Page 62 - Medicinal Chemistry Self Assessment

2.14 – remove bold from label
Section 2 Whole Molecule Drug Evaluation

O O
O
OH
H 3 C CH 3 1.15 Fluvoxamine
Cl

Fenofibric Acid

Fluvoxamine is an inhibitor of the serotonin reuptake transporter (SERT) and prevents the reuptake of serotonin

at the presynaptic membrane in the central nervous system. It is indicated for use in the treatment of depression.
1.15 and 2.15 – remove bold from label
Fluvoxamine is structurally unique relative to the rest of the serotonin selective reuptake inhibitor class of drugs.

A
B
C D

E

Fluvoxamine

1.15 and 2.15 – remove bold from label
1. Conduct a structural evaluation of fluvoxamine, focusing on the boxed functional groups, and use the

information in the grid to inform your answers to the questions that follow.
F C
3
Function
O Function Amino Acids That
Character CH
3
Interaction(s) Can Interact with the
Acidic, Basic, NH Possible with O Functional Group via
–
N
O
Character or Neutral O Function 3 Biological O
Hydrogen Bonding
Name of Hydrophilic Provide ↑ Solubility Target Interactions at
OH
Functional and/or pK When and/or at Physiological pH=7.4
Fluvoxamine maleate
a
Group Hydrophobic Relevant ↑ Absorption pH=7.4 None Is Acceptable
A

B
C

D

E

51