Page 102 - Medicinal Chemistry Self Assessment

Section 2 Whole Molecule Drug Evaluation

1.27 Zanamivir and Oseltamivir

1.27 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 d B infections.
influenza A and B infections.

Zanamivir

1. Identify all of the H of 7.2.
1. Identify all of the acidic and basic functional groups, provide the normal pK range for each functional
a
group, and identify if each functional group would be primarily ionized or unionized at a pulmonary
2. Identify all other water soluble functional groups that are present within the structure of zanamivir.
pH=7.2.
3. Based on your or capsule.
4. Zanamivir exerts its n. Using neuraminidase.
2. Identify all other water soluble functional groups that are present within the structure of zanamivir.

3. Based on your answers to questions 1 and 2, explain why zanamivir is administered as an oral inhaler
instead of an oral tablet or capsule.

4. Zanamivir exerts its antiviral action by inhibiting neuraminidase, a viral enzyme that is required for the
spread of the viral infection. A key component of neuraminidase’s action is the hydrolysis of N-acetylsialic
acid from surface viral glycoproteins. Shown below is the structure of N-acetylsialic acid bound to a glyco-
protein. Using this structure and the structure of zanamivir, provide an explanation of how zanamivir
Glycosidic bond
inhibits neuraminidase.
N-Acetylsialic acid bound to glycoprotein Zanamivir

5. Shown below is a, or similar to that of zanamivir?

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6. Shown below is the oseltamivir .