Testosterone propionate

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Testosterone propionate
Testosterone propionate.svg
Testosterone propionate molecule ball.png
Clinical data
Trade namesTestoviron, others
SynonymsTP; Testosterone propanoate; Testosterone 17β-propanoate; Propionyltestosterone; NSC-9166
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-lifeIntramuscular: 0.8 days[1][2]
ExcretionUrine
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.319 Edit this at Wikidata
Chemical and physical data
FormulaC22H32O3
Molar mass344.495 g/mol g·mol−1
3D model (JSmol)

Testosterone propionate, sold under the brand name Testoviron among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men.[3][1][4] It has also been used to treat breast cancer in women.[5] It is given by injection into muscle usually once every two to three days.[4][6][7]

Side effects of testosterone propionate 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).[8][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 propionate is a testosterone ester and a relatively short-acting prodrug of testosterone in the body.[6][3][1] Because of this, it is considered to be a natural and bioidentical form of testosterone.[9]

Testosterone propionate was discovered in 1936 and was introduced for medical use in 1937.[10][3] It was the first testosterone ester to be marketed, and was the major form of testosterone used in medicine until about 1960.[3][4] The introduction of longer-acting testosterone esters like testosterone enanthate, testosterone cypionate, and testosterone undecanoate starting in the 1950s resulted in testosterone propionate mostly being superseded.[3][4] As such, it is rarely used today.[4][11] In addition to its medical use, testosterone propionate is used to improve physique and performance.[4] The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 propionate is used primarily in androgen replacement therapy. It is specifically approved for the treatment of hypogonadism in men, breast cancer, low sexual desire, delayed puberty in boys, and menopausal symptoms.[12]

Side effects[edit]

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

Pharmacology[edit]

Pharmacodynamics[edit]

Relative androgenic to anabolic
activity in animals

Medication Ratio
Testosterone 1:1
Testosterone cypionate 1:1
Testosterone enanthate 1:1
Methyltestosterone 1:1
Fluoxymesterone 1:2
Oxymetholone 1:3
Oxandrolone 1:3–1:13
Nandrolone decanoate 1:2.5–1:4
Sources: See template.

Testosterone propionate 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]

Testosterone propionate is administered in oil via intramuscular injection.[1][2] It has a relatively short elimination half-life and mean residence time of 0.8 days and 1.5 days, respectively.[1][2] As such, it has a short duration of action and must be administered two to three times per week.[13]

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.

Chemistry[edit]

Testosterone propionate, or testosterone 17β-propanoate, is a synthetic androstane steroid and a derivative of testosterone.[14][15] It is an androgen ester; specifically, it is the C17β propionate (propanoate) ester of testosterone.[14][15]

Structural properties of major testosterone esters

Androgen Structure Ester Rel. MWb Rel. Tc Durationd
Position Moiety Type Lengtha Rank Group
Testosterone
Testosteron.svg
1.00 1.00 6 Short
Testosterone propionate
Testosterone propionate.svg
C17β Propanoic acid Straight-chain fatty acid 3 1.19 0.84 5 Short
Testosterone cypionate
Testosterone cypionate.svg
C17β Cyclopentylpropanoic acid Aromatic fatty acid – (~6) 1.43 0.70 4 Moderate
Testosterone enanthate
Testosterone enanthate.svg
C17β Heptanoic acid Straight-chain fatty acid 7 1.39 0.72 3 Moderate
Testosterone undecanoate
Testosterone undecanoate.svg
C17β Undecanoic acid Straight-chain fatty acid 11 1.58 0.63 2 Long
Testosterone buciclatee
Testosteronebuciclate structure.png
C17β Bucyclic acidf 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 molecular weight. c = Relative testosterone content by weight (i.e., relative androgenic potency). d = Duration by intramuscular or subcutaneous injection. e = Never marketed. f = Bucyclic acid = trans-4-Butylcyclohexane-1-carboxylic acid. Sources: See individual articles.

