Dimethyltrienolone

Dimethyltrienolone
Clinical data
Other names	RU-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 class	Androgen; Anabolic steroid; Progestogen
Identifiers
	IUPAC name (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	10110-86-8 ;
PubChem CID	101678228;
ChemSpider	23208745;
UNII	8GP0J5637H;
ChEMBL	ChEMBL128880;
Chemical and physical data
Formula	C20H26O2
Molar mass	298.426 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@@H]1CC2=CC(=O)CCC2=C3[C@@H]1[C@@H]4CC[C@]([C@]4(C=C3)C)(C)O;
	InChI 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 name RU-2420) is a synthetic, orally active, and extremely potent anabolic–androgenic steroid (AAS) and 17α-alkylated 19-nortestosterone (nandrolone) derivative which was never marketed for medical use.[1] It has among the highest known affinity of any AAS for the androgen (and progesterone) receptors,[2][3] and has been said to be perhaps the most potent AAS to have ever been developed.[1]

Pharmacology

Pharmacodynamics

Dimethyltrienolone is an extremely potent agonist of the androgen and progesterone receptors and hence AAS and progestogen.[1] In animal bioassays, it was shown to possess more than 100 times the anabolic and androgenic potency of the reference AAS methyltestosterone.[1] The drug is not a substrate for 5α-reductase and so is not potentiated or inactivated in so-called "androgenic" tissues like the prostate gland or skin.[1] It is also not a substrate for aromatase and so has no estrogenic activity.[1] Due to its lack of estrogenicity, dimethyltrienolone has no propensity for causing estrogenic side effects like gynecomastia.[1] Because of its C17α methyl group and very high resistance to hepatic metabolism, dimethyltrienolone is said to be exceedingly hepatotoxic.[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 (%). Reference ligands (100%) were progesterone for the PRTooltip progesterone receptor, testosterone for the ARTooltip androgen receptor, estradiol for the ERTooltip estrogen receptor, DEXATooltip dexamethasone for the GRTooltip glucocorticoid receptor, and aldosterone for the MRTooltip mineralocorticoid receptor.

Chemistry

Dimethyltrienolone, also known as 7α,17α-dimethyl-δ^9,11-19-nortestosterone or as 7α,17α-dimethylestra-4,9,11-trien-17β-ol-3-one, as well as 7α,17α-dimethyltrenbolone, is a synthetic estrane steroid and a 17α-alkylated derivative of nandrolone (19-nortestosterone).[1] It is the 7α,17α-dimethyl derivative of trenbolone and the 7α-methyl derivative of metribolone,[6] as well as the δ^9,11 analogue of metribolone and the δ^9,11, 17α-methylated derivative of trestolone.[1]

History

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

References

William Llewellyn (2009). Anabolics. Molecular Nutrition Llc. pp. 212–214. ISBN 978-0967930473.
Waszkowycz B, Clark DE, Frenkel D, Li J, Murray CW, Robson B, Westhead DR (1994). "PRO_LIGAND: an approach to de novo molecular design. 2. Design of novel molecules from molecular field analysis (MFA) models and pharmacophores". J. Med. Chem. 37 (23): 3994–4002. doi:10.1021/jm00049a019. PMID 7966160.
Loughney DA, Schwender CF (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.
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.
Ojasoo T, Delettré J, Mornon JP, Turpin-VanDycke C, Raynaud JP (1987). "Towards the mapping of the progesterone and androgen receptors". J. Steroid Biochem. 27 (1–3): 255–69. doi:10.1016/0022-4731(87)90317-7. PMID 3695484.
D. Ganten; D. Pfaff (6 December 2012). Actions of Progesterone on the Brain. Springer Science & Business Media. pp. 17–. ISBN 978-3-642-69728-9.
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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[Llewellyn2009-1] William Llewellyn (2009). Anabolics. Molecular Nutrition Llc. pp. 212–214. ISBN 978-0967930473.

[pmid7966160-2] Waszkowycz B, Clark DE, Frenkel D, Li J, Murray CW, Robson B, Westhead DR (1994). "PRO_LIGAND: an approach to de novo molecular design. 2. Design of novel molecules from molecular field analysis (MFA) models and pharmacophores". J. Med. Chem. 37 (23): 3994–4002. doi:10.1021/jm00049a019. PMID 7966160.

[pmid1291626-3] Loughney DA, Schwender CF (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.

[pmid7382482-4] 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.

[pmid3695484-5] Ojasoo T, Delettré J, Mornon JP, Turpin-VanDycke C, Raynaud JP (1987). "Towards the mapping of the progesterone and androgen receptors". J. Steroid Biochem. 27 (1–3): 255–69. doi:10.1016/0022-4731(87)90317-7. PMID 3695484.

[GantenPfaff2012-6] D. Ganten; D. Pfaff (6 December 2012). Actions of Progesterone on the Brain. Springer Science & Business Media. pp. 17–. ISBN 978-3-642-69728-9.

[Mathieu1967-7] 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.