20.58 Fluphenazine is an antipsychotic drug that is administered as an ester prodrug via intramuscular injection: N. 'N CF3 Fluphenazine decanoate The hydrophobic tail of the ester is deliberately designed to enable a slow release of the prodrug into the bloodstream, where the prodrug is rapidly hydrolyzed to produce the active drug. (a) Draw the structure of the active drug. (b) Draw the structure of and assign a systematic name for the carbox- ylic acid that is produced as a by-product of the hydrolysis step.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter28: Biomolecules: Nucleic Acids
Section28.SE: Something Extra
Problem 38AP
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20.58 Fluphenazine is an antipsychotic drug that is administered as
an ester prodrug via intramuscular injection:
CF3
Fluphenazine decanoate
The hydrophobic tail of the ester is deliberately designed to enable a slow
release of the prodrug into the bloodstream, where the prodrug is rapidly
hydrolyzed to produce the active drug.
(a) Draw the structure of the active drug.
(b) Draw the structure of and assign a systematic name for the carbox-
ylic acid that is produced as a by-product of the hydrolysis step.
Transcribed Image Text:20.58 Fluphenazine is an antipsychotic drug that is administered as an ester prodrug via intramuscular injection: CF3 Fluphenazine decanoate The hydrophobic tail of the ester is deliberately designed to enable a slow release of the prodrug into the bloodstream, where the prodrug is rapidly hydrolyzed to produce the active drug. (a) Draw the structure of the active drug. (b) Draw the structure of and assign a systematic name for the carbox- ylic acid that is produced as a by-product of the hydrolysis step.
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