Oxymetholone

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Oxymetholone
Oxymetholone.svg
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
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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.006.454
Chemical and physical data
Formula C21H32O3
Molar mass 332.48 g/mol
3D model (JSmol)
 NYesY (what is this?)  (verify)

Oxymetholone (brand names Anadrol, Anapolon, others) is a synthetic, orally active anabolic-androgenic steroid (AAS) and 17α-methylated derivative of dihydrotestosterone (DHT) which is marketed in the United States, Europe, and elsewhere in the world.[1][2]

Medical uses[edit]

The primary clinical applications of oxymetholone include treatment of osteoporosis and anemia, 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 anemia 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.[3] Similarly, there is a risk of side effects.[4][5] Despite very low binding affinity with the androgen receptor, oxymetholone is highly effective in promoting extensive gains in body mass,[citation needed] mostly by greatly improving protein synthesis. For this reason, it is often used by bodybuilders and athletes.

Side effects[edit]

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.[4] 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.[4] 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.[5]

Pharmacology[edit]

Like other AAS, oxymetholone is an agonist of the androgen receptor (AR).[6] It is not a substrate for 5α-reductase and is a poor substrate for 3α-hydroxysteroid dehydrogenase (3α-HSD), and therefore shows a high ratio of anabolic to androgenic activity.[6]

As a DHT derivative, oxymetholone is not a substrate for aromatase and hence cannot be aromatized into estrogenic metabolites.[6] 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.[6][7][8][9] It has been suggested that this may be due to direct binding to and activation of the estrogen receptor by oxymetholone.[6]

Oxymetholone does not possess any significant progestogenic activity.[6]

Chemistry[edit]

Oxymetholone, also known as 2-hydroxymethylene-17α-methyl-4,5α-dihydrotestosterone (2-hydroxymethylene-17α-methyl-DHT) or as 2-hydroxymethylene-17α-methylandrostan-17β-ol-3-one, is a synthetic androstane steroid and a 17α-alkylated derivative of DHT.

Synthesis[edit]

A chemical synthesis of oxymetholone is shown as follows:[citation needed]

Oxymetholone synthesis.svg

History[edit]

Oxymetholone was first described in a 1959 paper by scientists from Syntex.[10][11]

Society and culture[edit]

Generic name[edit]

Oxymetholone is the INN, USAN, BAN of the drug.

References[edit]

  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. ^ "Anadrol-50" (PDF). Meda Pharmaceuticals. December 2006. Retrieved 8 January 2012. 
  4. ^ a b c "Oxymetholone Side Effects". drugs.com. 
  5. ^ a b "Anadrol Official FDA Information, Side Effects and Uses". drugs.com. 
  6. ^ a b c d e f William Llewellyn (2009). Anabolics. Molecular Nutrition Llc. p. 149. ISBN 978-0967930473. 
  7. ^ Hengge UR, Stocks K, Wiehler H, Faulkner S, Esser S, Lorenz C, Jentzen W, Hengge D, Goos M, Dudley RE, Ringham G (2003). "Double-blind, randomized, placebo-controlled phase III trial of oxymetholone for the treatment of HIV wasting". AIDS. 17 (5): 699–710. PMID 12646793. doi:10.1097/01.aids.0000050853.71999.16. 
  8. ^ CORTESGALLEGOS, V., CASTANEDA, G., ALONSO, R., PEREZPASTEN, E., REYESLUGO, V., BARRON, C., ... & VILLALPANDO, S. (1982, January). SPONTANEOUS AND OXYMETHOLONE-INDUCED GYNECOMASTIA. In JOURNAL OF ANDROLOGY (Vol. 3, No. 1, pp. 33-33). C/O ALLEN PRESS, INC PO BOX 368, LAWRENCE, KS 66044: AMER SOC ANDROLOGY, INC.
  9. ^ VILLALPANDO, S., Mondragon, L., Barron, C., REYESLUGO, U., PEREZPASTEN, E., Alonso, R., ... & GALLEGOS, V. (1982, January). 5-ALPHA REDUCTASE BLOCKADE MAY BE RESPONSIBLE FOR SPONTANEOUS AND OXYMETHOLONE-INDUCED GYNECOMASTIA. In ARCHIVOS DE INVESTIGACION MEDICA (Vol. 13, No. 2, pp. S13-S13). SOCIAL APDO POSTAL 73-032, MEXICO DF 03020, MEXICO: INST MEXICANO SEGURO.
  10. ^ 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. 
  11. ^ 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.