Page 157 - Medicinal Chemistry Self Assessment

Medicinal Chemistry Self-Assessment Book: Batch Two
Chapters 1.10 and 2.10

Chapter 1.10/2.10 (remove bold from drug name)

146 Medicinal Chemistry Self Assessment

5. Approximately 60% of a cefprozil dose is recovered in the urine unchanged. Because impairment in
Cefprozil (Cefzil)
hepatic function increases the half-life of the drug by several hours, it is likely that cefprozil under-

goes a variety of metabolic transformations catalyzed by liver enzymes. For each of the metabolic
transformations A–F, identify which metabolic transformation has occurred and whether the product
Chpater 1.10/2.10 Corrected structure (product of E transformation)
formed was the result of a phase I or phase II metabolic transformation.

NH 2 H
H O N H H S
O N
H O O CH 3
O H
H H CO 2 H
N S
NH 2
O N OH
H O O CH 3
CO 2 H O H N H H S
H O 2
N
A B O CH 3
CO 2 H
C
NH 2 H
N H H S

O N
H O O CH 3
CO 2 H

NH 2 H H H F D
N S
E
O N
H O O CH 3 NH 2 H

O N H N H H S
O
O S O N
-O O O CH 3
OH O
CO 2 H
NH 2 H
N H H S

O N OH
H O O
CO 2 H

Answer

Name of Transformation Phase I or Phase II
A Oxidative deamination Phase I
B Aromatic hydroxylation Phase I
C Amide hydrolysis Phase I
D Sulfate conjugation Phase II
E Allylic oxidation Phase I
F Amino acid conjugation (with glycine) Phase II