Testosterone cypionate

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~(7-8) days i.m.Tooltip intramuscular injection)[1]
Excretion90% Urine; 6% feces[1]
Identifiers
IUPAC name
  • [(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
Chemical and physical data
FormulaC27H40O3
Molar mass412.614 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CCC4CCCC4)CCC5=CC(=O)CC[C@]35C
InChI
  • 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(AR); 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]

  1. ^ a b Cite error: The named reference Depo-Testosterone-Label was invoked but never defined (see the help page).
  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 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 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. ^ 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 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. ^ 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. ^ Cite error: The named reference Publishing2013 was invoked but never defined (see the help page).
  16. ^ Cite error: The named reference Hoberman2005 was invoked but never defined (see the help page).
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