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PF3012 > NSAIDs - chemistry > Flashcards

NSAIDs - chemistry Flashcards

1
Q

List the 4 key features of prostaglandins

A
  • eicosanoid fatty acid (C20)
  • cyclopentane ring
  • C7 side chain containing carboxylate (alpha chain)
  • C8 side chain containing hydroxyl group (beta chain)
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2
Q

What does PGE2 indicate

A
  • ketone at C9 and alpha OH at C11
  • 2 indicates 2 C=C bonds in chains
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3
Q

what enzyme converts phospholipids into AA

A

phospholipase A2

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4
Q

which class of drugs inhibits PLA2

A

glucocorticoids via lipocortin

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5
Q

what is the half life of PGG2 and PGH2

A

5 minutes (unstable) (precursors to PGs)

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6
Q

List the two reaction catalysed by COX 1 and COX 2

A
  • Oxygen addition to AA, forming Prostaglandin G2 (PGG2)
  • Reduction of PGG2 to PGH2
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7
Q

What enzymes are present in COX-1 active site

A

Ile-434 and Ile-523

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8
Q

What enzymes are present in COX-2 active site

A

Val-434 and Val-523

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9
Q

What is the major difference in physiological function between COX-1 and cox-2

A
  • little COX-2 present in resting cells, but expression is induced by cytokines
  • COX-1 functions to produce PG involved in normal cell activity
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10
Q

What does COX-3 do

A

Mediates pain and body temperature, not inflammation

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11
Q

What is the major metabolite of PGE2

A

13,14-dihyro-15-keto-PGE2

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12
Q

What are the steps in the metabolism of PGE2

A
  • oxidation of 15-OH to 15-ketone by prostaglandin 15-OH dehydrogenase
  • reduction of 13 double bond by delta 13 reductase
  • cleavage of alpha chain
  • oxidation of beta chain to carboxylic acid
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13
Q

What does PGF2alpha do

A
  • dinoprost
  • inhibits progesterone production
  • abortifacient
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14
Q

What is the synthetic equivalent to Dinoprost

A

carboprost tromethane
15 beta methyl prevents metabolic oxidation

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15
Q

What enzymes convert paracetamol to N-hydroxamide

A

CYP2E1 and CYP3A4

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16
Q

What is N-hydroxamide converted to

A

N-acetimidoquinone (NAPQI)

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17
Q

What is Parvolex

A

Acetylcysteine
- 200mg/ml IV within 12 hours

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18
Q

Paracote

A

Paracetamol 500mg/ L-methionine 100mg

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19
Q

What does aspirin inhibit

A

Inhibits COX and biosynthesis of TXA

20
Q

Side effects of aspirin

A

GI disturbances (dyspepsia, bleeding, ulceration)

21
Q

How does aspirin modify COX

A
  • covalently
  • acetylates serine residues in COX1 and COX2
  • irreversibly inactivates COX
22
Q

What is the name of the reaction in the synthesis of Aspirin

A

Kolbe-Schmidt

23
Q

list the 3 modes of action of diclofenac

A
  • inhibits COX
  • inhibits lipoxygenase pathway - decreased production of leukotrienes
  • inhibits arachidonic acid release
24
Q

List 3 formulations of diclofenac sodium

A

voltarol, difene, diclac

25
name the formulation of diclofenac potassium
cataflam
26
name the formulation of diclofenac diethylammonium
voltarol gel
27
what is in arthrotec?
diclofenac sodium with misoprostol
28
Rank ibuprofen, indometacin and aspirin in decreasing anti-inflammatory action
Indomethacin > ibuprofen > aspirin
29
which enantiomer is active
S, but sold as racemic mixture
30
How is ibuprofen metabolised?
omega, omega-1 and omega-2 oxidation
31
How is Naproxen metabolised
(S) enantiomer
32
What is naproxen metabolised to
6-O-desmethyl derivative
33
Name two formulations of Naproxen
Naprosyn Synflex (Naproxen sodium)
34
What is the preferred conformation of indomethacin
Preferred conformation places chlorophenyl non-coplanar with indole to avoid clash with 2-Me
35
Describe the metabolism of indomethacin
50% of dose is deactivated by CYP2C9 to 5-O-desmethyl
36
What class of NSAID is mefenamic acid?
N-arylanthranilic acid
37
How does meclofenamate sodium differ from mefenamic acid?
Increased anti-inflammatory action (25x) Better inhibitor of PG biosynthesis 2 x ortho-Cl twist the ring into a non-coplanar conformation
38
Describe the structure of an Oxicam
enol-containing benzothiazine carboxamide
39
Describe the MOA of oxicam
- inhibitor of COX enzymes - inhibits migration of polymorphonuclear cells - inhibits release of lysosomal enzymes
40
How is Piroxicam metabolised
Oxidation by CYP2C9
41
What is the brand name of Piroxicam
Feldene
42
What is the R1 group in coxibs
usually large sulfonyl or sulfamoyl
43
How are COX-2 selective coxibs linked to an increased risk of heart attack?
Linked to inhibition of PGI2 (prostacyclin) production
44
What do COX-1 and COX-2 mediate?
COX-1 mediates the production of PGs and platelet aggregate stimulator TXA2 COX-2 mediates the production of the platelet aggregate inhibitor PGI2
45
What is the ideal COXIB
Drug with high COX-2 inhibition and some COX-1 inhibition
46
How is celecoxib metabolised
Metabolic oxidation by CYP2C9 on 4'-Me

PF3012 (10 decks)

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