Esomeprazole

"Nexium" redirects here. For the defunct cult with the same pronunciation, see NXIVM.
For the similarly named medication esomeprazole is derived from, see omeprazole.

Esomeprazole
Clinical data
Pronunciation/ˌɛsoʊˈmɛprəˌzoʊl, -ˈmiː-, -ˌzɒl/[1]
Trade namesNexium, others[2]
AHFS/Drugs.comMonograph
MedlinePlusa699054
License data
Pregnancy
category
Routes of
administration		By mouth, intravenous
Drug classProton pump inhibitor
ATC code
Legal status
Legal status
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 Edit this at Wikidata
Chemical and physical data
FormulaC17H19N3O3S
Molar mass345.42 g·mol−1
3D model (JSmol)
  • 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 checkY
  • Key:SUBDBMMJDZJVOS-XMMPIXPASA-N checkY
 ☒NcheckY (what is this?)  (verify)

Esomeprazole, sold under the brand name Nexium [or Neksium] among others,[2] is a medication which reduces stomach acid.[11] It is used to treat gastroesophageal reflux disease, peptic ulcer disease, and Zollinger–Ellison syndrome.[11][12] Its effectiveness is similar to that of other proton pump inhibitors (PPIs).[13] It is taken by mouth or injection into a vein.[11]

Common side effects include headache, constipation, dry mouth, and abdominal pain.[11] Serious side effects may include angioedema, Clostridium difficile infection, and pneumonia.[11] Use in pregnancy appears to be safe, while safety during breastfeeding is unclear.[3] Esomeprazole is the (S)-(−)-enantiomer (or less specifically the S-isomer) of omeprazole.[11] It works by blocking H+/K+-ATPase in the parietal cells of the stomach.[11]

It was patented in 1993 and approved for medical use in 2000.[14] It is available as a generic medication and sold over the counter in a number of countries.[15][12] In 2021, it was the 125th most commonly prescribed medication in the United States, with more than 4 million prescriptions.[16][17] It is also available in lower dose formulations without a prescription in the United States,[18] the United Kingdom[19] as well as Australia, Canada, and New Zealand.[20]

  1. ^ "Esomeprazole". Merriam-Webster.com Dictionary. Merriam-Webster. Retrieved 21 January 2016.
  2. ^ a b "Esomeprazole Brand Names". BDdrugs.com. Bangladesh. 2011. Archived from the original on 7 February 2012.
  3. ^ a b "Esomeprazole Pregnancy and Breastfeeding Warnings". Drugs.com. Retrieved 3 March 2019.
  4. ^ "Esomeprazole". Therapeutic Goods Administration (TGA). 15 September 2017. Retrieved 19 July 2020.
  5. ^ "Toreso/Esocolam/Meprator/Esotor/Nesed/Esome/Esotrack (Torrent Australasia Pty Ltd)". Therapeutic Goods Administration (TGA). 16 February 2023. Retrieved 9 April 2023.
  6. ^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
  7. ^ "Nexium- esomeprazole magnesium capsule, delayed release Nexium- esomeprazole magnesium granule, delayed release". DailyMed. U.S. Library of Medicine. 7 June 2018. Retrieved 7 December 2020.
  8. ^ "Nexium 24HR- esomeprazole magnesium capsule, delayed release Nexium 24HR ClearMinis- esomeprazole magnesium capsule, delayed release". DailyMed. 26 May 2020. Retrieved 7 December 2020.
  9. ^ "Nexium I.V.- esomeprazole sodium injection". DailyMed. U.S. Library of Medicine. 27 November 2020. Retrieved 7 December 2020.
  10. ^ "Nexium Control EPAR". European Medicines Agency (EMA). 17 September 2018. Retrieved 14 January 2021.
  11. ^ a b c d e f g "Esomeprazole Magnesium Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
  12. ^ a b British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 78. ISBN 978-0-85711-338-2.
  13. ^ "[99] Comparative effectiveness of proton pump inhibitors | Therapeutics Initiative". 28 June 2016. Retrieved 14 July 2016.
  14. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 445. ISBN 978-3-527-60749-5.
  15. ^ Jones & Bartlett Learning (2017). 2018 Nurse's Drug Handbook. Jones & Bartlett Learning. p. 394. ISBN 978-1-284-12134-6.
  16. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  17. ^ "Esomeprazole - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  18. ^ Cite error: The named reference USA2020OTC was invoked but never defined (see the help page).
  19. ^ "About esomeprazole". 13 January 2022.
  20. ^ "Australian TGA Scheduling of Esomeprazole". 15 September 2017. Retrieved 1 August 2023.