Chemistry:Testosterone cypionate

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Short description: Chemical compound
Testosterone cypionate
Testosterone cypionate.svg
Testosterone cypionate molecule ball.png
Clinical data
Trade namesDepo-Testosterone, others
Other namesTC; TCPP; Testosterone cipionate; Testosterone cyclopentylpropionate; Testosterone cyclopentanepropionate; Testosterone 17β-cyclopentylpropionate
Routes of
administration		Intramuscular injection
Drug classAndrogen; Anabolic steroid; Androgen ester
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: very low
Intramuscular: very high
MetabolismLiver
Elimination half-life~8 days i.m.)[1]
Excretion90% Urine; 6% feces[1]
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC27H40O3
Molar mass412.614 g·mol−1
3D model (JSmol)

Testosterone cypionate, sold under the brand name Depo-Testosterone among others, 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][6] It is given by injection into muscle or subcutaneously, once every one to four weeks, depending on clinical indication.[4][7][8][9]

Side effects of testosterone cypionate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.[4] Testosterone supplementation is also known to reduce the threshold for aggressive behavior in men.[10] 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).[11][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 cypionate is a testosterone ester and a long-lasting prodrug of testosterone in the body.[7][2][3] Because of this, it is considered to be a natural and bioidentical form of testosterone.[12]

Testosterone cypionate was introduced for medical use in 1951.[13][14] Along with testosterone enanthate, testosterone undecanoate, and testosterone propionate, it is one of the most commonly used testosterone esters.[11][4] It is used mainly in the United States .[4] In addition to its medical use, testosterone cypionate 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 cypionate is used primarily in androgen replacement therapy.[15] It is currently FDA approved for the treatment of primary or hypogonadotropic hypogonadism (either congenital or acquired). Its safety in andropause (late-onset hypogonadism in men) has not yet been established.[1] It is currently used off-label for breast cancer, breast disorders, delayed puberty in boys, oligospermia (low sperm count), transmasculine hormone replacement therapy in transgender men,[9] and osteoporosis.[16][1]

Side effects

Side effects of testosterone cypionate include virilization among others.[4] It can also create conditions for heart attack, enlargement of prostate gland, liver malfunction, issues related to coagulation, pulmonary embolism, and polycythemia.[17] Diminished sperm production is a common side-effect of testosterone replacement therapy because of the decreased intra-testicular concentration of testosterone and suppression of the hypothalamic-pituitary-gonadal axis.[18]

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 cypionate 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

The pharmacokinetics of testosterone cypionate via depot intramuscular injection, including its elimination half-life and duration of action, are said to be extremely comparable to and hence essentially the same as those of testosterone enanthate.[4][3] As such, testosterone cypionate and testosterone enanthate are considered to be "functionally interchangeable" as medications.[4] For reference, testosterone enanthate has an elimination half-life of 4.5 days and a mean residence time of 8.5 days and requires frequent administration of approximately once per week.[19] Large fluctuations in testosterone levels result with it, with levels initially being elevated and supraphysiological.[19] The pharmacokinetics of testosterone cypionate have been studied and reported.[20]

Chemistry

Testosterone cypionate, or testosterone 17β-cyclopentylpropionate, is a synthetic androstane steroid and a derivative of testosterone.[21][22] It is an androgen ester; specifically, it is the C17β cyclopentylpropionate (cypionate) ester of testosterone.[21][22]

History

Testosterone cypionate was first synthesized in 1951[23] and was introduced for medical use in the United States the same year under the brand name Depo-Testosterone.[13][14]

Society and culture

Generic names

Testosterone cypionate is the generic name of the drug and its USP.[21][22][24][25] The drug does not have an INN, USAN, or BAN.[21][22][24][25] It has also been referred to as testosterone cipionate, as well as testosterone cyclopentylpropionate or testosterone cyclopentanepropionate.[21][22][24][25]

Brand names

Testosterone cypionate is or has been marketed under a variety of brand names, including:[21][22][24][25]

  • Andro Cyp
  • Andronaq LA
  • Andronate
  • Dep Andro
  • Dep Test
  • Deposteron
  • Depostomead
  • Depotest
  • Depo-Testosterone
  • Depovirin
  • Durandro
  • Duratest
  • Jectatest
  • Malogen CYP
  • Pertestis
  • Testa-C
  • Testadiate Depo
  • Testex Elmu Prolongatum
  • Testoject LA
  • Virilon

Availability

Testosterone cypionate is marketed in the United States .[4][22] It is not widely available outside of the United States, though it has been marketed in Canada , Australia , Spain , Brazil , and South Africa .[4][22]

Legal status

Testosterone cypionate, 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.[26][27]

