Drostanolone

Structural formula
General
Non-proprietary name	Drostanolone
other names	(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; Masteron; 17 β - hydroxy -2 α -methyl-5 α -androstan-3-one;
Molecular formula	C 20 H 32 O 2 ; C 23 H 36 O 3 (propionate);
External identifiers / databases
EC number	200-367-9
ECHA InfoCard	100,000,334
PubChem	6011
ChemSpider	5789
DrugBank	DB00858
Wikidata	Q422343
Drug information
ATC code	A14
Drug class	Anabolic steroids
properties
Molar mass	304.46 g · mol -1 ; 360.53 g · mol -1 (propionate);
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Drostanolone is a synthetically produced drug from the group of anabolic steroids with a strong androgenic (masculinizing) effect. Today, drostanolone is no longer of any medical importance, but is used improperly in the bodybuilder scene for the purpose of building muscle and increasing performance.

History of development and therapeutic use

Drostanolone was first synthesized by HJ Ringold in 1959, and it was launched in 1969 as "Drolban" for the treatment of inoperable breast cancer in women. Drostanolon is a synthetic derivative ( derivative ) of the physiologically occurring sex hormone dihydrotestosterone . As such, it is one of the androgens , a class of sex hormones . Medicinally, drostanolone was used as an ester of drostanolone propionate .

Due to severe side effects, it was withdrawn from the official market and replaced by other means. The last drug that was on the German market was “Masteron” from the Belgian company “Sarva-Syntex” . The distribution was stopped in 1997.

Mode of action

Drostanolone has a stronger effect than dihydrotestosterone (DHT). Like DHT, some of the substance is also inactivated by reduction to 17-ketosteroids and excreted in the urine. According to a study by the former manufacturer "Sarva-Syntex" , drostanolone has an anti-estrogenic effect similar to a selective estrogen receptor modulator . Furthermore Drostanolon acts mildly diuretic ( diuretic ) as it is on the aldosterone binding receptor, which is responsible for the water balance within the cells.

Drostanolone is a pure androgen and cannot be aromatized to estrogenic structures , so that no estrogenic effects arise. A gynecomastia should accordingly be precluded as a side effect. Recent studies indicate that drostanolone - typical for androgens - inhibits the storage capacity of certain fat cells for lipids (fats). Physiologically, this takes place via the inhibition of a signal transduction pathway that normally supports the function of fat cells ( adipocytes ).

Side effects

The noteworthy side effects of drostanolone include severe hair loss , acne , increased body hair growth, increased aggressiveness, influencing the body's own hormone production, increased blood pressure , changes in the tone of the voice (lower, male) and deterioration in blood lipid levels.

The hair loss that almost always occurs when it is misused by men can not be treated with drugs such as finasteride , since finasteride only prevents the conversion to dihydrotestosterone, but drostanolone is already a synthetic form of it. If taken for a long time, drostanolone can affect the central nervous system, cause sleep disorders and changes in the prostate .

Abuse in Sports

Due to its strongly androgenic properties, drostanolone is abused by advanced athletes in weight training and bodybuilding as a performance-enhancing preparation , for example to increase the bracing force. It also compresses and hardens the muscles. The substance classified as a doping agent is manufactured in "underground laboratories" and illegally sold.

In order to accelerate muscle growth even more and to maximize the increase in strength, Drostanolone is also mixed with other substances that are misused in weight training such as Trenbolone , Furazabol and / or Stanozolol . Such combinations, especially with stanozolol, are said to cause a particularly pronounced deterioration in blood lipid levels, which increases the risk of a heart attack . Unlike most other anabolic steroids, drostanolone is not harmful to the liver. Compared to Trenbolone, for example, Drostanolone is more androgenic and less anabolic. Adverse effects are often treated with spironolactone or tamoxifen with simultaneous discontinuation of drostanolone.

The trade in preparations containing drostanolone without permission is prohibited under the Medicines Act . Possession is also a criminal offense; according to the doping agent quantity regulation , anything over possession of 1015 mg is not a small amount. The active ingredient was placed on the prohibited list by the World Anti-Doping Agency (WADA).

literature

D. Sinner, Anabolic Steroids. The Black Book 2007 BMS-Verlag, Gronau 2007. ISBN 978-3-00-020944-4 . Page 108/109.

Individual evidence

↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

↑ Otto-Albrecht Neumüller (Ed.): Römpps Chemie-Lexikon. Volume 2: Cm-G. 8th revised and expanded edition. Franckh'sche Verlagshandlung, Stuttgart 1981, ISBN 3-440-04512-9 , p. 1015.

↑ H. J. Ringold, E. Batres, O. Halpern, E. Necoechea: Steroids. CV. ¹ 2-Methyl and 2-Hydroxymethylene-androstane Derivatives , J. Amer. Chem. Soc. 1959, 81, p. 427, doi: 10.1021 / ja01511a040 .

↑ Singh, R. et al. (2006): Testosterone inhibits adipogenic differentiation in 3T3-L1 cells: nuclear translocation of androgen receptor complex with beta-catenin and T-cell factor 4 may bypass canonical Wnt signaling to down-regulate adipogenic transcription factors. In: Endocrinology. Vol. 147, pp. 141-154. PMID 16210377 , doi: 10.1210 / en.2004-1649 .

↑ Substance Classification Bookle ( Memento of the original from September 27, 2013 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. (PDF; 703 kB). @1@ 2

[NV-1] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[Römpp-2] Otto-Albrecht Neumüller (Ed.): Römpps Chemie-Lexikon. Volume 2: Cm-G. 8th revised and expanded edition. Franckh'sche Verlagshandlung, Stuttgart 1981, ISBN 3-440-04512-9 , p. 1015.

[Ariens-3] H. J. Ringold, E. Batres, O. Halpern, E. Necoechea: Steroids. CV. ¹ 2-Methyl and 2-Hydroxymethylene-androstane Derivatives , J. Amer. Chem. Soc. 1959, 81, p. 427, doi: 10.1021 / ja01511a040 .

[4] Singh, R. et al. (2006): Testosterone inhibits adipogenic differentiation in 3T3-L1 cells: nuclear translocation of androgen receptor complex with beta-catenin and T-cell factor 4 may bypass canonical Wnt signaling to down-regulate adipogenic transcription factors. In: Endocrinology. Vol. 147, pp. 141-154. PMID 16210377 , doi: 10.1210 / en.2004-1649 .