Metenolone acetate

Metenolone acetate

Clinical data
Trade names	Primobolan, Primobolan S, Primonabol, Nibal
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
Synonyms	NSC-74226; SH-567; SQ-16496
CAS Number	434-05-9
PubChem CID	252372
ChemSpider	3946
UNII	W75590VPKQ
Chemical and physical data
Formula	C22H32O3
Molar mass	344.50 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. It has been used in the treatment of bone marrow diseases and anemia. Metenolone acetate is the C17β acetate ester and a prodrug of metenolone, and is the form of metenolone that is used orally; the form that is used via depot intramuscular injection is metenolone enanthate. Along with mesterolone, metenolone acetate is one of the few AAS that is orally active but is not 17α-alkylated.