Testosterone propionate

{{See also|Androgen replacement therapy#Medical uses|Anabolic steroid#Medical}}

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.{{Cite web|url=http://adisinsight.springer.com/drugs/800013172|title = Testosterone propionate | work = AdisInsight | publisher = Springer Nature Switzerland AG }}

{{Androgen replacement therapy formulations and dosages used in men}}

{{Androgen replacement therapy formulations and dosages used in women}}

{{Androgen/anabolic steroid dosages for breast cancer}}

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

{{See also|Anabolic steroid#Adverse effects|Androgen replacement therapy#Adverse effects}}

Side effects of testosterone propionate include virilization among others.

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

{{See also|Testosterone#Mechanism of action|Anabolic steroid#Pharmacology}}

{{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).

Testosterone propionate is administered in oil via intramuscular injection.{{cite journal | vauthors = Behre HM, Abshagen K, Oettel M, Hübler D, Nieschlag E | title = Intramuscular injection of testosterone undecanoate for the treatment of male hypogonadism: phase I studies | journal = European Journal of Endocrinology | volume = 140 | issue = 5 | pages = 414–419 | date = May 1999 | pmid = 10229906 | doi = 10.1530/eje.0.1400414 | s2cid = 22597244 | citeseerx = 10.1.1.503.1752 }} It has a relatively short elimination half-life and mean residence time of 2 days and 4 days, respectively. As such, it has a short duration of action and must be administered two to three times per week.{{cite book | vauthors = Lee C, Basaria S, Dobs AS | chapter = Hypogonadism and Hormone Replacement in Men with Cancers | veditors = Yeung SJ, Escalante CP, Gagel RF | title = Medical Care of Cancer Patients| chapter-url = https://books.google.com/books?id=XxfjqF1A0TkC&pg=PA247 |year=2009|publisher=PMPH-USA|isbn=978-1-60795-008-0|pages=247–}}

Intramuscular injection of testosterone propionate as an oil solution, aqueous suspension, and emulsion has been compared.{{cite book| vauthors = Hamburger C |title=Ciba Foundation Symposium - Steroid Hormone Administration (Book II of Colloquia on Endocrinology, Vol. 3)|chapter=17-Ketosteroid Excretion and Modes of Administering Testosterone Preparations|series=Novartis Foundation Symposia|year=1952|pages=304–322|publisher=John Wiley & Sons |issn=1935-4657|doi=10.1002/9780470715154.ch7|isbn=9780470715154}}

{{Pharmacokinetics of testosterone esters}}

{{Parenteral durations of androgens/anabolic steroids}}

{{See also|Androgen ester|List of androgen esters}}

Testosterone propionate, or testosterone 17β-propanoate, is a synthetic androstane steroid and a derivative of testosterone.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA641|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=641–642}}{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA1002|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=1002–1004}} It is an androgen ester; specifically, it is the C17β propionate (propanoate) ester of testosterone.

