Drostanolone propionate

Last updated
Drostanolone propionate
Drostanolone propionate.svg
Clinical data
Trade names Drolban, 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 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
Elimination half-life Intramuscular: 2 days [1]
Excretion Urine
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 InfoCard 100.007.550 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C23H36O3
Molar mass 360.538 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 Yes check.svgY
  • Key:NOTIQUSPUUHHEH-UXOVVSIBSA-N Yes check.svgY
   (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]

Contents

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
RouteMedicationFormDosage
Oral Methyltestosterone Tablet30–200 mg/day
Fluoxymesterone Tablet10–40 mg 3x/day
Calusterone Tablet40–80 mg 4x/day
Normethandrone Tablet40 mg/day
Buccal Methyltestosterone Tablet25–100 mg/day
Injection (IM or SC) Testosterone propionate Oil solution50–100 mg 3x/week
Testosterone enanthate Oil solution200–400 mg 1x/2–4 weeks
Testosterone cypionate Oil solution200–400 mg 1x/2–4 weeks
Mixed testosterone esters Oil solution250 mg 1x/week
Methandriol Aqueous suspension100 mg 3x/week
Androstanolone (DHT) Aqueous suspension300 mg 3x/week
Drostanolone propionateOil solution100 mg 1–3x/week
Metenolone enanthate Oil solution400 mg 3x/week
Nandrolone decanoate Oil solution50–100 mg 1x/1–3 weeks
Nandrolone phenylpropionate Oil solution50–100 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

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
MedicationRatioa
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

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 steroidStructureEsterRelative
mol. weight		Relative
AAS contentb		Durationc
PositionMoietyTypeLengtha
Boldenone undecylenate
Boldenone undecylenate.svg
C17β Undecylenic acid Straight-chain fatty acid111.580.63Long
Drostanolone propionate
Drostanolone propionate.svg
C17β Propanoic acid Straight-chain fatty acid31.180.84Short
Metenolone acetate
Metenolone acetate.svg
C17β Ethanoic acid Straight-chain fatty acid21.140.88Short
Metenolone enanthate
Metenolone enanthate.png
C17β Heptanoic acid Straight-chain fatty acid71.370.73Long
Nandrolone decanoate
Nandrolone decanoate.svg
C17β Decanoic acid Straight-chain fatty acid101.560.64Long
Nandrolone phenylpropionate
Nandrolone phenylpropionate.svg
C17β Phenylpropanoic acid Aromatic fatty acid– (~6–7)1.480.67Long
Trenbolone acetate
Trenbolone acetate.svg
C17β Ethanoic acid Straight-chain fatty acid21.160.87Short
Trenbolone enanthate d
Trenbolone enanthate.svg
C17β Heptanoic acid Straight-chain fatty acid71.410.71Long
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 BANM, while dromostanolone propionate is the USAN and USP; there is no INN 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 INN, BAN, and DCF while there is no USAN. [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]

Related Research Articles

<span class="mw-page-title-main">Methyltestosterone</span> Chemical compound

Methyltestosterone, sold under the brand names Android, Metandren, and Testred among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, at low doses as a component of menopausal hormone therapy for menopausal symptoms like hot flashes, osteoporosis, and low sexual desire in women, and to treat breast cancer in women. It is taken by mouth or held in the cheek or under the tongue.

<span class="mw-page-title-main">Oxandrolone</span> Androgen and anabolic steroid

Oxandrolone, sold under the brand names Oxandrin and Anavar, among others, is an androgen and anabolic steroid (AAS) medication which is used to help promote weight gain in various situations, to help offset protein catabolism caused by long-term corticosteroid therapy, to support recovery from severe burns, to treat bone pain associated with osteoporosis, to aid in the development of girls with Turner syndrome, and for other indications. It is taken by mouth.

<span class="mw-page-title-main">Oxymetholone</span> Androgen and anabolic steroid

Oxymetholone, sold under the brand names Anadrol and Anapolon among others, is an androgen and anabolic steroid (AAS) medication which is used primarily in the treatment of anemia. It is also used to treat osteoporosis, HIV/AIDS wasting syndrome, and to promote weight gain and muscle growth in certain situations. It is taken by mouth.

<span class="mw-page-title-main">Metenolone enanthate</span> Chemical compound

Metenolone enanthate, or methenolone enanthate, sold under the brand names Primobolan Depot and Nibal Injection, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It is given by injection into muscle. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly only available on the black market. A related drug, metenolone acetate, is taken by mouth.

<span class="mw-page-title-main">Ethylestrenol</span> Chemical compound

Ethylestrenol, also known as ethyloestrenol or ethylnandrol and sold under the brand names Maxibolin and Orabolin among others, is an androgen and anabolic steroid (AAS) medication which has been used in the past for a variety of indications such as to promote weight gain and to treat anemia and osteoporosis but has been discontinued for use in humans. It is still available for veterinary use in Australia and New Zealand however. It is taken by mouth.

<span class="mw-page-title-main">Norethandrolone</span> Chemical compound

Norethandrolone, sold under the brand names Nilevar and Pronabol among others, is an androgen and anabolic steroid (AAS) medication which has been used to promote muscle growth and to treat severe burns, physical trauma, and aplastic anemia but has mostly been discontinued. It is still available for use in France however. It is taken by mouth.

