Testosterone cypionate

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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
  • [(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
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] 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] 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).[10][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.[11]

Testosterone cypionate was introduced for medical use in 1951.[12][13] Along with testosterone enanthate, testosterone undecanoate, and testosterone propionate, it is one of the most commonly used testosterone esters.[10][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]

Testosterone cypionate is used primarily in androgen replacement therapy.[14] 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), hormone replacement therapy in transgender men,[9] and osteoporosis.[15][1]

Side effects[edit]

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.[16]

Pharmacology[edit]

Pharmacodynamics[edit]

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[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.[17] Large fluctuations in testosterone levels result with it, with levels initially being elevated and supraphysiological.[17] The pharmacokinetics of testosterone cypionate have been studied and reported.[18]

Chemistry[edit]

Testosterone cypionate, or testosterone 17β-cyclopentylpropionate, is a synthetic androstane steroid and a derivative of testosterone.[19][20] It is an androgen ester; specifically, it is the C17β cyclopentylpropionate (cypionate) ester of testosterone.[19][20]

History[edit]

Testosterone cypionate was first synthesized in 1951[21] and was introduced for medical use in the United States the same year under the brand name Depo-Testosterone.[12][13]

Society and culture[edit]

Generic names[edit]

Testosterone cypionate is the generic name of the drug and its USP.[19][20][22][23] The drug does not have an INN, USAN, or BAN.[19][20][22][23] It has also been referred to as testosterone cipionate, as well as testosterone cyclopentylpropionate or testosterone cyclopentanepropionate.[19][20][22][23]

Brand names[edit]

Testosterone cypionate is or has been marketed under a variety of brand names, including:[19][20][22][23]

  • 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]

Testosterone cypionate is marketed in the United States.[4][20] It is not widely available outside of the United States, though it has been marketed in Canada, Australia, Spain, Brazil, and South Africa.[4][20]

Legal status[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.[24][25]

References[edit]

  1. ^ a b c d Pfizer. "Depo-Testosterone; testosterone cypionate injection, USP" (PDF). U.S. Food and Drug Administration.CS1 maint: uses authors parameter (link)
  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.
  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.
  4. ^ a b c d e f g h i j k l m n William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 212–216. ISBN 978-0-9828280-1-4.
  5. ^ Costa, Laura Bregieiro Fernandes; Rosa-e-Silva, Ana Carolina Japur de Sá; Medeiros, Sebastião Freitas de; Nacul, Andrea Prestes; Carvalho, Bruno Ramalho de; Benetti-Pinto, Cristina Laguna; Yela, Daniela Angerame; Maciel, Gustavo Arantes Rosa; Soares Júnior, José Maria; Maranhão, Técia Maria de Oliveira (May 2018). "Recommendations for the Use of Testosterone in Male Transgender*". Revista Brasileira de Ginecologia e Obstetrícia. 40 (5): 275–280. doi:10.1055/s-0038-1657788. ISSN 0100-7203. 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.
  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. ^ a b Kicman AT (June 2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–21. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.
  11. ^ 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): 1318–43. doi:10.1210/jc.2016-1271. PMID 27032319.
  12. ^ a b William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 3170–. ISBN 978-0-8155-1856-3.
  13. ^ a b Hoberman J (21 February 2005). Testosterone Dreams: Rejuvenation, Aphrodisia, Doping. University of California Press. pp. 134–. ISBN 978-0-520-93978-3.
  14. ^ HRTGuru corp. "What is Testosterone Cypionate".CS1 maint: uses authors parameter (link)
  15. ^ "Testosterone cypionate drug profile". Adis Insight.
  16. ^ "Testosterone Cypionate Common Side Effects Reported by Real Users". Retrieved 2020-09-06.
  17. ^ 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.
  18. ^ Nankin HR (June 1987). "Hormone kinetics after intramuscular testosterone cypionate". Fertility and Sterility. 47 (6): 1004–9. doi:10.1016/S0015-0282(16)59237-1. PMID 3595893.
  19. ^ 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.
  20. ^ 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.
  21. ^ Dekansi J, Chapman RN (September 1953). "Testosterone phenyl propionate (TPP): biological trials with a new androgen". Br J Pharmacol Chemother. 8 (3): 271–7. doi:10.1111/j.1476-5381.1953.tb00793.x. PMC 1509286. PMID 13093945.
  22. ^ a b c d Morton I, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. ISBN 978-94-011-4439-1.
  23. ^ a b c d "Testosterone". Drugs.com International.
  24. ^ Karch SB (21 December 2006). Drug Abuse Handbook, Second Edition. CRC Press. pp. 30–. ISBN 978-1-4200-0346-8.
  25. ^ 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.