Oxymetholone

Oxymetholone
Clinical data
Trade names Androyd, Anadrol, Anapolon, Anasteronal, Hemogenin, Oxitosona, Roboral, Synasteron, Zenalosyn
AHFS/Drugs.com Consumer Drug Information
Pregnancy
category
  • X
Routes of
administration		 Oral
ATC code A14AA05 (WHO)
Legal status
Legal status
Pharmacokinetic data
Bioavailability 95%
Metabolism Hepatic
Biological half-life 8-9 hours
Excretion Urinary: 95%
Identifiers
Synonyms NSC-26198
CAS Number 434-07-1 N
PubChem (CID) 5281034
DrugBank DB06412 N
ChemSpider 4444502 YesY
UNII L76T0ZCA8K YesY
KEGG D00490 YesY
ChEBI CHEBI:7864 N
ChEMBL CHEMBL1200585 N
Chemical and physical data
Formula C21H32O3
Molar mass 332.48 g/mol
3D model (Jmol) Interactive image
 NYesY (what is this?)  (verify)

Oxymetholone (INN, USAN, BAN) (brand names Anadrol, Anapolon, others) is a synthetic, orally active anabolic-androgenic steroid (AAS) and 17α-methylated derivative of dihydrotestosterone (DHT) that is marketed in the United States, Europe, and elsewhere in the world.[1][2] It was first described in a 1959 paper by scientists from Syntex.[3][4] Its primary clinical applications include treatment of osteoporosis and anaemia, as well as stimulating muscle growth in malnourished or underdeveloped patients. The drug was approved for human use by the FDA. Later, non-steroidal drugs such as epoetin alfa were developed and proven to be more effective as a treatment for anaemia and osteoporosis without the side effects of oxymetholone. The drug remained available despite this and eventually found a new use in treating HIV wasting syndrome.

Presented most commonly as a 50 mg tablet, oxymetholone is one of the strongest androgenic steroids available.[5] Similarly, there is a risk of side effects.[6][7] Despite very low binding affinity with the androgen receptor, 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.

Side effects

The common side-effects of oxymetholone include depression, lethargy, headache, swelling, rapid 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.[6] In women, side effects also include acne, changes in menstrual periods, deepened voice, hair growth on the chin or chest, male pattern baldness, enlarged clitoris, and changes in sex drive.[6] Because of its 17α-alkylated structure, oxymetholone is highly 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.[7]

Chemistry

Oxymetholone is also known by the chemical names 2-hydroxymethylene-17α-methyl-4,5α-dihydrotestosterone (2-hydroxymethylene-17α-methyl-DHT) and 2-hydroxymethylene-17α-methylandrostan-17β-ol-3-one.

References

  1. ↑ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 924–. ISBN 978-1-4757-2085-3.
  2. ↑ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 779–. ISBN 978-3-88763-075-1.
  3. ↑ Pavlatos, AM; Fultz, O; Monberg, MJ; Vootkur, A; Pharmd (June 2001). "Review of oxymetholone: a 17alpha-alkylated anabolic-androgenic steroid.". Clinical therapeutics. 23 (6): 789–801; discussion 771. PMID 11440282.
  4. ↑ Zderic, John A.; Carpio, Humberto; Ringold, H. J. (January 1959). "Steroids. CVI. Synthesis of 7β-Methyl Hormone Analogs". Journal of the American Chemical Society. 81 (2): 432–436. doi:10.1021/ja01511a041.
  5. ↑ "Anadrol-50" (PDF). Meda Pharmaceuticals. December 2006. Retrieved 8 January 2012.
  6. 1 2 3 "Oxymetholone Side Effects". drugs.com.
  7. 1 2 "Anadrol Official FDA Information, Side Effects and Uses". drugs.com.


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