Page 244 - Medicinal Chemistry Self Assessment

Section 4 Whole Molecule Drug Evaluation

Answers

2.27 Zanamivir and Oseltamivir

2.27 Zanamivir and Oseltamivir
Shown below is the structure of zanamivir. This drug molecule is administered via oral inhalation for the treatment of
Shown below is the structure for the treatment of influenza A and B infections.
influenza A and B infections.

Zanamivir

Chapter 2.27
1. Identify all of the acidic and basic functional groups, provide the normal pK range for each functional
1. Identify all of the of 7.2.
a
group, and identify if each functional group would be primarily ionized or unionized at a pulmonary
Please replace the structure for the answer of Q1 with the one below.
Answer:
pH=7.2.

Answer

Carboxylic acid (Acidic functional group)
Carboxylic acid (Acidic functional group)
Normal pH range = 2.5 to 5
Normal pH range = 2.5 to 5
Would be primarily ionized at a pH of 7.2
Would be primarily ionized at a pH = 7.2

Guanidine (Basic functional group)
Normal pH range = 12 to 13
Guanidine (Basic functional group)
Normal pH range = 12 to 13
Would be primarily ionized at a pH of 7.2
Would be primarily ionized at a pH = 7.2
2. Identify all other water soluble functional groups that are present within the structure of zanamivir.

Answer:

Please replace the structure for the answer to Q6, part a with the one below (page 4, middle structure)
Primary hydroxyl group
Secondary hydroxyl group
(or primary alcohol) (or secondary alcohol)
Secondary hydroxyl group
(or secondary alcohol) Ether oxygen
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Amide
Product of Product of Product of ester

ester hydrolysis amide hydrolysis and amide hydrolysis

3. Based on your is administered as an oral inhaler instead of an oral tablet or capsule.