Page 103 - Medicinal Chemistry Self Assessment

1.27 Zanamivir and Oseltamivir
1.27 Zanamivir and Oseltamivir
Shown below is the d B infections.
Shown below is the d B infections.

1.27 Zanamivir and Oseltamivir
Shown below is the d B infections.

Zanamivir
Zanamivir

1. Identify all of the H of 7.2.
1. Identify all of the H of 7.2.
2. Identify all other water soluble functional groups that are present within the structure of zanamivir.
2. Identify all other water soluble functional groups that are present within the structure of zanamivir.
Medicinal Chemistry Self Assessment
92 3. Based on your or capsule.
3. Based on your or capsule.
4. Zanamivir exerts its n. Using neuraminidase.
Zanamivir

4. Zanamivir exerts its n. Using neuraminidase.

1. Identify all of the H of 7.2.
2. Identify all other water soluble functional groups that are present within the structure of zanamivir.
3. Based on your or capsule.
4. Zanamivir exerts its n. Using neuraminidase.

Glycosidic bond
Glycosidic bond
N-Acetylsialic acid bound to glycoprotein Zanamivir
N-Acetylsialic acid bound to glycoprotein Zanamivir

5. Shown below is a, or similar to that of zanamivir?
5. Shown below is a stereoisomer of zanamivir. Identify if the stereoisomer is an enantiomer, a diastereomer,
5. Shown below is a, or similar to that of zanamivir?
a geometric isomer, an epimer, and/or a conformational isomer. Predict whether this stereoisomer’s

pharmacological activity is likely to be more active, less active, or similar to that of zanamivir?

Glycosidic bond
N-Acetylsialic acid bound to glycoprotein Zanamivir

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

6. Shown below is the oseltamivir .
6. Shown below is the oseltamivir .

6. Shown below is the structure of oseltamivir and a list of five metabolic transformations. For each

metabolic transformation, indicate if it is a phase I or a phase II transformation and if oseltamivir has

a functional group present that can undergo the indicated transformation. When evaluating these
metabolic transformations, consider functional groups that are initially present within the structure
of oseltamivir as well as those that can be added/revealed through phase I metabolism. If you answer

YES, then draw the appropriate metabolite; if you answer NO, then provide a brief explanation as to
6. Shown below is the oseltamivir .
why this metabolic transformation is not possible for oseltamivir.

Metabolic Pathways
A. Hydrolysis
B. Allylic oxidation
C. Glucuronide conjugation

D. ω-Oxidation
E. Oxidative O-Dealkylation