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Methylestradiol

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Methylestradiol
Clinical data
Other names17α-Methylestra-1,3,5(10)-triene-3,17β-diol; NSC-52245
Routes of
administration		Oral
Identifiers
  • (8R,9S,13S,14S,17S)-13,17-Dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.005.572 Edit this at Wikidata
Chemical and physical data
FormulaC19H26O2
Molar mass286.40854 g/mol g·mol−1
3D model (JSmol)
  • CC12CCC3C(C1CCC2(C)O)CCC4=C3C=CC(=C4)O
  • InChI=1S/C19H26O2/c1-18-9-7-15-14-6-4-13(20)11-12(14)3-5-16(15)17(18)8-10-19(18,2)21/h4,6,11,15-17,20-21H,3,5,7-10H2,1-2H3/t15-,16-,17+,18+,19+/m1/s1
  • Key:JXQJDYXWHSVOEF-GFEQUFNTSA-N

Methylestradiol, or 17α-methylestradiol (17α-ME), is a semisynthetic, steroidal estrogen that has been sold in combination with normethandrone (methylestrenolone) under brand names including Ginecosid, Ginecoside, Mediol, Renodiol for the treatment of menopausal symptoms in Brazil, Venezuela, and Indonesia.[1][2][3] Due to the presence of the 17α-methyl group, methylestradiol cannot be deactivated by oxidation of the 17β-hydroxy group, resulting in improved metabolic stability and potency relative to estradiol analogously to ethinyl estradiol (17α-ethinylestradiol).[4] In addition to its clinical use, methylestradiol has been studied as a radiopharmaceutical.[5]

Methylestradiol is an active metabolite of the anabolic steroid methyltestosterone (17α-methyltestosterone), and is responsible for the estrogenic side effects of the drug such as gynecomastia.[4][6] Metandienone (17α-methyl-δ1-testosterone), another anabolic steroid, produces a similar but non-identical estrogenic metabolite.[6]

See also

References

  1. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 898–. ISBN 978-1-4757-2085-3.
  2. ^ Drugs.com. "Methylestradiol". Retrieved 2 January 2016.
  3. ^ IARC Working Group on the Evaluation of Carcinogenic Risks to Humans; World Health Organization; International Agency for Research on Cancer (2007). Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy. World Health Organization. pp. 389–. ISBN 978-92-832-1291-1.
  4. ^ a b Detlef Thieme; Peter Hemmersbach (18 December 2009). Doping in Sports. Springer Science & Business Media. pp. 470–. ISBN 978-3-540-79088-4.
  5. ^ Feenstra A, Vaalburg W, Nolten GM, Reiffers S, Talma AG, Wiegman T, van der Molen HD, Woldring MG (1983). "Estrogen receptor binding radiopharmaceuticals: II. Tissue distribution of 17 alpha-methylestradiol in normal and tumor-bearing rats". J. Nucl. Med. 24 (6): 522–8. PMID 6406650.
  6. ^ a b William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 533–. ISBN 978-0-9828280-1-4.



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