Nexium™

The Naming of Chiral Drugs. The nomenclature of chiral compounds is difficult and sometimes confusing. We have already introduced the prefixes R and S, (- -) and (—), and D and L. We have already seen many common names for drugs that have an implied chirality, as in methamphet-amine and ephedrine. The hyphenated prefixes R/S, D/L, and + / — render the alphabetic indexing of pharmaceutics problematic. One approach to this problem that has been used to help with this issue is to select drug names where the chirality has been imbedded into the common chemical name. One example that we have discussed is esomeprazole, 

FIGURE 5.1 o. Molecular structures of omeprazole enantiomers. (Prilosec and Nexium are registered trademarks of the AstraZenaca group of companies.) 

FIGURE 5.11. Molecular structure of the active enantiomer of atorvastatin. Lipitor is a registered trademark of Pfizer Inc.) 

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Esomeprazole (Nexium) Lansoprazole (Prevacid) Omeprazole (Prilosec) Panloprazole (Protonix) Rabeprazole (Aciphex)... 

Omeprazole Each particle in the capsule is protected by an acid stable content that must not be crushed. The granules in the capsule can be too large for tube administration. Change drug. Another proton-pump inhibitor with smaller granules such as Nexium or Prilosec/Losec MUPS. Special instructions are available... 

Acid reflux and heartburn are conditions that affect many of us from time to time. Exhibit 1.4 describes the proton pump inhibitor, Nexium, and its predecessor, Prilosec, and how they work as antiulcerants. 

Nexium (esomeprazole magnesium, AstraZeneca) is a drug termed as a proton pump inhibitor. It turns off the secretions of acid into the stomach. When less acid is produced, there is a reduced amount of acid that can flow back up from the stomach into the esophagus to cause reflux symptoms. 

It should be noted that there are normally three names associated with a drug the trade or proprietary name (e.g., Nexium), generic or nonproprietary name (esomeprazole), and a specific chemical name for the active ingredient. In the case of esomeprazole, the active ingredient is the S-isomer of benzimidazole. 

Sources Food and Drug Administration. Nexium. http //www.fda.gov/cder/foi/label/2006/ 021153s0221bl.pdf [accessed July 27,2007]. 

Esomeprazole (Nexium, AstraZeneca) proton pump inhibitor for the prevention of relapse in reflux esophagitis... 

Our second interesting case of chirality is an example of advertising trumping science. In this case, the molecule in question is known generically as esomeprazole and is marketed in the United States as Nexium, widely advertised as the purple pill. The story begins with a closely related molecule, omeprazole, marketed as Losec or Prilosec. 

Nexium containing esomeprazole (proton pump inhibitor) is marketed by AstraZeneca. 

Powder for injection, freeze-dried 20 and 40 Nexium I. V. (AstraZeneca) mg Rx)... 

Tagamet DS OTC) Esomeprazole (Nexium) Famotidine (Pepcid, Pepcid AC)... 

Esomeprazole (Nexium) [Gastric Acid Inhibitor/Proton Pump Inhibitor] Uses Short-term (4-8 wk) for erosive esophagitis/GERD H. pylori Infxn in combo w/ antibiotics Action Proton pump inhibitor, gastric acid Dose Adults. GERD/erosive gastritis 20 0 mg/d PO x 4-8 wk 20 0 mg IV 10-30 min inf or >3 min IV push, 10 d max Maint 20 mg/d... 

Nexium 21 (1.0) 23.6 (0.8) 22.9 (1.0) Block the enzyme that pumps H into the secretory side of the parietal cells of the stomach. 

Effexor 3.5 Nexium 4.6 Cozaar/ — Taxotere 2.0 Zyprexa 4.2 Singulair 3.0... 

Nexium Esomeprazole Mg Astrazenaca LP Delayed release pellets Capsule... 

E-mail web form Phone + 44 20 7304 5000 15 Stanhope Gate London W1K 1LN United Kingdom A company resulting from the merger of Swedish AB and the British Zeneca Group in 1999, it is the maker of Arimidex for treatment of certain types of breast cancer, Crestor for high cholesterol, and Nexium (the purple pill) for heartburn relief. 

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