Wikipedia

Testosterone enanthate

(Redirected from Testosterone enantate)

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 transsexual men[medical citation needed]. It is given by injection into muscle or subcutaneously usually once every one to four weeks.[5][7][2]

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[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
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

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]

Medical uses

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

Testosterone enanthate is used primarily in androgen replacement therapy.[4][15] 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.[16] It is also used in masculinizing hormone therapy for transgender men.[6]

Side effects

edit
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 5α-dihydrotestosterone in normal men.[17] 5α-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.[18][19] Testosterone enanthate can also be converted to estradiol (E2) by the aromatase enzyme,[20] which may lead to gynecomastia in males. Aromatase inhibitors, such as anastrozole, letrozole, exemestane, etc., can help to prevent the subsequent estrogenic activity of testosterone enanthate metabolites in the body.[20]

Pharmacology

edit

Pharmacodynamics

edit
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 prodrug of testosterone and is an androgen and anabolic–androgenic steroid (AAS). That is, it is an agonist of the androgen receptor (AR).

Testosterone enanthate 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.[21][22] Esterase enzymes break the ester bond in testosterone enantate, releasing free testosterone and enanthic acid through hydrolysis. This process ensures a sustained release of free bioavailable and bioactive testosterone in the body. Testosterone can either directly exert effects on target tissues or be metabolized by the 5α-reductase enzymes into 5α-dihydrotestosterone (DHT) or aromatized to estradiol (E2).[21] Aromatization in this context is the process where testosterone is converted to estradiol (E2) by the enzyme aromatase (CYP19A1 in humans). This conversion involves changing the structure of testosterone to include an aromatic ring A of a steroid nucleus, making it an estrogen, a so-called female hormone, which plays various roles in the body, such as regulating reproductive functions and bone density. If not aromatized (not converted into an estrogen), both testosterone and DHT are bioactive and bind to an androgen receptor; however, DHT has a stronger binding affinity than testosterone and may have more androgenic effect in certain tissues (such as prostate gland, skin and hair follicles)[23] at lower levels.[21]

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] When testosterone enanthate is dissolved in an oil (such as castor oil), the oil acts as a depot, or reservoir, that slowly releases the drug into the bloodstream. This slow release is due to the oil's viscosity and the gradual breakdown of the ester bond by esterase enzymes. The oil creates a barrier that slows the diffusion of testosterone enanthate into the surrounding tissues, resulting in a more controlled and prolonged release compared to injecting pure testosterone enanthate.[24][25] The rate at which testosterone enanthate is released from oils can vary based on the oil's viscosity and other properties such as drug solubility in the oil.[26][27][28][29]

Chemistry

edit
See also: Androgen ester and List of androgen esters

Testosterone enanthate, or testosterone 17β-heptanoate, is a synthetic androstane steroid and a derivative of testosterone.[30][31] It is an androgen ester; specifically, it is the C17β enanthate (heptanoate) ester of testosterone.[30][31]

History

edit

Testosterone enanthate was described as early as 1952[32] and was first introduced for medical use in the United States in 1954 under the brand name Delatestryl.[14][4]

Society and culture

edit

Generic names

edit

Testosterone enanthate is the generic name of the drug and its USANTooltip United States Adopted Name and BANTooltip British Approved Name.[30][31][33][34] It has also referred to as testosterone heptanoate.[30][31][33][34]

Brand names

edit

Testosterone enanthate is marketed primarily under the brand name Delatestryl.[30][31][33][34]

It is or has been marketed under a variety of other brand names as well, including, among others:[30][31][33][34][35]

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

Availability

edit
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.[36][31][34] Testosterone enanthate (testosterone heptanoate) is often available in concentrations of 200 mg per milliliter of fluid.[37]

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.[38][39]

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.[40]

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.[41]

