7α-Methylestradiol

7α-Methylestradiol (7α-Me-E2), also known as 7α-methylestra-1,3,5(10)-triene-3,17β-diol, is a synthetic estrogen and an active metabolite of the androgen/anabolic steroids trestolone/Methandienone.[1][2][3] It is considered to be responsible for the estrogenic activity of trestolone.[2][3] The compound shows about the same affinity for the estrogen receptor as estradiol.[1]

Relative affinities (%) of 7α-methylestradiol and related steroids[1][4][5][6]
CompoundPRTooltip Progesterone receptorARTooltip Androgen receptorERTooltip Estrogen receptorGRTooltip Glucocorticoid receptorMRTooltip Mineralocorticoid receptorSHBGTooltip Sex hormone-binding globulinCBGTooltip Corticosteroid binding globulin
Estradiol2.67.91000.60.138.7<0.1
7α-Methylestradiol1–315–25101<1<1 ? ?
Trestolone50–75100–125 ?<1 ? ? ?
Values are percentages (%). Reference ligands (100%) were progesterone for the PRTooltip progesterone receptor, testosterone for the ARTooltip androgen receptor, E2 for the ERTooltip estrogen receptor, DEXATooltip dexamethasone for the GRTooltip glucocorticoid receptor, aldosterone for the MRTooltip mineralocorticoid receptor, DHTTooltip dihydrotestosterone for SHBGTooltip sex hormone-binding globulin, and cortisol for CBGTooltip Corticosteroid-binding globulin.
Not to be confused with Methylestradiol.
7α-Methylestradiol
Clinical data
Other names7α-Methyl-E2; 7α-Me-E2; 7α-Methylestra-1,3,5(10)-triene-3,17β-diol
Drug classEstrogen
Identifiers
  • (7R,8R,9S,13S,14S,17S)-7,13-Dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
CAS Number
PubChem CID
UNII
Chemical and physical data
FormulaC19H26O2
Molar mass286.415 g·mol−1
3D model (JSmol)
  • [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(O)C=C3C[C@@H](C)[C@@]21[H]
  • InChI=1/C19H26O2/c1-11-9-12-10-13(20)3-4-14(12)15-7-8-19(2)16(18(11)15)5-6-17(19)21/h3-4,10-11,15-18,20-21H,5-9H2,1-2H3/t11-,15-,16+,17+,18-,19+/s2
  • Key:DXWWYJWUFULMAP-BQXDHOISNA-N

See also

References
  1. Raynaud JP, Ojasoo T, Bouton MM, Philibert D (1979). "Receptor Binding as a Tool in the Development of New Bioactive Steroids". Drug Design. pp. 169–214. doi:10.1016/B978-0-12-060308-4.50010-X. ISBN 9780120603084.
  2. García-Becerra R, Ordaz-Rosado D, Noé G, Chávez B, Cooney AJ, Larrea F (February 2012). "Comparison of 7α-methyl-19-nortestosterone effectiveness alone or combined with progestins on androgen receptor mediated-transactivation". Reproduction. 143 (2): 211–219. doi:10.1530/REP-11-0171. PMID 22065861.
  3. Attardi BJ, Pham TC, Radler LC, Burgenson J, Hild SA, Reel JR (June 2008). "Dimethandrolone (7alpha,11beta-dimethyl-19-nortestosterone) and 11beta-methyl-19-nortestosterone are not converted to aromatic A-ring products in the presence of recombinant human aromatase". The Journal of Steroid Biochemistry and Molecular Biology. 110 (3–5): 214–222. doi:10.1016/j.jsbmb.2007.11.009. PMC 2575079. PMID 18555683.
  4. 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.
  5. Ojasoo T, Raynaud JP (November 1978). "Unique steroid congeners for receptor studies". Cancer Research. 38 (11 Pt 2): 4186–4198. PMID 359134.
  6. Raynaud JP, Bouton MM, Moguilewsky M, Ojasoo T, Philibert D, Beck G, et al. (January 1980). "Steroid hormone receptors and pharmacology". Journal of Steroid Biochemistry. 12: 143–157. doi:10.1016/0022-4731(80)90264-2. PMID 7421203.
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