View source for RU-2309

{{Short description|Chemical compound}}
{{Drugbox
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| IUPAC_name = (8''S'',13''S'',14''S'',17''S'')-13-ethyl-17-hydroxy-17-methyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[''a'']phenanthren-3-one
| image = RU-2309.svg
| width = 225px
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| class = [[Androgen]]; [[Anabolic steroid]]
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| PubChem = 124385827
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| ChemSpiderID = 23208646
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| synonyms = 18-Methylmetribolone; 17α-Methyltetrahydrogestrinone; 17α-Methyl-THG; ∆<sup>9,11</sup>-17α,18-dimethyl-19-nortestosterone; 17α,18-Dimethylestr-4,9,11-trien-17β-ol-3-one
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| C=20 | H=26 | O=2
| SMILES = CC[C@]12C=CC3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@]2(C)O
| StdInChI_Ref =
| StdInChI = 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
| StdInChIKey_Ref =
| StdInChIKey = KTIKZXSPPAGDBN-FYQPLNBISA-N
}}
'''RU-2309''', also known as '''18-methylmetribolone''', '''δ<sup>9,11</sup>-17α,18-dimethyl-19-nortestosterone''', or '''17α,18-dimethylestr-4,9,11-trien-17β-ol-3-one''', is a [[17α-alkylated anabolic steroid|17α-alkylated]] [[androgen]]/[[anabolic steroid]] (AAS) of the [[19-nortestosterone]] group which was never marketed.<ref name="pmid7382482">{{cite journal | vauthors = Delettré J, Mornon JP, Lepicard G, Ojasoo T, Raynaud JP | title = Steroid flexibility and receptor specificity | journal = J. Steroid Biochem. | volume = 13 | issue = 1 | pages = 45–59 | date = January 1980 | pmid = 7382482 | doi = 10.1016/0022-4731(80)90112-0 }}</ref><ref name="pmid359134">{{cite journal | vauthors = Ojasoo T, Raynaud JP | title = Unique steroid congeners for receptor studies | journal = Cancer Res. | volume = 38 | issue = 11 Pt 2 | pages = 4186–98 | date = November 1978 | pmid = 359134 | url = http://cancerres.aacrjournals.org/content/38/11_Part_2/4186.short}}</ref><ref name="pmid1291626">{{cite journal | vauthors = Loughney DA, Schwender CF | title = A comparison of progestin and androgen receptor binding using the CoMFA technique | journal = J. Comput. Aided Mol. Des. | volume = 6 | issue = 6 | pages = 569–81 | date = December 1992 | pmid = 1291626 | doi = 10.1007/bf00126215| bibcode = 1992JCAMD...6..569L | s2cid = 22004130 }}</ref> It is the C18 [[methyl group|methyl]] or C13β [[ethyl group|ethyl]] [[chemical derivative|derivative]] of [[metribolone]].<ref name="pmid7382482" /><ref name="pmid359134" /> 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]].<ref name="Office2012">{{cite book|author=U. s. Government Printing Office|title=Food and Drugs, Part 1300 to End|url=https://books.google.com/books?id=piqKQFmlay8C&pg=PA6|date=29 May 2012|publisher=Government Printing Office|isbn=978-0-16-090721-0|pages=6–}}</ref> Hence, it could also be referred to as '''17α-methyl-THG'''.<ref name="Office2012" /> RU-2309 shows high [[affinity (pharmacology)|affinity]] for the [[androgen receptor|androgen]], [[progesterone receptor|progesterone]], and [[glucocorticoid receptor]]s.<ref name="pmid7382482" /><ref name="pmid359134" /><ref name="pmid1291626" />
==See also==
* [[List of androgens/anabolic steroids]]
==References==
{{Reflist}}
{{Androgen receptor modulators}}
{{Glucocorticoid receptor modulators}}
{{Progesterone receptor modulators}}
[[Category:Tertiary alcohols]]
[[Category:Anabolic–androgenic steroids]]
[[Category:Estranes]]
[[Category:Glucocorticoids]]
[[Category:Hepatotoxins]]
[[Category:Ketones]]
[[Category:Progestogens]]
{{Steroid-stub}}
{{Genito-urinary-drug-stub}}