Metenolone acetate

Metenolone acetate
Clinical data
Other names	NSC-74226; SH-567; SQ-16496
Routes of; administration	Oral
Identifiers
	IUPAC name [(5S,8R,9S,10S,13S,14S,17S)-1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate;
CAS Number	434-05-9;
PubChem CID	252372;
ChemSpider	3946;
UNII	W75590VPKQ;
CompTox Dashboard (EPA)	DTXSID40963004 ;
ECHA InfoCard	100.006.453
Chemical and physical data
Formula	C22H32O3
Molar mass	344.495 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=CC(=O)C[C@H]2[C@]1([C@H]3CC[C@]4([C@H]([C@@H]3CC2)CC[C@@H]4OC(=O)C)C)C;
	InChI InChI=1S/C22H32O3/c1-13-11-16(24)12-15-5-6-17-18-7-8-20(25-14(2)23)21(18,3)10-9-19(17)22(13,15)4/h11,15,17-20H,5-10,12H2,1-4H3/t15-,17-,18-,19-,20-,21-,22-/m0/s1; Key:PGAUJQOPTMSERF-QWQRBHLCSA-N;

Metenolone acetate (INN), or methenolone acetate (USAN, BANM) (brand names Primobolan, Primobolan S, Primonabol, Nibal), also known as 1-methyl-4,5α-dihydro-δ¹-testosterone 17β-acetate (1-methyl-δ¹-DHT 17β-acetate) or 1-methylandrost-1,4-dien-17β-ol-3-one 17β-acetate, is a synthetic, orally active anabolic-androgenic steroid (AAS) and derivative of dihydrotestosterone (DHT) that is marketed in Europe, Australia, and Mexico.^[1]^[2]^[3] It has been used in the treatment of bone marrow diseases and anemia.^[3] Metenolone acetate is the C17β acetate ester and a prodrug of metenolone,^[1]^[2] and is the form of metenolone that is used orally; the form that is used via depot intramuscular injection is metenolone enanthate.^[2] Along with mesterolone, metenolone acetate is one of the few AAS that is orally active but is not 17α-alkylated.^[4]

References

^ ^a ^b J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 784–. ISBN 978-1-4757-2085-3.
^ ^a ^b ^c Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 660–661. ISBN 978-3-88763-075-1.
^ ^a ^b I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 178–. ISBN 978-94-011-4439-1.
^ Kicman AT (June 2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–21. doi:10.1038/bjp.2008.165. PMID 18500378.