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ANTI-INFLAMMATORY AGENTS
• Drugs that relieve pain, reduce inflammation
and reduce temperature
• Blocks the production of Prostaglandins which
is responsible for pain and swelling of
inflammatory conditions.
Mechanism of Action
• Prostaglandins are the mediators of
inflammation.
• NSAIDs are irreversible inhibitors of
cyclooygenase activity thus they prevent the
formation of prostaglandins and reduces the
symptoms of inflammation.
Classification
• Salicylates- aspirin, sodium salicylate
• Propionic acid derivative (profens)- ibuprofen, naproxen
• Indole derivative- indomethacin, sulindac
• Pyrrole acetic acid derivative- ketorolac, tolmetin,
zomepirac
• Anthranilates (fenamates)- diclofenac, mefenamic acid
• Oxicam derivative- piroxicam
• Phenylpyrazolones- phenylbutazone, antipyrine
Salicylates
• Derivatives of 2-hydroxy benzoic acid.
• Used as analgesic to relieve pain.
• MOA- inhibit cyclooxygenase and reduce levels of PGE2
SAR-
• -COOH & -OH replacement decreases activity
• Reduction of –COOH to –CONH2, retains analgesic property
but devoid of anti-inflammatory activity. Eg Slicylamide
• -OH at meta or para to –COOH decreases activity
• Halogen on aromatic ring inceases activity as well as toxicity.
• Substitution of hydrophobic aryl group at 5th position
improves activity.
COOH
OH
SALICYLIC ACID
Synthesis of Salicylic acid
Sodium Salicylate
• MOA-
• Blocks synthesis of PG by inhibiting
cyclooxygenase which converts arachidonic
acid to cyclic endoperoxides,precursor of PG
• Uses- relieve pain, fever, treatment of gout
OH
O
-
Na
+
O
ASPIRIN
• MOA-
• Inhibit COX-1 & COX-2 and decrease formation of PG
and thromboxane
• Uses- relief pain, inflammation associated with
rheumatoid arthritis, osteoarthritis
• Side effects- effects of overdose tinitus, hypokalemia,
hypoglycemia, hypotention
OCOCH 3
OH
O
Synthesis of Aspirin
PROPIONIC ACID DERIVATIVE (PROFENS)
• Contain chiral carbon in the alpha position of acetic acid side
chain
IBUPROFEN
• Non selective Inhhibitor of COX which is used for PG synthesis.
• Uses-treatment of rheumatoid arthritis, osteoarthritis,
management of desmenorrhea, spondylytis, gout.
• Adverse effect- edema, nausea, vomiting, peptic ulcer, GI
bleeding
COOH
CH3
CH3
C
H3
NAPROXEN
• MOA
• Inhibit COX-1 and COX-2
• Uses-treatment of rheumatoid arthritis, osteoarthritis,
management of desmenorrhea, spondylitis, gout.
• AE- nephrotoxicity, drowsiness, nausea, vomiting
COOH
CH3
H3CO
INDOLE DERIVATIVE
N
X
COOH
R
2
R
1
N
H3CO
COOH
CH3
O
Cl
INDOMETHACIN
F
COOH
CH3
S
C
H3
O SULINDAC
SAR
• Carboxyl group is essential for anti-inflammatory
activity.
• Substitution at R1, C6H4CH2>CH3>H
• Presence of indole Nitrogen is not essential, 1-
benzylidenylindene analogue is also active. Eg
sulindac
• 5-methoxy in indomethacin is imp.
• Presence of Cl or F at para position of phenyl is imp.
For antiinflammatory activity.
INDOMETHACINE
• MOA
• Inhibit COX 1 and COX 2
• Inhibit Phospholipase A2 enzyme responsible for releasing
arachidonic acid from phospholipids.