History[edit]

Testosterone esters were synthesized for the first time in 1936, and were found to have greatly improved potency relative to testosterone.[10] Among the esters synthesized, testosterone propionate was the most potent, and for this reason, was selected for further development, subsequently being marketed.[10] Testosterone propionate was introduced in 1937 by Schering AG in Germany under the brand name Testoviron.[4] It was the first ester of testosterone to be introduced,[3] and was the major form of testosterone used medically before 1960.[4] In the 1950s, longer-acting testosterone esters like testosterone enanthate and testosterone cypionate were introduced and superseded testosterone propionate.[3] Although rarely used nowadays due to its short duration,[11] testosterone propionate remains medically available.[4]

Society and culture[edit]

Generic names[edit]

Testosterone propionate is the generic name of the drug and its USAN and BAN.[14][15][16][17] It has also been referred to as testosterone propanoate or as propionyltestosterone.[14][15][16][17]

Brand names[edit]

Testosterone propionate is or has been marketed under a variety of brand names including Agrovirin, Andronate, Andrusol-P, Masenate, Neo-Hombreol, Oreton, Perandren, Synandrol, Testoviron, and numerous others.[14][15][16][17]

Availability[edit]

Testosterone propionate appears to no longer be available in the United States.[18]

Legal status[edit]

Testosterone propionate, 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.[19][20]

References[edit]

  1. ^ a b c d e Eberhard Nieschlag; Hermann M. Behre; Susan Nieschlag (13 January 2010). Andrology: Male Reproductive Health and Dysfunction. Springer Science & Business Media. pp. 441–446. ISBN 978-3-540-78355-8.
  2. ^ a b c Behre HM, Abshagen K, Oettel M, Hübler D, Nieschlag E (1999). "Intramuscular injection of testosterone undecanoate for the treatment of male hypogonadism: phase I studies". Eur. J. Endocrinol. 140 (5): 414–9. CiteSeerX 10.1.1.503.1752. doi:10.1530/eje.0.1400414. PMID 10229906.
  3. ^ a b c d e f g Eberhard Nieschlag; Hermann M. Behre; Susan Nieschlag (26 July 2012). Testosterone: Action, Deficiency, Substitution. Cambridge University Press. pp. 9, 315–. ISBN 978-1-107-01290-5.
  4. ^ a b c d e f g h i j k l m n William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 357–361, 413, 426, 607. ISBN 978-0-9828280-1-4.
  5. ^ Bolour S, Braunstein G (2005). "Testosterone therapy in women: a review". Int. J. Impot. Res. 17 (5): 399–408. doi:10.1038/sj.ijir.3901334. PMID 15889125.
  6. ^ a b Kenneth L. Becker (2001). Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. pp. 1185, 1187. ISBN 978-0-7817-1750-2.
  7. ^ Anita H. Payne; Matthew P. Hardy (28 October 2007). The Leydig Cell in Health and Disease. Springer Science & Business Media. pp. 423–. ISBN 978-1-59745-453-7.
  8. ^ Kicman AT (2008). "Pharmacology of anabolic steroids". Br. J. Pharmacol. 154 (3): 502–21. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.
  9. ^ Santoro N, Braunstein GD, Butts CL, Martin KA, McDermott M, Pinkerton JV (2016). "Compounded Bioidentical Hormones in Endocrinology Practice: An Endocrine Society Scientific Statement". J. Clin. Endocrinol. Metab. 101 (4): 1318–43. doi:10.1210/jc.2016-1271. PMID 27032319.
  10. ^ a b c Korenchevsky V, Dennison M, Eldridge M (1937). "The prolonged treatment of castrated and ovariectomized rats with testosterone propionate". Biochem. J. 31 (3): 475–85. doi:10.1042/bj0310475. PMC 1266958. PMID 16746360.
  11. ^ a b Christopher R. Chapple; William D. Steers (10 May 2011). Practical Urology: Essential Principles and Practice: Essential Principles and Practice. Springer Science & Business Media. pp. 228–. ISBN 978-1-84882-034-0.
  12. ^ http://adisinsight.springer.com/drugs/800013172
  13. ^ Yeung SJ, Escalante CP, Gagel RF (2009). Medical Care of Cancer Patients. PMPH-USA. pp. 247–. ISBN 978-1-60795-008-0.
  14. ^ a b c d e J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 641–642. ISBN 978-1-4757-2085-3.
  15. ^ a b c d e Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1002–1004. ISBN 978-3-88763-075-1.
  16. ^ a b c I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. ISBN 978-94-011-4439-1.
  17. ^ a b c "Testosterone".
  18. ^ "Drugs@FDA: FDA Approved Drug Products". United States Food and Drug Administration. Retrieved 16 November 2016.
  19. ^ Steven B. Karch, MD, FFFLM (21 December 2006). Drug Abuse Handbook, Second Edition. CRC Press. pp. 30–. ISBN 978-1-4200-0346-8.CS1 maint: Multiple names: authors list (link)
  20. ^ Linda Lane Lilley; Julie S. Snyder; Shelly Rainforth Collins (5 August 2016). Pharmacology for Canadian Health Care Practice. Elsevier Health Sciences. pp. 50–. ISBN 978-1-77172-066-3.

External links[edit]