Page 83 - Medicinal Chemistry Self Assessment

72 Medicinal Chemistry Self Assessment

5. As stated above, barbiturates exert their mechanism of action by interacting with the GABA recep-
A
tors. Assume that the following amino acids are involved in this binding: Val, Phe, Ser, Asn, and Lys.
Using the functional groups present within the structure of secobarbital, identify five specific binding
interactions between secobarbital and the side chains of the amino acids indicated.

Chapters 1.21 and 2.21
6. Shown below are known metabolites of butabarbital, secobarbital, and phenobarbital. Identify the
Please replace the indicated structure in Question 6 in both 1.21 and 2.21 (the one that is part of the question)
metabolic transformations that are required to produce each metabolite and indicate if they are
phase I or phase II transformations. Would you expect any of these metabolites to retain their
with the one below. Both structures had an identical error.
pharmacological activity? Why or why not?

Metabolite of Metabolite of Metabolite of
butabarbital secobarbital phenobarbital

Chapter 2.22

Please replace the structure for the answer to Question 3 in Chapter 2.22 with the one below.

Intramolecular
Hydrogen Bond
Intramolecular
Hydrogen Bond

Pravastatin
Fluvastatin