Drostanolone propionate

Drostanolone propionate
Clinical data
Trade namesDrolban, Masteril, Masteron, others
Other namesDromostanolone 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 classAndrogen; Anabolic steroid; Androgen ester
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: 0–2%
Intramuscular: 100%
Protein bindingHigh
MetabolismHepatic
Elimination half-lifeIntramuscular: 2 days[1]
ExcretionUrine
Identifiers
  • (2R,5S,8R,9S,10S,13S,14S,17S)-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
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.007.550 Edit this at Wikidata
Chemical and physical data
FormulaC23H36O3
Molar mass360.538 g·mol−1
3D model (JSmol)
  • 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
  • InChI=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 checkY
  • Key:NOTIQUSPUUHHEH-UXOVVSIBSA-N checkY
  (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

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 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.

Androgen/anabolic steroid dosages for breast cancer
Route Medication Form Dosage
Oral Methyltestosterone Tablet 30–200 mg/day
Fluoxymesterone Tablet 10–40 mg 3x/day
Calusterone Tablet 40–80 mg 4x/day
Normethandrone Tablet 40 mg/day
Buccal Methyltestosterone Tablet 25–100 mg/day
Injection (IMTooltip intramuscular injection or SCTooltip subcutaneous injection) Testosterone propionate Oil solution 50–100 mg 3x/week
Testosterone enanthate Oil solution 200–400 mg 1x/2–4 weeks
Testosterone cypionate Oil solution 200–400 mg 1x/2–4 weeks
Mixed testosterone esters Oil solution 250 mg 1x/week
Methandriol Aqueous suspension 100 mg 3x/week
Androstanolone (DHT) Aqueous suspension 300 mg 3x/week
Drostanolone propionate Oil solution 100 mg 1–3x/week
Metenolone enanthate Oil solution 400 mg 3x/week
Nandrolone decanoate Oil solution 50–100 mg 1x/1–3 weeks
Nandrolone phenylpropionate Oil solution 50–100 mg/week
Note: Dosages are not necessarily equivalent. Sources: See template.

Non-medical uses

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

Side effects

See also: Anabolic steroid § Adverse effects

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 (200 mg/twice a week),[8] 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.[9][1]

Pharmacology

Pharmacodynamics

Androgenic vs. anabolic activity ratio
of androgens/anabolic steroids
Medication Ratioa
Testosterone ~1:1
Androstanolone (DHT) ~1:1
Methyltestosterone ~1:1
Methandriol ~1:1
Fluoxymesterone 1:1–1:15
Metandienone 1:1–1:8
Drostanolone 1:3–1:4
Metenolone 1:2–1:30
Oxymetholone 1:2–1:9
Oxandrolone 1:3–1:13
Stanozolol 1:1–1:30
Nandrolone 1:3–1:16
Ethylestrenol 1:2–1:19
Norethandrolone 1:1–1:20
Notes: In rodents. Footnotes: a = Ratio of androgenic to anabolic activity. Sources: See template.

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.[10]

Pharmacokinetics

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

See also: List of androgens/anabolic steroids and List of androgen esters

Drostanolone propionate, or drostanolone 17β-propionate, is a synthetic androstane steroid and a derivative of DHT.[11][12][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.[11][12][1]

Structural properties of major anabolic steroid esters
Anabolic steroid Structure Ester Relative
mol. weight		 Relative
AAS contentb		 Durationc
Position Moiety Type Lengtha
Boldenone undecylenate
C17β Undecylenic acid Straight-chain fatty acid 11 1.58 0.63 Long
Drostanolone propionate
C17β Propanoic acid Straight-chain fatty acid 3 1.18 0.84 Short
Metenolone acetate
C17β Ethanoic acid Straight-chain fatty acid 2 1.14 0.88 Short
Metenolone enanthate
C17β Heptanoic acid Straight-chain fatty acid 7 1.37 0.73 Long
Nandrolone decanoate
C17β Decanoic acid Straight-chain fatty acid 10 1.56 0.64 Long
Nandrolone phenylpropionate
C17β Phenylpropanoic acid Aromatic fatty acid – (~6–7) 1.48 0.67 Long
Trenbolone acetate
C17β Ethanoic acid Straight-chain fatty acid 2 1.16 0.87 Short
Trenbolone enanthated
C17β Heptanoic acid Straight-chain fatty acid 7 1.41 0.71 Long
Footnotes: a = Length of ester in carbon atoms for straight-chain fatty acids or approximate length of ester in carbon atoms for aromatic fatty acids. b = Relative androgen/anabolic steroid content by weight (i.e., relative androgenic/anabolic potency). c = Duration by intramuscular or subcutaneous injection in oil solution. d = Never marketed. Sources: See individual articles.

History

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

Generic names

Drostanolone propionate is the generic name of the drug and its BANMTooltip British Approved Name, while dromostanolone propionate is the USANTooltip United States Adopted Name and USPTooltip United States Pharmacopeia; there is no INNTooltip International Nonproprietary Name for this form.[11][12][13] The generic name of the unesterified form of the drug is drostanolone or dromostanolone and the former is its INNTooltip International Nonproprietary Name, BANTooltip British Approved Name, and DCFTooltip Dénomination Commune Française while there is no USANTooltip United States Adopted Name.[11][12][13][2]

Brand names

Drostanolone propionate was marketed under a variety of brand names including Drolban, Masterid, Masteril, Masteron, Masterone, Mastisol, Metormon, Permastril, and Prometholone.[11][12][1]

Availability

Drostanolone propionate appears to no longer be marketed.[1][2] It was previously available in the United States, Europe, and Japan.[12][1] In Europe, it was specifically marketed in the United Kingdom, Germany, Belgium, France, Spain, Portugal, Italy, and Bulgaria.[12][1]

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

References

  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 Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 517–. ISBN 978-0-9828280-1-4.
  2. ^ a b c "Anabolic Agents". Drugs.com.
  3. ^ 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.
  4. ^ a b Ringold HJ, 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. Bibcode:1959JAChS..81..427R. 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 Karch SB (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 propionate (Masteron) administration - The Dose for Treating Breast Cancer". Masterone. 2020-01-24. Archived from the original on 2020-10-01. Retrieved 2021-02-23.
  9. ^ Solimini R, Rotolo MC, Mastrobattista L, Mortali C, Minutillo A, Pichini S, et al. (March 2017). "Hepatotoxicity associated with illicit use of anabolic androgenic steroids in doping". European Review for Medical and Pharmacological Sciences. 21 (1 Suppl): 7–16. PMID 28379599.
  10. ^ "Drostanolone (PIM 901)". www.inchem.org. Retrieved 2016-03-15.
  11. ^ a b c d e Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 652–. ISBN 978-1-4757-2085-3.
  12. ^ 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.
  13. ^ a b Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 106–. ISBN 978-94-011-4439-1.