Drostanolone propionate

{{Short description|Chemical compound}} {{Drugbox | verifiedrevid = 447772837 | IUPAC_name = (2''R'',5''S'',8''R'',9''S'',10''S'',13''S'',14''S'',17''S'')-17-hydroxy-2,10,13-trimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[''a'']phenanthren-3-one | image = Drostanolone propionate.svg | image_class = skin-invert-image | width = 250px

| tradename = Drolban, Masteril, Masteron, others | pregnancy_AU =  | pregnancy_US =  | pregnancy_category = X | legal_AU =  | legal_CA = Schedule IV | legal_UK =  | legal_US = Schedule III | legal_status = | routes_of_administration = Intramuscular injection<ref name="Llewellyn2011" /> | class = Androgen; Anabolic steroid; Androgen ester

| IUPHAR_ligand = 6947 | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 58-19-5 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 7DR7H00HDT | ATC_prefix = A14 | ATC_suffix = | PubChem = 224004 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB00858 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 194604 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 31523 | synonyms = Dromostanolone propionate; NSC-12198; Drostanolone 17β-propionate; 2α-Methyl-4,5α-dihydrotestosterone 17β-propionate; 2α-Methyl-DHT propionate; 2α-Methyl-5α-androstan-17β-ol-3-one 17β-propionate

| C=23 | H=36 | O=3 | SMILES = CCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(C[C@H](C(=O)C4)C)C)C | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C23H36O3/c1-5-21(25)26-20-9-8-17-16-7-6-15-12-19(24)14(2)13-23(15,4)18(16)10-11-22(17,20)3/h14-18,20H,5-13H2,1-4H3/t14-,15+,16+,17+,18+,20+,22+,23+/m1/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = NOTIQUSPUUHHEH-UXOVVSIBSA-N }}  '''Drostanolone propionate''', or '''dromostanolone propionate''', sold under the brand names '''Drolban''', '''Masteril''', and '''Masteron''' among others, is an androgen and anabolic steroid (AAS) medication which was used to treat breast cancer in women but is now no longer marketed.<ref name="Llewellyn2011">{{cite book |url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT517 |title=Anabolics |vauthors=Llewellyn W |publisher=Molecular Nutrition Llc |year=2011 |isbn=978-0-9828280-1-4 |pages=517– |quote=Drostanolone (also known as dromostanolone) is a modified form of dihydrotestosterone. It differs by the introduction of a methyl group at carbon-2 (alpha), which considerably increases the anabolic strength of the steroid by heightening its resistance to metabolism by the 3-hydroxysteroid dehydrogenase enzyme in skeletal muscle tissue.}}</ref><ref name="Drugs.com">{{cite web | title = Anabolic Agents | url = https://www.drugs.com/international/dromostanolone.html | work = Drugs.com }}</ref> It is given by injection into muscle.<ref name="Llewellyn2011" />

Side effects of drostanolone propionate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.<ref name="Llewellyn2011" /> It has no risk of liver damage.<ref name="Llewellyn2011" /> 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).<ref name="Llewellyn2011" /><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> It has moderate anabolic effects and weak androgenic effects, which give it a mild side effect profile and make it especially suitable for use in women.<ref name="Llewellyn2011" /> The drug has no estrogenic effects.<ref name="Llewellyn2011" /> Drostanolone propionate is an androgen ester and a long-lasting prodrug of drostanolone in the body.<ref name="Llewellyn2011" />

Drostanolone propionate was first described in 1959 and was introduced for medical use in 1961.<ref name="Llewellyn2011" /><ref name="RingoldBatres1959" /><ref name="Publishing2013" /> In addition to its medical use, drostanolone propionate is used to 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" /><ref name="FFFLM2006" />

==Medical uses== The principal clinical indication of drostanolone propionate in the United States as well as international markets was the treatment of advanced inoperable breast cancer in women.<ref name="Llewellyn2011" />

