Pivampicillin is a methylpivoxyl ester of ampicillin. It is prepared as a pro-drug to improve the lipophilic characteristics of the antibiotic and thus its bioavailability. In the body, the pivalic ester is hydrolyzed allowing the release of ampicillin. With this information: a) Draw the structure of ampicillin (the hydrolysis product of pivampicillin). b) Show the complete mechanism for the hydrolysis in acid medium of the ester (shown in red).

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
icon
Related questions
icon
Concept explainers
Question
Pivampicillin is a methylpivoxyl ester of
ampicillin. It is prepared as a pro-drug to
improve the lipophilic characteristics of the
antibiotic and thus its bioavailability. In the
body, the pivalic ester is hydrolyzed allowing
the release of ampicillin. With this information:
a) Draw the structure of ampicillin (the
hydrolysis product of pivampicillin).
b) Show the complete mechanism for the
hydrolysis in acid medium of the ester (shown
in red).
NH2H
N
Pivampicillin
Transcribed Image Text:Pivampicillin is a methylpivoxyl ester of ampicillin. It is prepared as a pro-drug to improve the lipophilic characteristics of the antibiotic and thus its bioavailability. In the body, the pivalic ester is hydrolyzed allowing the release of ampicillin. With this information: a) Draw the structure of ampicillin (the hydrolysis product of pivampicillin). b) Show the complete mechanism for the hydrolysis in acid medium of the ester (shown in red). NH2H N Pivampicillin
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 4 steps with 3 images

Blurred answer
Knowledge Booster
Carbohydrates
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY