|Trade names||Androyd, Anadrol, Anapolon, Anasteronal, Hemogenin, Oxitosona, Roboral, Synasteron, Zenalosyn|
|AHFS/Drugs.com||Consumer Drug Information|
|Biological half-life||8-9 hours|
|Chemical and physical data|
|Molar mass||332.48 g/mol|
|3D model (JSmol)|
|(what is this?)|
|This article needs additional citations for verification. (January 2012) (Learn how and when to remove this template message)|
Oxymetholone (brand names Anadrol, Anapolon, others) is a synthetic, orally active anabolic-androgenic steroid (AAS) and 17α-methylated derivative of dihydrotestosterone (DHT) which is marketed in the United States, Europe, and elsewhere in the world.
The drug was approved for human use by the FDA. Later, non-steroidal drugs such as epoetin alfa were developed and proven to be more effective as a treatment for anemia and osteoporosis without the side effects of oxymetholone. The drug remained available despite this and eventually found a new use in treating HIV wasting syndrome.
Presented most commonly as a 50 mg tablet, oxymetholone is one of the strongest androgenic steroids available. Similarly, there is a risk of side effects. Despite very low binding affinity with the androgen receptor, oxymetholone is highly effective in promoting extensive gains in body mass, mostly by greatly improving protein synthesis. For this reason, it is often used by bodybuilders and athletes.
The common side effects of oxymetholone include depression, lethargy, headache, swelling, rapid weight gain, priapism, changes in skin color, urination problems, nausea, vomiting, stomach pain (if taken on an empty stomach), loss of appetite, jaundice, breast swelling in men, feeling restless or excited, insomnia, and diarrhea. In women, side effects also include acne, changes in menstrual periods, deepened voice, hair growth on the chin or chest, male pattern baldness, enlarged clitoris, and changes in sex drive. Because of its 17α-alkylated structure, oxymetholone is highly hepatotoxic. Long term use of the drug can cause a variety of serious ailments, including hepatitis, liver cancer, and cirrhosis; therefore periodic liver function tests are recommended for those taking oxymetholone.
Like other AAS, oxymetholone is an agonist of the androgen receptor (AR). 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.
As a DHT derivative, oxymetholone is not a substrate for aromatase and hence cannot be aromatized into estrogenic metabolites. However, uniquely among DHT derivatives, oxymetholone is nonetheless associated with relatively high estrogenicity, and is known to have the potential to produce estrogenic side effects such as gynecomastia (rarely) and water retention. It has been suggested that this may be due to direct binding to and activation of the estrogen receptor by oxymetholone.
Oxymetholone, also known as 2-hydroxymethylene-17α-methyl-4,5α-dihydrotestosterone (2-hydroxymethylene-17α-methyl-DHT) or as 2-hydroxymethylene-17α-methylandrostan-17β-ol-3-one, is a synthetic androstane steroid and a 17α-alkylated derivative of DHT.
Society and culture
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