Page 180 - Medicinal Chemistry Self Assessment

Section 4 Whole Molecule Drug Evaluation
2.14 – remove bold from label

Answers

O O
O
OH
H 3 C CH 3 2.15 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. Conduct a structural evaluation of fluvoxamine, focusing on the boxed functional groups, and use the
1.15 and 2.15 – remove bold from label
information in the grid to inform your answers to the questions that follow.

Answer F C
3
Function
O
Character CH 3 Amino Acids That
Function
Acidic, Basic, N O NH 3 – O O Can Interact with the
O
Character or Neutral Function Interaction(s) Functional Group via
Possible with Hydrogen Bonding
OH
Name of Hydrophilic Provide Fluvoxamine maleate Biological Target Interactions at
↑ Solubility

Functional and/or pK When and/or at Physiological pH=7.4
a
Group Hydrophobic Relevant ↑ Absorption pH=7.4 None Is Acceptable
A Halogenated Hydrophilic (F) Neutral Solubility (F) Dipole–dipole Ser, Thr, Tyr, Cys, Asn, Gln,
aliphatic alkane Hydrophobic (R) Absorption (R) H-bonding (A) Trp, His

Ion–dipole (as the
dipole)

B Aromatic hydro- Hydrophobic Neutral Absorption Hydrophobic None
carbon van der Waals
π-π Stacking

C Aliphatic alkane Hydrophobic (R) Neutral Absorption Hydrophobic None

van der Waals

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