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The Purple Pill


Annette W. Neuman
Department of Chemistry
Oxford College of Emory University


This interrupted case study is designed to teach students about chirality and the pH scale in the context of medicinal chemistry. Students read about a college student who wakes in the middle of the night with chest pains. Upon examination in the emergency room, she is determined to be suffering from gastroesophageal reflux disorder (GERD). Students learn about the drug esomeprazole (Nexium) and its stereochemical relationship to its precursor, omeprazole (Prilosec). They also learn about the pH scale as they investigate the mechanism of action of these drugs. Students are asked to read about the development and activity of esomeprazole and write a brief essay arguing whether esomeprazole is an improvement over omeprazole. This case may be used in a survey course of general, organic, and biochemistry or can be modified for use in a sophomore-level organic chemistry course, an introductory pharmacology course, an upper-level medicinal chemistry course, or a general biology course.

  • Define the following terms: differential diagnosis, mechanism of action, pH, and racemic mixture.
  • Find generic names, brand names, chemical structures, and indications of small molecule drugs.
  • Briefly describe the mechanism of action of proton pump inhibitors.
  • Compare the acidity of solutions using their pH.
  • Explain why different enantiomers of the same molecule may have different activities in the body.
  • Assess the ethics of pharmaceutical companies.
Keywords: Electrocardiogram; GI cocktail; gastroesophageal reflux disorder; GERD; omeprazole; esomeprazole; mechanism of action; pH; proton pump; inhibitor; enantiomer; racemic mixture; stereochemistry; chiral center; differential diagnosis; drug; Prilosec; Nexium
Topical Area: Ethics
Educational Level: Undergraduate lower division, Undergraduate upper division
Formats: PDF
Type/Method: Interrupted
Language: English
Subject Headings: Chemistry (General)   Biology (General)   Medicinal Chemistry   Organic Chemistry   Pharmacy / Pharmacology  
Date Posted: 3/11/2019
Date Modified: N/A
Copyright: Copyright held by the National Center for Case Study Teaching in Science, University at Buffalo, State University of New York. Please see our usage guidelines, which outline our policy concerning permissible reproduction of this work.

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