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   » » Wiki: Oxymetholone
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Oxymetholone, sold under the brand names Anadrol and Anapolon among others, is an and (AAS) medication which is used primarily in the treatment of .

(2025). 9780982828014, Molecular Nutrition Llc. .
It is also used to treat , HIV/AIDS , and to promote and in certain situations. It is taken by mouth.

of oxymetholone include increased as well as of like , , and . It can also cause . The drug is a synthetic androgen and anabolic steroid and hence is an of the androgen receptor (AR), the biological target of androgens like and dihydrotestosterone (DHT). It has strong effects and weak effects.

Oxymetholone was first prescribed in 1959 and was introduced for medical use but was discontinued in 1961 due its high lipid toxicity. It is used mostly in the . In addition to its medical use, oxymetholone is used to improve physique and performance. The drug is a controlled substance in many countries and so non-medical use is generally illicit.


Medical uses
The primary clinical applications of oxymetholone include treatment of and , as well as stimulating muscle growth in malnourished or underdeveloped patients. However, in the , the only remaining -approved indication is the treatment of .

Following the introduction of oxymetholone, drugs such as were developed and shown to be more effective as a treatment for and without the of oxymetholone. The drug remained available despite this and eventually found a new use in treating HIV/AIDS .

Presented most commonly as a 50 mg tablet, oxymetholone has been said to be one of the "strongest" and "most powerful" AAS available for medical use. Similarly, there is a risk of side effects. 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 and .


Non-medical uses
Oxymetholone is used for physique- and performance-enhancing purposes by , , and .


Side effects
The common of oxymetholone include depression, , , swelling, fast and excessive , , changes in skin color, urination problems, , , (if taken on an empty stomach), loss of appetite, , in men, feeling restless or excited, , and . In women, side effects also include , changes in , , , pattern hair loss, , and changes in . Because of its 17α-alkylated structure, oxymetholone is . Long term use of the drug can cause a variety of serious ailments, including , liver cancer, and ; therefore periodic liver function tests are recommended for those taking oxymetholone.


Pharmacology

Pharmacodynamics
Like other AAS, oxymetholone is an of the androgen receptor (AR). It is not a substrate for 5α-reductase (as it is already 5α-reduced) and is a poor substrate for 3α-hydroxysteroid dehydrogenase (3α-HSD), and therefore shows a high ratio of to activity.

As a DHT derivative, oxymetholone is not a substrate for and hence cannot be aromatized into estrogenic . 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 (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 does not possess any significant activity.


Pharmacokinetics
There is limited information available on the of oxymetholone. It appears to be well-absorbed with oral administration. Oxymetholone has very low affinity for human serum sex hormone-binding globulin (SHBG), less than 5% of that of testosterone and less than 1% of that of DHT. The drug is in the by at the C2 position, at the C3 position, at the C17 position, and conjugation.
(2015). 9780323311038, Elsevier Health Sciences. .
The C2 hydroxymethylene group of oxymetholone can be to form (17α-methyl-DHT), which may contribute to the effects of oxymetholone. The elimination half-life of oxymetholone is unknown. Oxymetholone and its are eliminated in the .


Chemistry
Oxymetholone, also known as 2-hydroxymethylene-17α-methyl-4,5α-dihydrotestosterone (2-hydroxymethylene-17α-methyl-DHT) or as 2-hydroxymethylene-17α-methyl-5α-androstan-17β-ol-3-one, is a synthetic and a 17α-alkylated derivative of DHT.
(2014). 9781475720853, Springer. .
(2000). 9783887630751, Taylor & Francis. .


History
Oxymetholone was first described in a 1959 paper by scientists from . It was introduced for medical use by and Imperial Chemical Industries in the under the brand name Anapolon by 1961. Oxymetholone was also introduced under the brand names Adroyd () by 1961 and Anadrol (Syntex) by 1962. The drug was marketed in the in the early 1960s.


Society and culture

Generic names
Oxymetholone is the of the drug and its , , , , and , while oxymétholone is its .
(2012). 9789401144391, Springer Science & Business Media. .


Brand names
Oxymetholone has been marketed under a variety of brand names including Anadrol, Anadroyd, Anapolon, Anasterona, Anasteronal, Anasterone, Androlic, Androyd, Hemogenin, Nastenon, Oxitoland, Oxitosona, Oxyanabolic, Oxybolone, Protanabol, Roboral, Synasterobe, Synasteron, and Zenalosyn.
(2012). 9783642663536, Springer Science & Business Media. .


Availability

United States
Oxymetholone is one of the few AAS that remains available for medical use in the . The others (as of August 2023) are testosterone, testosterone cypionate, testosterone enanthate, testosterone undecanoate, methyltestosterone, , and


Other countries
The availability of oxymetholone is fairly limited and seems to be scattered into isolated markets in , , and and . It is known to be available in , , , , , , and . At least historically, it has also been available in , the , , the , , , The UAE, , , and .


Legal status
Oxymetholone, along with other AAS, is a schedule III controlled substance in the under the Controlled Substances Act.
(2006). 9781420003468, CRC Press. .


Further reading
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