1. Progestins Overall Organization of the Topic
Structure and function of natural progestin
- Progesterone
Nomenclature of progestational steroids
Biosynthesis and metabolism of progesterone
Progesterone Agonists
Generalizations on Structure-Activity Relationships
Progesterone antagonist
- RU-486
2/23/2019
MEDC 603 Steroids

2. Progestins Progest-4-ene-3,20-dione Progesterone 2/23/2019
MEDC 603 Steroids

3. Inhibits follicular maturation and ovulation
Functions of Progesterone
Maintains pregnancy
Inhibits follicular maturation and ovulation
prevents spontaneous uterine contraction
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MEDC 603 Steroids

4. Progesterone Metabolism
Reduction C-20
Reduction
C-4, C-3
Reduction C-20
Reduction
C-4, C-3
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MEDC 603 Steroids

5. Progesterone Agonists
1. Derivatization of the 17 - position
17a-hydroxyprogesterone caproate
Click here to view the 3D structure of 17-substitution
2/23/2019
MEDC 603 Steroids

6. Medroxyprogesterone acetate
Progesterone Agonists
2. Derivatization of A/B rings
Medroxyprogesterone acetate
(Oral Activity = 12-25)
Megestrol acetate
Chlomadinone acetate
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MEDC 603 Steroids

7. Progesterone Agonists
3. Testosterone Derivatives
Ethisterone
Dimethisterone
Relative Oral Activity = 1
Relative Oral Activity = 12
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MEDC 603 Steroids

8. Progesterone Agonists
Nortestosterone Derivatives
Norethindrone
Norgestrel
Relative Oral Activity = 5-10
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MEDC 603 Steroids

9. Either a progesterone or a testosterone skeleton
Generalizations on Structure-Activity Relationships
for Oral Progestational Activity
Steroid skeleton
Unsaturated A ring
Either a progesterone or a testosterone skeleton
If testosterone derivative, 17-ethinyl substitution
19-nor substitution is useful
2/23/2019
MEDC 603 Steroids

10. Progesterone Antagonist
RU-486: Mifepristone
2/23/2019
MEDC 603 Steroids