Page 58 - Medicinal Chemistry Self Assessment

Section 2 Whole Molecule Drug Evaluation

1.14 Fenofibrate and Gemfibrozil

Fenofibrate is a member of the fibrate class of anti-hyperlipidemic agents. It is used as adjunctive therapy to diet in the
management of dyslipidemias, including in the treatment of severe hypertriglyceridemia. The specific mechanism(s)
by which fenofibrate decreases triglyceride and total cholesterol levels, as well as increases the levels of high density
lipoproteins (HDL), is unknown. What we do know is that the decrease in very low density lipoproteins (VLDLs)
1.14 and 2.14 (drug name – remove bold)
results from fenofibrate stimulation of lipoprotein lipase.

Fenofibrate Gemfibrozil

1. Conduct a complete structural evaluation of fenofibrate and use the information in the grid to inform
Letter “C” – add bold
your answers to the questions that follow.

Function
Amino Acids That
Character Function Can Interact with the
Character Acidic, Basic, or Function Interaction(s) Functional Group via
Name of Hydrophilic Neutral ↑ Solubility Possible with Biological Hydrogen Bonding
Functional and/or Provide pK and/or Target at Physiological Interactions at pH=7.4
a
Group Hydrophobic When Relevant ↑ Absorption C pH=7.4 None Is Acceptable

2.14 – remove bold from label

B F

A C D

E

Fenofibrate

2.14 – remove bold from label
47

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

Inactive Active