Testosterone propionate

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Testosterone propionate
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Clinical data
Trade namesTestoviron, others
Other namesTP; Testosterone propanoate; Testosterone 17β-propanoate; Propionyltestosterone; NSC-9166
Routes of
administration		Intramuscular injection, buccal
Drug classAndrogen; Anabolic steroid; Androgen ester
Legal status
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Pharmacokinetic data
BioavailabilityOral: very low
Intramuscular: very high
MetabolismLiver
Elimination half-lifeIntramuscular: 0.8 days (~20 hours)[1][2][3]
ExcretionUrine
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] propanoate
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Chemical and physical data
FormulaC22H32O3
Molar mass344.495 g·mol−1
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  • CCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
  • InChI=1S/C22H32O3/c1-4-20(24)25-19-8-7-17-16-6-5-14-13-15(23)9-11-21(14,2)18(16)10-12-22(17,19)3/h13,16-19H,4-12H2,1-3H3/t16-,17-,18-,19-,21-,22-/m0/s1
  • Key:PDMMFKSKQVNJMI-BLQWBTBKSA-N
Data page
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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.[4][1][5] It has also been used to treat breast cancer in women.[6] It is given by injection into muscle usually once every two to three days.[5][7][8]

Side effects of testosterone propionate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.[5] Testosterone supplementation is also known to reduce the threshold for aggressive behavior in men.[9] 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][5] It has strong androgenic effects and moderate anabolic effects, which make it useful for producing masculinization and suitable for androgen replacement therapy.[5] Testosterone propionate is a testosterone ester and a relatively short-acting prodrug of testosterone in the body.[7][4][1] Because of this, it is considered to be a natural and bioidentical form of testosterone.[11]

Testosterone propionate was discovered in 1936 and was introduced for medical use in 1937.[12][4] It was the first testosterone ester to be marketed, and was the major form of testosterone used in medicine until about 1960.[4][5] 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.[4][5] As such, it is rarely used today.[5][13] In addition to its medical use, testosterone propionate is used to improve physique and performance.[5] The drug is a controlled substance in many countries and so non-medical use is generally illicit.[5]

Medical uses

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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.[14]

Template:Androgen replacement therapy formulations and dosages used in men

Template:Androgen replacement therapy formulations and dosages used in women

Template:Androgen/anabolic steroid dosages for breast cancer

Available forms

Testosterone propionate is usually provided as an oil solution for use by intramuscular injection.[5] It was also previously available as an 30 mg or 50 mg aqueous suspension.[15] Buccal tablets of testosterone propionate were previously available as well.[5]

Side effects

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Side effects of testosterone propionate include virilization among others.[5]

Testosterone propionate is often a painful injection, which is attributed to its short ester chain.[5]

Pharmacology

Pharmacodynamics

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Template:Relative androgenic to anabolic activity in animals

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

Testosterone propionate is administered in oil via intramuscular injection.[1][2] It has a relatively short elimination half-life and mean residence time of 2 days and 4 days, respectively.[1][2] As such, it has a short duration of action and must be administered two to three times per week.[16]

Intramuscular injection of testosterone propionate as an oil solution, aqueous suspension, and emulsion has been compared.[17]

Template:Pharmacokinetics of testosterone esters

Template:Parenteral durations of androgens/anabolic steroids

Chemistry

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Testosterone propionate, or testosterone 17β-propanoate, is a synthetic androstane steroid and a derivative of testosterone.[18][19] It is an androgen ester; specifically, it is the C17β propionate (propanoate) ester of testosterone.[18][19]

Template:Structural properties of major testosterone esters

History

Testosterone esters were synthesized for the first time in 1936, and were found to have greatly improved potency relative to testosterone.[12] Among the esters synthesized, testosterone propionate was the most potent, and for this reason, was selected for further development, subsequently being marketed.[12] Testosterone propionate was introduced in 1937 by Schering AG in Germany under the brand name Testoviron.[5] It was the first commercially available form of testosterone, and the first testosterone ester, to be introduced.[4][20] The medication was the major form of testosterone used medically before 1960.[5] Buccal testosterone propionate tablets were introduced for medical use in the mid-to-late 1940s under the brand name Oreton Buccal Tablets.[21][22][23] An aqueous suspension of testosterone propionate was marketed by Ciba by 1950.[24] In the 1950s, longer-acting testosterone esters like testosterone enanthate and testosterone cypionate were introduced and superseded testosterone propionate.[4] Although rarely used nowadays due to its short duration,[13] testosterone propionate remains medically available.[5]

Society and culture

Generic names

Testosterone propionate is the generic name of the drug and its USANTooltip United States Adopted Name and BANTooltip British Approved Name.[18][19][25][26] It has also been referred to as testosterone propanoate or as propionyltestosterone.[18][19][25][26]

