Esomeprazole

• CAS: 119141-88-7
• Catalog Number: ACM119141887
• Category: Main Products
• Molecular Weight: 345.42
• Molecular Formula: C₁₇H₁₉N₃O₃S
• Synonyms: Esomeprazole(Na, Mg);(5-methoxy-1H-benzimidazol-2-yl)[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfoniumolate;(S)-Esomeprazole;Esomeprazole(Mg);5-Methoxy-2-((S)-((4-methoxy-3,5-dimethyl-2- pyridinyl)methyl)sulfinyl)-1H-benzimidazole;6-Methoxy-2-[(R)-(4-methoxy-3,5-dimethyl-pyridin-2-yl)methylsulfinyl]-1H-benzoimidazole;Esomeprazole;EsoMeprazole EC Pellets 22%
• IUPAC Name: 6-methoxy-2-[(S)-(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1H-benzimidazole
• Canonical SMILES: CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C(N2)C=C(C=C3)OC
• InChI Key: SUBDBMMJDZJVOS-DEOSSOPVSA-N
• Boiling Point: 600ºC at 760mmHg
• Flash Point: 316.7ºC
• Density: 1.37g/cm³
• Exact Mass: 345.11500

Case Study

Comparison of the Efficacy of Esomeprazole and Omeprazole

Waheed Asghar, et al. DARU Journal of Pharmaceutical Sciences, 2015, 23, 1-7.

Esomeprazole (S enantiomer) and omeprazole (parent racemate) have been used to treat symptoms of gastroesophageal reflux disease (GERD) and conditions associated with excessive gastric acid secretion. In order to comparatively study the efficacy of the two, this work conducted a web search for randomized controlled trials comparing head-to-head omeprazole and esomeprazole, and out of 1171 studies, 14 were deemed eligible.
Results and discussion
· There was no notable difference in treatment effectiveness between omeprazole and esomeprazole in triple therapy for H. pylori treatment, according to both intention-to-treat (OR', 1.06; CI, 0.83, 1.36; p = 0.63) and per-protocol analysis (OR', 1.07; CI, 0.84, 1.36; p = 0.57).
· In treating gastro-oesophageal reflux disease, esomeprazole showed a slight superiority over the racemate omeprazole (OR', 1.18; CI, 1.01, 1.38; p = 0.04). The two medications demonstrated similar efficacy in all measures of intragastric pH except for the percentage of patients maintaining a 24-hour gastric pH above 4 (1.57; CI, 1.04, 2.381; p = 0.03).
· In summary, despite some differences in GERD control and bioavailability, esomeprazole offers little or no significant therapeutic advantage over omeprazole.

A Study of Esomeprazole and Aspirin in the Treatment of Barrett's Esophagus

Jankowski, Janusz AZ, et al. The Lancet, 2018, 392(10145), 400-408.

To evaluate the efficacy of high-dose esomeprazole proton pump inhibitor (PPI) and aspirin in improving outcomes in patients with Barrett's esophagus, a randomized factorial trial was conducted.
Experimental methods and results
· Study Design and Patient Randomization: The trial employed a 2×2 factorial design and was conducted at 84 centers in the UK and one center in Canada. Patients with Barrett's esophagus of 1 cm or more were randomized 1:1:1:1 to receive high-dose or low-dose PPI, with or without aspirin, for a minimum of 8 years.
· Study Recruitment and Follow-up: A total of 2557 patients were recruited between March 10, 2005, and March 1, 2009. The median follow-up and treatment duration was 8.9 years, with 99.9% of planned data collected, resulting in 20,095 follow-up years.
· Treatment Outcomes: Of the 313 primary events observed, high-dose PPI was found to be superior to low-dose PPI. Aspirin alone was not significantly better than no aspirin, but when patients using non-steroidal anti-inflammatory drugs were censored, aspirin was found to be significantly better than no aspirin. Combining high-dose PPI with aspirin had the strongest effect compared to low-dose PPI without aspirin.

Custom Q&A

What is the molecular formula of esomeprazole?

The molecular formula of esomeprazole is C17H19N3O3S.

What are the synonyms for esomeprazole?

The synonyms for esomeprazole include (S)-Omeprazole, (S)-(-)-Omeprazole, (-)-Omeprazole, and 119141-88-7.

What is the molecular weight of esomeprazole?

The molecular weight of esomeprazole is 345.4 g/mol.

What is the role of esomeprazole in the body?

Esomeprazole has multiple roles in the body, including being an inhibitor of gastric acid secretion, histamine antagonist, and an anti-ulcer drug.

What conditions is esomeprazole used for?

Esomeprazole is used for the treatment of gastro-oesophageal reflux disease (GERD), dyspepsia, peptic ulcer disease, and Zollinger-Ellison syndrome.

What is the brand name of esomeprazole?

The brand name of esomeprazole is Nexium.

What class of medication does esomeprazole belong to?

Esomeprazole belongs to the proton pump inhibitor (PPI) class of medications.

How does esomeprazole work to reduce stomach acid secretion?

Esomeprazole works by covalently binding to sulfhydryl groups of cysteines found on the (H+, K+)-ATPase enzyme at the secretory surface of gastric parietal cells, leading to inhibition of both basal and stimulated gastric acid secretion.

Are there any differences between esomeprazole and its racemate, omeprazole?

Esomeprazole is the S-isomer of omeprazole, which is a racemate of the S- and R-enantiomer. In vitro studies have shown that esomeprazole exhibits similar efficacy in inhibiting acid secretion compared to omeprazole.

What is the potential association of esomeprazole with cardiovascular events?

PPIs, including esomeprazole, have been associated with an increased risk of cardiovascular events in patients with unstable coronary syndromes. This may be due to the inhibition of dimethylarginine dimethylaminohydrolase (DDAH) activity, leading to an accumulation of the nitric oxide synthase inhibitor ADMA.