• Uses
• Rheumatoid arthritis, osteoarthritis, spondylitis
N
H3CO
COOH
CH3
O
Cl
INDOMETHACIN
SULINDAC
• MOA
• Inhibit COX 1 and COX 2 which leads to inhibition of
PG
• Uses
• Rheumatoid arthritis, osteoarthritis, spondylitis, gout
F
COOH
CH3
S
C
H3
O SULINDAC
PYRROLE ACETIC ACID DERIVATIVE
O
N
OH
O
KETOROLAC
N
O
H
O CH3
C
H3 O
TOLMETIN
ZOMEPIRAC
N
O
H
O Cl
C
H3 O
CH3
TOLMETIN
• MOA
• Inhibit PG Synthesis
• Uses
• Rheumatoid arthritis, osteoarthritis,
spondylitis
N
O
H
O CH3
C
H3 O
TOLMETIN
ZOMEPIRAC
• MOA
• Decrease PG Synthesis
• Withdrawn from market due to its adverse
effect, anaphylactic reactions.
ZOMEPIRAC
N
O
H
O Cl
C
H3 O
CH3
KETOROLAC
• MOA
• Inhibit COX-1 and COX-2 LEADS TO INHIBITION
OF PG Synthesis
• Uses
• Potent NSAID used to treat moderate to
severe pain O
N
OH
O
KETOROLAC
OXICAM DERIVATIVE
PIROXICAM
• NSAID used to relieve symptoms of painful
inflammatory conditions like arthritis
• Inhibit COX-1, Prevents production of PG
involved in mediation of swelling and pain.
N
NH
O
S
O O
OH
ANTHRANILATES (FENAMATES)
• N-aryl substituted derivatives of anthranilic acid.
• SAR
• Position of –COOH is imp. For activity
• Replacement of –COOH by tetrazole retains the activity.
• Substitution on anthranilic acid ring reduces the activity.
• Replacement of –NH , no acticity
COOH
NH
DICLOFENAC
• Inhibit COX-1 and COX-2
• Uses-treatment of rheumatoid arthritis,
osteoarthritis
• Adverse effect- hepatotoxicity
COOH
NH
Cl
Cl
Mefenamic acid
• Inhibit COX-1 and COX-2
• Uses-used for mild to moderate pain and
primary dysmenorrhea
HOOC
NH
C
H3
CH3
PHENYLPYRAZOLONES
N
N
O
O CH3
PHENYLBUTAZONES
N
N
CH3
O
C
H3
ANTIPYRINE
PHENYLBYTAZONE
• Inactivate PG synthase through peroxide
mediated deactivation
• Reduce production of PG.
• Use- spondylitis
N
N
O
O CH3
PHENYLBUTAZONES
ANTIPYRINE
• Inhibit COX-1 AND COX-2 involved in PG
synthesis.
• Analgesic
N
N
CH3
O
C
H3
ANTIPYRINE

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Presentation on Non Steroidal Anti-inflammatory Agents

  • 1. ANTI-INFLAMMATORY AGENTS • Drugs that relieve pain, reduce inflammation and reduce temperature • Blocks the production of Prostaglandins which is responsible for pain and swelling of inflammatory conditions.
  • 3. • Prostaglandins are the mediators of inflammation. • NSAIDs are irreversible inhibitors of cyclooygenase activity thus they prevent the formation of prostaglandins and reduces the symptoms of inflammation.
  • 4. Classification • Salicylates- aspirin, sodium salicylate • Propionic acid derivative (profens)- ibuprofen, naproxen • Indole derivative- indomethacin, sulindac • Pyrrole acetic acid derivative- ketorolac, tolmetin, zomepirac • Anthranilates (fenamates)- diclofenac, mefenamic acid • Oxicam derivative- piroxicam • Phenylpyrazolones- phenylbutazone, antipyrine
  • 5. Salicylates • Derivatives of 2-hydroxy benzoic acid. • Used as analgesic to relieve pain. • MOA- inhibit cyclooxygenase and reduce levels of PGE2 SAR- • -COOH & -OH replacement decreases activity • Reduction of –COOH to –CONH2, retains analgesic property but devoid of anti-inflammatory activity. Eg Slicylamide • -OH at meta or para to –COOH decreases activity • Halogen on aromatic ring inceases activity as well as toxicity. • Substitution of hydrophobic aryl group at 5th position improves activity. COOH OH SALICYLIC ACID
