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
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 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] It is given by injection into muscle or subcutaneously, once every one to four weeks, depending on clinical indication.[4][6][7][8]

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).[9][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.[6][2][3] Because of this, it is considered to be a natural and bioidentical form of testosterone.[10]

Testosterone cypionate was introduced for medical use in 1951.[11][12] Along with testosterone enanthate, testosterone undecanoate, and testosterone propionate, it is one of the most commonly used testosterone esters.[9][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. 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,[8] and osteoporosis.[13][1]

Medications and dosages used in masculinizing hormone therapy for transgender men

Medication Brand names Type Route Dosage
Testosterone undecanoate Andriol, Jatenzo Androgen Oral 40–80 mg/2–3x day (with meals)
Testosterone Striant Androgen Buccal 30 mg 2x/day
Natesto Nasal spray 11 mg 3x/day
AndroGel, others Transdermal gel 25–100 mg/day
Androderm, others Transdermal patch 2.5–10 mg/day
Axiron Axillary solution 30–120 mg/day
Testopel Subcutaneous implant 150–600 mg/3–6 months
Testosterone enanthate Delatestryl, others Androgen Injection (IM or SC) 50–100 mg/week or 100–250 mg/2–4 weeks
Testosterone cypionate Depo-Testosterone, others Androgen Injection (IM or SC) 50–100 mg/week or 100–250 mg/2–4 weeks
Testosterone isobutyrate Agovirin Depot Androgen Injection (IM or SC) 50–100 mg/week
Mixed testosterone estersa Sustanon 250, others Androgen Injection (IM or SC) 250 mg/2–3 weeks or 500 mg/3–6 weeks
Testosterone undecanoate Aveed, Nebido, others Androgen Injection (IM or SC) 750–1,000 mg/10–14 weeks
GnRH analogue Various GnRH modulator Parenteral (various) Variable
Elagolix Orilissa GnRH antagonist Oral 150 mg/day or 200 mg/twice a day
Medroxyprogesterone acetateb Provera, others Progestin Oral 5–10 mg/day
Depo-Provera, others Injection (IM) 150 mg/3 months
Depo-SubQ Provera 104 Injection (SC) 104 mg/3 months
Lynestrenolb Orgametril, others Progestin Oral 5–10 mg/day
Finasteridec Propecia, Proscar 5α-Reductase inhibitor Oral 1 mg/day
Dutasteridec Avodart 5α-Reductase inhibitor Oral 0.5 mg/day
Footnotes: a = Specifically 12% testosterone propionate, 24% testosterone phenylpropionate, 24% testosterone isocaproate, and 40% testosterone decanoate. b = For suppression of menses only. c = For prevention/treatment of scalp hair loss only. Sources: See template.

Androgen replacement therapy formulations and dosages used in women

Route Medication Form(s) Major brand name(s) Dosage
Oral Testosterone (micronized)d Tablet N/A 2.5 mg/day
Testosterone undecanoatea Capsule Andriol, Jatenzo 40–80 mg 1x/1–2 days
Methyltestosteroneb Tablet Metandren; Estratest 0.5–10 mg/day
Fluoxymesterone Tablet Halotestin 1 mg 1x/1–2 days
Normethandronea,b Tablet Ginecoside 5 mg/day
Tibolonea Tablet Livial 1.25–2.5 mg/day
Prasterone (DHEA)c Tablet N/A 25–100 mg/day
Sublingual Testosteroned Tablet N/A 0.25–0.5 mg/day
Methyltestosterone Tablet Metandren 0.25 mg/day
Transdermal Testosteronea Patch Intrinsa 150–300 μg/day
Testosterone Cream; Gel AndroGel 5–10 mg/day
Vaginal Testosteroned Cream; Gel N/A ? mg 1x/1–3 days
Testosteroned Suppository N/A 1 mg 1x/2 days
Prasterone (DHEA) Insert Intrarosa 6.5 mg/day
Intramuscular Testosterone enanthateb Oil Delatestryl; Primodian Depot 25–100 mg 1x/4–6 weeks
Testosterone cypionateb Oil Depo-Testost.; Depo-Testadiol 25–100 mg 1x/4–6 weeks
Testosterone isobutyratea,b Water Femandren M, Folivirin 25–50 mg 1x/4–6 weeks
Testosterone EBHb,e Oil Climacteron 150 mg 1x/4–8 weeks
Nandrolone decanoate Oil Deca-Durabolin 25–50 mg 1x/6–12 weeks
Prasterone enanthatea,b Oil Gynodian Depot 200 mg 1x/4–6 weeks
Subcutaneous Testosterone Implant Testopel 50–100 mg 1x/3–6 months
Footnotes: a = Not available or no longer available in the United States. b = Alone and/or in combination with an estrogen. c = Over-the-counter. d = Compounded only. e = Discontinued. Sources: See template.

