Page 46 - Medicinal Chemistry Self Assessment

Section 2 Whole Molecule Drug Evaluation

1.10 Cefprozil

Cefprozil is a second-generation cephalosporin that exhibits good Gram (+) activity with improved Gram (–) activity
Medicinal Chemistry Self-Assessment Book: Batch Two
as compared to the first-generation cephalosporins. Effective against the majority of bacteria that cause upper and
Chapters 1.10 and 2.10
lower respiratory infections, as well as skin infections, cefprozil was a first-line anti-infective agent until an increase in

the incidence of resistance and the development of newer agents decreased its “favored” status.
Chapter 1.10/2.10 (remove bold from drug name)

Cefprozil (Cefzil)

1. Conduct a complete structural evaluation of cefprozil and use the information in the grid to inform your
Chpater 1.10/2.10 Corrected structure (product of E transformation)
answers to the questions that follow.

NH 2 H
H O Function N H H S Function
Character Interaction(s) Amino Acids That
O
Character Acidic, Basic, Function H O Possible with N Can Interact with
CH
O
3
O
Functional Group via
↑ Solubility
Name of Hydrophilic or Neutral H H H Biological Target CO 2 H
S
Functional and/or Provide pK N and/or at Physiological H-Bonding (at pH=7.4)
NH
a
2
Group Hydrophobic When Relevant ↑ Absorption pH=7.4 None is Acceptable
N
O
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 H H
N S
O N
H O O CH 3
CO 2 H
D
NH 2 H F
N H H S
E
O N
H O O CH 3 NH 2 H
O 35 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