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Testosterone cypionate

From Wikipedia, the free encyclopedia

Testosterone cypionate
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.Tooltip intramuscular injection)[1]
Excretion90% Urine; 6% feces[1]
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] 3-cyclopentylpropanoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.335 Edit this at Wikidata
Chemical and physical data
FormulaC27H40O3
Molar mass412.614 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CCC4CCCC4)CCC5=CC(=O)CC[C@]35C
  • InChI=1S/C27H40O3/c1-26-15-13-20(28)17-19(26)8-9-21-22-10-11-24(27(22,2)16-14-23(21)26)30-25(29)12-7-18-5-3-4-6-18/h17-18,21-24H,3-16H2,1-2H3/t21-,22-,23-,24-,26-,27-/m0/s1
  • Key:HPFVBGJFAYZEBE-ZLQWOROUSA-N

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] including 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] Testosterone cypionate is converted by the body to testosterone that has both androgenic effects and anabolic effects, which make it useful for producing masculinization and suitable for androgen replacement therapy;[4] still, the relative potency of these effects can depend on various factors and is a topic of ongoing research.[12][13] Testosterone can either directly exert effects on target tissues or be metabolized by 5α-reductase into DHT or aromatized to estradiol (E2).[12] 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.[12] 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.[14]

Testosterone cypionate was introduced for medical use in 1951.[15][16] 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

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

Testosterone cypionate is used primarily in androgen replacement therapy.[17] It is currently FDA approved for the treatment of primary or hypogonadotropic hypogonadism (either congenital or acquired). The drug's safety in andropause (late-onset hypogonadism in men) has not yet been established,[1] and there are concerns that it may escalate the risks of benign prostatic hyperplasia, prostate cancer and heart diseases.[18] 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.[19][1]

Side effects

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

Side effects of testosterone cypionate include virilization among others.[4] 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.[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 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).

Testosterone cypionate is converted by the body to testosterone that has both androgenic effects and anabolic effects;[4] still, the relative potency of these effects can depend on various factors and is a topic of ongoing research.[12][13] Testosterone can either directly exert effects on target tissues or be metabolized by 5α-reductase into dihydrotestosterone (DHT) or aromatized to estradiol (E2).[12] 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.[12]

Pharmacokinetics

[edit]

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.[21] Large fluctuations in testosterone levels result with it, with levels initially being elevated and supraphysiological.[21] The pharmacokinetics of testosterone cypionate have been studied and reported.[22]

Chemistry

[edit]
See also: Androgen ester and List of androgen esters

Testosterone cypionate, or testosterone 17β-cyclopentylpropionate, is a synthetic androstane steroid and a derivative of testosterone.[23][24] It is an androgen ester; specifically, it is the C17β cyclopentylpropionate (cypionate) ester of testosterone.[23][24]

History

[edit]

Testosterone cypionate was first synthesized in 1951[25] and was introduced for medical use in the United States the same year under the brand name Depo-Testosterone.[15][16]

Society and culture

[edit]

Generic names

[edit]

Testosterone cypionate is the generic name of the drug and its USPTooltip United States Pharmacopeia.[23][24][26][27] The drug does not have an INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, or BANTooltip British Approved Name.[23][24][26][27] It has also been referred to as testosterone cipionate, as well as testosterone cyclopentylpropionate or testosterone cyclopentanepropionate.[23][24][26][27]

Brand names

[edit]

Testosterone cypionate is or has been marketed under a variety of brand names, including:[23][24][26][27]

  • 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

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

Testosterone cypionate is marketed in the United States.[4][24] It is not widely available outside of the United States, though it has been marketed in Canada, Australia, Spain, Brazil, and South Africa.[4][24]

[edit]

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.[28][29]

