Methylestradiol

Methylestradiol

File:Methylestradiol.svg
Systematic (IUPAC) name
(8R,9S,13S,14S,17S)-13,17-Dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
Clinical data
Routes of administration	Oral
Identifiers
CAS Number	302-76-1
PubChem	CID: 66413
ChemSpider	59787
Synonyms	17α-Methylestra-1,3,5(10)-triene-3,17β-diol; NSC-52245
Chemical data
Formula	C19H26O2
Molecular mass	286.40854 g/mol
SMILES CC12CCC3C(C1CCC2(C)O)CCC4=C3C=CC(=C4)O
InChI 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. 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). In addition to its clinical use, methylestradiol has been studied as a radiopharmaceutical.

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. Metandienone (17α-methyl-δ¹-testosterone), another anabolic steroid, produces a similar but non-identical estrogenic metabolite.

See also

• Cloxestradiol