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
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MEDC 603 Steroids

2. Estrogenic Steroids Structure and Nomenclature of Natural Estrogens
Estradiol Estrone Estriol
intramuscular intramuscular oral
100% % %
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
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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
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MEDC 603 Steroids

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

5. Synthetic Estrogenic
Estradiol look-alikes
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MEDC 603 Steroids

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

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

8. Synthetic Estrogenic
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MEDC 603 Steroids

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

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