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Dimethyltrienolone

From Wikipedia, the free encyclopedia
Anabolic–androgenic steroid
Pharmaceutical compound
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 mass298.426 g·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)derivative which was never marketed formedical use.[1] It has among the highest knownaffinity of 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 potentagonist of theandrogen andprogesterone receptors and hence AAS andprogestogen.[1] Inanimalbioassays, it was shown to possess more than 100 times theanabolic andandrogenicpotency of the reference AASmethyltestosterone.[1] The drug is not asubstrate for5α-reductase and so is not potentiated or inactivated in so-called "androgenic"tissues like theprostate gland orskin.[1] It is also not a substrate foraromatase and so has noestrogenic activity.[1] Due to its lack of estrogenicity, dimethyltrienolone has no propensity for causing estrogenicside effects likegynecomastia.[1] Because of its C17αmethyl group and very high resistance tohepaticmetabolism, dimethyltrienolone is said to be exceedinglyhepatotoxic.[1]

Relative affinities (%) of dimethyltrienolone and related steroids[4][5]
CompoundChemical namePRTooltip Progesterone receptorARTooltip Androgen receptorERTooltip Estrogen receptorGRTooltip Glucocorticoid receptorMRTooltip Mineralocorticoid receptor
TestosteroneT1.0100<0.10.170.9
Nandrolone19-NT20154<0.10.51.6
Trenbolone9,11-19-NT74197<0.12.91.33
Trestolone7α-Me-19-NT50–75100–125?<1?
Normethandrone17α-Me-19-NT100146<0.11.50.6
Metribolone9,11-17α-Me-19-NT208204<0.12618
Mibolerone7α,17α-DiMe-19-NT214108<0.11.42.1
Dimethyltrienolone9,11-7α,17α-DiMe-19-NT3061800.12252
Values are percentages (%). Referenceligands (100%) wereprogesterone for thePRTooltip progesterone receptor,testosterone for theARTooltip androgen receptor,estradiol for theERTooltip estrogen receptor,DEXATooltip dexamethasone for theGRTooltip glucocorticoid receptor, andaldosterone for theMRTooltip mineralocorticoid receptor.

Chemistry

[edit]
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 asyntheticestranesteroid and a17α-alkylatedderivative ofnandrolone (19-nortestosterone).[1] It is the 7α,17α-dimethyl derivative oftrenbolone and the 7α-methyl derivative ofmetribolone,[6] as well as the δ9,11analogue ofmetribolone and 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.ISBN 978-0967930473.
  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.PMID 7966160.
  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.PMID 1291626.S2CID 22004130.
  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.PMID 7382482.
  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.PMID 3695484.
  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–.ISBN 978-3-642-69728-9.
  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.
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
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