Androgen/anabolic steroid dosages for breast cancer

Route/form Androgen Dosage
Oral Methyltestosterone 30–200 mg/day
Fluoxymesterone 10–40 mg 3x/day
Calusterone 40 mg 4x/day
Normethandrone 40 mg/day
IM injection Testosterone propionate 50–100 mg 3x/week
Testosterone enanthate 200–400 mg 1x/2–4 weeks
Testosterone cypionate 200–400 mg 1x/2–4 weeks
Methandriol (aq. susp.) 100 mg 3x/week
Androstanolone (aq. susp.) 300 mg 3x/week
Drostanolone propionate 100 mg 3x/week
Nandrolone decanoate 50–100 mg 1x/1–3 weeks
Nandrolone phenylpropionate 50–100 mg/week
Notes: Dosages are not necessarily equivalent. Sources: See template.

Side effects[edit]

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

Pharmacology[edit]

Pharmacodynamics[edit]

Androgenic vs. anabolic activity
of androgens/anabolic steroids

Medication Ratioa
Testosterone 2:1–1:2
Dihydrotestosterone 3:1–1:2
Methyltestosterone ~1:1
Fluoxymesterone 2:1–1:15
Metandienone 2:1–1:8
Drostanolone 1:3
Metenolone 1:2–1:30
Oxymetholone 1:2–1:9
Oxandrolone 1:3–1:13
Stanozolol 2:1–1:30
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.[14] Large fluctuations in testosterone levels result with it, with levels initially being elevated and supraphysiological.[14] The pharmacokinetics of testosterone cypionate have been studied and reported.[15]

Pharmacokinetics of testosterone esters

Testosterone ester Form Route of administration Elimination half-life Mean residence time
Testosterone undecanoate Oil-filled capsules Oral 1.6 hours 3.7 hours
Testosterone propionate Oil solution Intramuscular injection 0.8 days 1.5 days
Testosterone enanthate Castor oil solution Intramuscular injection 4.5 days 8.5 days
Testosterone undecanoate Tea seed oil solution Intramuscular injection 20.9 days 34.9 days
Testosterone undecanoate Castor oil solution Intramuscular injection 33.9 days 36.0 days
Testosterone buciclatea Aqueous suspension Intramuscular injection 29.5 days 60.0 days
Notes: Testosterone cypionate has very similar pharmacokinetics to TE. Footnotes: a = Never marketed. Sources: See template.

Parenteral durations of androgens/anabolic steroids

Compound Brand name(s) Type Duration
Testosterone (aq. susp.) Andronaq, Sterotate, Virosterone Androgen 2–3 days
Testosterone propionate Androteston, Perandren, Testoviron Androgen 3–4 days
Testosterone phenylpropionate Testolent Androgen 8 days
Testosterone isobutyrate (aq. susp.) Agovirin Depot, Perandren M Androgen 14 days
Mixed testosterone estersa Triolandren Androgen 10–20 days
Mixed testosterone estersb Testosid Depot Androgen 14–20 days
Testosterone enanthate Delatestryl Androgen 14–20 days
Testosterone cypionate Depovirin Androgen 14–20 days
Mixed testosterone estersc Sustanon 250 Androgen 28 days
Testosterone undecanoate Aveed, Nebido Androgen 100 days
Testosterone buciclate (aq. susp.)d 20 Aet-1, CDB-1781e Androgen 90–120 days
Nandrolone phenylpropionate Durabolin Anabolic 10 days
Nandrolone decanoate Deca Durabolin Anabolic 21 days
Methandriol (aq. susp.) Notandron, Protandren Androgen 8 days
Methandriol bisenanthoyl acetate Notandron Depot Androgen 16 days
Metenolone acetate Primobolan Anabolic 3 days
Metenolone enanthate Primobolan Depot Anabolic 14 days
Note: All are via i.m. injection of oil solution unless noted otherwise. Footnotes: a = TP, TV, and TUe. b = TP and TKL. c = TP, TPP, TiCa, and TD. d = Studied, but never marketed. e = Developmental code names. Sources: See template.

