Oxymetholone

Systematic (IUPAC) name
17β-Hydroxy-2-hydroxymethylidene-17α-methyl-3-androstanone
Clinical data
AHFS/Drugs.com	Consumer Drug Information
Pregnancy category	X
Legal status	Schedule III (US)
Routes of administration	Oral
Pharmacokinetic data
Bioavailability	95%
Metabolism	Hepatic
Biological half-life	8-9 hours
Excretion	Urinary:95%
Identifiers
CAS Registry Number	434-07-1 N
ATC code	A14AA05
PubChem	CID: 5281034
ChemSpider	4444502 Y
UNII	L76T0ZCA8K Y
KEGG	D00490 Y
ChEBI	CHEBI:7864 N
ChEMBL	CHEMBL1200585 N
Chemical data
Formula	C21H32O3
Molecular mass	332.48 g/mol
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
N (what is this?)  (verify)

Oxymetholone, marketed as Anadrol and Anapolon, is a synthetic anabolic steroid developed in 1960 by Zoltan 'Anadrol Z' F.^{[citation needed]} 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.^[1] Similarly, there is a risk of side effects.^[2][3] 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.^[2] 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.^[2] 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.^[3] It is dangerous to take oxymetholone in high dosages (100mg+) for periods of time exceeding four weeks.

References[edit]