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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
Q

name the formulation of diclofenac potassium

A

cataflam

26
Q

name the formulation of diclofenac diethylammonium

A

voltarol gel

27
Q

what is in arthrotec?

A

diclofenac sodium with misoprostol

28
Q

Rank ibuprofen, indometacin and aspirin in decreasing anti-inflammatory action

A

Indomethacin > ibuprofen > aspirin

29
Q

which enantiomer is active

A

S, but sold as racemic mixture

30
Q

How is ibuprofen metabolised?

A

omega, omega-1 and omega-2 oxidation

31
Q

How is Naproxen metabolised

A

(S) enantiomer

32
Q

What is naproxen metabolised to

A

6-O-desmethyl derivative

33
Q

Name two formulations of Naproxen

A

Naprosyn
Synflex (Naproxen sodium)

34
Q

What is the preferred conformation of indomethacin

A

Preferred conformation places chlorophenyl non-coplanar with indole to avoid clash with 2-Me

35
Q

Describe the metabolism of indomethacin

A

50% of dose is deactivated by CYP2C9 to 5-O-desmethyl

36
Q

What class of NSAID is mefenamic acid?

A

N-arylanthranilic acid

37
Q

How does meclofenamate sodium differ from mefenamic acid?

A

Increased anti-inflammatory action (25x)
Better inhibitor of PG biosynthesis
2 x ortho-Cl twist the ring into a non-coplanar conformation

38
Q

Describe the structure of an Oxicam

A

enol-containing benzothiazine carboxamide

39
Q

Describe the MOA of oxicam

A
  • inhibitor of COX enzymes
  • inhibits migration of polymorphonuclear cells
  • inhibits release of lysosomal enzymes
40
Q

How is Piroxicam metabolised

A

Oxidation by CYP2C9

41
Q

What is the brand name of Piroxicam

A

Feldene

42
Q

What is the R1 group in coxibs

A

usually large sulfonyl or sulfamoyl

43
Q

How are COX-2 selective coxibs linked to an increased risk of heart attack?

A

Linked to inhibition of PGI2 (prostacyclin) production

44
Q

What do COX-1 and COX-2 mediate?

A

COX-1 mediates the production of PGs and platelet aggregate stimulator TXA2
COX-2 mediates the production of the platelet aggregate inhibitor PGI2

45
Q

What is the ideal COXIB

A

Drug with high COX-2 inhibition and some COX-1 inhibition

46
Q

How is celecoxib metabolised

A

Metabolic oxidation by CYP2C9 on 4’-Me

PF3012 (10 decks)

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