Chemistry and Actions

1. Progesterone
Dr. Jasmine Chaudhary
Associate Prof.
MMCP, MM(DU)
Mullana

2. PROGESTERONE
Lecture by Dr. Jasmine Chaudhary

3. Anterior Pituatory Gland
FSH
(Follicle Stimulating Hormone)
Prolactin
LH
(Leutinising Hormone)
Normal growth of
ovarian follicle
Maturation of follicle
and formation of
corpus luteum
Maintains secretory
activity of corpus
luteum to release
progesterone
Lecture by Dr. Jasmine Chaudhary

4. Lecture by Dr. Jasmine Chaudhary

5. PROGESTERONE (PROGESTINS)
 Steroid al hormone secreted by corpus luteum of ovary and
placenta which prepare uterus for implantation of fertilized
ovum, to maintain pregnancy and to promote development of
mammary gland.
 Corpus luteum secretes progesterone to suppress secretion of
FSH and LH by feedback inhibitory mechanism and thus
prevent ovulation during pregnancy.
 It also inhibits release of oxytocin and thus prevents abortion.
Lecture by Dr. Jasmine Chaudhary

6. SOURCE
Plant source: Discorea maxicana contains steroid diosgenin
and converted to progesterone.
In mammals, it is .synthesized from Cholesterol as precusor
Cholesterol Pregnenolone Progesterone
Lecture by Dr. Jasmine Chaudhary

7. Chemically, progesterone is Pregn-4-en-3,20-dione
Lecture by Dr. Jasmine Chaudhary

8. SAR
Progesterone is not orally effective due to its complete degradation
in liver so synthetic progestins were synthesized.
Progesterone Pregnanediol (metabolite)
So following class derivatives were synthesized :
 17α-hydroxy progesterone
 19-nortestosterone
Lecture by Dr. Jasmine Chaudhary

9. Modification at 17 α-hydroxy progesterone
 Steroidal nucleus is essential for activity.
 Activity of 17α-hydroxy progesterone can be enhanced by
 Unsaturation at 6 or 7 position e.g. Chlormadinone acetate.
CH3
CH3
CH3
O
O
OCOCH3
Cl
Chlormadinone
acetate Lecture by Dr. Jasmine Chaudhary

10.  Substitution of methyl or halogen at 6th carbon. E.g. Medroxy
progesterone acetate.
 Introduction of methyl group at 11 position.
These all factors prolong duration of action also.
 Substitution of F-group at 21 position prevent hydroxylation
and enhance oral effectiveness.
 Inversion of configuration at position 10 in progesterone gives
retroprogesterone which is more active orally as well as
parentrally.
CH3
CH3
CH3
O
O
OCOCH3
CH3
Medroxyprogesterone acetate
Lecture by Dr. Jasmine Chaudhary

11. Modifications at 19-nortestosterone nucleus
•Introduction of alkyl group at C-17 blocks oxidation to inactive
compound and increase progesterone activity. E.g. Ethisterone.
•Removal of 19-methyl group decrease androgenic activity. E.g.
Norethisterone
CH3
OH
O
CH
H
CH3
CH3
OH
O
CH
Lecture by Dr. Jasmine Chaudhary

12.  Substituting methyl group at C-18 increases activity. E.g.
Norgesterol
 Unsaturation of Ring B and C increase activity.
 Introduction of halogen or methyl at 6 or 7 position increase
activity. E.g. Dimethisterone.
OH
O
CH
C
H3
H
CH3
CH3
OH
O
CCH3
CH3
Lecture by Dr. Jasmine Chaudhary

13. Uses
 Prevents abortion.
 Treatment of dysmennorhoea.
 In diagnosis of pregnancy (Main hormone detected is HCG)
 In carcinoma of breast.
 It support pregnancy and fertility and to treat gynecological
disorders.
Side Effects
 Nausea & vomiting
 Drowsiness
 Irregular bleeding
Lecture by Dr. Jasmine Chaudhary