B. Pharm. 5th sem. 3rd year Medicinal chemistry-II structures and chemistry of corticosteroid.

1. CHEMISTRY OF
CORTICOSTEROIDS
Raj K. Prasad (Gold Medalist)
M. Pharm. (P’ceutical Chemistry)

2. CORTICOSTEROIDS
• All corticosteroids are derivatives of
cyclopentanophenanthrene with keto-groups at C3 and C20
and an unsaturated bond between C4 and C5.
 Corticosteroids do not heal illnesses, but they are widely
used in various conditions when it is necessary to utilize
their anti-inflammatory, immunosuppressant, and
mineralocorticoid properties.
 They are used in replacement therapy for patients who have
adrenal insufficiency.

3. Glucocorticoids
(Moderate to low salt retention):

4. Glucocorticoids
 Glucocorticoids (GC) are endogenous compounds that have
an effect on carbohydrate, lipid, and protein metabolism, and
which exhibit anti-inflammatory, desensitizing, and
antiallergy action.
 They are immunodepressants, and they also possess anti-
shock and anti-toxic action.

5. example
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6. Mineralocorticoids
(High salt retention): 6

7. Mineralocorticoids (MC)
• Mineralocorticoids (MC) are endogenous compounds
that have an effect on fluid and electrolytic balance in
the body, mainly by promoting sodium retention in the
kidney.
Eg. aldosterone, 11-deoxycorticosterone, 11-deoxy-17-
oxycorticosterone.

8. CORTISONE
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10. CORTISONE
 It is a naturally occurring cortisone with good
systemic anti-inflammatory activity and low-to-
moderate salt-retention activity after its in vivo
conversion to hydrocortisone acetate.
 This conversion is mediated by 11β-hydroxysteroid
dehydrogenase.
 Its plasma half-life is only about 30 minutes,
compared with 90 minutes to 3 hours for
hydrocortisone.

11. USES
 Cortisone is used for inflammatory processes, allergies, and
adrenal insufficiency.
 It also used in collagen diseases, Addison disease, severe
shock, allergic conditions, chronic lymphocytic leukemia, and
many other indications.
 Cortisone acetate is relatively ineffective topically, mainly
because it must be reduced in vivo to hydrocortisone.

12. HYDROCORTISONE
(11β,17α,21-trihydroxypregn-4-en-3,20-dione)

13. Uses
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14. Uses
 Hydrocortisone drugs are used for severe inflammation,
shock, primary or secondary renal insufficiency, adrenal
insufficiency, ulcerative colitis, and rheumatoid, gouty, and
psoriatic arthritis, collagen and dermatological diseases,
allergic conditions, ophthalmologic and gastrointestinal
diseases, and respiratory tract diseases.

15. PREDNISOLONE
(11β,17α,21-trihydroxypregna-1,4-dien-
3,20-dione)
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16.  Prednisolone differs from prednisone in that the
keto-group at C11 of prednisone is replaced by a
hydroxyl group.
 Prednisolone is available in various salts and
esters to maximize its therapeutic utility like
Prednisolone acetate, Prednisolone sodium
phosphate, Prednisolone sodium succinate etc.

17. 17

18. Uses
Prednisolone is used for the same indications as all corticosteroids:
•Rheumatism,
•Polyarthritis,
•Bronchial asthma,
•Neurodermatitis,
•And eczema.
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19. BETAMETHASONE
Betamethasone, which
differs from
dexamethasone only in
configuration of the 16-
methyl group was made
available for the treatment
of rheumatic diseases and
dermatologic disorders.
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20. Structure
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21. Uses
•Betamethasone is primarily used
locally to treat dermatitis and eczema,
and also as an anti-itch agent.

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DEXAMETHASONE
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23. Structure
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24.  The distinctive characteristic of
dexamethasone is the presence of a fluorine
atom at C9 of the steroid ring.
 A 16a-methyl group decreases the reactivity of
the 20-keto group to carbonyl reagents and
increases the stability of the drug in human
plasma in vitro.

25. Uses
 Dexamethasone is used for the same
indications as all corticosteroids; however, it
exhibits a significantly more powerful anti-
inflammatory and anti-allergic action.
 It is used for circulatory collapse—shock during
or after surgical operations, trauma, blood loss,
myocardial infarction, and burns.
 It is also used in severe infections—toxemia,
vascular collapse in meningococcosis,
septicemia, diphtheria, typhoid fever, and
peritonitis.
 It is used in severe allergic conditions—
asthmatic status, laryngeal edema, severe
anaphylactic reactions to medicinal drugs, and
pyrogenic reactions.
Raj K. prasd 25

26. RAJ
THANK YOU
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