Oxymetholone

Overview

Oxymetholone, sold under the brand names Anadrol and Anapolon among others, is an androgen and anabolic steroid (AAS) medication which is used primarily in the treatment of anemia. It is also used to treat osteoporosis, HIV/AIDS wasting syndrome, and to promote weight gain and muscle growth in certain situations. It is taken by mouth.[1][2][3] WP

Side effects of oxymetholone include increased sexual desire as well as symptoms of masculinization like acne, increased hair growth, and voice changes. It can also cause liver damage. The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). It has strong anabolic effects and weak androgenic effects.[1][2][4] WP

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 United States. 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.[1][5–8] WP

Uses, dosage and effects

Medical uses

The primary clinical applications of oxymetholone include treatment of anemia and osteoporosis, as well as stimulating muscle growth in malnourished or underdeveloped patients. However, in the United States, the only remaining FDA (Food and Drug Administration)-approved indication is the treatment of anemia.[1][9] WP

Following the introduction of oxymetholone, nonsteroidal drugs such as epoetin alfa were developed and shown 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/AIDS wasting syndrome.[1] WP

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 bodybuilders and athletes.[1][10][11][12] WP

Non-medical uses

Oxymetholone is used for physique- and performance-enhancing purposes by competitive athletes, bodybuilders, and powerlifters.[1] WP

Risks and side effects

Side effects

The common side effects of oxymetholone include depression, lethargy, headache, swelling, fast and excessive 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, voice deepening, hair growth on the chin or chest, pattern hair loss, enlarged clitoris, and changes in libido. Because of its 17α-alkylated structure, oxymetholone is 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.[1][11][12] WP

Pharmacology

Pharmacodynamics

Like other AAS, oxymetholone is an agonist 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 anabolic to androgenic activity.[1] WP

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 does not possess any significant progestogenic activity.[1][13][14][15] WP

Pharmacokinetics

There is limited information available on the pharmacokinetics 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 metabolized in the liver by oxidation at the C2 position, reduction at the C3 position, hydroxylation at the C17 position, and conjugation. The C2 hydroxymethylene group of oxymetholone can be cleaved to form mestanolone (17α-methyl-DHT), which may contribute to the effects of oxymetholone. The elimination half-life of oxymetholone is unknown. Oxymetholone and its metabolites are eliminated in the urine.[1][2][16][17] WP

History

History

Oxymetholone was first described in a 1959 paper by scientists from Syntex. It was introduced for medical use by Syntex and Imperial Chemical Industries in the United Kingdom under the brand name Anapolon by 1961. Oxymetholone was also introduced under the brand names Adroyd (Parke-Davis) by 1961 and Anadrol (Syntex) by 1962. The drug was marketed in the United States in the early 1960s.[1][5][6][7][18][19][20] WP

Legal status

Generic names

Oxymetholone is the generic name of the drug and its INN (International Nonproprietary Name), USAN (United States Adopted Name), USP (United States Pharmacopeia), BAN (British Approved Name), and JAN (Japanese Accepted Name), while oxymétholone is its DCF (Dénomination Commune Française).[8][21][22][23] WP

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.[1][8][21][22][24] WP

United states

Oxymetholone is one of the few AAS that remains available for medical use in the United States. The others (as of August 2023) are testosterone, testosterone cypionate, testosterone enanthate, testosterone undecanoate, methyltestosterone, fluoxymesterone, and nandrolone[25] WP

Other countries

The availability of oxymetholone is fairly limited and seems to be scattered into isolated markets in Europe, Asia, and North and South America. It is known to be available in Turkey, Greece, Moldova, Iran, Thailand, Brazil, and Paraguay. At least historically, it has also been available in Canada, the United Kingdom, Belgium, the Netherlands, Spain, Poland, The UAE, Israel, Hong Kong, and India.[1][8][22] WP

Legal status

Oxymetholone, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act.[26] WP

Chemistry

Formula

C21H32O3 PC

CAS number

434-07-1 PC

Molar mass (g/mol)

