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Pivampicillin is a penicillin prodrug: Pivampicillin N O N

Chapter 21, Problem 21.68

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QUESTION:

Pivampicillin is a penicillin prodrug: Pivampicillin N O N S O 2 HNH O O O O The prodrug ester group (in red) enables a more rapid delivery of the prodrug to the bloodstream, where the ester group is subsequently hydrolyzed by enzymes, releasing the active drug. (a) Draw the structure of the active drug. (b) What is the name of the active drug (see the Medically Speaking box at the end of Section 21.12)?

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QUESTION:

Pivampicillin is a penicillin prodrug: Pivampicillin N O N S O 2 HNH O O O O The prodrug ester group (in red) enables a more rapid delivery of the prodrug to the bloodstream, where the ester group is subsequently hydrolyzed by enzymes, releasing the active drug. (a) Draw the structure of the active drug. (b) What is the name of the active drug (see the Medically Speaking box at the end of Section 21.12)?

ANSWER:

Step 1 of 3

Consider the following structure:

The prodrug ester moiety (highlighted in red) allows the drug to be rapidly delivered to the bloodstream, where it is hydrolyzed by enzymes. This releases the active drug.

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