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Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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
Transcribed Image Text:Lumiracoxib has been associated with bioactivation resulting in
the formation of a toxic intermediate leading to drug associated liver damage.
Lumiracoxib--an NSAID
CH3
Show a structural formula to indicate how lumiracoxib could be metabolized and
bioactivated into a reactive NAPQI-like reactive intermediate that will account for its liver
toxicity. Remember that in CYP450 catalyzed phase 1 drug metabolism the para-
hydroxylation of an aromatic amine (an aniline derivative) is a very common metabolic
reaction. If lumiracoxib was first p-hydroxylated the the p-hydroxylated product again
oxidized by CYP 450what might result? Use the production of NAPQI that I presented
as a model for the 2nd step.

Transcribed Image Text:Would a structural alert have been appropriate for this structure? Justify your answer.
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