Methylestradiol

Source: Wikipedia, the free encyclopedia.
Not to be confused with 7α-Methylestradiol.
Methylestradiol
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
  • (8R,9S,13S,14S,17S)-13,17-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
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, sold under the brand names Ginecosid, Ginecoside, Mediol, and Renodiol, is an

progestin and androgen/anabolic steroid medication.[3][4] Methylestradiol is taken by mouth.[1]

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

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

breakthrough bleeding.[5]

Pharmacology

Pharmacodynamics

Methylestradiol is an

affinity for the estrogen receptor than estradiol or ethinylestradiol.[6]

Methylestradiol is an

fluid retention.[10][11][12]

Relative affinities (%) of methylestradiol and related steroids
Compound PRTooltip Progesterone receptor ARTooltip Androgen receptor ERTooltip Estrogen receptor GRTooltip Glucocorticoid receptor MRTooltip Mineralocorticoid receptor SHBGTooltip Sex hormone-binding globulin
CBG
Tooltip Corticosteroid binding globulin
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 ? ?
Sources: Values are percentages (%). Reference
CBGTooltip Corticosteroid-binding globulin. Sources: [13][6][14][15]

Pharmacokinetics

Due to the presence of its C17α

metabolic stability and potency relative to estradiol.[10] This is analogous to the case of ethinylestradiol and its C17α ethynyl group.[10]

Chemistry

See also: List of estrogens

Methylestradiol, or 17α-methylestradiol (17α-ME), also known as 17α-methylestra-1,3,5(10)-triene-3,17β-diol, is a

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).[16]

History

Methylestradiol was first marketed, alone as Follikosid and in combination with methyltestosterone as Klimanosid, in 1955.[17][18][19][20]

Society and culture

Generic names

Methylestradiol has not been assigned an

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. ^
    PMID 13673847
    .
  2. ^
    ISBN 978-1-4757-2085-3
    .
  3. ^ a b c d e f g h i j k "Methylestradiol". Drugs.com. Retrieved 2 January 2016.
  4. ^
    ISBN 978-92-832-1291-1
    .
  5. ^
    ISBN 978-3-642-67570-6
    .
  6. ^
    PMID 359134
    .
  7. PMID 6406650
    .
  8. ^ Unlisted Drugs. Pharmaceutical Section, Special Libraries Association. 1982. 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. S2CID 38008851
    .
  10. ^
    ISBN 978-3-540-79088-4
    .
  11. ISBN 978-0-9828280-1-4
    .
  12. PMID 1964199
    .
  13. ISBN 9780120603084
    .
  14. PMID 3695484
    .
  15. PMID 7421203
    .
  16. ^ Falconi G, Rossi GL, Ercoli A (September 1970). James VH (ed.). Quinestrol and other cyclopentyl ethers of estrogenic steroids: different rates of storage in body fat. Third International Congress on Hormonal Steroids, Hamburg. International Congress Series No. 210. Amsterdam, Excerpta Medica. pp. 218–219. Archived from the original on 28 March 2018.
  17. S2CID 1678069
    .
  18. ISBN 978-3-7091-5694-0
    .
  19. ISBN 978-3-662-36329-4
    .
  20. ^ Helwig B (1956). Moderne Arzneimittel: eine Spezialitätenkunde nach Indikationsgebieten für Ärzte und Apotheker. Wissenschaftliche Verlagsgesellschaft. p. 240.
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