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Dimethyltrienolone

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Dimethyltrienolone
Clinical data
Other namesRU-2420; 7α,17α-Dimethyltrenbolone; 7α,17α-Dimethyl-δ9,11-19-nortestosterone; 7α,17α-Dimethylestra-4,9,11-trien-17β-ol-3-one
Routes of
administration		By mouth
Drug classAndrogen;Anabolic steroid;Progestogen
Identifiers
  • (7R,8S,13S,14S,17S)-17-hydroxy-7,13,17-trimethyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC20H26O2
Molar mass298.426g·mol−1
3D model (JSmol)
  • C[C@@H]1CC2=CC(=O)CCC2=C3[C@@H]1[C@@H]4CC[C@]([C@]4(C=C3)C)(C)O
  • InChI=1S/C20H26O2/c1-12-10-13-11-14(21)4-5-15(13)16-6-8-19(2)17(18(12)16)7-9-20(19,3)22/h6,8,11-12,17-18,22H,4-5,7,9-10H2,1-3H3/t12-,17+,18-,19+,20+/m1/s1
  • Key:MEMDJKLEPFFNQS-ZGPIAVDESA-N

Dimethyltrienolone(developmental code nameRU-2420) is asynthetic,orally active,and extremelypotentanabolic–androgenic steroid(AAS) and17α-alkylated19-nortestosterone(nandrolone)derivativewhich was never marketed formedical use.[1]It has among the highest knownaffinityof any AAS for theandrogen(andprogesterone)receptors,[2][3]and has been said to be perhaps the most potent AAS to have ever been developed.[1]

Pharmacology

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Pharmacodynamics

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Dimethyltrienolone is an extremely potentagonistof theandrogenandprogesterone receptorsand hence AAS andprogestogen.[1]Inanimalbioassays,it was shown to possess more than 100 times theanabolicandandrogenicpotencyof the reference AASmethyltestosterone.[1]The drug is not asubstratefor5α-reductaseand so is not potentiated or inactivated in so-called "androgenic"tissueslike theprostate glandorskin.[1]It is also not a substrate foraromataseand so has noestrogenicactivity.[1]Due to its lack of estrogenicity, dimethyltrienolone has no propensity for causing estrogenicside effectslikegynecomastia.[1]Because of its C17αmethyl groupand very high resistance tohepaticmetabolism,dimethyltrienolone is said to be exceedinglyhepatotoxic.[1]

Relative affinities (%) of dimethyltrienolone and related steroids[4][5]
Compound Chemical name PRTooltip Progesterone receptor ARTooltip Androgen receptor ERTooltip Estrogen receptor GRTooltip Glucocorticoid receptor MRTooltip Mineralocorticoid receptor
Testosterone T 1.0 100 <0.1 0.17 0.9
Nandrolone 19-NT 20 154 <0.1 0.5 1.6
Trenbolone ∆9,11-19-NT 74 197 <0.1 2.9 1.33
Trestolone 7α-Me-19-NT 50–75 100–125 ? <1 ?
Normethandrone 17α-Me-19-NT 100 146 <0.1 1.5 0.6
Metribolone ∆9,11-17α-Me-19-NT 208 204 <0.1 26 18
Mibolerone 7α,17α-DiMe-19-NT 214 108 <0.1 1.4 2.1
Dimethyltrienolone ∆9,11-7α,17α-DiMe-19-NT 306 180 0.1 22 52
Values are percentages (%). Referenceligands(100%) wereprogesteronefor thePRTooltip progesterone receptor,testosteronefor theARTooltip androgen receptor,estradiolfor theERTooltip estrogen receptor,DEXATooltip dexamethasonefor theGRTooltip glucocorticoid receptor,andaldosteronefor theMRTooltip mineralocorticoid receptor.

Chemistry

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See also:List of androgens/anabolic steroids

Dimethyltrienolone, also known as 7α,17α-dimethyl-δ9,11-19-nortestosterone or as 7α,17α-dimethylestra-4,9,11-trien-17β-ol-3-one, as well as 7α,17α-dimethyltrenbolone, is asyntheticestranesteroidand a17α-alkylatedderivativeofnandrolone(19-nortestosterone).[1]It is the 7α,17α-dimethyl derivative oftrenboloneand the 7α-methyl derivative ofmetribolone,[6]as well as the δ9,11analogueofmetriboloneand the δ9,11,17α-methylated derivative oftrestolone.[1]

History

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Dimethyltrienolone was first described in 1967.[1][7]It was never marketed for medical use.[1]

See also

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References

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  1. ^abcdefghijklWilliam Llewellyn (2009).Anabolics.Molecular Nutrition Llc. pp. 212–214.ISBN978-0967930473.
  2. ^Waszkowycz B, Clark DE, Frenkel D, Li J, Murray CW, Robson B, Westhead DR (November 1994). "PRO_LIGAND: an approach to de novo molecular design. 2. Design of novel molecules from molecular field analysis (MFA) models and pharmacophores".Journal of Medicinal Chemistry.37(23): 3994–4002.doi:10.1021/jm00049a019.PMID7966160.
  3. ^Loughney DA, Schwender CF (December 1992). "A comparison of progestin and androgen receptor binding using the CoMFA technique".Journal of Computer-Aided Molecular Design.6(6): 569–581.Bibcode:1992JCAMD...6..569L.doi:10.1007/bf00126215.PMID1291626.S2CID22004130.
  4. ^Delettré J, Mornon JP, Lepicard G, Ojasoo T, Raynaud JP (January 1980). "Steroid flexibility and receptor specificity".Journal of Steroid Biochemistry.13(1): 45–59.doi:10.1016/0022-4731(80)90112-0.PMID7382482.
  5. ^Ojasoo T, Delettré J, Mornon JP, Turpin-VanDycke C, Raynaud JP (1987). "Towards the mapping of the progesterone and androgen receptors".Journal of Steroid Biochemistry.27(1–3): 255–269.doi:10.1016/0022-4731(87)90317-7.PMID3695484.
  6. ^Rabe T, Kesel L, Runnebaum B (6 December 2012)."Antiprogestins".In Ganten D, Pfaff D (eds.).Actions of Progesterone on the Brain.Springer Science & Business Media. pp. 17–.ISBN978-3-642-69728-9.
  7. ^Mathieu J (1967).Proceedings of the International Symposium on Drug Research, Montreal, Canada, June 12-14, 1967.Chemical Institute of Canada, Medical Chemistry Group, Montreal, Canada. p. 134.
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