7α-Methylestradiol

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Not to be confused with Methylestradiol.
7α-Methylestradiol
7α-Methylestradiol.svg
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

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 steroid trestolone.[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]
Compound PR AR ER GR MR SHBG CBG
Estradiol 2.6 7.9 100 0.6 0.13 8.7 <0.1
7α-Methylestradiol 1–3 15–25 101 <1 <1 ? ?
Trestolone 50–75 100–125 ? <1 ? ? ?
Values are percentages (%). Reference ligands (100%) were progesterone for the PR, testosterone for the AR, E2 for the ER, DEXA for the GR, aldosterone for the MR, DHT for SHBG, and cortisol for CBG.

See also[edit]

References[edit]

  1. ^ a b c Raynaud, J.P.; Ojasoo, T.; Bouton, M.M.; 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. ^ a b García-Becerra R, Ordaz-Rosado D, Noé G, Chávez B, Cooney AJ, Larrea F (2012). "Comparison of 7α-methyl-19-nortestosterone effectiveness alone or combined with progestins on androgen receptor mediated-transactivation". Reproduction. 143 (2): 211–9. doi:10.1530/REP-11-0171. PMID 22065861.
  3. ^ a b Attardi BJ, Pham TC, Radler LC, Burgenson J, Hild SA, Reel JR (June 2008). "Dimethandrolone (7,11β-dimethyl-19-nortestosterone) and 11β-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): 214–22. 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". J. Steroid Biochem. 27 (1–3): 255–69. doi:10.1016/0022-4731(87)90317-7. PMID 3695484.
  5. ^ Ojasoo T, Raynaud JP (November 1978). "Unique steroid congeners for receptor studies". Cancer Res. 38 (11 Pt 2): 4186–98. PMID 359134.
  6. ^ Raynaud JP, Bouton MM, Moguilewsky M, Ojasoo T, Philibert D, Beck G, Labrie F, Mornon JP (January 1980). "Steroid hormone receptors and pharmacology". J. Steroid Biochem. 12: 143–57. doi:10.1016/0022-4731(80)90264-2. PMID 7421203.



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