Hormonal treatment is part of the complex therapy for some kind of tumors, particularly the ones associated with hormone-active tissues like breast or prostate cancer. Some types of breast cancer cells, expressing estrogen receptors (called ER+ cancers), use estrogen for their growth and dissemination. That is why drugs that block estrogen receptors or decrease their expression on the cell membrane, antiestrogens, could limit the tumor spread and size. Drostanolone propionate has been FDA approved<ref>{{Cite web|url=http://www.accessdata.fda.gov/scripts/cder/ob/docs/obdetail.cfm?Appl_No=012936&TABLE1=OB_DISC|archive-url=https://web.archive.org/web/20160624230136/http://www.accessdata.fda.gov/scripts/cder/ob/docs/obdetail.cfm?Appl_No=012936&TABLE1=OB_DISC|url-status=dead|archive-date=June 24, 2016|title=Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations|website=www.accessdata.fda.gov|access-date=2016-03-15}}</ref> as an antiestrogenic drug for the treatment of breast cancer. By the time of its release, there were not many alternatives for patients with breast cancer and drostanolone propionate was a revolution for these patients. As it has lower androgenic rate compared to testosterone, the risk of virilization is much lighter. Due to this fact, women, who usually do not respond well to any AAS, were having much greater chance to survive cancer. Drostanolone propionate can also be used for breast tumors that do not respond well to other treatments or also as palliative care for advanced incurable tumors. The effects of the product depend of course on the dose and period of administration. The risk of virilization becomes greater with high doses and continuous administration period.

==Non-medical uses== Drostanolone propionate is or has been used for physique- and performance-enhancing purposes by competitive athletes, bodybuilders, and powerlifters.<ref name="Llewellyn2011" />

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

Drostanolone propionate produces considerably less virilization in women compared to equal doses of testosterone propionate.<ref name="Llewellyn2011" /> However, since the given dosage for breast cancer was relatively high (200 mg/twice a week),<ref>{{Cite web|date=2020-01-24|title=Drostanolone propionate (Masteron) administration - The Dose for Treating Breast Cancer|url=https://masterone.online/know-the-masteron-administration.html|url-status=live|access-date=2021-02-23|website=Masterone|language=en-US|archive-url=https://web.archive.org/web/20201001115527/https://masterone.online/know-the-masteron-administration.html |archive-date=2020-10-01 }}</ref> mild virilization including oily skin, acne, voice deepening, hirsutism, and clitoral enlargement could still occur, and marked virilization could manifest with long-term therapy.<ref name="Llewellyn2011" /> The drug has no estrogenic activity and hence has no propensity for causing gynecomastia (in males) or fluid retention.<ref name="Llewellyn2011" /> Drostanolone propionate is not known to pose a risk of hepatotoxicity.<ref>{{cite journal | vauthors = Solimini R, Rotolo MC, Mastrobattista L, Mortali C, Minutillo A, Pichini S, Pacifici R, Palmi I | display-authors = 6 | title = Hepatotoxicity associated with illicit use of anabolic androgenic steroids in doping | journal = European Review for Medical and Pharmacological Sciences | volume = 21 | issue = 1 Suppl | pages = 7–16 | date = March 2017 | pmid = 28379599 }}</ref><ref name="Llewellyn2011" />

==Pharmacology==

===Pharmacodynamics=== {{Relative androgenic to anabolic activity in animals}}

Drostanolone propionate is a prodrug of drostanolone.<ref name="Llewellyn2011" /> Like other AAS, drostanolone is an agonist of the androgen receptor (AR).<ref name="Llewellyn2011" /> It is not a substrate for 5α-reductase and is a poor substrate for 3α-hydroxysteroid dehydrogenase (3α-HSD), and therefore shows a high ratio of anabolic to androgenic activity.<ref name="Llewellyn2011" /> As a DHT derivative, drostanolone is not a substrate for aromatase and hence cannot be aromatized into estrogenic metabolites.<ref name="Llewellyn2011" /> While no data are available on the progestogenic activity of drostanolone, it is thought to have low or no such activity similarly to other DHT derivatives.<ref name="Llewellyn2011" /> Since the drug is not 17α-alkylated, it is not known to cause hepatotoxicity.<ref name="Llewellyn2011" />

Drostanolone propionate, via its active form drostanolone, interacts with the AR and activates a cascade of genetic changes, including increased protein synthesis (anabolism) and decreased amino acid degradation (catabolism). It also induces a reduction or inhibition of prolactin or estrogen receptors in the breasts, which is linked to its antitumor effects.<ref name="INCHEM">{{Cite web|url=http://www.inchem.org/documents/pims/pharm/pim901.htm|title=Drostanolone (PIM 901)|website=www.inchem.org|access-date=2016-03-15}}</ref>{{Better citation needed|reason=The current source does not mention these claims.|date=June 2025}}

