Oxymetholone

Oxymetholone
Clinical data
Trade names	Anadrol, Anapolon, others
Other names	CI-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.com	Consumer Drug Information
Pregnancy; category	X;
Dependence; liability	Moderate
Addiction; liability	Moderate
Routes of; administration	By mouth
Drug class	Androgen; Anabolic steroid
ATC code	A14AA05 (WHO) ;
Legal status
Legal status	BR: Class C5 (Anabolic steroids); CA: Schedule IV; UK: Class C; US: Schedule III;
Pharmacokinetic data
Bioavailability	Well-absorbed
Metabolism	Liver
Elimination half-life	Unknown
Excretion	Urine
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	434-07-1 ;
PubChem CID	5281034;
DrugBank	DB06412 ;
ChemSpider	4444502 ;
UNII	L76T0ZCA8K;
KEGG	D00490 ;
ChEBI	CHEBI:7864 ;
ChEMBL	ChEMBL1200585 ;
CompTox Dashboard (EPA)	DTXSID5023794 ;
ECHA InfoCard	100.006.454
Chemical and physical data
Formula	C21H32O3
Molar mass	332.484 g·mol−1
3D model (JSmol)	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 ; Key:ICMWWNHDUZJFDW-DHODBPELSA-N ;
	(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]

^ ^a ^b "Anabolic steroid misuse". nhs.uk. 2022-11-04. Retrieved 2024-07-12.
^ 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.
^ ^a ^b ^c Cite error: The named reference pmid6539197 was invoked but never defined (see the help page).
^ ^a ^b ^c Cite error: The named reference HochadelMosby2015 was invoked but never defined (see the help page).
^ ^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.
^ ^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.
^ "Oxymetholone Powder Uses". aea.ltd. Retrieved 2022-12-17.
^ 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.
^ Cite error: The named reference ZdericCarpio1959 was invoked but never defined (see the help page).
^ Cite error: The named reference ProcRSocMed1961 was invoked but never defined (see the help page).
^ Cite error: The named reference BrMedJ1961 was invoked but never defined (see the help page).
^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).

[d982-1] "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.

[pmid6539197-3] Cite error: The named reference pmid6539197 was invoked but never defined (see the help page).

[HochadelMosby2015-4] Cite error: The named reference HochadelMosby2015 was invoked but never defined (see the help page).

[Llewellyn2011-5] ^ ^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.

[pmid11440282-6] 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.

[pmid18500378-8] 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.

[ZdericCarpio1959-9] Cite error: The named reference ZdericCarpio1959 was invoked but never defined (see the help page).

[ProcRSocMed1961-10] Cite error: The named reference ProcRSocMed1961 was invoked but never defined (see the help page).

[BrMedJ1961-11] Cite error: The named reference BrMedJ1961 was invoked but never defined (see the help page).

[Drugs.com-12] Cite error: The named reference Drugs.com was invoked but never defined (see the help page).

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Oxymetholone

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