Clinical data | |
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Trade names | Ginecosid, Ginecoside, Mediol, Renodiol |
Other names | NSC-52245; 17α-Methylestradiol; 17α-ME; 17α-Methylestra-1,3,5(10)-triene-3,17β-diol |
Routes of administration | By mouth[1] |
Drug class | Estrogen |
Identifiers | |
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CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
KEGG | |
ChEBI | |
ChEMBL | |
ECHA InfoCard | 100.005.572 |
Chemical and physical data | |
Formula | C19H26O2 |
Molar mass | 286.415 g·mol−1 |
3D model (JSmol) | |
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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]
Methylestradiol is used in combination with the progestin and androgen/anabolic steroid normethandrone (methylestrenolone) in the treatment of menopausal symptoms.[3][4]
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 of methylestradiol include nausea, breast tension, edema, and breakthrough bleeding.[5]
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]
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 | ? | ? |
Sources: 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 . Sources: [13][6][14][15] |
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]
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 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).[16]
Methylestradiol was first marketed, alone as Follikosid and in combination with methyltestosterone as Klimanosid, in 1955.[17][18][19][20]
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]
Methylestradiol is or has been marketed under the brand names Ginecosid, Ginecoside, Mediol, and Renodiol, all in combination with normethandrone.[3][2]
Methylestradiol is or has been marketed in Brazil, Venezuela, and Indonesia.[3]