Estrogenic Steroids

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
• - Schulers hypothesis
• Estrogen antagonists
• - clomiphene and tamoxifen

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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- 3,17b-diol
estr-1,3,5-triene- 3,16a,17b-triol
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Estrogenic Steroids
Physiological Activity of Natural Estrogens

• Reproduction and development of female sex
  organs
• Role in ovulation and pregnancy
• Role in bone density modulation

4
Biosynthesis and Metabolism of Estradiol
cholesterol
pregnenolone testosterone
estriol
estrone estradiol
conjugation to glucuronides, sulfates, etc.
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Synthetic Estrogenic
Estradiol look-alikes
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Synthetic Estrogenic
Diethyl-Stilbestrols (DES)
Ethinyl-estradiol R H
Diethylstilbestrol Mestranol R CH3
Chlorotrianisene
Dienestrol
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Synthetic Estrogenic
Schulers Hypothesis for Synthetic Estrogens
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Synthetic Estrogenic
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Estrogen Antagonists
Triphenylethylene Derivatives Partial Agonists
Chlorotrianisene (estrogenic)
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Estrogen Antagonists
Estrogen Derivatives
Selective Estrogen Receptor Modulators (SERM)
tissue specific activity