RU-2309

RU-2309, also known as 18-methylmetribolone, δ^9,11-17α,18-dimethyl-19-nortestosterone, or 17α,18-dimethylestr-4,9,11-trien-17β-ol-3-one, is a 17α-alkylated androgen/anabolic steroid (AAS) of the 19-nortestosterone group which was never marketed.^[1][2][3] It is the C18 methyl or C13β ethyl derivative of metribolone.^[1][2] The compound is closely related to tetrahydrogestrinone (THG), which has the same chemical structure as RU-2309 except for possessing an ethyl group at the C17α position instead of a methyl group.^[4] Hence, it could also be referred to as 17α-methyl-THG.^[4] RU-2309 shows high affinity for the androgen, progesterone, and glucocorticoid receptors.^[1][2][3]

RU-2309

Clinical data
Other names	18-Methylmetribolone; 17α-Methyltetrahydrogestrinone; 17α-Methyl-THG; ∆9,11-17α,18-dimethyl-19-nortestosterone; 17α,18-Dimethylestr-4,9,11-trien-17β-ol-3-one
Drug class	Androgen; Anabolic steroid
Identifiers
IUPAC name (8S,13S,14S,17S)-13-ethyl-17-hydroxy-17-methyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
PubChem CID	124385827
ChemSpider	23208646
Chemical and physical data
Formula	C20H26O2
Molar mass	298.426 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC[C@]12C=CC3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@]2(C)O
InChI InChI=1S/C20H26O2/c1-3-20-11-8-16-15-7-5-14(21)12-13(15)4-6-17(16)18(20)9-10-19(20,2)22/h8,11-12,17-18,22H,3-7,9-10H2,1-2H3/t17-,18+,19+,20+/m1/s1 Key:KTIKZXSPPAGDBN-FYQPLNBISA-N

See also

• List of androgens/anabolic steroids

References

1. Delettré J, Mornon JP, Lepicard G, Ojasoo T, Raynaud JP (January 1980). "Steroid flexibility and receptor specificity". J. Steroid Biochem. 13 (1): 45–59. doi:10.1016/0022-4731(80)90112-0. PMID 7382482.
2. Ojasoo T, Raynaud JP (November 1978). "Unique steroid congeners for receptor studies". Cancer Res. 38 (11 Pt 2): 4186–98. PMID 359134.
3. Loughney DA, Schwender CF (December 1992). "A comparison of progestin and androgen receptor binding using the CoMFA technique". J. Comput. Aided Mol. Des. 6 (6): 569–81. Bibcode:1992JCAMD...6..569L. doi:10.1007/bf00126215. PMID 1291626. S2CID 22004130.
4. U. s. Government Printing Office (29 May 2012). Food and Drugs, Part 1300 to End. Government Printing Office. pp. 6–. ISBN 978-0-16-090721-0.