Omeprazole

Omeprazole, sold under the brand names Prilosec and Losec, among others, is a medication used in the treatment of gastroesophageal reflux disease (GERD), peptic ulcer disease, and Zollinger–Ellison syndrome. It is also used to prevent upper gastrointestinal bleeding in people who are at high risk. Omeprazole is a proton-pump inhibitor (PPI) and its effectiveness is similar to that of other PPIs. It can be taken by mouth or by injection into a vein. It is also available in the fixed-dose combination medication omeprazole/sodium bicarbonate as Zegerid and as Konvomep.

Omeprazole
Clinical data
Pronunciation/ˈmɛprəzl/
Trade namesLosec, Prilosec, others
AHFS/Drugs.comMonograph
MedlinePlusa693050
License data
Pregnancy
category
  • AU: B3
Routes of
administration
By mouth, intravenous
Drug classProton-pump inhibitor
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability35–76%
Protein binding95%
MetabolismLiver (CYP2C19, CYP3A4)
Elimination half-life1–1.2 hours
Excretion80% (urine)
20% (bile via feces)
Identifiers
  • 5-Methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-benzimidazole
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.122.967
Chemical and physical data
FormulaC17H19N3O3S
Molar mass345.42 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
Density1.4±0.1 g/cm3
Melting point156 °C (313 °F)
  • CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C(N2)C=C(C=C3)OC
  • 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) Y
  • Key:SUBDBMMJDZJVOS-UHFFFAOYSA-N Y
  (verify)

Common side effects include nausea, vomiting, headaches, abdominal pain, and increased intestinal gas. Serious side effects may include Clostridium difficile colitis, an increased risk of pneumonia, an increased risk of bone fractures, and the potential of masking stomach cancer. Whether it is safe for use in pregnancy is unclear. It works by blocking the release of stomach acid.

Omeprazole was patented in 1978, and approved for medical use in 1988. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2021, it was the eighth-most commonly prescribed medication in the United States, with more than 54 million prescriptions. It is also available without a prescription in the United States.

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