Oxymetholone

Oxymetholone
Clinical data
Trade namesAnadrol, Anapolon, others
Other namesCI-406; NSC-26198; 2-Hydroxymethylene-17α-methyl-4,5α-dihydrotestosterone; 2-Hydroxymethylene-17α-methyl-DHT; 2-Hydroxymethylene-17α-methyl-5α-androstan-17β-ol-3-one
AHFS/Drugs.comConsumer Drug Information
Pregnancy
category
  • X
Dependence
liability		Moderate [1]
Addiction
liability		Moderate [1]
Routes of
administration		By mouth
Drug classAndrogen; Anabolic steroid
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityWell-absorbed[3]
MetabolismLiver[3][4]
Elimination half-lifeUnknown[4]
ExcretionUrine[3][4]
Identifiers
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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.454
Chemical and physical data
FormulaC21H32O3
Molar mass332.484 g·mol−1
3D model (JSmol)
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?)  (verify)

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.[5][6] It is also used to treat osteoporosis, HIV/AIDS wasting syndrome, and to promote weight gain[7] and muscle growth in certain situations.[5] It is taken by mouth.[5][6]

Side effects of oxymetholone include increased sexual desire as well as symptoms of masculinization like acne, increased hair growth, and voice changes.[5] It can also cause liver damage.[5][6] 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).[5][8] It has strong anabolic effects and weak androgenic effects.[5]

Oxymetholone was first prescribed in 1959 and was introduced for medical use but was discontinued in 1961 due its high lipid toxicity.[5][9][10][11] It is used mostly in the United States.[5][12] In addition to its medical use, oxymetholone is used to improve physique and performance.[5] The drug is a controlled substance in many countries and so non-medical use is generally illicit.[5]

  1. ^ a b "Anabolic steroid misuse". nhs.uk. 2022-11-04. Retrieved 2024-07-12.
  2. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  3. ^ a b c Cite error: The named reference pmid6539197 was invoked but never defined (see the help page).
  4. ^ a b c Cite error: The named reference HochadelMosby2015 was invoked but never defined (see the help page).
  5. ^ a b c d e f g h i j k William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 323–334. ISBN 978-0-9828280-1-4.
  6. ^ a b c Pavlatos AM, Fultz O, Monberg MJ, Vootkur A (June 2001). "Review of oxymetholone: a 17alpha-alkylated anabolic-androgenic steroid". Clinical Therapeutics. 23 (6): 789–801, discussion 771. doi:10.1016/s0149-2918(01)80070-9. PMID 11440282.
  7. ^ "Oxymetholone Powder Uses". aea.ltd. Retrieved 2022-12-17.
  8. ^ Kicman AT (June 2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–21. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.
  9. ^ Cite error: The named reference ZdericCarpio1959 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference ProcRSocMed1961 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference BrMedJ1961 was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
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