References

  1. ↑ 1.0 1.1 1.2 1.3 "Depo-Testosterone; testosterone cypionate injection, USP". Pfizer. U.S. Food and Drug Administration. https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/085635s029lbl.pdf. 
  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 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. ↑ 4.00 4.01 4.02 4.03 4.04 4.05 4.06 4.07 4.08 4.09 4.10 4.11 4.12 4.13 Anabolics. Molecular Nutrition Llc. 2011. pp. 212–216. ISBN 978-0-9828280-1-4. https://books.google.com/books?id=afKLA-6wW0oC&pg=PT212. 
  5. ↑ "Recommendations for the Use of Testosterone in Male Transgender". Revista Brasileira de Ginecologia e Obstetricia 40 (5): 275–280. May 2018. doi:10.1055/s-0038-1657788. PMID 29913543. 
  6. ↑ "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. 
  7. ↑ 7.0 7.1 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. 
  8. ↑ Lexicon of Psychiatry, Neurology, and the Neurosciences. Lippincott Williams & Wilkins. 2000. pp. 974–. ISBN 978-0-7817-2468-5. https://books.google.com/books?id=ea_QVG2BFy8C&pg=PA974. 
  9. ↑ 9.0 9.1 "Endocrine Treatment of Gender-Dysphoric/Gender-Incongruent Persons: An Endocrine Society Clinical Practice Guideline". The Journal of Clinical Endocrinology and Metabolism 102 (11): 3869–3903. November 2017. doi:10.1210/jc.2017-01658. PMID 28945902. 
  10. ↑ "Is testosterone linked to human aggression? A meta-analytic examination of the relationship between baseline, dynamic and manipulated testosterone on human aggression.". Hormones and Behavior 123: 104644. 2020. doi:10.1016/j.yhbeh.2019.104644. PMID 31785281. http://clok.uclan.ac.uk/33858/1/33858Geniole%20et%20al%20Revised%20Oct%2030%202019.pdf. 
  11. ↑ 11.0 11.1 "Pharmacology of anabolic steroids". British Journal of Pharmacology 154 (3): 502–521. June 2008. doi:10.1038/bjp.2008.165. PMID 18500378. 
  12. ↑ "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. 
  13. ↑ 13.0 13.1 William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 3170–. ISBN 978-0-8155-1856-3. https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA3170. 
  14. ↑ 14.0 14.1 Testosterone Dreams: Rejuvenation, Aphrodisia, Doping. University of California Press. 21 February 2005. pp. 134–. ISBN 978-0-520-93978-3. https://books.google.com/books?id=6HhZ4IeoTwoC&pg=PA134. 
  15. ↑ "What is Testosterone Cypionate". HRTGuru corp.. 19 July 2016. https://hrtguru.com/shop/testosterone-cypionate. 
  16. ↑ "Testosterone cypionate - Pfizer". Adis Insight. Springer Nature Switzerland AG. http://adisinsight.springer.com/drugs/800012376. 
  17. ↑ "Testosterone Cypionate Common Side Effects Reported by Real Users" (in en-US). cypionate.info. https://cypionate.info/side-effects.html. 
  18. ↑ "Testosterone Is a Contraceptive and Should Not Be Used in Men Who Desire Fertility". The World Journal of Men's Health 37 (1): 45–54. January 2019. doi:10.5534/wjmh.180036. PMID 30350483. 
  19. ↑ 19.0 19.1 The Leydig Cell in Health and Disease. Springer Science & Business Media. 28 October 2007. pp. 423–. ISBN 978-1-59745-453-7. https://books.google.com/books?id=x4ttqKIAOg0C&pg=PA423. 
  20. ↑ "Hormone kinetics after intramuscular testosterone cypionate". Fertility and Sterility 47 (6): 1004–1009. June 1987. doi:10.1016/S0015-0282(16)59237-1. PMID 3595893. 
  21. ↑ 21.0 21.1 21.2 21.3 21.4 21.5 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. 
  22. ↑ 22.0 22.1 22.2 22.3 22.4 22.5 22.6 22.7 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. 
  23. ↑ "Testosterone phenyl propionate (TPP): biological trials with a new androgen". British Journal of Pharmacology and Chemotherapy 8 (3): 271–277. September 1953. doi:10.1111/j.1476-5381.1953.tb00793.x. PMID 13093945. 
  24. ↑ 24.0 24.1 24.2 24.3 Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 6 December 2012. ISBN 978-94-011-4439-1. https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA270. 
  25. ↑ 25.0 25.1 25.2 25.3 "Testosterone". Drugs.com International. https://www.drugs.com/international/testosterone.html. 
  26. ↑ 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. 
  27. ↑ 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. 

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