Page 39 - Medicinal Chemistry Self Assessment

Medicinal Chemistry Self-Assessment Book: Batch Two
Chapters 1.8 and 2.8

Chapter 1.8/2.8 (remove bold from drug name x2)
E
D F
A
B

28 Medicinal Chemistry Self Assessment

Aliskiren
C
2. Aliskiren is marketed as the pure 2S, 4S, 5S, 7S enantiomer. Circle all of the chiral carbon atoms and

determine if diastereomeric or geometric isomers are possible.

Aliskiren

3. Although aliskiren is administered orally, its oral bioavailability is ~2.5% and is very poorly absorbed.

Using the information in the structure evaluation grid, provide a structural rationale for this unfortu-

nate property.

4. Approximately 25% of the absorbed dose of aliskiren is excreted in the urine unchanged. It is

unknown how much of an absorbed dose is metabolized, and several metabolites from CYP3A4

mediated transformations have been identified. Several possible metabolic products are illustrated.

Identify which metabolic transformation has occurred and whether or not it represents an oxidative

transformation.