Non-Narcotic Analgesics Med Chem (Dr. Adams)

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Last updated 8:27 PM on 8/29/26
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29 Terms

1
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stereochemistry based on the substituents at C-9 and C-11 positions

The notation for prostaglandins is PGXₙ.

What does X express?

<p>The notation for prostaglandins is PGXₙ. </p><p>What does X express?</p>
2
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number of double bonds

The notation for prostaglandins is PGXₙ.

What does n express?

<p>The notation for prostaglandins is PGXₙ. </p><p>What does n express?</p>
3
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D

The notation for prostaglandins is PGXₙ. What stereochemistry has an -OH at 9-C?

<p>The notation for prostaglandins is PGXₙ. What stereochemistry has an -OH at 9-C?</p>
4
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E

The notation for prostaglandins is PGXₙ. What stereochemistry has an -OH at 11-C?

<p>The notation for prostaglandins is PGXₙ. What stereochemistry has an -OH at 11-C?</p>
5
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F

The notation for prostaglandins is PGXₙ. What stereochemistry has an -OH at 9-C & 11-C?

<p>The notation for prostaglandins is PGXₙ. What stereochemistry has an -OH at 9-C & 11-C?</p>
6
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15α-hydroxyl group ("down")

Prostaglandins have 20 carbons and are derived from arachidonic acid. What group is 15-C required to have?

<p>Prostaglandins have 20 carbons and are derived from arachidonic acid. What group is 15-C required to have?</p>
7
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trans double bond

Prostaglandins have 20 carbons and are derived from arachidonic acid. What stereochemistry must 13-C have?

<p>Prostaglandins have 20 carbons and are derived from arachidonic acid. What stereochemistry must 13-C have?</p>
8
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COX-4

Which COX isoform does not exist?

9
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COX-2 has 2 valines

Observe the active site of COX-1 and COX-2. Why does COX-2 have a larger active site?

<p>Observe the active site of COX-1 and COX-2. Why does COX-2 have a larger active site?</p>
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COX-1 has 2 isoleucines

Observe the active site of COX-1 and COX-2. Why does COX-1 have a smaller active site?

<p>Observe the active site of COX-1 and COX-2. Why does COX-1 have a smaller active site?</p>
11
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True

T/F: NSAIDs are all are organic acids with pKₐs in the 3-5 range

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False

T/F: Aminophenols have anti-inflammatory properties

<p>T/F: Aminophenols have anti-inflammatory properties</p>
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acidic group

Which functional group on NSAIDs is essential for COX inhibition?

<p>Which functional group on NSAIDs is essential for COX inhibition?</p>
14
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1

How many carbons must separate the acid and aromatic ring of NSAIDs?

<p>How many carbons must separate the acid and aromatic ring of NSAIDs?</p>
15
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methyl or propioaryl

Which R1 group on NSAIDs increases anti-inflammatory properties?

<p>Which R1 group on NSAIDs increases anti-inflammatory properties?</p>
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S

Which NSAID enantiomer of R1 is associated with activity in ibuprofen?

<p>Which NSAID enantiomer of R1 is associated with activity in ibuprofen?</p>
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lipophilic

Which R2 group on NSAIDs increases activity?

<p>Which R2 group on NSAIDs increases activity?</p>
18
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Salicylates (e.g. aspirin)

Which non-opioid analgesic class is required to have a carboxylic acid and a group ortho to the acid (usually a phenol)?

<p>Which non-opioid analgesic class is required to have a carboxylic acid and a group ortho to the acid (usually a phenol)?</p>
19
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True

T/F: Unlike NSAIDs, salicylates are uricosuric and anti-pyretic

<p>T/F: Unlike NSAIDs, salicylates are uricosuric and anti-pyretic</p>
20
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conversion to easily hydrolysable ester

What modification to aspirin occurs to become salicylic acid?

<p>What modification to aspirin occurs to become salicylic acid?</p>
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H

What group on R1 is characteristic of acetic NSAIDs e.g. indomethacin?

<p>What group on R1 is characteristic of acetic NSAIDs e.g. indomethacin?</p>
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methyl

What group on R1 is characteristic of propionic NSAIDs e.g. ibuprofen?

<p>What group on R1 is characteristic of propionic NSAIDs e.g. ibuprofen?</p>
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True

T/F: Nabumetone is a prodrug that is metabolized into a structural analog of naproxen

<p>T/F: Nabumetone is a prodrug that is metabolized into a structural analog of naproxen</p>
24
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carboxylic acid

Unlike other NSAIDs, oxicams lack which group?

<p>Unlike other NSAIDs, oxicams lack which group?</p>
25
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sulfone

COX-2 selectivity requires the utilization of binding to the side pocket of COX-2. What functional group on COX-2 inhibitor achieves this?

<p>COX-2 selectivity requires the utilization of binding to the side pocket of COX-2. What functional group on COX-2 inhibitor achieves this?</p>
26
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less GI side effects

Nabumetone is a prodrug. What are the benefits of using an NSAID prodrug?

27
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5-C

Adding a group to which carbon increases potency and anti-inflammatory properties of salicylates?

<p>Adding a group to which carbon increases potency and anti-inflammatory properties of salicylates?</p>
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Reye's syndrome

Why are salicylates contraindicated in children and teenagers with viral infections +/- fever?

29
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False

T/F: NSAIDs have a side effect of hepatotoxicity. There is a higher likelihood with CYP induction and/or GSH depletion