Page 60 - Medicinal Chemistry Self Assessment

1.14 Fenofibrate and Gemfibrozil 49

5. Provide a structural rationale for why oxidative O-dealkylation does not occur.

6. Fenofibrate and gemfibrozil have dramatically different elimination half-lives (20–22 hours and 1.5
hours respectively). Identify the possible metabolic transformations for gemfibrozil and provide a
1.14 and 2.14 (drug name – remove bold)
justification for the significant difference in this pharmacokinetic parameter.

Fenofibrate Gemfibrozil

Letter “C” – add bold

C

2.14 – remove bold from label

B F

A C D

E

Fenofibrate

2.14 – remove bold from label

O O CH O O
3
Ester
O Hydrolysis O
O CH 3 OH
H 3 C CH 3 H 3 C CH 3
Cl Cl

Inactive Active