Oxymetholone

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Structural formula
Structural formula of oxymetholone
General
Non-proprietary name Oxymetholone
other names
  • 17 β- hydroxy-2- (hydroxymethylene) -17-methyl-5 α -androstan-3-one
  • Anasteron
Molecular formula C 21 H 32 O 3
Brief description

whitish, odorless, crystalline powder

External identifiers / databases
CAS number 434-07-1
EC number 207-098-6
ECHA InfoCard 100.006.454
PubChem 5281034
ChemSpider 4444502
DrugBank DB06412
Wikidata Q420864
Drug information
ATC code

A14 AA05

properties
Molar mass 332.48 g · mol -1
Physical state

firmly

Melting point

178-180 ° C

solubility
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
08 - Dangerous to health

Caution

H and P phrases H: 351-361
P: 281
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Oxymetholone is a synthetic drug selected from the group of the anabolic steroids and is a derivative ( derivative ) of the physiologically occurring sex hormone dihydrotestosterone .

history

Oxymetholone was developed and marketed by the Syntex company in 1960 . The field of application at that time was in the treatment of anemia , as the active ingredient has the ability to increase the number of red blood cells. Syntex stopped producing the product in 1993, as newer active ingredients had proven to be more effective and better tolerated in the treatment of anemia. In 1998, oxymetholone was temporarily re-launched on the market by the pharmaceutical company Unimed , as it had proven to be an effective means of increasing body weight in diseases such as AIDS , which are associated with severe weight loss.

Mode of action

As a derivative of dihydrotestosterone (DHT), oxymetholone cannot convert to estrogen in the human body , but in contrast to DHT, it does cause fat tissue to accumulate and water to be stored in the body. The reason for this is an activation of estrogen receptors by oxymetholone and the resulting estrogen-typical effects. Oxymetholone also stimulates the formation and development of red blood cells ( erythropoiesis ).

Abuse in Sports

Oxymetholone is known as a doping agent mainly under the name Anapolon. Due to its pronounced anabolic and androgenic effects, it is abused by doping strength athletes, bodybuilders, wrestlers, boxers, etc. to achieve a rapid increase in strength. It is considered to be one of the most effective, but also most harmful steroids. An effect already occurs after the first dose.

Since 2005 oxymetholone is on the prohibited list The 2005 Prohibited List of the World Anti-Doping Agency ( WADA ). Possession of more than 100 mg is assessed as a not small amount according to the German Medicines Act , according to the doping agent quantity regulation .

Side effects

Oxymetholone has a number of side effects, including:

  • Liver dysfunction (studies suggest liver cancer with prolonged use)
  • Jaundice
  • Increase in blood pressure
  • oily skin and severe acne
  • Accelerated hair loss that cannot be treated with finasteride
  • strong headache
  • nausea
  • Vomit
  • stomach pain
  • insomnia
  • diarrhea
  • Epistaxis
  • general malaise
  • heavy sweating
  • Worsening of blood lipids
  • impaired thyroid function

swell

Individual evidence

  1. ↑ a b c d e entry on oxymetholone. In: Römpp Online . Georg Thieme Verlag, accessed on June 23, 2011.
  2. ↑ a b Oxymetholone data sheet from Sigma-Aldrich , accessed on May 9, 2017 ( PDF ).
  3. ↑ a b Entry on oxymetholone in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  4. ^ JAMA, Journal of the American Medical Association. Vol. 240, p. 243, 1978.
  5. ↑ Drugs in Japan Vol. 6 , p. 156, 1982.
  6. ↑ FTW Publishing - Steroid Info Oxymetholone, 2006.