Omeprazole

For the similarly named medication derived from omeprazole, see esomeprazole.

Omeprazole
Clinical data
Pronunciation/oʊˈmɛprəzoʊl/
Trade namesLosec, Prilosec, others[1][2]
AHFS/Drugs.comMonograph
MedlinePlusa693050
License data
Pregnancy
category
Routes of
administration		By mouth, intravenous
Drug classProton-pump inhibitor
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability35–76%[6][7]
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 Edit this at Wikidata
Chemical and physical data
FormulaC17H19N3O3S
Molar mass345.42 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
Density1.4±0.1[8] 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) checkY
  • Key:SUBDBMMJDZJVOS-UHFFFAOYSA-N checkY
  (verify)

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.[1] It is also used to prevent upper gastrointestinal bleeding in people who are at high risk.[1] Omeprazole is a proton-pump inhibitor (PPI) and its effectiveness is similar to that of other PPIs.[9] It can be taken by mouth or by injection into a vein.[1][10] It is also available in the fixed-dose combination medication omeprazole/sodium bicarbonate as Zegerid[11][12] and as Konvomep.[13]

Common side effects include nausea, vomiting, headaches, abdominal pain, and increased intestinal gas.[1][14] Serious side effects may include Clostridioides difficile colitis, an increased risk of pneumonia, an increased risk of bone fractures, and the potential of masking stomach cancer.[1] Whether it is safe for use in pregnancy is unclear.[1] It works by blocking the release of stomach acid.[1]

Omeprazole was patented in 1978 and approved for medical use in 1988.[15][16] It is on the World Health Organization's List of Essential Medicines.[17] It is available as a generic medication.[1] In 2022, it was the ninth most commonly prescribed medication in the United States, with more than 52 million prescriptions.[18][19] It is also available without a prescription in the United States.[20][21]

  1. ^ a b c d e f g h i "Omeprazole". The American Society of Health-System Pharmacists. Archived from the original on 19 February 2011. Retrieved 21 October 2018.
  2. ^ Cite error: The named reference Drugs.com international was invoked but never defined (see the help page).
  3. ^ "Omeprazole Use During Pregnancy". Drugs.com. 11 April 2019. Archived from the original on 15 February 2020. Retrieved 15 February 2020.
  4. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  5. ^ "Product monograph brand safety updates". Health Canada. 7 July 2016. Retrieved 1 April 2024.
  6. ^ "Prilosec- omeprazole magnesium capsule, delayed release Prilosec- omeprazole magnesium granule, delayed release". DailyMed. 22 December 2016. Archived from the original on 27 December 2019. Retrieved 15 February 2020.
  7. ^ Vaz-da-Silva M, Loureiro AI, Nunes T, Maia J, Tavares S, Falcão A, et al. (2005). "Bioavailability and bioequivalence of two enteric-coated formulations of omeprazole in fasting and fed conditions". Clinical Drug Investigation. 25 (6): 391–399. doi:10.2165/00044011-200525060-00004. PMID 17532679. S2CID 22082780. Archived from the original on 13 March 2013. Retrieved 21 October 2018.
  8. ^ "Omeprazole MSDS". Archived from the original on 19 April 2017. Retrieved 21 October 2018.
  9. ^ "[99] Comparative effectiveness of proton pump inhibitors | Therapeutics Initiative". 28 June 2016. Archived from the original on 30 October 2020. Retrieved 14 July 2016.
  10. ^ "Omeprazole 40 mg Powder for Solution for Infusion". EMC. 10 February 2016. Archived from the original on 7 April 2016. Retrieved 21 October 2018.
  11. ^ "Zegerid- omeprazole and sodium bicarbonate powder, for suspension Zegerid- omeprazole and sodium bicarbonate capsule". DailyMed. 4 March 2022. Retrieved 16 December 2022.
  12. ^ "Zegerid OTC- omeprazole and sodium bicarbonate capsule, gelatin coated". DailyMed. 5 December 2022. Retrieved 16 December 2022.
  13. ^ "Konvomep- omeprazole and sodium bicarbonate kit". DailyMed. 30 August 2022. Retrieved 21 January 2023.
  14. ^ Cite error: The named reference Dav2015 was invoked but never defined (see the help page).
  15. ^ "Drug Approval Package: Prilosec (Omeprazole) NDA# 019-810s38s50s5". U.S. Food and Drug Administration (FDA). 30 March 2001. Archived from the original on 1 April 2021. Retrieved 5 October 2022.
  16. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 445. ISBN 9783527607495. Archived from the original on 3 August 2020. Retrieved 29 June 2020.
  17. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  18. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  19. ^ "Omeprazole Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  20. ^ "Questions and Answers on Prilosec OTC (omeprazole)". U.S. Food and Drug Administration (FDA). 3 November 2018. Archived from the original on 28 August 2021. Retrieved 2 March 2020.
  21. ^ "Drug Approval Package: Prilosec (Omeprazole Magnesium) NDA #021229". U.S. Food and Drug Administration (FDA). Archived from the original on 24 January 2022. Retrieved 6 October 2022.