Oxabolone

Oxabolone is a synthetic anabolic-androgenic steroid (AAS) of the nandrolone (19-nortestosterone) group which was never marketed.^[1][2][3] It can be formulated as the cipionate ester prodrug oxabolone cipionate, which, in contrast, has been marketed for medical use.^[1][2][3]

Oxabolone

Clinical data
Other names	4-Hydroxy-19-nortestosterone; 4,17β-Dihydroxyestr-4-en-3-one; 19-Norandrost-4-ene-4,17β-diol-3-one
Routes of administration	Intramuscular injection (as oxabolone cipionate)
Drug class	Androgen; Anabolic steroid
Identifiers
IUPAC name (8R,9S,10R,13S,14S,17S)-4,17-dihydroxy-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
CAS Number	4721-69-1
ChemSpider	16736429
UNII	51RPF719WE
CompTox Dashboard (EPA)	DTXSID50878357
ECHA InfoCard	100.022.920
Chemical and physical data
Formula	C18H26O3
Molar mass	290.403 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C4CC[C@H]3C(/CC[C@@H]1[C@@H]3CC[C@]2(C)[C@@H](O)CC[C@@H]12)=C4/O
InChI InChI=1S/C18H26O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h10-12,14,16,20-21H,2-9H2,1H3/t10-,11-,12-,14+,16+,18+/m1/s1 Key:GXHBCWCMYVTJOW-YGRHGMIBSA-N

Oxabolone is on the World Anti-Doping Agency's list of prohibited substances,^[4] and is therefore banned from use in most major sports.

The 17α-methylated analogue of oxabolone is methylhydroxynandrolone (4-hydroxy-17α-methyl-19-nortestosterone) and the 17α- and 19-methylated derivative of oxabolone is oxymesterone (4-hydroxy-17α-methyltestosterone).^[1][2][3]