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| | Oxymetholone Chemical Properties |
| Melting point | 172-180°C | | alpha | 34 º | | Boiling point | 409.59°C (rough estimate) | | density | 1.0834 (rough estimate) | | refractive index | 38 ° (C=1, CHCl3) | | storage temp. | 2-8°C | | solubility | H2O: ≤0.5 mg/mL | | pka | 5.28±0.70(Predicted) | | form | solid | | color | white to light yellow | | Water Solubility | <0.1 g/100 mL at 23 ºC | | Merck | 6967 | | Stability: | Stability May be light sensitive. Combustible. Incompatible with strong oxidizing agents. | | InChIKey | ICMWWNHDUZJFDW-CCTJMHFWSA-N | | CAS DataBase Reference | 434-07-1(CAS DataBase Reference) | | NIST Chemistry Reference | Oxymetholone(434-07-1) | | EPA Substance Registry System | Oxymetholone (434-07-1) |
| | Oxymetholone Usage And Synthesis |
| description | Oxymetholone is an orally active synthetic anabolic steroid and a 17alpha-methylated derivative of dihydrotestosterone, with androgenic activity. Although oxymetholone has low affinity for binding the androgen receptor (AR), it strongly activates AR-mediated signaling, which stimulates both protein synthesis and erythropoietin production. This agent may stimulate muscle growth, induce hemoglobin production and red blood cell formation, and promote increased bone density. | | Mechanism of Action | The influence of testosterone in humans takes on two main pathways: generation of the androgen receptor as 5α-dihydrotestosterone (DHT) or directly, and by transformation into estradiol and generation of specific estrogen receptors. Unrestrained receptors are transferred into the cytoplasm of the selected tissue cells where it bonds with the androgen receptors, or it is reduced to DHT by 5α-reductase. The binding points are referred to as hormone response elements, and they determine the transcriptional activity of specific genes, which result in the androgenic effects.
| | Indication | Oxymetholone is indicated for the treatment of anemias that are resultant of ineffective red cell production, such as myelofibrosis, acquired aplastic anemia, congenital aplastic anemia and hypoplastic anemia. The drug should not be prescribed as a replacement for other supplementary measures such as antibacterial therapy, pyridoxine deficiency or vitamin B12, folic acid, rectification of iron, transfusion and the correct use of corticosteroids.
| | Dosage | The recommended dose of Oxymetholone is 1-5mg/kg administered daily based on the patient’s body weight. The most effective dose is 1-2mg/kg per day, but a patient may necessitate higher doses, which can be individualized.
Response to Oxymetholone is not immediate hence a minimum trial period of 3-6months should be indicated. In instances of remission, some patients thrive without the medication whereas an established dosage can support some with lower dose indications. For patients with congenital aplastic anemia, a regular maintenance dose should be prescribed.
| | Contraindications | Oxymetholone should not be prescribed for patients with severe kidney or liver disease, female breast cancer with the affirmation of high calcium levels in the blood, male breast cancer, prostate cancer, and if one is pregnant.
Oxymetholone is also contraindicated in patients who have coronary artery disease, diabetes, blood clotting or bleeding disorder, enlarged prostate, high levels of triglycerides or cholesterol, cognitive heart failure or if they are taking blood thinners such as Jantoven, Coumadin and Warfarin. The drug is also contraindicated in patients who are hypersensitive to Oxymetholone, patients with nephrosis and those with adverse hepatic dysfunction.
| | Side Effects | Common side effects associated with Oxymetholone use in men and women include diarrhea, vomiting, nausea, insomnia, feeling excited or restless, increased or reduced libido, breast tenderness/swelling, male pattern baldness and acne.
In men, Oxymetholone may result in bladder irritability, a reduction in original volume, epididymitis, chronic priapism, impotence, testicular oligospermia and atrophy, and suppression of testicular function.
