Estrogenic Steroids Overall Organization of the Topic Structure and nomenclature of natural estrogens - Estradiol, estrone, and estriol Biosynthesis and metabolism of estradiol Synthetic estrogens - Schuler’s hypothesis Estrogen antagonists - clomiphene and tamoxifen 12/6/2018 MEDC 603 Steroids

Estrogenic Steroids Structure and Nomenclature of Natural Estrogens Estradiol Estrone Estriol intramuscular intramuscular oral 100% 33% 1.6% estr-1,3,5-triene- 3,17b-diol 3-hydroxy-estr-1,3,5 -triene-17-one estr-1,3,5-triene- 3,16a,17b-triol 12/6/2018 MEDC 603 Steroids

Estrogenic Steroids Physiological Activity of Natural Estrogens Reproduction and development of female sex organs Role in ovulation and pregnancy Role in bone density modulation 12/6/2018 MEDC 603 Steroids

Biosynthesis and Metabolism of Estradiol cholesterol pregnenolone testosterone estriol estrone estradiol conjugation to glucuronides, sulfates, etc…. 12/6/2018 MEDC 603 Steroids

Synthetic Estrogenic Estradiol look-alikes 12/6/2018 MEDC 603 Steroids

Synthetic Estrogenic Diethyl-Stilbestrols (DES) Ethinyl-estradiol R = H Diethylstilbestrol Mestranol R = CH3 Chlorotrianisene Dienestrol 12/6/2018 MEDC 603 Steroids

Synthetic Estrogenic Schuler’s Hypothesis for Synthetic Estrogens 12/6/2018 MEDC 603 Steroids

Synthetic Estrogenic 12/6/2018 MEDC 603 Steroids

Estrogen Antagonists Triphenylethylene Derivatives – Partial Agonists Chlorotrianisene (estrogenic) 12/6/2018 MEDC 603 Steroids

Estrogen Antagonists Estrogen Derivatives Selective Estrogen Receptor Modulators (SERM) – tissue specific activity 12/6/2018 MEDC 603 Steroids