Chemistry:Methylestradiol

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Short description: Chemical compound
Methylestradiol
Methylestradiol.svg
Methylestradiol molecule ball.png
Clinical data
Trade namesGinecosid, Ginecoside, Mediol, Renodiol
Other namesNSC-52245; 17α-Methylestradiol; 17α-ME; 17α-Methylestra-1,3,5(10)-triene-3,17β-diol
Routes of
administration		By mouth[1]
Drug classEstrogen
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC19H26O2
Molar mass286.415 g·mol−1
3D model (JSmol)

Methylestradiol, sold under the brand names Ginecosid, Ginecoside, Mediol, and Renodiol, is an estrogen medication which is used in the treatment of menopausal symptoms.[2][3][4] It is formulated in combination with normethandrone, a progestin and androgen/anabolic steroid medication.[3][4] Methylestradiol is taken by mouth.[1]

Side effects of methylestradiol include nausea, breast tension, edema, and breakthrough bleeding among others.[5] It is an estrogen, or an agonist of the estrogen receptors, the biological target of estrogens like estradiol.[6]

Methylestradiol is or has been marketed in Brazil , Venezuela, and Indonesia.[3] In addition to its use as a medication, methylestradiol has been studied for use as a radiopharmaceutical for the estrogen receptor.[7]

Medical uses

Methylestradiol is used in combination with the progestin and androgen/anabolic steroid normethandrone (methylestrenolone) in the treatment of menopausal symptoms.[3][4]

Available forms

Methylestradiol is marketed in combination with normethandrone in the form of oral tablets containing 0.3 mg methylestradiol and 5 mg normethandrone.[8][9]

Side effects

Side effects of methylestradiol include nausea, breast tension, edema, and breakthrough bleeding.[5]

Pharmacology

Pharmacodynamics

Methylestradiol is an estrogen, or an agonist of the estrogen receptor.[6] It shows somewhat lower affinity for the estrogen receptor than estradiol or ethinylestradiol.[6]

Methylestradiol is an active metabolite of the androgens/anabolic steroids methyltestosterone (17α-methyltestosterone), metandienone (17α-methyl-δ1-testosterone), and normethandrone (17α-methyl-19-nortestosterone), and is responsible for their estrogenic side effects, such as gynecomastia and fluid retention.[10][11][12]

Relative affinities (%) of methylestradiol and related steroids
Compound PR AR ER GR MR SHBG CBG
Estradiol 2.6 7.9 100 0.6 0.13 8.7 <0.1
Ethinylestradiol 15–25 1–3 112 1–3 <1 ? ?
Methylestradiol 3–10, 15–25 1–3 67 1–3 <1 ? ?
Methyltestosterone 3 45, 100–125 ? 1–5 ? 5 ?
Normethandrone 100 146 <0.1 1.5 0.6 ? ?

Pharmacokinetics

Due to the presence of its C17α methyl group, methylestradiol cannot be deactivated by oxidation of the C17β hydroxyl group, resulting in improved metabolic stability and potency relative to estradiol.[10] This is analogous to the case of ethinylestradiol and its C17α ethynyl group.[10]

Chemistry

Methylestradiol, or 17α-methylestradiol (17α-ME), also known as 17α-methylestra-1,3,5(10)-triene-3,17β-diol, is a synthetic estrane steroid and a derivative of estradiol.[2][3] It is specifically the derivative of estradiol with a methyl group at the C17α positions.[2][3] Closely related steroids include ethinylestradiol (17α-ethynylestradiol) and ethylestradiol (17α-ethylestradiol).[2] The C3 cyclopentyl ether of methylestradiol has been studied and shows greater oral potency than methylestradiol in animals, similarly to quinestrol (ethinylestradiol 3-cyclopentyl ether) and quinestradol (estriol 3-cyclopentyl ether).[13]

History

Methylestradiol was first marketed, alone as Follikosid and in combination with methyltestosterone as Klimanosid, in 1955.[14][15][16][17]

Society and culture

Generic names

Methylestradiol has not been assigned an INN or other formal name designations.[2][3] Its generic name in English and German is methylestradiol, in French is méthylestradiol, and in Spanish is metilestadiol.[3] It is also known as 17α-methylestradiol.[3]

Brand names

Methylestradiol is or has been marketed under the brand names Ginecosid, Ginecoside, Mediol, and Renodiol, all in combination with normethandrone.[3][2]

