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)

Safety Information

Hazard Codes 

T,Xn

Risk Statements 

40-63

Safety Statements 

53-22-26-36/37/39-36

WGK Germany 

3

RTECS 

BV8060000

HS Code 

29372900

Hazardous Substances Data

434-07-1(Hazardous Substances Data)

Toxicity

TDLo orl-hmn: 46 mg/kg/14W-I:LIV JAMAAP 240,243,78

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.

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