Oxymetholone is a potent oral anabolic steroid derived from dihydrotestosterone. More specifically, it is a close cousin of methyldihydrotestosterone (mestanolone), differing only by the addition of a 2-hydroxymethylene group. This creates a steroid with considerably different activity than mestanolone, however, such that it is very difficult to draw comparisons between the two. For starters, oxymetholone is a very potent anabolic hormone. Dihydrotestosterone and mestanolone are both very weak in this regard, owing to the fact that these molecules are not very stable in the high enzyme (3-alpha hydroxysteroid dehydrogenase) environment of muscle tissue. Oxymetholone remains highly active here instead, as is reported in standard animal assay tests demonstrating a significantly higher anabolic activity than testosterone or methyltestosterone. Such assays suggest the androgenicity of oxymetholone is also very low (1/4th to 1/7th its anabolic activity), although real world results in humans suggest it is decidedly higher than that.

Oxymetholone is considered by many to be the most powerful steroid commercially available. A steroid novice experimenting with this agent is likely to gain 20 to 30 pounds of massive bulk, and it can often be accomplished within 6 weeks of use. This steroid produces a lot of water retention, so a good portion of this gain is going to be water weight. This is often of little consequence to the user, who may be feeling very big and strong while taking oxymetholone. Although the smooth look that results from water retention is often not attractive, it can aid quite a bit to the level of size and strength gained. The muscle is fuller, will contract better, and is provided a level of protection in the form of extra water held into and around connective tissues. This will allow for more elasticity, and will hopefully decrease the chance for injury when lifting heavy. It should be noted, however, that a very rapid gain in mass might also place too much stress on your connective tissues. The tearing of pectoral and biceps tissue is commonly associated with heavy lifting while massing up on steroids, and oxymetholone is a common offender. There can be such a thing as gaining too fast.

History:

Oxymetholone was first described in 1959. The agent was released in the United States as a prescription drug during the early 1960’s, sold under the brand names Anadrol-50 (Syntex) and Androyd (Parke Davis & Co.). Syntex developed the agent, and would hold patent rights to it until their expiration many years later. The drug was originally approved for use in conditions where anabolic action was necessary. Indicated uses included geriatric debilitation, chronic underweight states, pre- and postoperative preservation of lean mass, convalescence from infection, gastrointestinal disease, osteoporosis, and general catabolic conditions. The recommended dose for such uses was usually 2.5 mg three times per day. The drug was originally supplied in a 2.5 mg, 5 mg, or 10 mg tablet.

Structural Characteristics:

Oxymetholone is a modified form of dihydrotestosterone. It differs by 1) the addition of a methyl group at carbon 17- alpha, which helps protect the hormone during oral administration, and 2) the introduction of a 2- hydroxymethylene group, which inhibits its metabolism by the 3-hsd enzyme and greatly enhances the anabolic and relative biological activity of methyldihydrotestosterone.

Side Effects (Estrogenic):

Oxymetholone is a highly estrogenic steroid. Gynecomastia is often a concern during treatment, and may present itself quite early into a cycle (particularly when higher doses are used). At the same time water retention can become a problem, causing a notable loss of muscle definition as both subcutaneous water retention and fat levels build. To avoid strong estrogenic side effects, it may be necessary to use an anti-estrogen such as Nolvadex® or Clomid®. It is important to note that oxymetholone does not directly convert to estrogen in the body. This steroid is a derivative of dihydrotestosterone, and as such cannot be aromatized.

Anti-aromatase compounds such as Cytadren and Arimidex® will, likewise, not effect the relative estrogenicity of this steroid. Some have suggested that the high level of estrogenic activity in oxymetholone is actually due to the drug acting as a progestin, similar to nandrolone. The side effects of both estrogens and progestins can be very similar, which might have made this explanation a plausible one. There was a medical study examining the progestational activity of oxymetholone, however, and it determined that there was no such activity present.386 With such findings, it seems most plausible that oxymetholone can activate the estrogen receptor, similar to, but more profoundly than, the estrogenic androgen methandriol.

Side Effects (Androgenic):

Although oxymetholone is classified as an anabolic steroid, androgenic side effects are still possible with this substance. These may include bouts of oily skin, acne, and body/facial hair growth. Higher doses are more likely to cause such side effects. Anabolic/androgenic steroids may also aggravate male pattern hair loss. Women are additionally warned of the potential virilizing effects of anabolic/androgenic steroids. These may include a deepening of the voice, menstrual irregularities, changes in skin texture, facial hair growth, and clitoral enlargement. While Anadrol is classified as an anabolic steroid, it does retain a notable androgenic component.

It is interesting to note that oxymetholone does exhibit some tendency to convert to dihydrotestosterone in the body, although this does not occur via the 5-alpha reductase enzyme. Oxymetholone is already a dihydrotestosteronebased steroid, so no such alteration can take place. Aside from the added c-17 alpha alkylation (discussed below), oxymetholone differs from DHT only by the addition of a 2- hydroxymethylene group. This grouping can be removed metabolically, reducing oxymetholone to the potent androgen 17alpha-methyl dihydrotestosterone (mestanolone).387 There is little doubt that this biotransformation contributes at least on some level to the androgenic nature of this steroid. Note that since 5-alpha reductase is not involved, the relative androgenicity of oxymetholone is not affected by the concurrent use of finasteride or dutasteride.

Side Effects (Hepatotoxicity):

Oxymetholone is a c17-alpha alkylated compound. This alteration protects the drug from deactivation by the liver, allowing a very high percentage of the drug entry into the bloodstream following oral administration. C17-alpha alkylated anabolic/androgenic steroids can be hepatotoxic. Prolonged or high exposure may result in liver damage. In rare instances life-threatening dysfunction may develop. It is advisable to visit a physician periodically during each cycle to monitor liver function and overall health. Intake of c17- alpha alkylated steroids is commonly limited to 6-8 weeks, in an effort to avoid escalating liver strain. Oxymetholone has a saturated A-ring, which slightly reduces its relative hepatotoxicity.388 Still, this agent, particularly at the doses commonly used, can present substantial hepatotoxicity to the user. Studies administering 50 mg or 100 mg daily to 31 elderly men for 12 weeks produced significant increases in liver enzymes (transaminases AST and ALT) only in patients taking 100 mg. A second study administering 50 mg daily to 30 patients for up to and exceeding one year (in some patients) has demonstrated elevations in y-glutamyltransferase (GGT) in 17% of patients, significant increases in bilirubin in 10%, and serum albumin increases in 20%.389 One patient developed a liver tumor that could have been peliosis hepatitis, a lifethreatening adverse event characterized by blood filled cysts in the liver. A small number of other cases of peliosis hepatitis have been linked to oxymetholone, suggesting the potential for hepatotoxicity should still be carefully considered before use.

The use of a liver detoxification supplement such as Liver Stabil, Liv-52, or Essentiale Forte is advised while taking any hepatotoxic anabolic/androgenic steroids.

Technical

• (Oxymetholone)
• [17 beta-hydroxy-2-hydroxymethylene-17 alpha-methyl-5 alpha-androstan-3-one]
• Molecular Weight: 332.482
• Molecular Formula: C21H32O3
• Melting Point: 178-180C
• Manufacturer: Syntex (Originally)
• Release Date: 1960
• Effective Dose: 100mgs (optimal)
• Active Life: <16hours
• Detection Time: up to 8 weeks
• Androgenic: Anabolic Ratio: 45:320