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Estrogenic Steroids

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.

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Estrogenic Steroids

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  1. 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 MEDC 603 Steroids

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

  3. Estrogenic Steroids Physiological Activity of Natural Estrogens • Reproduction and development of female sex organs • Role in ovulation and pregnancy • Role in bone density modulation MEDC 603 Steroids

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

  5. Synthetic Estrogenic Estradiol look-alikes MEDC 603 Steroids

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

  7. Synthetic Estrogenic Schuler’s Hypothesis for Synthetic Estrogens MEDC 603 Steroids

  8. Synthetic Estrogenic MEDC 603 Steroids

  9. Estrogen Antagonists Triphenylethylene Derivatives – Partial Agonists Chlorotrianisene (estrogenic) MEDC 603 Steroids

  10. Estrogen Antagonists Estrogen Derivatives Selective Estrogen Receptor Modulators (SERM) – tissue specific activity MEDC 603 Steroids

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