Esomeprazole

Esomeprazole, sold under the brand name Nexium [or Neksium] among others, is a medication which reduces stomach acid. It is used to treat gastroesophageal reflux disease, peptic ulcer disease, and Zollinger–Ellison syndrome. Its effectiveness is similar to that of other proton pump inhibitors (PPIs). It is taken by mouth or injection into a vein.

Esomeprazole
Clinical data
Pronunciation/ˌɛsˈmɛprəˌzl, -ˈm-, -ˌzɒl/
Trade namesNexium, others
AHFS/Drugs.comMonograph
MedlinePlusa699054
License data
Pregnancy
category
  • AU: B3
Routes of
administration
By mouth, intravenous
Drug classProton pump inhibitor
ATC code
Legal status
Legal status
  • AU: S2 (Pharmacy medicine) /  S4 (Prescription Only Medicine)
  • CA: ℞-only
  • UK: General sales list (GSL, OTC)
  • US: OTC / Rx-only
  • EU: OTC
Pharmacokinetic data
Bioavailability50 to 90%
MetabolismLiver (CYP2C19, CYP3A4)
Elimination half-life1–1.5 hours
Excretion80% Kidney
20% Feces
Identifiers
  • (S)-(−)-5-Methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-3H-benzoimidazole
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.149.048
Chemical and physical data
FormulaC17H19N3O3S
Molar mass345.42 g·mol−1
3D model (JSmol)
SMILES
  • COc1ccc2nc([nH]c2c1)[S@](=O)Cc1ncc(C)c(OC)c1C
  • InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)/t24-/m1/s1 Y
  • Key:SUBDBMMJDZJVOS-XMMPIXPASA-N Y
 NY (what is this?)  (verify)

Common side effects include headache, constipation, dry mouth, and abdominal pain. Serious side effects may include angioedema, Clostridium difficile infection, and pneumonia. Use in pregnancy appears to be safe, while safety during breastfeeding is unclear. Esomeprazole is the (S)-(−)-enantiomer (or less specifically the S-isomer) of omeprazole. It works by blocking H+/K+-ATPase in the parietal cells of the stomach.

It was patented in 1993 and approved for medical use in 2000. It is available as a generic medication and sold over the counter in a number of countries. In 2021, it was the 125th most commonly prescribed medication in the United States, with more than 4 million prescriptions. It is also available in lower dose formulations without a prescription in the United States, the United Kingdom as well as Australia, Canada, and New Zealand.

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