<span class="mw-page-title-main">Mesterolone</span> Chemical compound

Mesterolone, sold under the brand name Proviron among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels. It has also been used to treat male infertility, although this use is controversial. It is taken by mouth.

<span class="mw-page-title-main">Mestanolone</span> Chemical compound

Mestanolone, also known as methylandrostanolone and sold under the brand names Androstalone and Ermalone among others, is an androgen and anabolic steroid (AAS) medication which is mostly no longer used. It is still available for use in Japan however. It is taken by mouth.

<span class="mw-page-title-main">Selective androgen receptor modulator</span> Class of pharmaceutical drugs

Selective androgen receptor modulators (SARMs) are a class of drugs that act on the androgen receptor selectively in the muscle and bone.

<span class="mw-page-title-main">Metribolone</span> Chemical compound

Metribolone is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated nandrolone (19-nortestosterone) derivative which was never marketed for medical use but has been widely used in scientific research as a hot ligand in androgen receptor (AR) ligand binding assays (LBAs) and as a photoaffinity label for the AR. More precisely, metribolone is the 17α-methylated derivative of trenbolone. It was investigated briefly for the treatment of advanced breast cancer in women in the late 1960s and early 1970s, but was found to produce signs of severe hepatotoxicity at very low dosages, and its development was subsequently discontinued.

<span class="mw-page-title-main">Drostanolone</span> Chemical compound

Drostanolone, or dromostanolone, is an anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was never marketed. An androgen ester prodrug of drostanolone, drostanolone propionate, was formerly used in the treatment of breast cancer in women under brand names such as Drolban, Masteril, and Masteron. This has also been used non-medically for physique- or performance-enhancing purposes.

<span class="mw-page-title-main">1-Testosterone</span> Chemical compound

1-Testosterone, also known as δ1-dihydrotestosterone (δ1-DHT), as well as dihydroboldenone, is a synthetic anabolic–androgenic steroid (AAS) and a 5α-reduced derivative of boldenone (Δ1-testosterone). It differs from testosterone by having a 1(2)-double bond instead of a 4(5)-double bond in its A ring. It was legally sold online in the United States until 2005, when it was reclassified as a Schedule III drug.

<span class="mw-page-title-main">Methasterone</span> Chemical compound

Methasterone, also known as methyldrostanolone and known by the nickname Superdrol, is a synthetic and orally active anabolic–androgenic steroid (AAS) which was never marketed for medical use. It was sold legally for 9 years as a body building supplement. Because of this lengthy time being legal it has more studies and references than most other designer steroids.

<span class="mw-page-title-main">Epitiostanol</span> Chemical compound

Epitiostanol, sold under the brand name Thiodrol, is an injected antiestrogen and anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was described in the literature in 1965 and has been marketed in Japan as an antineoplastic agent for the treatment of breast cancer since 1977.

<span class="mw-page-title-main">Trimethyltrienolone</span> Chemical compound

Trimethyltrienolone (TMT), also known by its developmental code name R-2956 or RU-2956, is an antiandrogen medication which was never introduced for medical use but has been used in scientific research.

<span class="mw-page-title-main">Methylepitiostanol</span> Chemical compound

Methylepitiostanol, known by the nicknames Epistane, Hemapolin, Havoc, and Epi Plex, is a synthetic and orally active anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was first described in the literature in 1974 but was never marketed for medical use. It is the 17α-methylated derivative of epitiostanol, an AAS and antiestrogen which was formerly used in the treatment of breast cancer in Japan. Similarly to mepitiostane, methylepitiostanol is an orally active variant of epitiostanol. Due to its C17α methyl group, the drug is considered to have a high potential for hepatotoxicity.

<span class="mw-page-title-main">Metenolone acetate</span> Chemical compound

Metenolone acetate, or methenolone acetate, sold under the brand names Primobolan and Nibal, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It is taken by mouth. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available. A related drug, metenolone enanthate, is given by injection into muscle.

<span class="mw-page-title-main">Androstanolone</span> Androgenic and anabolic steroid medication

Androstanolone, or stanolone, also known as dihydrotestosterone (DHT) and sold under the brand name Andractim among others, is an androgen and anabolic steroid (AAS) medication and hormone which is used mainly in the treatment of low testosterone levels in men. It is also used to treat breast development and small penis in males. Compared to testosterone, androstanolone (DHT) is less likely to aromatize into estrogen, and therefore it shows less pronounced estrogenic side effects, such as gynecomastia and water retention. On the other hand, androstanolone (DHT) show more significant androgenic side effects, such as acne, hair loss and prostate enlargement.

<span class="mw-page-title-main">Structure–activity relationships of anabolic steroids</span>

The structure–activity relationships (SAR) of anabolic steroids (AAS) have been extensively studied.

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 517–. ISBN   978-0-9828280-1-4.
  2. 1 2 3 "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. 1 2 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. doi:10.1021/ja01511a040. ISSN   0002-7863.
  5. 1 2 William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1402–. ISBN   978-0-8155-1856-3.
  6. 1 2 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. 1 2 3 4 5 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. 1 2 3 4 5 6 7 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 377–. ISBN   978-3-88763-075-1.
  13. 1 2 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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.