332.5 PC

IUPAC name (computed by PubChem)

(2Z,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-2-(hydroxymethylidene)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one PC

SMILES

C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CC[C@@H]4[C@@]3(C/C(=C/O)/C(=O)C4)C PC

InChIKey

ICMWWNHDUZJFDW-DHODBPELSA-N PC

PubChem CID

5281034

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other William Llewellyn. Anabolics. 2011
2. Journal / agency Pavlatos AM, Fultz O, Monberg MJ, Vootkur A. Review of oxymetholone: a 17alpha-alkylated anabolic-androgenic steroid. Clinical Therapeutics. June 2001. doi:10.1016/s0149-2918(01)80070-9 · PMID 11440282
3. Other Oxymetholone Powder Uses
4. Journal / agency Kicman AT. Pharmacology of anabolic steroids. British Journal of Pharmacology. June 2008. doi:10.1038/bjp.2008.165 · PMID 18500378 · PMC2439524
5. Journal / agency Zderic JA, Carpio H, Ringold HJ. Steroids. CVI. Synthesis of 7β-Methyl Hormone Analogs. Journal of the American Chemical Society. January 1959. doi:10.1021/ja01511a041
6. Journal / agency Advertisements. Proceedings of the Royal Society of Medicine. 1961. PMC1870224
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8. Other Oxymetholone
9. Journal / agency Oxymetholone
10. Other Anadrol-50. December 2006
11. Other Oxymetholone Side Effects
12. Other Anadrol Official FDA Information, Side Effects and Uses
13. Journal / agency Hengge UR, Stocks K, Wiehler H, Faulkner S, Esser S, Lorenz C, Jentzen W, Hengge D, Goos M, Dudley RE, Ringham G. Double-blind, randomized, placebo-controlled phase III trial of oxymetholone for the treatment of HIV wasting. AIDS. March 2003. doi:10.1097/00002030-200303280-00008 · PMID 12646793
14. Journal / agency Cortesgallegos V, Castaneda G, Alonso R, Perezpasten E, Reyeslugo V, Barron C, Mondragon L, Villalpando S. Spontaneous and Oxymetholone-Induced Gynecomastia. Journal of Andrology. January 1982
15. Journal / agency Villalpando S, Mondragon L, Barron C, Reyeslugo U, Perezpasten E, Alonso R, Castaneda G, Gallegos V. 5-Alpha Reductase Blockade May Be Responsible for Spontaneous and Oxymetholone-Induced Gynecomastia. Archivos de Investigacion Medica. January 1982
16. Journal / agency Saartok T, Dahlberg E, Gustafsson JA. Relative binding affinity of anabolic-androgenic steroids: comparison of the binding to the androgen receptors in skeletal muscle and in prostate, as well as to sex hormone-binding globulin. Endocrinology. June 1984. doi:10.1210/endo-114-6-2100 · PMID 6539197
17. Other Hochadel, Maryanne. Mosby's Drug Reference for Health Professions. 1 April 2015
18. Journal / agency Locum R. Latest Pharmaceutical Preparations. The Central African Journal of Medicine. 1961
19. Journal / agency Clark GM. New drugs in rheumatic disease. Arthritis and Rheumatism. August 1962. doi:10.1002/art.1780050411 · PMID 13879693
20. Journal / agency Matusow, Paul D. If - Then; C.A.M.S.I.; In the future. Dalhousie Medical Journal. 1962
21. Other Elks J. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 14 November 2014
22. Other Index Nominum 2000: International Drug Directory. January 2000
23. Other Morton IK, Hall JM. Concise Dictionary of Pharmacological Agents: Properties and Synonyms. 6 December 2012
24. Other Kochakian, Charles D. Anabolic-Androgenic Steroids. 6 December 2012
25. Journal / agency Drugs@FDA: FDA Approved Drug Products
26. Other Karch SB. Drug Abuse Handbook, Second Edition. 21 December 2006

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.