View source for Testosterone propionate

{{short description|Chemical compound}}
{{Drugbox
| Verifiedfields = 
| Watchedfields = 
| verifiedrevid = 
| IUPAC_name = [(8''R'',9''S'',10''R'',13''S'',14''S'',17''S'')-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[''a'']phenanthren-17-yl] propanoate
| image = Testosterone propionate.svg
| image_class = skin-invert-image
| width = 250px
| image2 = Testosterone propionate molecule ball.png
| width2 = 250px

<!--Clinical data-->
| tradename = Testoviron, others
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = 
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = Schedule IV
| legal_UK = 
| legal_US = Schedule III
| legal_status = 
| routes_of_administration = [[Intramuscular injection]], [[buccal administration|buccal]]
| class = [[Androgen]]; [[Anabolic steroid]]; [[Androgen ester]]

<!--Pharmacokinetic data-->
| bioavailability = [[Oral administration|Oral]]: very low<br />[[Intramuscular injection|Intramuscular]]: very high
| protein_bound = 
| metabolism = [[Liver]]
| elimination_half-life = [[Intramuscular injection|Intramuscular]]: 0.8 days (~20 hours)<ref name="NieschlagBehre2010" /><ref name="pmid10229906" /><ref name="RastrelliReisman2019">{{cite book| vauthors = Rastrelli G, Reisman Y, Ferri S, Prontera O, Sforza A, Maggi M, Corona G |title=Sexual Medicine|chapter=Testosterone Replacement Therapy|year=2019|pages=79–93|publisher=Springer |doi=10.1007/978-981-13-1226-7_8|isbn=978-981-13-1225-0|s2cid=240176927 }}</ref>
| excretion = [[Urine]]

<!--Identifiers-->
| CAS_number_Ref = 
| CAS_number = 57-85-2
| CAS_supplemental = 
| ATC_prefix = 
| ATC_suffix = 
| PubChem = 5995
| DrugBank_Ref = 
| DrugBank = DB01420
| ChemSpiderID_Ref = 
| ChemSpiderID = 5774
| UNII = WI93Z9138A
| ChEBI = 9466
| ChEMBL = 1170
| KEGG = D00959
| synonyms = TP; Testosterone propanoate; Testosterone 17β-propanoate; Propionyltestosterone; NSC-9166

<!--Chemical data-->
| C=22 | H=32 | O=3
| SMILES = CCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
| StdInChI_Ref = 
| StdInChI = 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
| StdInChIKey_Ref = 
| StdInChIKey = PDMMFKSKQVNJMI-BLQWBTBKSA-N
}}
<!-- Definition and medical uses -->
'''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 [[male hypogonadism|low testosterone levels in men]].<ref name="NieschlagBehre2012">{{cite book| vauthors = Behre HM, Nieschlag E | chapter = Testosterone preparations for clinical use in males | veditors = Nieschlag E, Behre HM, Nieschlag S |title=Testosterone: Action, Deficiency, Substitution|chapter-url=https://books.google.com/books?id=MkrAPaQ4wJkC&pg=PA315|date=26 July 2012|publisher=Cambridge University Press|isbn=978-1-107-01290-5|pages=9,315–}}</ref><ref name="NieschlagBehre2010">{{cite book | vauthors = Nieschlag E, Behre HM | chapter = Testosterone Therapy | veditors = Nieschlag E, Behre HM, Nieschlag S |title=Andrology: Male Reproductive Health and Dysfunction| chapter-url = https://books.google.com/books?id=mEgckDNkonUC&pg=PA441 |date=13 January 2010|publisher=Springer Science & Business Media|isbn=978-3-540-78355-8|pages=441–446}}</ref><ref name="Llewellyn2011">{{cite book| vauthors =  Llewellyn W |title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT357|year=2011|publisher=Molecular Nutrition Llc|isbn=978-0-9828280-1-4|pages=357–361,413,426,607,677}}</ref> It has also been used to treat [[breast cancer]] in women.<ref name="pmid15889125">{{cite journal | vauthors = Bolour S, Braunstein G | title = Testosterone therapy in women: a review | journal = International Journal of Impotence Research | volume = 17 | issue = 5 | pages = 399–408 | year = 2005 | pmid = 15889125 | doi = 10.1038/sj.ijir.3901334 | s2cid = 6461717 | doi-access =  }}</ref> It is given by [[intramuscular injection|injection into muscle]] usually once every two to three days.<ref name="Llewellyn2011" /><ref name="Becker2001">{{cite book| vauthors = Becker KL |title=Principles and Practice of Endocrinology and Metabolism|url=https://books.google.com/books?id=FVfzRvaucq8C&pg=PA1185|year=2001|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-1750-2|pages=1185,1187}}</ref><ref name="PayneHardy2007">{{cite book| vauthors = Payne AH, Hardy MP |title=The Leydig Cell in Health and Disease|url=https://books.google.com/books?id=x4ttqKIAOg0C&pg=PA423|date=28 October 2007|publisher=Springer Science & Business Media|isbn=978-1-59745-453-7|pages=423–}}</ref>

