Oxymetholone

Oxymetholone
Clinical data
Trade names	Androyd, Anadrol, Anapolon, Anasteronal, Hemogenin, Oxitosona, Roboral, Synasteron, Zenalosyn
Other names	NSC-26198
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
Elimination half-life	8-9 hours
Excretion	Urinary: 95%
Identifiers
	IUPAC name 2-Hydroxymethylene-17α-methylandrostan-17β-ol-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	332.48 g/mol 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 ;
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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.^[1]^[2] It was first described in a 1959 paper by scientists from Syntex.^[3]^[4] 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.^[5] Similarly, there is a risk of side effects.^[6]^[7] 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

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.^[6] 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.^[6] 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.^[7]

Chemistry

Oxymetholone is also known by the chemical names 2-hydroxymethylene-17α-methyl-4,5α-dihydrotestosterone (2-hydroxymethylene-17α-methyl-DHT) and 2-hydroxymethylene-17α-methylandrostan-17β-ol-3-one.

References

^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 924–. ISBN 978-1-4757-2085-3.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 779–. ISBN 978-3-88763-075-1.
^ Pavlatos, AM; Fultz, O; Monberg, MJ; Vootkur, A; Pharmd (June 2001). "Review of oxymetholone: a 17alpha-alkylated anabolic-androgenic steroid". Clinical therapeutics. 23 (6): 789–801, discussion 771. PMID 11440282.
^ Zderic, John A.; Carpio, Humberto; Ringold, H. J. (January 1959). "Steroids. CVI. Synthesis of 7β-Methyl Hormone Analogs". Journal of the American Chemical Society. 81 (2): 432–436. doi:10.1021/ja01511a041.
^ "Anadrol-50" (PDF). Meda Pharmaceuticals. December 2006. Retrieved 8 January 2012.
^ ^a ^b ^c "Oxymetholone Side Effects". drugs.com.
^ ^a ^b "Anadrol Official FDA Information, Side Effects and Uses". drugs.com.

[Elks2014-1] J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 924–. ISBN 978-1-4757-2085-3.

[IndexNominum2000-2] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 779–. ISBN 978-3-88763-075-1.

[2001rev-3] Pavlatos, AM; Fultz, O; Monberg, MJ; Vootkur, A; Pharmd (June 2001). "Review of oxymetholone: a 17alpha-alkylated anabolic-androgenic steroid". Clinical therapeutics. 23 (6): 789–801, discussion 771. PMID 11440282.

[4] Zderic, John A.; Carpio, Humberto; Ringold, H. J. (January 1959). "Steroids. CVI. Synthesis of 7β-Methyl Hormone Analogs". Journal of the American Chemical Society. 81 (2): 432–436. doi:10.1021/ja01511a041.

[5] "Anadrol-50" (PDF). Meda Pharmaceuticals. December 2006. Retrieved 8 January 2012.

[drugs1-6] "Oxymetholone Side Effects". drugs.com.

[drugs2-7] "Anadrol Official FDA Information, Side Effects and Uses". drugs.com.

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