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	PR	AR	ER	GR	MR
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 PR, testosterone for the AR, estradiol for the ER, DEXA for the GR, and aldosterone for the MR.

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]

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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. doi:10.1007/bf00126215. PMID 1291626.
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. doi:10.1007/bf00126215. PMID 1291626.

[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.