Methylestradiol

Methylestradiol

Clinical data
Trade names	Ginecosid, Ginecoside, Mediol, Renodiol
Synonyms	17α-Methylestra-1,3,5(10)-triene-3,17β-diol; NSC-52245
Routes of administration	Oral
Identifiers
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
CAS Number	302-76-1
PubChem CID	66413
ChemSpider	59787
Chemical and physical data
Formula	C19H26O2
Molar mass	286.40854 g/mol
3D model (JSmol)	Interactive image
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), an anabolic-androgenic steroid and progestin and , 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 ethinylestradiol (17α-ethynylestradiol). In addition to its clinical use, methylestradiol has been studied as a radiopharmaceutical.

Methylestradiol is an active metabolite of the anabolic-androgenic steroids methyltestosterone (17α-methyltestosterone) and metandienone (17α-methyl-δ¹-testosterone) and is responsible for their estrogenic side effects such as gynecomastia (breast development) and fluid retention.