Page 148 - Medicinal Chemistry Self Assessment

Section 4 Whole Molecule Drug Evaluation

Answers

2.9 Aripiprazole

2.9 Aripiprazole
2.9 Aripiprazole

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

Aripiprazole
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 would be primarily ionized or unionized at a urine pH of 5.6.
a
1. Identify all of would be primarily ionized or unionized at a urine pH of 5.6.
fied functional groups, and identify if each functional group would be primarily ionized or unionized at a
Answer
urine pH=5.6.
Answer

Answer

Tertiary amine (Basic functional group)
Tertiary amine (Basic functional group) H O
Normal pH range = 9 to 11
Normal pH range = 9 to 11 = N H O
Would be primarily ionized at a pH 5.6
=
Would be primarily ionized at a pH 5.6 N
Cl Cl O
Cl Cl O
N N
N N Aripiprazole
Aripiprazole
Aromatic amine (Aniline, Basic functional group)
Normal pH range = 2 to 5
Aromatic amine (Aniline, Basic functional group)
=
Would be primarily unionized at a pH 5.6
Normal pH range = 2 to 5
=
Would be primarily unionized at a pH 5.6
2. Identify all of the of aripiprazole.
Answer
2. Identify all of the of aripiprazole.
3.
Answer
3. Alkyl (aliphatic) chain
(Lipid soluble)
Alkyl (aliphatic) chain
137
Ether oxygen
Halogens (Lipid soluble) (Water soluble) O Amide
(Lipid soluble) Ether oxygen H (Water soluble)
Halogens (Water soluble) N O Amide
(Water soluble)
(Lipid soluble) H Hydrocarbon portion
Cl Cl O N of bicyclic ring
(Lipid soluble)
Hydrocarbon portion
Aromatic (phenyl) ring Cl Cl O
(Lipid soluble) N N of bicyclic ring
Aromatic (phenyl) ring (Lipid soluble)
(Lipid soluble) N N Aripiprazole

Aripiprazole
Alkyl (aliphatic) chain
(Lipid soluble)

Alkyl (aliphatic) chain
(Lipid soluble)