Structure via PubChem · Public domain (PubChem)
oxymetholone
Sign in to saveAlso known as 17β-Hydroxy-2-hydroxymethylidene-17α-methyl-3-androstanone, Oximetolona, Oxymetholon, Oxymétholone, Oxymetholonum
Key facts
- Drug.C
- 21
- Drug.H
- 32
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 462267488
- Drug.IUPAC_name
- (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
- Drug.image
- Oxymetholone.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 250px
- Drug.tradename
- Anadrol, Anapolon, others
- Drug.pregnancy_category
- X
- Drug.legal_BR
- C5
- Drug.legal_CA
- Schedule IV
- Drug.legal_UK
- Class C
- Drug.legal_US
- Schedule III
- Drug.dependency_liability
- Moderate
- Drug.addiction_liability
- Moderate
- Drug.routes_of_administration
- By mouth
via Wikipedia infobox
Chemical data
- Formula
- C21H32O3
- Molecular weight
- 332.5 g/mol
- IUPAC name
- (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
- 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
- InChIKey
- ICMWWNHDUZJFDW-DHODBPELSA-N
- XLogP
- 4.4
- Polar surface area
- 57.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1972
- Admin. routes
- oral
via ChEMBL · EBI
Research
529 papers- Oxymetholone.BETA : bulletin of experimental treatments for AIDS : a publication of the San Francisco AIDS Foundation · 1998
- Oxymetholone.Report on carcinogens : carcinogen profiles · 2004
- Oxymetholone.Report on carcinogens : carcinogen profiles · 2011
- Oxymetholone.Report on carcinogens : carcinogen profiles · 2002
- Review of oxymetholone: a 17alpha-alkylated anabolic-androgenic steroid.Clinical therapeutics · 2001
via PubMed
Wikidata facts
- Mass
- 332.235145
- Has use
- medication
Show 5 more facts
- chemical formula
- C₂₁H₃₂O₃
- canonical SMILES
- CC12CCC3C(C1CCC2(C)O)CCC4C3(CC(=CO)C(=O)C4)C
- isomeric 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
- medical condition treated
- anemia
- Commons category
- Oxymetholone
via Wikidata · CC0
~7 min read
Encyclopedic overview
17 sectionsContents
- Medical uses
- Non-medical uses
- Side effects
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Generic names
- Brand names
- Availability
- United States
- Other countries
- Legal status
- References
- Further reading
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.
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.
Excerpted from Wikipedia’s “oxymetholone” article, available under the CC BY-SA 4.0 licence.