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Course: Medicinal Chemistry Course Code: BBICBI404R04/BICBI404R01 Instructor: Karthi Shanmugam

This document contains a problem set for a medicinal chemistry course. It includes 4 problems related to calculating drug receptor occupancy, drug ionization based on pKa values and pH, and identifying ionizable functional groups on various drug structures. The problems provide structures of drugs like terazosin, aspirin, cefotaxime, nitrofurantoin, atenolol, ezetimibe, and natamycin. Acidic and basic functional groups and their pKa values are given, along with different pH conditions representing environments like the stomach, intestine, urine and plasma. Students are asked to calculate percent ionization and receptor occupancy and identify whether groups would be primarily ionized or unionized given the pH scenarios.

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Karthi Shanmugam
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65 views

Course: Medicinal Chemistry Course Code: BBICBI404R04/BICBI404R01 Instructor: Karthi Shanmugam

This document contains a problem set for a medicinal chemistry course. It includes 4 problems related to calculating drug receptor occupancy, drug ionization based on pKa values and pH, and identifying ionizable functional groups on various drug structures. The problems provide structures of drugs like terazosin, aspirin, cefotaxime, nitrofurantoin, atenolol, ezetimibe, and natamycin. Acidic and basic functional groups and their pKa values are given, along with different pH conditions representing environments like the stomach, intestine, urine and plasma. Students are asked to calculate percent ionization and receptor occupancy and identify whether groups would be primarily ionized or unionized given the pH scenarios.

Uploaded by

Karthi Shanmugam
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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Course: Medicinal Chemistry

Course Code: BBICBI404R04/BICBI404R01


Instructor: Karthi Shanmugam

CIA-1 Problem Set Page 1


Problem #1 Terazosin is an antagonist at the alpha1-adrenergic receptor, it has an equilibrium dissociation
constant 1.0 nM. Epinephrine is an antagonist at the alpha1-adrenergic receptor and has an equilibrium
dissociation constant of 100nM. Calculate the percentage of receptors occupied for each drug under the following
conditions. Plot the relationship between concentration of the drug and receptor occupancy.

Terazosin % receptor occupied? Epinephrine % receptor occupied?


0.5 nM 50.0 nM
1.0 nM 100.0 nM
4.0 nM 400.0 nM
10.0 nM 1000.0 nM

CIA-1 Problem Set Page 2


Problem #2 The pKa of aspirin, a weak acid is 3.5. Calculate the degree of ionization of aspirin in the stomach
and intestine if the pH of the contents of the stomach is 1 and the pH of the contents in the intestine is 6.

CIA-1 Problem Set Page 3


Problem #3 Shown below are the structures of cefotaxime, nitrofurantoin, atenolol, and ezetimibe. Each of
these drug molecules contains one ionizable functional group. The pKa value of cefotaxime is 3.4,
nitrofurantoin is 7.1, and atenolol is 9.6.
a. Match the pKa values provided with the appropriate functional groups of the corresponding drugs+. For
each functional groups, 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 pH=1.8, a urinary pH=6.1, or a plasma pH=7.4. Provide an explanation for your responses for
cefotaxime at a plasma pH=7.4, nitrofurantoin at a urinary pH=6.1, and atenolol at a stomach pH=1.8.

CIA-1 Problem Set Page 4


CIA-1 Problem Set Page 5
Problem #4 Shown below is the structure of natamycin. It contains two functional groups that could be
potentially ionized. The pKa values for natamycin are 4.6 and 8.4.

a. Match the pKa values provided to the appropriate functional groups and identify if the functional group
is acidic or basic.
b. Using the Henderson-Hasselbalch equation, calculate the percent ionization that occurs for each of
these functional groups at an intestinal pH=6.2.

CIA-1 Problem Set Page 6


CIA-1 Problem Set Page 7
CIA-1 Problem Set Page 8

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