Omeprazole

Omeprazole

Clinical data
Pronunciation	/oʊˈmɛprəzoʊl/
Trade names	Losec, Prilosec, Zegerid, others
AHFS/Drugs.com	Monograph
License data	US FDA: Omeprazole
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Routes of administration	by mouth, IV
ATC code	A02BC01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: General sales list (GSL, OTC) US: OTC
Pharmacokinetic data
Bioavailability	35–76%
Protein binding	95%
Metabolism	Hepatic (CYP2C19, CYP3A4)
Biological half-life	1–1.2 hours
Excretion	80% (urine) 20% (feces)
Identifiers
IUPAC name 5-Methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-benzimidazole
CAS Number	73590-58-6 Y
PubChem (CID)	4594
IUPHAR/BPS	4279
DrugBank	DB00338 Y
ChemSpider	4433 Y
UNII	KG60484QX9 Y
KEGG	D00455 Y
ChEBI	CHEBI:7772 Y
ChEMBL	CHEMBL1503 Y
PDB ligand ID	1C6 (PDBe, RCSB PDB)
ECHA InfoCard	100.122.967
Chemical and physical data
Formula	C17H19N3O3S
Molar mass	345.42 g/mol
3D model (Jmol)	Interactive image
Chirality	Racemic mixture
Melting point	156 °C (313 °F)
SMILES Cc1c(OC)c(C)cnc1CS(=O)c2nc3ccc(OC)cc3n2
InChI 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

Omeprazole, sold under the brand names Prilosec and Losec among others, is a medication used in the treatment of gastroesophageal reflux disease, peptic ulcer disease, and Zollinger–Ellison syndrome. It is also used to prevent upper gastrointestinal bleeding in people who are at high risk. It can be taken by mouth or injected into a vein.

Common side effects include nausea, vomiting, headaches, 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. It is unclear if it is safe for use in pregnancy. Omeprazole is a proton pump inhibitor and as such blocks the release of stomach acid.

Omeprazole was discovered in 1979. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication. The wholesale cost in the developing world as of 2014 is US$0.01 to US$0.07 per dose. In the United States it costs on average US$0.50 per pill.

Omeprazole can be used in the treatment of gastroesophageal reflux disease (GERD), peptic ulcers, erosive esophagitis, and Zollinger-Ellison syndrome.