Testosterone enanthate
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Clinical data | |
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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 | |
Legal status |
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Pharmacokinetic data | |
Bioavailability | Oral: very low Intramuscular: high |
Metabolism | Liver |
Elimination half-life | Intramuscular: 4–5 days[2] |
Excretion | Urine |
Identifiers | |
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CAS Number | |
ECHA InfoCard | 100.005.686 |
Chemical and physical data | |
Formula | C26H40O3 |
Molar mass | 400.603 g·mol−1 |
3D model (JSmol) | |
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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 transgender men.[6] 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]
Testosterone enanthate was introduced for medical use in 1954.[10][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]
Medical uses
[edit]Testosterone enanthate is used primarily in androgen replacement therapy.[4][11] It is the most widely used form of testosterone in androgen replacement therapy.[4] 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.[12] It is also used in masculinizing hormone therapy for transgender men.[6]
Side effects
[edit]Side effects of testosterone enanthate include virilization among others.[5] Approximately 10 percent of testosterone enanthate will be converted to dihydrotestosterone in normal men.[13] 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 IGFBP.[14][15] Testosterone enanthate can also be converted to estradiol by aromatase,[16] which may lead to gynecomastia in males. Aromatase inhibitors can help to prevent the estrogenic activity of testosterone enanthate in the body.[16]
Pharmacology
[edit]Pharmacodynamics
[edit]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).
Testosterone cypionate is converted by the body to testosterone that has both androgenic effects and anabolic effects;[5] still, the relative potency of these effects can depend on various factors and is a topic of ongoing research.[17][18] Testosterone can either directly exert effects on target tissues or be metabolized by 5α-reductase into dihydrotestosterone (DHT) or aromatized to estradiol (E2).[17] Both testosterone and DHT bind to an androgen receptor; however, DHT has a stronger binding affinity than testosterone and may have more androgenic effect in certain tissues at lower levels.[17]
Pharmacokinetics
[edit]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.[2] 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.[2]
Chemistry
[edit]Testosterone enanthate, or testosterone 17β-heptanoate, is a synthetic androstane steroid and a derivative of testosterone.[19][20] It is an androgen ester; specifically, it is the C17β enanthate (heptanoate) ester of testosterone.[19][20]
History
[edit]Testosterone enanthate was described as early as 1952[21] and was first introduced for medical use in the United States in 1954 under the brand name Delatestryl.[10][4]
Society and culture
[edit]Generic names
[edit]Testosterone enanthate is the generic name of the drug and its USAN and BAN .[19][20][22][23] It has also referred to as testosterone heptanoate.[19][20][22][23]
Brand names
[edit]Testosterone enanthate is marketed primarily under the brand name Delatestryl.[19][20][22][23]
It is or has been marketed under a variety of other brand names as well, including, among others:[19][20][22][23][24]
- Andro LA
- Andropository
- Cypionat
- Cypoprime
- Depandro
- Durathate
- Everone
- Testocyp
- Testostroval
- Testrin
- Testro LA
- Xyosted
- pharmaqo labs
Availability
[edit]Testosterone enanthate is available in the United States and widely elsewhere throughout the world.[25][20][23] Testosterone enanthate (testosterone heptanoate) is often available in concentrations of 200 mg per milliliter of fluid.[26]
Legal status
[edit]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.[27][28]
Research
[edit]As of October 2017, an auto-injection formulation of testosterone enanthate was in preregistration for the treatment of hypogonadism in the United States.[29]
Xyosted
[edit]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.[30]
References
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- ^ a b c d 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 e f g 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 i j 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.
- ^ a b Irwig MS (April 2017). "Testosterone therapy for transgender men". The Lancet. Diabetes & Endocrinology. 5 (4): 301–311. doi:10.1016/S2213-8587(16)00036-X. PMID 27084565.
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- ^ a b "Testosterone Enanthate". Pharmaceutical Manufacturing Encyclopedia. Vol. T. William Andrew Publishing. 2007. p. 35t. doi:10.1016/B978-0-8155-1526-5.50024-6. ISBN 978-0-8155-1526-5.
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- ^ "DELATESTRYL Package Insert" (PDF). Indevus Pharmaceuticals, Inc. Archived (PDF) from the original on 2017-02-16. Retrieved 2017-12-11.
- ^ "DHT (dihydrotestosterone): What is DHT's role in baldness?". 28 July 2017. Archived from the original on 8 October 2019. Retrieved 9 May 2019.
- ^ Ashton WS, Degnan BM, Daniel A, Francis GL (1995). "Testosterone increases insulin-like growth factor-1 and insulin-like growth factor-binding protein". Annals of Clinical and Laboratory Science. 25 (5): 381–388. PMID 7486812.
- ^ Hoeh MP, Levine LA (March 2015). "Management of Recurrent Ischemic Priapism 2014: A Complex Condition with Devastating Consequences". Sexual Medicine Reviews. 3 (1): 24–35. doi:10.1002/smrj.37. PMID 27784569. S2CID 24028084.
- ^ a b Ishikawa T, Glidewell-Kenney C, Jameson JL (February 2006). "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. doi:10.1016/j.jsbmb.2005.09.004. PMID 16386416. S2CID 25849126.
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- ^ "Antares Receives Fda Approval of Xyostedtm (Testosterone Enanthate) Injection for Testosterone Replacement Therapy in Adult Males" (PDF). Archived (PDF) from the original on 2019-05-04. Retrieved 2019-05-05.