===Pharmacokinetics=== Drostanolone propionate is not active via the oral route and must be administered via intramuscular injection.<ref name="Llewellyn2011" /> The elimination half-life of the drug via this route is approximately 2 days.<ref name="Llewellyn2011" /> It has a much longer elimination half-life via intramuscular injection than drostanolone.<ref name="Llewellyn2011" /> Drostanolone propionate is metabolized into drostanolone, which is the active form.<ref name="Llewellyn2011" />

==Chemistry== {{See also|List of androgens/anabolic steroids|List of androgen esters}}

Drostanolone propionate, or drostanolone 17β-propionate, is a synthetic androstane steroid and a derivative of DHT.<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=PA652|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=652–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA377|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=377–}}</ref><ref name="Llewellyn2011" /> It is the C17β propionate (propanoate) ester of drostanolone, which itself is 2α-methyl-4,5α-dihydrotestosterone (2α-methyl-DHT) or 2α-methyl-5α-androstan-17β-ol-3-one.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" />

==History== Drostanolone and drostanolone propionate were first described in 1959.<ref name="Llewellyn2011" /><ref name="RingoldBatres1959">{{cite journal| vauthors = Ringold HJ, Batres E, Halpern O, Necoechea E |title=Steroids. CV.12-Methyl and 2-Hydroxymethylene-androstane Derivatives|journal=Journal of the American Chemical Society|volume=81|issue=2|year=1959|pages=427–432|issn=0002-7863|doi=10.1021/ja01511a040|bibcode=1959JAChS..81..427R }}</ref> The related AAS oxymetholone and methasterone (methyldrostanolone) were first described in the same paper as well.<ref name="Llewellyn2011" /> Drostanolone propionate was introduced for medical use in the United States in 1961 and in Europe shortly thereafter.<ref name="Publishing2013">{{cite book|author=William Andrew Publishing|title=Pharmaceutical Manufacturing Encyclopedia, 3rd Edition|url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA1402|date=22 October 2013|publisher=Elsevier|isbn=978-0-8155-1856-3|pages=1402–}}</ref>

==Society and culture==

===Generic names=== ''Drostanolone propionate'' is the generic name of the drug and its {{abbrlink|BANM|British Approved Name}}, while ''dromostanolone propionate'' is the {{abbrlink|USAN|United States Adopted Name}} and {{abbrlink|USP|United States Pharmacopeia}}; there is no {{abbrlink|INN|International Nonproprietary Name}} for this form.<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=PA106|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=106–}}</ref> The generic name of the unesterified form of the drug is ''drostanolone'' or ''dromostanolone'' and the former is its {{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|BAN|British Approved Name}}, and {{abbrlink|DCF|Dénomination Commune Française}} while there is no {{abbrlink|USAN|United States Adopted Name}}.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="MortonHall2012" /><ref name="Drugs.com" />

===Brand names=== Drostanolone propionate was marketed under a variety of brand names including Drolban, Masterid, Masteril, Masteron, Masterone, Mastisol, Metormon, Permastril, and Prometholone.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" />

===Availability=== Drostanolone propionate appears to no longer be marketed.<ref name="Llewellyn2011" /><ref name="Drugs.com" /> It was previously available in the United States, Europe, and Japan.<ref name="IndexNominum2000" /><ref name="Llewellyn2011" /> In Europe, it was specifically marketed in the United Kingdom, Germany, Belgium, France, Spain, Portugal, Italy, and Bulgaria.<ref name="IndexNominum2000" /><ref name="Llewellyn2011" />

===Legal status=== Drostanolone propionate, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act.<ref name="FFFLM2006">{{cite book| vauthors = Karch SB |title=Drug Abuse Handbook, Second Edition|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>

== References == {{Reflist|2}}

== External links == * [https://steroidscanada.org/product/masteron-propionate-2/ Masteron Propionate Genetix Pharma]

Category:Androgen esters Category:Androgens Category:Androstanes Category:Hormonal antineoplastic drugs Category:Ketones Category:Prodrugs Category:Propionate esters