4846 Mestranol The 3-methyl ether of ethinyl estradiol. It must be demethylated to be biologically active. It is used as the estrogen component of many combination ORAL contraceptives. 72-33-3 6291 C21H26O2 White powder. 150.5°C 3.77e-03 g/L Mestranol is the 3-methyl ether of ethinylestradiol. Ethinylestradiol, is a synthetic derivative of estradiol. Ethinylestradiol is orally bio-active and the estrogen used in almost all modern formulations of combined oral contraceptive pills. It binds to (and activates) the estrogen receptor. Mestranol is a biologically inactive prodrug of ethinylestradiol to which it is demethylated in the liver with a conversion efficiency of 70%. Estrogens diffuse into their target cells and interact with a protein receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH). No indication of carcinogenicity to humans (not listed by IARC). Mestranol was used as one of the first oral contraceptives. 2014-09-11T05:16:50Z 2014-12-24T20:26:57Z Mestranol C07618 6784 DB01357 true [H][C@]12CC[C@](O)(C#C)[C@]1(C)CC[C@@]1([H])C3=CC=C(OC)C=C3CC[C@]21[H] C21H26O2 InChI=1/C21H26O2/c1-4-21(22)12-10-19-18-7-5-14-13-15(23-3)6-8-16(14)17(18)9-11-20(19,21)2/h1,6,8,13,17-19,22H,5,7,9-12H2,2-3H3/t17-,18-,19+,20+,21+/s2 InChIKey=IMSSROKUHAOUJS-ZTUUXWJNNA-N 310.4299 310.193280076 Exogenous Solid HMDB15446 CHEMBL1201151 6054