com/books?id=mEgckDNkonUC&pg=PA442. 
  4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 4.6 4.7 4.8 Anabolics. Molecular Nutrition Llc. 2011. pp. 208–211. ISBN 978-0-9828280-1-4. https://books.google.com/books?id=afKLA-6wW0oC&pg=PT208. 
  5. ↑ 5.0 5.1 "Testosterone therapy for transgender men". The Lancet. Diabetes & Endocrinology 5 (4): 301–311. April 2017. doi:10.1016/S2213-8587(16)00036-X. PMID 27084565. 
  6. ↑ 6.0 6.1 Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. 2001. pp. 1185, 1187. ISBN 978-0-7817-1750-2. https://books.google.com/books?id=FVfzRvaucq8C&pg=PA1185. 
  7. ↑ 7.0 7.1 "Pharmacology of anabolic steroids". British Journal of Pharmacology 154 (3): 502–521. June 2008. doi:10.1038/bjp.2008.165. PMID 18500378. 
  8. ↑ "Compounded Bioidentical Hormones in Endocrinology Practice: An Endocrine Society Scientific Statement". The Journal of Clinical Endocrinology and Metabolism 101 (4): 1318–1343. April 2016. doi:10.1210/jc.2016-1271. PMID 27032319. 
  9. ↑ 9.0 9.1 "Testosterone Enanthate". p. 35t. https://books.google.com/books?id=_J2ti4EkYpkC&pg=PAPA3171.  in William Andrew Publishing (2007). "T". Pharmaceutical Manufacturing Encyclopedia. pp. 1t–242t. doi:10.1016/B978-0-8155-1526-5.50024-6. ISBN 978-0-8155-1526-5. 
  10. ↑ "Testosterone Enanthate raw powder (CAS 315-37-7) ≥98% | AASraw" (in en-US). aasraw. https://www.aasraw.com/products/testosterone-enanthate/. 
  11. ↑ "DELATESTRYL Package Insert". Indevus Pharmaceuticals, Inc.. https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/009165s031lbl.pdf. 
  12. ↑ "DHT (dihydrotestosterone): What is DHT's role in baldness?". 28 July 2017. https://www.medicalnewstoday.com/articles/68082.php. 
  13. ↑ "Testosterone increases insulin-like growth factor-1 and insulin-like growth factor-binding protein". Annals of Clinical and Laboratory Science 25 (5): 381–388. 1995. PMID 7486812. 
  14. ↑ "Management of Recurrent Ischemic Priapism 2014: A Complex Condition with Devastating Consequences". Sexual Medicine Reviews 3 (1): 24–35. March 2015. doi:10.1002/smrj.37. PMID 27784569. 
  15. ↑ 15.0 15.1 "Aromatase-independent testosterone conversion into estrogenic steroids is inhibited by a 5 alpha-reductase inhibitor". The Journal of Steroid Biochemistry and Molecular Biology 98 (2–3): 133–138. February 2006. doi:10.1016/j.jsbmb.2005.09.004. PMID 16386416. 
  16. ↑ 16.0 16.1 16.2 16.3 16.4 16.5 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 641–642. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA641. 
  17. ↑ 17.0 17.1 17.2 17.3 17.4 17.5 17.6 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1002–1004. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA1002. 
  18. ↑ "Über protrahiert wirksame Androgene". Festschrift zum 75. Geburtstag. Springer. 1952. pp. 85–92. doi:10.1007/978-3-642-49902-9_11. ISBN 978-3-642-49610-3. 
  19. ↑ 19.0 19.1 19.2 19.3 "Testosterone". Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 6 December 2012. p. 270. ISBN 978-94-011-4439-1. https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA270. 
  20. ↑ 20.0 20.1 20.2 20.3 20.4 "Testosterone". October 1, 2018. https://www.drugs.com/international/testosterone.html. 
  21. ↑ "Testosterone cypionate profile and most popular brands in USA" (in en). http://downsizefitness.com/rankings/testosterone-cypionate/. 
  22. ↑ "Drugs@FDA: FDA Approved Drug Products". United States Food and Drug Administration. http://www.accessdata.fda.gov/scripts/cder/daf/. 
  23. ↑ "Testosterone enanthate". Drugbank. https://www.drugbank.ca/drugs/DB13944. 
  24. ↑ Drug Abuse Handbook, Second Edition. CRC Press. 21 December 2006. pp. 30–. ISBN 978-1-4200-0346-8. https://books.google.com/books?id=ZjrMBQAAQBAJ&pg=PA30. 
  25. ↑ Pharmacology for Canadian Health Care Practice. Elsevier Health Sciences. 5 August 2016. pp. 50–. ISBN 978-1-77172-066-3. https://books.google.com/books?id=dNgoDwAAQBAJ&pg=PA50. 
  26. ↑ "Testosterone enanthate auto-injection - Antares Pharma". February 5, 2018. https://adisinsight.springer.com/drugs/800037740. 
  27. ↑ "Antares Receives Fda Approval of Xyostedtm (Testosterone Enanthate) Injection for Testosterone Replacement Therapy in Adult Males". https://www.antarespharma.com/application/files/2715/3835/7488/XYOSTED_FDA_Approval_Final.pdf. 

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