Availability

Methylestradiol is or has been marketed in Brazil , Venezuela, and Indonesia.[3]

References

  1. ↑ 1.0 1.1 "[Oral hormonal treatment with methylestrene-olone & methylestradiol as early pregnancy tests]" (in de). Die Medizinische 4 (21): 1032–1033. May 1959. PMID 13673847. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 898–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA898. 
  3. ↑ 3.00 3.01 3.02 3.03 3.04 3.05 3.06 3.07 3.08 3.09 3.10 "Methylestradiol". Drugs.com. https://www.drugs.com/international/methylestradiol.html. 
  4. ↑ 4.0 4.1 4.2 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. https://books.google.com/books?id=aGDU5xibtNgC&pg=PA389. 
  5. ↑ 5.0 5.1 "Clinical Effects of Estrogens". Functional Morphologic Changes in Female Sex Organs Induced by Exogenous Hormones. 1980. pp. 67–71. doi:10.1007/978-3-642-67568-3_10. ISBN 978-3-642-67570-6. 
  6. ↑ 6.0 6.1 6.2 Cite error: Invalid <ref> tag; no text was provided for refs named pmid359134
  7. ↑ "Estrogen receptor binding radiopharmaceuticals: II. Tissue distribution of 17 alpha-methylestradiol in normal and tumor-bearing rats". Journal of Nuclear Medicine 24 (6): 522–528. June 1983. PMID 6406650. 
  8. ↑ Unlisted Drugs. Pharmaceutical Section, Special Libraries Association.. 1982. https://books.google.com/books?id=BhxtAAAAMAAJ. "Batynid. C. Each dragee contains: normethandrone, 5 mg.; and methylestradiol, 0.3 mg. E. (Formerly) Gynaekosid. M. Boehringer Biochemia, Florence. A. Estrogenic; Rx of secondary amenorrhea. R. Notiz Med Farm 32;295, Nov-Dec 81." 
  9. ↑ "Amenorrhea as a leading symptom of choriocarcinoma". The Journal of Obstetrics and Gynaecology of the British Commonwealth 73 (1): 153–155. February 1966. doi:10.1111/j.1471-0528.1966.tb05137.x. PMID 5948541. 
  10. ↑ 10.0 10.1 10.2 Doping in Sports. Springer Science & Business Media. 18 December 2009. pp. 470–. ISBN 978-3-540-79088-4. https://books.google.com/books?id=R-hIC-caIn8C&pg=PA470. 
  11. ↑ Anabolics. Molecular Nutrition Llc. 2011. pp. 533–. ISBN 978-0-9828280-1-4. https://books.google.com/books?id=afKLA-6wW0oC&pg=PT533. 
  12. ↑ "Reappraisal of the health risks associated with the use of high doses of oral and injectable androgenic steroids". NIDA Research Monograph 102: 142–177. 1990. PMID 1964199. 
  13. ↑ "Quinestrol and other cyclopentyl ethers of estrogenic steroids: different rates of storage in body fat.". Third International Congress on Hormonal Steroids, Hamburg. Amsterdam, Excerpta Medica. September 1970. pp. 218–219. https://www.popline.org/node/474468. 
  14. ↑ "Neue Spezialitäten". Klinische Wochenschrift 33 (31–32): 773–774. 1955. doi:10.1007/BF01473523. ISSN 0023-2173. 
  15. ↑ Konservative Therapie der Frauenkrankheiten: Anzeigen, Grenzen und Methoden Einschliesslich der Rezeptur. Springer-Verlag. 8 March 2013. pp. 20–. ISBN 978-3-7091-5694-0. https://books.google.com/books?id=Hte1BgAAQBAJ&pg=PA20. 
  16. ↑ Hagers Handbuch der pharmazeutischen Praxis: Für Apotheker, Arzneimittelhersteller, Drogisten, Ärzte u. Medizinalbeamte. Springer-Verlag. 14 December 2013. pp. 1156–1157,1164. ISBN 978-3-662-36329-4. https://books.google.com/books?id=8bLwBgAAQBAJ&pg=PA1156. 
  17. ↑ Moderne Arzneimittel: eine Spezialitätenkunde nach Indikationsgebieten für Ärzte und Apotheker. Wissenschaftliche Verlagsgesellschaft. 1956. p. 240. https://books.google.com/books?id=cdfQAAAAMAAJ. 



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