Page 42 - Medicinal Chemistry Self Assessment

Section 2 Whole Molecule Drug Evaluation

1.9 Aripiprazole

1.9 Aripiprazole

Shown below is the structure of aripiprazole, a serotonin receptor modulator used for the treatment of depression,
schizophrenia, autism, mania, and bipolar disorder.
Shown below is the structure of aripiprazole, a serotonin receptor modulator used for the treatment of depression,
schizophrenia, autism, mania, and bipolar disorder.

O
H
N

Cl Cl O

N N

Aripiprazole

1. Identify all of the acidic and basic functional groups, provide the normal pK range for each of the identi-
1. Identify all of the pH of 5.6.
a
fied functional groups, and identify if each functional group would be primarily ionized or unionized at a
2. solubility of aripiprazole.
urine pH=5.6.
3. Using yur answers previously listed.
4. Drug hly aripiprazole and either tolbutamide or losartan?
2. Identify all of the remaining functional groups, and indicate how each group contributes to the overall
water solubility or the overall lipid solubility of aripiprazole.

3. Using your answers from the previous two questions, provide an explanation as to why aripiprazole can be
administered orally for the indications previously listed.

Tolbutamide

Losartan

5. Assume that at a physiological pH of 7.4.

D
31
A
C
B

Aripiprazole