<!-- Side effects and mechanism of action -->
[[Side effect]]s of testosterone propionate include [[symptom]]s of [[virilization|masculinization]] like [[acne]], [[hirsutism|increased hair growth]], [[voice deepening|voice changes]], and increased [[libido|sexual desire]].<ref name="Llewellyn2011" /> Testosterone supplementation is also known to reduce the threshold for [[aggressive behavior]] in men.<ref name="pmid31785281">{{cite journal | vauthors = Geniole SN, Bird BM, McVittie JS, Purcell RB, Archer J, Carré JM | title = Is testosterone linked to human aggression? A meta-analytic examination of the relationship between baseline, dynamic, and manipulated testosterone on human aggression | journal = Hormones and Behavior | volume = 123 | pages = 104644 | date = July 2020 | doi = 10.1016/j.yhbeh.2019.104644 | pmid = 31785281 | s2cid = 208515589 | url = http://clok.uclan.ac.uk/33858/1/33858Geniole%20et%20al%20Revised%20Oct%2030%202019.pdf }}</ref> The drug is a [[synthetic compound|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).<ref name="pmid18500378">{{cite journal | vauthors = Kicman AT | title = Pharmacology of anabolic steroids | journal = British Journal of Pharmacology | volume = 154 | issue = 3 | pages = 502–521 | date = June 2008 | pmid = 18500378 | pmc = 2439524 | doi = 10.1038/bjp.2008.165 }}</ref><ref name="Llewellyn2011" /> It has strong [[androgen]]ic effects and moderate [[anabolic]] effects, which make it useful for producing masculinization and suitable for [[androgen replacement therapy]].<ref name="Llewellyn2011" /> Testosterone propionate is a [[testosterone ester]] and a relatively short-acting [[prodrug]] of [[testosterone (medication)|testosterone]] in the body.<ref name="Becker2001" /><ref name="NieschlagBehre2012" /><ref name="NieschlagBehre2010" /> Because of this, it is considered to be a natural and bioidentical form of testosterone.<ref name="pmid27032319">{{cite journal | vauthors = Santoro N, Braunstein GD, Butts CL, Martin KA, McDermott M, Pinkerton JV | title = Compounded Bioidentical Hormones in Endocrinology Practice: An Endocrine Society Scientific Statement | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 101 | issue = 4 | pages = 1318–1343 | date = April 2016 | pmid = 27032319 | doi = 10.1210/jc.2016-1271 | doi-access = free }}</ref>

<!-- History, society, and culture -->
Testosterone propionate was discovered in 1936 and was introduced for medical use in 1937.<ref name="pmid16746360" /><ref name="NieschlagBehre2012" /> It was the first testosterone ester to be marketed, and was the major form of testosterone used in medicine until about 1960.<ref name="NieschlagBehre2012" /><ref name="Llewellyn2011" /> 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.<ref name="NieschlagBehre2012" /><ref name="Llewellyn2011" /> As such, it is rarely used today.<ref name="Llewellyn2011" /><ref name="ChappleSteers2011" /> In addition to its medical use, testosterone propionate is used to [[performance-enhancing substance|improve physique and performance]].<ref name="Llewellyn2011" /> The drug is a [[controlled substance]] in many countries and so non-medical use is generally illicit.<ref name="Llewellyn2011" />

==Medical uses==
{{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]], [[hypoactive sexual desire disorder|low sexual desire]], [[delayed puberty]] in boys, and [[menopause|menopausal]] [[symptom]]s.<ref name="AdisInsight">{{Cite web|url=http://adisinsight.springer.com/drugs/800013172|title = Testosterone propionate | work = AdisInsight | publisher = Springer Nature Switzerland AG }}</ref>

{{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}}

===Available forms===
Testosterone propionate is usually provided as an [[oil solution]] for use by intramuscular injection.<ref name="Llewellyn2011" /> It was also previously available as an 30&nbsp;mg or 50&nbsp;mg [[aqueous suspension]].<ref name="Kahr2013" /> [[Buccal administration|Buccal]] [[tablet (pharmacy)|tablet]]s of testosterone propionate were previously available as well.<ref name="Llewellyn2011" />

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

[[Side effect]]s of testosterone propionate include [[virilization]] among others.<ref name="Llewellyn2011" />

Testosterone propionate is often a painful injection, which is attributed to its short ester chain.<ref name="Llewellyn2011" />

==Pharmacology==

===Pharmacodynamics===
{{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).

