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7α-Methylestradiol

From Wikipedia, the free encyclopedia
Chemical compound
Not to be confused withMethylestradiol.
Pharmaceutical compound
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
PubChemCID
ChemSpider
UNII
ChEMBL
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 as7α-methylestra-1,3,5(10)-triene-3,17β-diol, is asyntheticestrogen and anactive metabolite of theandrogen/anabolic steroidTrestolone.[1][2][3] It is considered to be responsible for theestrogenic activity of trestolone.[2][3] The compound shows about higheraffinity for theandrogen receptor thanestradiol.[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 (%). Referenceligands (100%) wereprogesterone for thePRTooltip progesterone receptor,testosterone for theARTooltip androgen receptor,E2 for theERTooltip estrogen receptor,DEXATooltip dexamethasone for theGRTooltip glucocorticoid receptor,aldosterone for theMRTooltip mineralocorticoid receptor,DHTTooltip dihydrotestosterone forSHBGTooltip sex hormone-binding globulin, andcortisol forCBGTooltip Corticosteroid-binding globulin.

Synthesis

[edit]

The chemical synthesis of the 17-acetate ester starting fromtrestolone acetate has been described (but this is old work).[7] Alternative procedures exist, e.g.[8]

7α-Methylestradiol can be used to prepare 7 alpha-methyl-19-nor-androstatrienes such as for example a compound that is called 3-oxo-7a-methyl-17b-acetoxy-17a-ethynyl-4-9,11-19-norandrostatriene.[9]

See also

[edit]

References

[edit]
  1. ^abcRaynaud 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. ^abGarcía-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. ^abAttardi 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.
  7. ^, FR1434172 (1966 to Novartis AG, BASF Schweiz AG).
  8. ^Georg Dr Anner, Jaroslav Dr Kalvoda, & Peter Dr Wieland, CH451931 (1968 to Ciba-Geigy).
  9. ^Georg Dr Anner & Peter Dr Wieland, CH509996 (1971 to Ciba-Geigy).
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
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