Chemistry[edit]

Testosterone cypionate, or testosterone 17β-cyclopentylpropionate, is a synthetic androstane steroid and a derivative of testosterone.[16][17] It is an androgen ester; specifically, it is the C17β cyclopentylpropionate (cypionate) ester of testosterone.[16][17]

Structural properties of major testosterone esters

Androgen Structure Ester Relative
mol. weight
Relative
T contentb
Durationc
Position Moiety Type Lengtha Rank Group
Testosterone
Testosteron.svg
1.00 1.00 11 Short
Testosterone propionate
Testosterone propionate.svg
C17β Propanoic acid Straight-chain fatty acid 3 1.19 0.84 10 Short
Testosterone isobutyrate
Testosterone isobutyrate.svg
C17β Isobutyric acid Aromatic fatty acid – (~3) 1.24 0.80 9 Moderate
Testosterone cypionate
Testosterone cypionate.svg
C17β Cyclopentylpropanoic acid Aromatic fatty acid – (~6) 1.43 0.70 8 Moderate
Testosterone phenylpropionate
Testosterone phenpropionate.svg
C17β Phenylpropanoic acid Aromatic fatty acid – (~6) 1.46 0.69 7 Moderate
Testosterone isocaproate
Testosterone isocaproate.svg
C17β Isohexanoic acid Branched-chain fatty acid – (~5) 1.34 0.75 6 Moderate
Testosterone caproate
Testosterone caproate.svg
C17β Hexanoic acid Straight-chain fatty acid 6 1.35 0.75 5 Moderate
Testosterone enanthate
Testosterone enanthate.svg
C17β Heptanoic acid Straight-chain fatty acid 7 1.39 0.72 4 Moderate
Testosterone decanoate
Testosterone decanoate.svg
C17β Decanoic acid Straight-chain fatty acid 10 1.53 0.65 3 Long
Testosterone undecanoate
Testosterone undecanoate.svg
C17β Undecanoic acid Straight-chain fatty acid 11 1.58 0.63 2 Long
Testosterone buciclated
Testosteronebuciclate structure.png
C17β Bucyclic acide Aromatic carboxylic acid – (~9) 1.58 0.63 1 Long
Footnotes: a = Length of ester in carbon atoms for straight-chain fatty acids or approximate length of ester in carbon atoms for aromatic fatty acids. b = Relative testosterone content by weight (i.e., relative androgenic/anabolic potency). c = Duration by intramuscular or subcutaneous injection in oil solution (except TiB and TB, which are in aqueous suspension). d = Never marketed. e = Bucyclic acid = trans-4-Butylcyclohexane-1-carboxylic acid. Sources: See individual articles.

History[edit]

Testosterone cypionate was introduced for medical use in the United States in 1951 under the brand name Depo-Testosterone.[11][12]

Society and culture[edit]

Generic names[edit]

Testosterone cypionate is the generic name of the drug and its USP.[16][17][18][19] The drug does not have an INN, USAN, or BAN.[16][17][18][19] It has also been referred to as testosterone cipionate, as well as testosterone cyclopentylpropionate or testosterone cyclopentanepropionate.[16][17][18][19]

Brand names[edit]

Testosterone cypionate is or has been marketed under a variety of brand names, including:[16][17][18][19]

  • 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][17] It is not widely available outside of the United States, though it has been marketed in Canada, Australia, Spain, Brazil, and South Africa.[4][17]

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.[20][21]

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. ^ 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.
  6. ^ a b Becker KL (2001). Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. pp. 1185, 1187. ISBN 978-0-7817-1750-2.
  7. ^ Ayd FJ (2000). Lexicon of Psychiatry, Neurology, and the Neurosciences. Lippincott Williams & Wilkins. pp. 974–. ISBN 978-0-7817-2468-5.
  8. ^ 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.
  9. ^ 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.
  10. ^ 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.
  11. ^ a b William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 3170–. ISBN 978-0-8155-1856-3.
  12. ^ a b Hoberman J (21 February 2005). Testosterone Dreams: Rejuvenation, Aphrodisia, Doping. University of California Press. pp. 134–. ISBN 978-0-520-93978-3.
  13. ^ "Testosterone cypionate drug profile". Adis Insight.
  14. ^ 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.
  15. ^ Nankin HR (June 1987). "Hormone kinetics after intramuscular testosterone cypionate". Fertility and Sterility. 47 (6): 1004–9. PMID 3595893.
  16. ^ 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.
  17. ^ 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.
  18. ^ 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.
  19. ^ a b c d "Testosterone". Drugs.com International.
  20. ^ Karch SB (21 December 2006). Drug Abuse Handbook, Second Edition. CRC Press. pp. 30–. ISBN 978-1-4200-0346-8.
  21. ^ 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.