===Pharmacokinetics===
Testosterone propionate is administered in oil via [[intramuscular injection]].<ref name="NieschlagBehre2010" /><ref name="pmid10229906">{{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 }}</ref> It has a relatively short [[elimination half-life]] and [[mean residence time]] of 2 days and 4&nbsp;days, respectively.<ref name="NieschlagBehre2010" /><ref name="pmid10229906" /> As such, it has a short [[duration of action]] and must be administered two to three times per week.<ref name="YeungEscalante2009">{{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–}}</ref>

Intramuscular injection of testosterone propionate as an [[oil solution]], [[aqueous suspension]], and [[emulsion]] has been compared.<ref name="Hamburger1952">{{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}}</ref>

{{Pharmacokinetics of testosterone esters}}

{{Parenteral durations of androgens/anabolic steroids}}

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

Testosterone propionate, or testosterone 17β-propanoate, is a [[synthetic compound|synthetic]] [[androstane]] [[steroid]] and a [[chemical derivative|derivative]] of [[testosterone (medication)|testosterone]].<ref name="Elks2014">{{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}}</ref><ref name="IndexNominum2000">{{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}}</ref> It is an [[androgen ester]]; specifically, it is the C17β [[propionate]] (propanoate) [[ester]] of testosterone.<ref name="Elks2014" /><ref name="IndexNominum2000" />

{{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.<ref name="pmid16746360">{{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 }}</ref> Among the esters synthesized, testosterone propionate was the most potent, and for this reason, was selected for further development, subsequently being marketed.<ref name="pmid16746360" /> Testosterone propionate was introduced in 1937 by [[Schering AG]] in [[Germany]] under the brand name Testoviron.<ref name="Llewellyn2011" /> It was the first commercially available form of testosterone, and the first testosterone ester, to be introduced.<ref name="NieschlagBehre2012" /><ref name="pmid13849734">{{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 }}</ref> The medication was the major form of testosterone used medically before 1960.<ref name="Llewellyn2011" /> [[Buccal administration|Buccal]] testosterone propionate [[tablet (pharmacy)|tablet]]s were introduced for medical use in the mid-to-late 1940s under the brand name Oreton Buccal Tablets.<ref>{{cite book|title=The Mississippi Doctor|url=https://books.google.com/books?id=YvkfAQAAMAAJ|year=1946 | page = 7 }}</ref><ref>{{cite book|title=The Midwestern Druggist ...|url=https://books.google.com/books?id=K-IrAQAAMAAJ|year=1948|page=28}}</ref><ref name="JAPA1949">{{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}}</ref> An [[aqueous suspension]] of testosterone propionate was marketed by [[Ciba Specialty Chemicals|Ciba]] by 1950.<ref name="pmid14777285">{{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 }}</ref> In the 1950s, longer-acting testosterone esters like testosterone enanthate and testosterone cypionate were introduced and superseded testosterone propionate.<ref name="NieschlagBehre2012" /> Although rarely used nowadays due to its short duration,<ref name="ChappleSteers2011">{{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–}}</ref> testosterone propionate remains medically available.<ref name="Llewellyn2011" />

==Society and culture==

===Generic names===
''Testosterone propionate'' is the [[generic term|generic name]] of the drug and its {{abbrlink|USAN|United States Adopted Name}} and {{abbrlink|BAN|British Approved Name}}.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012">{{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}}</ref><ref name="Drugs.com">{{Cite web | url=https://www.drugs.com/international/testosterone.html | title=Testosterone | work = Drugs.com }}</ref> It has also been referred to as ''testosterone propanoate'' or as ''propionyltestosterone''.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" />

===Brand names===
Testosterone propionate is or has been marketed under a variety of brand names, including, among numerous others:<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" />

* Agrovirin
* Andronate
* Andrusol-P
* Anertan<ref name="Kahr2013">{{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–}}</ref>
* Masenate
* Neo-Hombreol
* Oreton
* Perandren
* Synandrol
* Testoviron

===Availability===
Testosterone propionate is no longer available commercially in the [[United States]] except via a compounding pharmacy.<ref name="Drugs@FDA">{{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/}}</ref>

===Legal status===
Testosterone propionate, along with other AAS, is a [[Controlled Substances Act#Schedule III controlled substances|schedule III]] [[controlled substance]] in the [[United States]] under the [[Controlled Substances Act]] and a [[Controlled Drugs and Substances Act#Schedule IV|schedule IV]] controlled substance in [[Canada]] under the [[Controlled Drugs and Substances Act]].<ref name="FFFLM2006">{{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–}}</ref><ref name="LilleySnyder2016">{{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–}}</ref>

== References ==
{{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]]