References

edit
  1. ^ "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.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ a b 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.
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.
  10. ^ https://academic.oup.com/jcem/article/107/3/614/6410585
  11. ^ "Testosterone enantate - Knowledge and References".
  12. ^ https://academic.oup.com/humupd/article/10/5/409/769303
  13. ^ 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.
  14. ^ 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. Archived from the original on 2024-10-04. Retrieved 2024-07-12.
  15. ^ "Testosterone Enanthate raw powder (CAS 315-37-7) ≥98% | AASraw". aasraw. Archived from the original on 2022-11-20. Retrieved 2022-11-20.
  16. ^ "DELATESTRYL Package Insert" (PDF). Indevus Pharmaceuticals, Inc. Archived (PDF) from the original on 2017-02-16. Retrieved 2017-12-11.
  17. ^ "DHT (dihydrotestosterone): What is DHT's role in baldness?". 28 July 2017. Archived from the original on 8 October 2019. Retrieved 9 May 2019.
  18. ^ 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.
  19. ^ 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.
  20. ^ 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.
  21. ^ a b c Čeponis J, Wang C, Swerdloff RS, Liu PY (2017). "Anabolic and Metabolic Effects of Testosterone and Other Androgens: Direct Effects and Role of Testosterone Metabolic Products". Thyroid Diseases. Endocrinology. pp. 1–22. doi:10.1007/978-3-319-29456-8_11-1. ISBN 978-3-319-29195-6. Archived from the original on 2024-04-07. Retrieved 2024-04-06.
  22. ^ Kuhn CM (2002). "Anabolic steroids". Recent Prog Horm Res. 57: 411–34. doi:10.1210/rp.57.1.411. PMID 12017555.
  23. ^ Swerdloff RS, Dudley RE, Page ST, Wang C, Salameh WA (2017). "Dihydrotestosterone: Biochemistry, Physiology, and Clinical Implications of Elevated Blood Levels". Endocrine Reviews. 38 (3): 220–254. doi:10.1210/er.2016-1067. PMC 6459338. PMID 28472278.
  24. ^ "Archived copy" (PDF). Archived (PDF) from the original on 2017-02-16. Retrieved 2017-12-11.{{cite web}}: CS1 maint: archived copy as title (link)
  25. ^ "Testosterone enanthate". Archived from the original on 2019-06-29. Retrieved 2024-11-06.
  26. ^ "Archived copy". Archived from the original on 2024-05-23. Retrieved 2024-11-06.{{cite web}}: CS1 maint: archived copy as title (link)
  27. ^ Larsen SW, Thing MA, Larsen C (2012). "Oily (Lipophilic) Solutions and Suspensions". Long Acting Injections and Implants. Springer. pp. 113–135. doi:10.1007/978-1-4614-0554-2_7. ISBN 978-1-4614-0553-5. Archived from the original on 2023-04-10. Retrieved 2024-11-06.
  28. ^ Yang D, Li W, Fang L, Liu C (2019). "Investigation of Controlled Release Molecular Mechanism of Oil Phase in Spilanthol Emulsion: Development and in Vitro, in Vivo Characterization". AAPS Pharmscitech. 20 (6): 227. doi:10.1208/s12249-019-1454-4. PMID 31222590.
  29. ^ https://www.jpharmsci.org/article/S0022-3549(15)38234-4/abstract
  30. ^ a b c d e f Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 641–642. ISBN 978-1-4757-2085-3.
  31. ^ a b c d e f g Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1002–1004. ISBN 978-3-88763-075-1. Archived from the original on 2024-10-04. Retrieved 2017-12-13.
  32. ^ Junkmann K (1952). "Über protrahiert wirksame Androgene" [Over protracted effective androgens]. Festschrift zum 75. Geburtstag. Springer. pp. 85–92. doi:10.1007/978-3-642-49902-9_11. ISBN 978-3-642-49610-3.
  33. ^ a b c d Morton IK, Hall JM (6 December 2012). "Testosterone". Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. p. 270. ISBN 978-94-011-4439-1. Archived from the original on 4 October 2024. Retrieved 11 May 2019.
  34. ^ a b c d e "Testosterone". Drugs.com. October 1, 2018. Archived from the original on November 13, 2016. Retrieved December 5, 2018.
  35. ^ "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.
  36. ^ "Drugs@FDA: FDA Approved Drug Products". United States Food and Drug Administration. Archived from the original on 16 November 2016. Retrieved 17 December 2016.
  37. ^ "Testosterone enanthate". Drugbank. Archived from the original on 2019-06-29. Retrieved 2019-05-09.
  38. ^ Karch SB (21 December 2006). Drug Abuse Handbook, Second Edition. CRC Press. pp. 30–. ISBN 978-1-4200-0346-8.
  39. ^ Lilley LL, Snyder JS, Collins SR (5 August 2016). Pharmacology for Canadian Health Care Practice. Elsevier Health Sciences. pp. 50–. ISBN 978-1-77172-066-3.
  40. ^ "Testosterone enanthate auto-injection - Antares Pharma". AdisInsight. February 5, 2018. Archived from the original on September 9, 2017. Retrieved December 5, 2018.
  41. ^ "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.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Testosterone_enanthate&oldid=1257137066"