{{Structural properties of major testosterone esters}}

Testosterone esters were synthesized for the first time in 1936, and were found to have greatly improved potency relative to testosterone.{{cite journal | vauthors = Korenchevsky V, Dennison M, Eldridge M | title = The prolonged treatment of castrated and ovariectomized rats with testosterone propionate | journal = The Biochemical Journal | volume = 31 | issue = 3 | pages = 475–485 | date = March 1937 | pmid = 16746360 | pmc = 1266958 | doi = 10.1042/bj0310475 }} Among the esters synthesized, testosterone propionate was the most potent, and for this reason, was selected for further development, subsequently being marketed. Testosterone propionate was introduced in 1937 by Schering AG in Germany under the brand name Testoviron. It was the first commercially available form of testosterone, and the first testosterone ester, to be introduced.{{cite journal | vauthors = Escamilla RF | title = Newer hormonal preparations | journal = California Medicine | volume = 92 | issue = 2 | pages = 121–124 | date = February 1960 | pmid = 13849734 | pmc = 1578009 }} The medication was the major form of testosterone used medically before 1960. Buccal testosterone propionate tablets were introduced for medical use in the mid-to-late 1940s under the brand name Oreton Buccal Tablets.{{cite book|title=The Mississippi Doctor|url=https://books.google.com/books?id=YvkfAQAAMAAJ|year=1946 | page = 7 }}{{cite book|title=The Midwestern Druggist ...|url=https://books.google.com/books?id=K-IrAQAAMAAJ|year=1948|page=28}}{{cite journal|title=New Prescription Products|journal=Journal of the American Pharmaceutical Association (Practical Pharmacy Ed.)|volume=10|issue=4|year=1949|pages=198–206|issn=0095-9561|doi=10.1016/S0095-9561(16)31795-9}} An aqueous suspension of testosterone propionate was marketed by Ciba by 1950.{{cite journal | vauthors = Østergaard E | title = Employment of androgens in gynecology | journal = Acta Obstetricia et Gynecologica Scandinavica | volume = 30 | issue = 1 | pages = 106–127 | date = 1950 | pmid = 14777285 | doi = 10.3109/00016345009154942 | s2cid = 30737118 }} In the 1950s, longer-acting testosterone esters like testosterone enanthate and testosterone cypionate were introduced and superseded testosterone propionate. Although rarely used nowadays due to its short duration,{{cite book| vauthors = Chapple CR, Steers WD |title=Practical Urology: Essential Principles and Practice: Essential Principles and Practice|url=https://books.google.com/books?id=A9m8TkdCUqEC&pg=PA228|date=10 May 2011|publisher=Springer Science & Business Media|isbn=978-1-84882-034-0|pages=228–}} testosterone propionate remains medically available.

Testosterone propionate is the generic name of the drug and its {{abbrlink|USAN|United States Adopted Name}} and {{abbrlink|BAN|British Approved Name}}.{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA270|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1}}{{Cite web | url=https://www.drugs.com/international/testosterone.html | title=Testosterone | work = Drugs.com }} It has also been referred to as testosterone propanoate or as propionyltestosterone.

Testosterone propionate is or has been marketed under a variety of brand names, including, among numerous others:

• Agrovirin
• Andronate
• Andrusol-P
• Anertan{{cite book| vauthors = Kahr H |title=Konservative Therapie der Frauenkrankheiten: Anzeigen, Grenzen und Methoden Einschliesslich der Rezeptur|url=https://books.google.com/books?id=Hte1BgAAQBAJ&pg=PA21|date=8 March 2013|publisher=Springer-Verlag|isbn=978-3-7091-5694-0|pages=21–}}
• Masenate
• Neo-Hombreol
• Oreton
• Perandren
• Synandrol
• Testoviron

Testosterone propionate is no longer available commercially in the United States except via a compounding pharmacy.{{cite web | title = Drugs@FDA: FDA Approved Drug Products | publisher = United States Food and Drug Administration | access-date = 16 November 2016 | url = https://www.accessdata.fda.gov/scripts/cder/daf/}}

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.{{cite book | vauthors = Bicerano J, Karch SB | chapter = Criminalistics: Introduction to Controlled Substances | veditors = Karch SB |title=Drug Abuse Handbook | edition = Second | chapter-url = https://books.google.com/books?id=ZjrMBQAAQBAJ&pg=PA30 |date=21 December 2006|publisher=CRC Press|isbn=978-1-4200-0346-8|pages=30–}}{{cite book| vauthors = Lilley LL, Snyder JS, Rainforth SC |title=Pharmacology for Canadian Health Care Practice|url=https://books.google.com/books?id=dNgoDwAAQBAJ&pg=PA50|date=5 August 2016|publisher=Elsevier Health Sciences|isbn=978-1-77172-066-3|pages=50–}}

{{Reflist}}

{{Testosterone}}

{{Androgens and antiandrogens}}

{{Androgen receptor modulators}}

{{Estrogen receptor modulators}}

Category:Anabolic–androgenic steroids

Category:Androstanes

Category:Cyclic ketones

Category:Propionate esters

Category:Testosterone esters