Drostanolone propionate

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Drostanolone propionate
Drostanolone propionate.svg
Clinical data
Trade names Drolban, Masteril, Masteron, others
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
Pregnancy
category
  • X
Routes of
administration
Intramuscular injection[1]
Drug class Androgen; Anabolic steroid; Androgen ester
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability Oral: 0–2%
Intramuscular: 100%
Protein binding High
Metabolism Hepatic
Biological half-life Intramuscular: 2 days[1]
Excretion Urine
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
ChEBI
ECHA InfoCard 100.007.550
Chemical and physical data
Formula C23H36O3
Molar mass 360.53 g/mol
3D model (JSmol)
  (verify)

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.[1][2] It is given by injection into muscle.[1]

Side effects of drostanolone propionate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.[1] It has no risk of liver damage.[1] 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).[1][3] 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.[1] The drug has no estrogenic effects.[1] Drostanolone propionate is an androgen ester and a long-lasting prodrug of drostanolone in the body.[1]

Drostanolone propionate was first described in 1959 and was introduced for medical use in 1961.[1][4][5] In addition to its medical use, drostanolone propionate is used to improve physique and performance.[1] The drug is a controlled substance in many countries and so non-medical use is generally illicit.[1][6]

Medical uses[edit]

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.[1]

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[7] as an antiestrogenic drug for the treatment of breast cancer. By the time of its release, there were not many alternatives for patients suffering from 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[edit]

Drostanolone propionate is or has been used for physique- and performance-enhancing purposes by competitive athletes, bodybuilders, and powerlifters.[1]

Side effects[edit]

Drostanolone propionate produces considerably less virilization in women compared to equal doses of testosterone propionate.[1] However, since the given dosage for breast cancer was relatively high (300 mg), mild virilization including oily skin, acne, voice deepening, hirsutism, and clitoral enlargement could still occur, and marked virilization could manifest with long-term therapy.[1] The drug has no estrogenic activity and hence has no propensity for causing gynecomastia (in males) or fluid retention.[1] Drostanolone propionate is not known to pose a risk of hepatotoxicity.[1]

Pharmacology[edit]

Pharmacodynamics[edit]

Drostanolone propionate is a prodrug of drostanolone.[1] Like other AAS, drostanolone is an agonist of the androgen receptor (AR).[1] 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.[1] As a DHT derivative, drostanolone is not a substrate for aromatase and hence cannot be aromatized into estrogenic metabolites.[1] 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.[1] Since the drug is not 17α-alkylated, it is not known to cause hepatotoxicity.[1]

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.[8]

Pharmacokinetics[edit]

Drostanolone propionate is not active via the oral route and must be administered via intramuscular injection.[1] The elimination half-life of the drug via this route is approximately 2 days.[1] It has a much longer elimination half-life via intramuscular injection than drostanolone.[1] Drostanolone propionate is metabolized into drostanolone, which is the active form.[1]

Chemistry[edit]

Drostanolone propionate, or drostanolone 17β-propionate, is a synthetic androstane steroid and a derivative of DHT.[9][10][1] 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.[9][10][1]

History[edit]

Drostanolone and drostanolone propionate were first described in 1959.[1][4] The related AAS oxymetholone and methasterone (methyldrostanolone) were first described in the same paper as well.[1] Drostanolone propionate was introduced for medical use in the United States in 1961 and in Europe shortly thereafter.[5]

Society and culture[edit]

Generic names[edit]

Drostanolone propionate is the generic name of the drug and its BANM, while dromostanolone propionate is the USAN and USP; there is no INN for this form.[9][10][11] The generic name of the unesterified form of the drug is drostanolone or dromostanolone and the former is its INN, BAN, and DCF while there is no USAN.[9][10][11][2]

Brand names[edit]

Drostanolone propionate was marketed under a variety of brand names including Drolban, Masterid, Masteril, Masteron, Masterone, Mastisol, Metormon, Permastril, and Prometholone.[9][10][1]

Availability[edit]

Drostanolone propionate appears to no longer be marketed.[1][2] It was previously available in the United States, Europe, and Japan.[10][1] In Europe, it was specifically marketed in the United Kingdom, Germany, Belgium, France, Spain, Portugal, Italy, and Bulgaria.[10][1]

Legal status[edit]

Drostanolone propionate, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act.[6]

References[edit]

  1. ^ a b c d e f g h i j k l m n o p q r s t u v w x y z aa ab ac ad ae af ag ah ai aj ak William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 517–. ISBN 978-0-9828280-1-4. 
  2. ^ a b c https://www.drugs.com/international/dromostanolone.html
  3. ^ Kicman AT (2008). "Pharmacology of anabolic steroids". Br. J. Pharmacol. 154 (3): 502–21. doi:10.1038/bjp.2008.165. PMC 2439524Freely accessible. PMID 18500378. 
  4. ^ a b Ringold, H. J.; Batres, E.; Halpern, O.; Necoechea, E. (1959). "Steroids. CV.12-Methyl and 2-Hydroxymethylene-androstane Derivatives". Journal of the American Chemical Society. 81 (2): 427–432. doi:10.1021/ja01511a040. ISSN 0002-7863. 
  5. ^ a b William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1402–. ISBN 978-0-8155-1856-3. 
  6. ^ a b Steven B. Karch, MD, FFFLM (21 December 2006). Drug Abuse Handbook, Second Edition. CRC Press. pp. 30–. ISBN 978-1-4200-0346-8. 
  7. ^ "Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations". www.accessdata.fda.gov. Retrieved 2016-03-15. 
  8. ^ "Drostanolone (PIM 901)". www.inchem.org. Retrieved 2016-03-15. 
  9. ^ a b c d e J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 652–. ISBN 978-1-4757-2085-3. 
  10. ^ a b c d e f g Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 377–. ISBN 978-3-88763-075-1. 
  11. ^ a b I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 106–. ISBN 978-94-011-4439-1. 

External links[edit]