Testosterone enanthate

Source: Wikipedia, the free encyclopedia.
Testosterone enanthate
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[2]
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
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

transgender men.[6] It is given by injection into muscle or subcutaneously usually once every one to four weeks.[5][7][2]

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

See also: Androgen replacement therapy § Medical uses, and Anabolic steroid § Medical

Testosterone enanthate is used primarily in

transgender men.[6]

Side effects

See also: Anabolic steroid § Adverse effects, and Androgen replacement therapy § Adverse effects

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

Pharmacodynamics

See also: Testosterone § Mechanism of action, and Anabolic steroid § Pharmacology
Androgenic vs. anabolic activity ratio
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

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

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

Testosterone enanthate has an

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

See also: Androgen ester and List of androgen esters

Testosterone enanthate, or testosterone 17β-heptanoate, is a

enanthate (heptanoate) ester of testosterone.[19][20]

History

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

Generic names

Testosterone enanthate is the

generic name of the drug and its USANTooltip United States Adopted Name and BANTooltip British Approved Name.[19][20][22][23] It has also referred to as testosterone heptanoate.[19][20][22][23]

Brand names

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

See also: List of androgens/anabolic steroids available in the United States

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

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

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

On October 1, 2018, the U.S.

subcutaneous testosterone enanthate product for testosterone replacement therapy in adult males.[30]

References

  1. FDA
    . Retrieved 22 Oct 2023.
  2. ^
    ISBN 978-1-58829-754-9
    .
  3. ^
    ISBN 978-1-107-01290-5. Archived
    from the original on 7 April 2024. Retrieved 3 January 2018.
  4. ^
    ISBN 978-3-540-78355-8. Archived
    from the original on 14 January 2023. Retrieved 19 November 2016.
  5. ^
    ISBN 978-0-9828280-1-4. Archived
    from the original on 2024-04-07. Retrieved 2018-01-03.
  6. ^
    PMID 27084565
    .
  7. ^
    ISBN 978-0-7817-1750-2. Archived
    from the original on 2024-04-07. Retrieved 2018-01-03.
  8. ^
    PMID 18500378
    .
  9. PMID 27032319
    .
  10. ^
    ISBN 978-0-8155-1526-5
    .
  11. ^ "Testosterone Enanthate raw powder (CAS 315-37-7) ≥98% | AASraw". aasraw. Archived from the original on 2022-11-20. Retrieved 2022-11-20.
  12. ^ "DELATESTRYL Package Insert" (PDF). Indevus Pharmaceuticals, Inc. Archived (PDF) from the original on 2017-02-16. Retrieved 2017-12-11.
  13. ^ "DHT (dihydrotestosterone): What is DHT's role in baldness?". 28 July 2017. Archived from the original on 8 October 2019. Retrieved 9 May 2019.
  14. PMID 7486812
    .
  15. S2CID 24028084
    .
  16. ^
    S2CID 25849126
    .
  17. ^
    ISBN 978-3-319-29195-6. Archived
    from the original on 2024-04-07. Retrieved 2024-04-06.
  18. PMID 12017555
    .
  19. ^
    ISBN 978-1-4757-2085-3
    .
  20. ^
    ISBN 978-3-88763-075-1
    .
  21. ISBN 978-3-642-49610-3
    .
  22. ^
    ISBN 978-94-011-4439-1
    .
  23. ^ a b c d e "Testosterone". Drugs.com. October 1, 2018. Archived from the original on November 13, 2016. Retrieved December 5, 2018.
  24. ^ "Testosterone cypionate profile and most popular brands in USA". Anabolic Steroids Ratings and Reviews - downsizefitness.com. Archived from the original on 2020-09-26. Retrieved 2020-09-06.
  25. ^ "Drugs@FDA: FDA Approved Drug Products". United States Food and Drug Administration. Archived from the original on 16 November 2016. Retrieved 17 December 2016.
  26. ^ "Testosterone enanthate". Drugbank. Archived from the original on 2019-06-29. Retrieved 2019-05-09.
  27. ISBN 978-1-4200-0346-8
    .
  28. ISBN 978-1-77172-066-3
    .
  29. ^ "Testosterone enanthate auto-injection - Antares Pharma". AdisInsight. February 5, 2018. Archived from the original on September 9, 2017. Retrieved December 5, 2018.
  30. ^ "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.
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