Prolonged Oxymetholone use can result in blood-filled cysts or tumors in the spleen or the liver. One may need to consult a doctor if they experience painful urination, loss of appetite, jaundice, dark urine, fast weight gain in the midsection or the face, clay-colored stools, pain on the upper section of the stomach and nausea.
| | Warnings | Oxymetholone should not be prescribed for patients who are allergic to the drug. This drug should not be prescribed for patients who are under 18 years unless it is under strict supervision by a doctor, where the doctor will also take x-rays of the patient every 6 months to ascertain that Oxymetholone is not affecting the child’s bone development.
| | Description | Oxymetholone is a synthetic, orally active anabolic-androgenic steroid (AAS) and 17α-methylated derivative of dihydrotestosterone (DHT). It is mainly used for the treatment of osteroporosis and anemia (low red blood cell count). It can also stimulate the muscle growth in malnourished or underdeveloped patients. It also has the potential to treat the HIV wasting syndrome. Oxymetholone can also lead to an even buildup in strength, which is its secondary characteristics, making it an excellent steroid to be coupled with other anabolic steroids to yield synergetic effect.
| | Chemical Properties | Oxymetholone is an odorless white to pale yellow crystalline solid or powder. Insoluble in water, easily soluble in chloroform, soluble in dioxane, vegetable oil, slightly soluble in ethanol and ether. It is sensitive to light (Akron 2009). It is structurally related to the male hormone testosterone (IARC 1977, NTP 1999). | | Uses | Oxymetholone is used in treatment of myelofibrosis and
myelosuppression. This drug can provoke bone marrow cells
and rise the blood cells in the peripheral blood vessels. It has
been approved by the US Food and Drug Administration for
the treatment of anemia caused by deficient red cell
production. It is effective in catabolic states, replacement of
male sex steroids in men who have androgen deficiency, and
in eugonadal male and female patients with acquired
immunodeficiency syndrome-associated wasting. | | Definition | ChEBI: Oxymetholone is a 3-oxo-5alpha- steroid that is 4,5alpha-dihydrotestosterone which is substituted by a hydroxymethylidene group at position 2 and by a methyl group at the 17alpha position. A synthetic androgen, it was mainly used for the treatment of anaemias until being replaced by treatments with fewer side effects. It has a role as an anabolic agent, an androgen and an anti-anaemic agent. It is a 17beta-hydroxy steroid, an enone, a tertiary alcohol, an enol, an anabolic androgenic steroid and a 3-oxo-5alpha-steroid. | | Brand name | Anadrol (Alaven). | | General Description | Oxymetholone is an odorless white to creamy white crystalline powder. It is approved for the treatment of various anemias. | | Air & Water Reactions | Insoluble in water. | | Reactivity Profile | Oxymetholone may be sensitive to light. | | Health Hazard | SYMPTOMS: Symptoms of exposure to Oxymetholone may include cholestatic jaundice, hepatocellular neoplasms and peliosis hepatitis. Prepubertal exposure may cause phallic enlargement and increased frequency of erection. Postpubertal exposure may cause inhibition of testicular function, testicular atrophy, oligospermia, impotence, chronic priapism, epididymitis, bladder irritability, clitoral enlargement, menstrual irregularities, increased or decreased libido, excitation, insomnia, nausea, vomiting, diarrhea, leukemia, gynecomastia, deepening of the voice in women, hirsutism and male-pattern baldness in women, acne, edema, retention of serum electrolytes and decreased glucose tolerance. It may also cause higher risk of developing liver cell tumors. Other symptoms include abnormal liver function tests, salt and water retention and masculinization, particularly of the female fetus. | | Fire Hazard | Flash point data for Oxymetholone are not available. Oxymetholone is probably combustible. | | Safety Profile | Confirmed human carcinogen producing liver tumors. Human systemic effects by ingestion: impaired liver function. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes. See also TESTOSTERONE. | | Potential Exposure | Oxymetholone is a controlled substance
(US), hormone and a systemic anabolic steroid. | | Carcinogenicity | Oxymetholone is reasonably anticipated to be a human carcinogenbased on limited evidence of carcinogenicity in humans. | | Environmental Fate | Oxymetholone may release into the environment through
various waste streams. If released to air, oxymetholone does
not absorb light at wavelengths >290 nm and therefore is
not expected to be susceptible to direct photolysis by
sunlight. If released to soil, oxymetholone is expected to have
moderate mobility. Occupational exposure to oxymetholone
may occur via dermal contact with this compound at workplaces
where oxymetholone is produced. It can be overused
intentionally in humans as a performance enhancement drug
in athletes. | | Shipping | UN3077 Environmentally hazardous substances,
solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous
material, Technical Name Required. | | Toxicity evaluation | Acute and Short-Term Toxicity (or Exposure)
Animal/Human
No exact data exist for carcinogenicity of oxymetholone in
human and animal. Oxymetholone is generally presumed to be
a nongenotoxic. This statement is based primarily on the results of mutagenicity test, repeated-dose toxicology studies, and the
predicted results of a 2-year rat carcinogenicity bioassay.
