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(Solved): 1. Shown below are the structures of cefotaxime, nitrofurantoin, atenolol, and ezetimibe. Each of ...



1. Shown below are the structures of cefotaxime, nitrofurantoin, atenolol, and ezetimibe. Each of these drug molecules contai

1. Shown below are the structures of cefotaxime, nitrofurantoin, atenolol, and ezetimibe. Each of these drug molecules contains one ionizable functional group. The \( \mathrm{pK}_{\mathrm{a}} \) values have been provided. a. Match the \( \mathrm{pK}_{\mathrm{a}} \) values provided with the appropriate functional groups. For each functional group, identify the name of the group and whether it is acidic or basic. b. For each functional group indicate whether it would be primarily ionized or primarily unionized at a stomach \( \mathrm{pH}=1.8 \), a urinary \( \mathrm{pH}=6.1 \), or a plasma \( \mathrm{pH}=7.4 \). Provide an explanation for your responses for cefotaxime at a plasma \( \mathrm{pH}=7.4 \), nitrofurantoin at a urinary \( \mathrm{pH}=6.1 \), and atenolol at a stomach \( \mathrm{pH}=1.8 \). Cefotaxime \( \mathrm{pK}_{\mathrm{a}}=3.4 \) Nitrofurantoin 2. In the previous question, we examined four \( \mathrm{pK}_{\mathrm{a}} \) values in three different environments for a total of 12 different scenarios. Which of these 12 scenarios allow you to use the Rule of Nines to calculate the percent of ionization of the functional group in the specific environment? Identify the specific scenarios and use the Rule of Nines to calculate the percent of the functional group that would be ionized.


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Solution: Key points: If the pH < pKa the group is protonated, if pH > pKa the group is deprotonated and if pH = pKa the group is 50% protonated and 50% deprotonated. 1. a. The functional groups are identified and circled in the below image. Drug pKa
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