References

[edit]
  1. ^ a b c d "Depo-Testosterone; testosterone cypionate injection, USP" (PDF). Pfizer. U.S. Food and Drug Administration. Archived (PDF) from the original on 2017-02-16. Retrieved 2017-12-11.
  2. ^ 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.
  3. ^ a b c 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 27 October 2017.
  4. ^ a b c d e f g h i j k l m n o Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 212–216. ISBN 978-0-9828280-1-4.
  5. ^ Costa LB, Rosa-E-Silva AC, Medeiros SF, Nacul AP, Carvalho BR, Benetti-Pinto CL, et al. (May 2018). "Recommendations for the Use of Testosterone in Male Transgender". Revista Brasileira de Ginecologia e Obstetricia. 40 (5): 275–280. doi:10.1055/s-0038-1657788. PMC 10316880. PMID 29913543.
  6. ^ 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.
  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. ^ Ayd FJ (2000). Lexicon of Psychiatry, Neurology, and the Neurosciences. Lippincott Williams & Wilkins. pp. 974–. ISBN 978-0-7817-2468-5.
  9. ^ a b Hembree WC, Cohen-Kettenis PT, Gooren L, Hannema SE, Meyer WJ, Murad MH, et al. (November 2017). "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. doi:10.1210/jc.2017-01658. PMID 28945902.
  10. ^ Geniole SN (2020). "Is testosterone linked to human aggression? A meta-analytic examination of the relationship between baseline, dynamic and manipulated testosterone on human aggression" (PDF). Hormones and Behavior. 123: 104644. doi:10.1016/j.yhbeh.2019.104644. PMID 31785281. S2CID 208515589. Archived (PDF) from the original on 2023-10-01. Retrieved 2023-07-06.
  11. ^ 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.
  12. ^ a b c d e f 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.
  13. ^ a b Kuhn CM (2002). "Anabolic steroids". Recent Prog Horm Res. 57: 411–34. doi:10.1210/rp.57.1.411. PMID 12017555.
  14. ^ 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.
  15. ^ a b Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. William Andrew Publishing. 22 October 2013. pp. 3170–. ISBN 978-0-8155-1856-3.
  16. ^ a b Hoberman J (21 February 2005). Testosterone Dreams: Rejuvenation, Aphrodisia, Doping. University of California Press. pp. 134–. ISBN 978-0-520-93978-3.
  17. ^ "What is Testosterone Cypionate". HRTGuru corp. 19 July 2016. Archived from the original on 6 September 2020. Retrieved 9 April 2020.
  18. ^ Snyder P (December 2022). "Testosterone treatment of late-onset hypogonadism - benefits and risks". Rev Endocr Metab Disord. 23 (6): 1151–1157. doi:10.1007/s11154-022-09712-1. PMID 35266057.
  19. ^ "Testosterone cypionate - Pfizer". Adis Insight. Springer Nature Switzerland AG. Archived from the original on 2019-07-03. Retrieved 2017-12-11.
  20. ^ Patel AS, Leong JY, Ramos L, Ramasamy R (January 2019). "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. doi:10.5534/wjmh.180036. PMC 6305868. PMID 30350483.
  21. ^ a b Payne AH, Hardy MP (28 October 2007). The Leydig Cell in Health and Disease. Springer Science & Business Media. pp. 423–. ISBN 978-1-59745-453-7. Archived from the original on 7 April 2024. Retrieved 27 October 2017.
  22. ^ Nankin HR (June 1987). "Hormone kinetics after intramuscular testosterone cypionate". Fertility and Sterility. 47 (6): 1004–1009. doi:10.1016/S0015-0282(16)59237-1. PMID 3595893.
  23. ^ 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.
  24. ^ a b c d e f g h Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1002–1004. ISBN 978-3-88763-075-1.
  25. ^ Dekanski J, Chapman RN (September 1953). "Testosterone phenyl propionate (TPP): biological trials with a new androgen". British Journal of Pharmacology and Chemotherapy. 8 (3): 271–277. doi:10.1111/j.1476-5381.1953.tb00793.x. PMC 1509286. PMID 13093945.
  26. ^ a b c d Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. ISBN 978-94-011-4439-1.
  27. ^ a b c d "Testosterone". Drugs.com International. Archived from the original on 2016-11-13. Retrieved 2017-10-27.
  28. ^ Karch SB (21 December 2006). Drug Abuse Handbook, Second Edition. CRC Press. pp. 30–. ISBN 978-1-4200-0346-8.
  29. ^ 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.
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