Use of oxymetholone by a pregnant mother can cause
virilization of a female fetus. Oxymetholone overdose
produces symptoms such as nausea and vomiting. Most of the
signs and symptoms appear after chronic toxicity. Patients are
expected to recover rapidly after acute overdose but there are
few data. ‘Body builders’ use doses many times the standard
therapeutic doses for these compounds but do not suffer acute
toxic effects.
Chronic Toxicity (or Exposure)
Human
Liver injury, jaundice, and gynecomastia can occur. Acne,
abnormal lipids, cardiovascular disease (including stroke and
myocardial infarction), abnormal glucose tolerance, muscular
hypertrophy in both sexes, and psychiatric disorder can happen
during or after prolonged treatment. Hypertension, left
ventricular hypertrophy, and premature coronary artery disease
have been reported. Also, stroke, aggressive behavior, depression,
mania, psychotic symptoms of hallucination, and delusion
in anabolic steroid abusers are seen. Fluid and electrolyte
impairments and retention of sodium and water in users lead
to edema. Hypercalcemia and insulin resistance with a fall in
glucose tolerance have been reported.
Chronic Toxicity (or Exposure)
Human
Liver injury, jaundice, and gynecomastia can occur. Acne,
abnormal lipids, cardiovascular disease (including stroke and
myocardial infarction), abnormal glucose tolerance, muscular
hypertrophy in both sexes, and psychiatric disorder can happen
during or after prolonged treatment. Hypertension, left
ventricular hypertrophy, and premature coronary artery disease
have been reported. Also, stroke, aggressive behavior, depression,
mania, psychotic symptoms of hallucination, and delusion
in anabolic steroid abusers are seen. Fluid and electrolyte
impairments and retention of sodium and water in users lead
to edema. Hypercalcemia and insulin resistance with a fall in
glucose tolerance have been reported.
Reproductive Toxicity
Women develop signs of virilism with increased facial hair,
male pattern baldness, acne, deepening of the voice, irregular
menses, and clitoral enlargement. Prostatic hypertrophy,
impotence, and small doses of anabolic steroids are said to
increase libido, but larger doses lead to azospermia and
impotence. Testicular atrophy is a common clinical feature of
long-term abuse of anabolic steroids. | | Incompatibilities | Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explosions.
Keep away from alkaline materials, strong bases,
strong acids, oxoacids, and epoxides. May be combustible
and light-sensitive. | | Waste Disposal | It is inappropriate and
possibly dangerous to the environment to dispose of
expired or waste pharmaceuticals by flushing them down
the toilet or discarding them to the trash. Household
quantities of expired or waste pharmaceuticals may be
mixed with wet cat litter or coffee grounds, doublebagged
in plastic, discard in trash. Larger quantities
shall carefully take into consideration applicable DEA,
EPA, and FDA regulations. If possible return the
pharmaceutical to the manufacturer for proper disposal
being careful to properly label and securely package the
material. Alternatively, the waste pharmaceutical shall be
labeled, securely packaged and transported by a state
licensed medical waste contractor to dispose by burial
in a licensed hazardous or toxic waste landfill or
incinerator. |
| | Oxymetholone Preparation Products And Raw materials |
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