Brand names

Testosterone propionate is or has been marketed under a variety of brand names, including, among numerous others:[18][19][25][26]

  • Agrovirin
  • Andronate
  • Andrusol-P
  • Anertan[15]
  • Masenate
  • Neo-Hombreol
  • Oreton
  • Perandren
  • Synandrol
  • Testoviron

Availability

Testosterone propionate is no longer available commercially in the United States except via a compounding pharmacy.[27]

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.[28][29]

References

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  1. ^ a b c d e Page Module:Citation/CS1/styles.css has no content.Nieschlag E, Behre HM (13 January 2010). "Testosterone Therapy". In Nieschlag E, Behre HM, Nieschlag S (eds.). Andrology: Male Reproductive Health and Dysfunction. Springer Science & Business Media. pp. 441–446. ISBN 978-3-540-78355-8.
  2. ^ a b c Page Module:Citation/CS1/styles.css has no content.Behre HM, Abshagen K, Oettel M, Hübler D, Nieschlag E (May 1999). "Intramuscular injection of testosterone undecanoate for the treatment of male hypogonadism: phase I studies". European Journal of Endocrinology. 140 (5): 414–419. CiteSeerX 10.1.1.503.1752. doi:10.1530/eje.0.1400414. PMID 10229906. S2CID 22597244.
  3. ^ Page Module:Citation/CS1/styles.css has no content.Rastrelli G, Reisman Y, Ferri S, Prontera O, Sforza A, Maggi M, Corona G (2019). "Testosterone Replacement Therapy". Sexual Medicine. Springer. pp. 79–93. doi:10.1007/978-981-13-1226-7_8. ISBN 978-981-13-1225-0. S2CID 240176927.
  4. ^ a b c d e f g Page Module:Citation/CS1/styles.css has no content.Behre HM, Nieschlag E (26 July 2012). "Testosterone preparations for clinical use in males". In Nieschlag E, Behre HM, Nieschlag S (eds.). Testosterone: Action, Deficiency, Substitution. Cambridge University Press. pp. 9, 315–. ISBN 978-1-107-01290-5.
  5. ^ a b c d e f g h i j k l m n o p q Page Module:Citation/CS1/styles.css has no content.Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 357–361, 413, 426, 607, 677. ISBN 978-0-9828280-1-4.
  6. ^ Page Module:Citation/CS1/styles.css has no content.Bolour S, Braunstein G (2005). "Testosterone therapy in women: a review". International Journal of Impotence Research. 17 (5): 399–408. doi:10.1038/sj.ijir.3901334. PMID 15889125. S2CID 6461717.
  7. ^ a b Page Module:Citation/CS1/styles.css has no content.Becker KL (2001). Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. pp. 1185, 1187. ISBN 978-0-7817-1750-2.
  8. ^ Page Module:Citation/CS1/styles.css has no content.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.
  9. ^ Page Module:Citation/CS1/styles.css has no content.Geniole SN, Bird BM, McVittie JS, Purcell RB, Archer J, Carré JM (July 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.
  10. ^ Page Module:Citation/CS1/styles.css has no content.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.
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  12. ^ a b c Page Module:Citation/CS1/styles.css has no content.Korenchevsky V, Dennison M, Eldridge M (March 1937). "The prolonged treatment of castrated and ovariectomized rats with testosterone propionate". The Biochemical Journal. 31 (3): 475–485. doi:10.1042/bj0310475. PMC 1266958. PMID 16746360.
  13. ^ a b Page Module:Citation/CS1/styles.css has no content.Chapple CR, Steers WD (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.
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  15. ^ a b Page Module:Citation/CS1/styles.css has no content.Kahr H (8 March 2013). Konservative Therapie der Frauenkrankheiten: Anzeigen, Grenzen und Methoden Einschliesslich der Rezeptur. Springer-Verlag. pp. 21–. ISBN 978-3-7091-5694-0.
  16. ^ Page Module:Citation/CS1/styles.css has no content.Lee C, Basaria S, Dobs AS (2009). "Hypogonadism and Hormone Replacement in Men with Cancers". In Yeung SJ, Escalante CP, Gagel RF (eds.). Medical Care of Cancer Patients. PMPH-USA. pp. 247–. ISBN 978-1-60795-008-0.
  17. ^ Page Module:Citation/CS1/styles.css has no content.Hamburger C (1952). "17-Ketosteroid Excretion and Modes of Administering Testosterone Preparations". Ciba Foundation Symposium - Steroid Hormone Administration (Book II of Colloquia on Endocrinology, Vol. 3). Novartis Foundation Symposia. John Wiley & Sons. pp. 304–322. doi:10.1002/9780470715154.ch7. ISBN 978-0-470-71515-4. ISSN 1935-4657. {{cite book}}: ISBN / Date incompatibility (help)
  18. ^ a b c d e Page Module:Citation/CS1/styles.css has no content.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.
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