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	CA: Schedule IV US: Schedule III
Pharmacokinetic data
Bioavailability	95%
Metabolism	Hepatic
Biological half-life	8-9 hours
Excretion	Urinary: 95%
Identifiers
IUPAC name 2-Hydroxymethylene-17α-methylandrostan-17β-ol-3-one
Synonyms	NSC-26198
CAS Number	434-07-1^N
PubChem (CID)	5281034
DrugBank	DB06412^N
ChemSpider	4444502^Y
UNII	L76T0ZCA8K^Y
KEGG	D00490^Y
ChEBI	CHEBI:7864^N
ChEMBL	CHEMBL1200585^N
ECHA InfoCard	100.006.454
Chemical and physical data
Formula	C₂₁H₃₂O₃
Molar mass	332.48 g/mol
3D model (Jmol)	Interactive image
SMILES O=C4/C(=C\O)C[C@]1([C@@H](CC[C@@H]2[C@@H]1CC[C@]3([C@H]2CC[C@@]3(O)C)C)C4)C
InChI InChI=1S/C21H32O3/c1-19-11-13(12-22)18(23)10-14(19)4-5-15-16(19)6-8-20(2)17(15)7-9-21(20,3)24/h12,14-17,22,24H,4-11H2,1-3H3/b13-12-/t14-,15+,16-,17-,19-,20-,21-/m0/s1^Y Key:ICMWWNHDUZJFDW-DHODBPELSA-N^Y
^NY (what is this?)

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. It was first described in a 1959 paper by scientists from Syntex. 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. Similarly, there is a risk of side effects. 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.

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