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

2
Estrogenic Steroids
Structure and Nomenclature of Natural Estrogens
Estradioll 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
3
Biosynthesis and Metabolism of Estradiol
cholesterol
pregnenolone testosterone
estriol
estrone estradiol
conjugation to glucuronides, sulfates, etc.
4
Synthetic Estrogenic
ethinyl-estradiol
diethylstilbestrol
chlorotrianisene
dienestrol
5
Synthetic Estrogenic
Schulers Hypothesis for Synthetic Estrogens
6
Synthetic Estrogenic
7
Estrogen Antagonists
chlorotrianisene
clomiphene (estrogenic)

(anti-estrogenic)
tamoxifen (anti-estrogenic)