  • 7. Sodium Salicylate • MOA- • Blocks synthesis of PG by inhibiting cyclooxygenase which converts arachidonic acid to cyclic endoperoxides,precursor of PG • Uses- relieve pain, fever, treatment of gout OH O - Na + O
  • 8. ASPIRIN • MOA- • Inhibit COX-1 & COX-2 and decrease formation of PG and thromboxane • Uses- relief pain, inflammation associated with rheumatoid arthritis, osteoarthritis • Side effects- effects of overdose tinitus, hypokalemia, hypoglycemia, hypotention OCOCH 3 OH O
  • 10. PROPIONIC ACID DERIVATIVE (PROFENS) • Contain chiral carbon in the alpha position of acetic acid side chain IBUPROFEN • Non selective Inhhibitor of COX which is used for PG synthesis. • Uses-treatment of rheumatoid arthritis, osteoarthritis, management of desmenorrhea, spondylytis, gout. • Adverse effect- edema, nausea, vomiting, peptic ulcer, GI bleeding COOH CH3 CH3 C H3
  • 11. NAPROXEN • MOA • Inhibit COX-1 and COX-2 • Uses-treatment of rheumatoid arthritis, osteoarthritis, management of desmenorrhea, spondylitis, gout. • AE- nephrotoxicity, drowsiness, nausea, vomiting COOH CH3 H3CO
  • 13. SAR • Carboxyl group is essential for anti-inflammatory activity. • Substitution at R1, C6H4CH2>CH3>H • Presence of indole Nitrogen is not essential, 1- benzylidenylindene analogue is also active. Eg sulindac • 5-methoxy in indomethacin is imp. • Presence of Cl or F at para position of phenyl is imp. For antiinflammatory activity.
  • 14. INDOMETHACINE • MOA • Inhibit COX 1 and COX 2 • Inhibit Phospholipase A2 enzyme responsible for releasing arachidonic acid from phospholipids. • Uses • Rheumatoid arthritis, osteoarthritis, spondylitis N H3CO COOH CH3 O Cl INDOMETHACIN
  • 15. SULINDAC • MOA • Inhibit COX 1 and COX 2 which leads to inhibition of PG • Uses • Rheumatoid arthritis, osteoarthritis, spondylitis, gout F COOH CH3 S C H3 O SULINDAC
  • 16. PYRROLE ACETIC ACID DERIVATIVE O N OH O KETOROLAC N O H O CH3 C H3 O TOLMETIN ZOMEPIRAC N O H O Cl C H3 O CH3
  • 17. TOLMETIN • MOA • Inhibit PG Synthesis • Uses • Rheumatoid arthritis, osteoarthritis, spondylitis N O H O CH3 C H3 O TOLMETIN
  • 18. ZOMEPIRAC • MOA • Decrease PG Synthesis • Withdrawn from market due to its adverse effect, anaphylactic reactions. ZOMEPIRAC N O H O Cl C H3 O CH3
  • 19. KETOROLAC • MOA • Inhibit COX-1 and COX-2 LEADS TO INHIBITION OF PG Synthesis • Uses • Potent NSAID used to treat moderate to severe pain O N OH O KETOROLAC
  • 20. OXICAM DERIVATIVE PIROXICAM • NSAID used to relieve symptoms of painful inflammatory conditions like arthritis • Inhibit COX-1, Prevents production of PG involved in mediation of swelling and pain. N NH O S O O OH
  • 21. ANTHRANILATES (FENAMATES) • N-aryl substituted derivatives of anthranilic acid. • SAR • Position of –COOH is imp. For activity • Replacement of –COOH by tetrazole retains the activity. • Substitution on anthranilic acid ring reduces the activity. • Replacement of –NH , no acticity COOH NH
  • 22. DICLOFENAC • Inhibit COX-1 and COX-2 • Uses-treatment of rheumatoid arthritis, osteoarthritis • Adverse effect- hepatotoxicity COOH NH Cl Cl
  • 23. Mefenamic acid • Inhibit COX-1 and COX-2 • Uses-used for mild to moderate pain and primary dysmenorrhea HOOC NH C H3 CH3
  • 25. PHENYLBYTAZONE • Inactivate PG synthase through peroxide mediated deactivation • Reduce production of PG. • Use- spondylitis N N O O CH3 PHENYLBUTAZONES
  • 26. ANTIPYRINE • Inhibit COX-1 AND COX-2 involved in PG synthesis. • Analgesic N N CH3 O C H3 ANTIPYRINE