Esomeprazole

Source: Wikipedia, the free encyclopedia.
"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
Proton 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
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,

injection into a vein.[11]

Common side effects include headache, constipation, dry mouth, and abdominal pain.

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][a] 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.

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]

Medical use

The primary uses of esomeprazole are gastroesophageal reflux disease, treatment and maintenance of

NSAID therapy, and treatment of gastrointestinal ulcers associated with Crohn's disease.[21][22]

Gastroesophageal reflux disease

Gastroesophageal reflux disease (GERD) is a condition in which the digestive acid in the stomach comes in contact with the esophagus. The irritation caused by this disorder is known as heartburn.[23] Long-term contact between gastric acids and the esophagus can cause permanent damage to the esophagus and is associated with Barrett's esophagus.[24] Esomeprazole reduces the production of digestive acids, thus reducing their effect on the esophagus.

Duodenal ulcers

Esomeprazole is combined with the antibiotics

peptic and duodenal ulcers
.

Efficacy

A 2006 meta analysis concluded that compared to other proton pump inhibitors, esomeprazole confers a modest overall benefit in esophageal healing and symptom relief. When broken down by disease severity, the benefit of esomeprazole relative to other proton pump inhibitors was negligible in people with mild disease (number needed to treat 50[clarification needed]), but appeared more in those with severe disease (number needed to treat 8[clarification needed]).[25] A second meta analysis also found increases in erosive esophageal healing (>95% healing rate) when compared to standardized doses in broadly selected patient populations.[26] A 2017 study found esomeprazole to be among a number of effective PPIs.[27]

Adverse effects

Common side effects include headache, diarrhea, nausea, flatulence, decreased appetite, constipation, dry mouth, and abdominal pain. More severe side effects are severe allergic reactions, chest pain, dark urine, fast heartbeat, fever, paresthesia, persistent sore throat, severe stomach pain, unusual bruising or bleeding, unusual tiredness, and yellowing of the eyes or skin.[28]

Proton pump inhibitors may be associated with a greater risk of hip fractures

diarrhoea.[30] Patients are frequently administered the drugs in intensive care as a protective measure against ulcers, but this use is also associated with a 30% increase in occurrence of pneumonia.[31]

Long-term use of proton pump inhibitors in patients treated for Helicobacter pylori has been shown to dramatically increase the risk of gastric cancer.[32]

Acute tubulointerstitial nephritis is a possible adverse reaction when using proton pump inhibitors.[9]

Interactions

Esomeprazole is a competitive inhibitor of the enzyme CYP2C19, and may therefore interact with drugs that depend on it for metabolism, such as diazepam and warfarin; the concentrations of these drugs may increase if they are used concomitantly with esomeprazole.[33] Conversely, clopidogrel (Plavix) is an inactive prodrug that partially depends on CYP2C19 for conversion to its active form; inhibition of CYP2C19 blocks the activation of clopidogrel, thus reducing its effects.[34][35]

Drugs that depend on stomach pH for absorption may interact with esomeprazole; drugs that depend on an acidic environment (such as ketoconazole or atazanavir) will be poorly absorbed, whereas drugs that are broken down in acidic environments (such as erythromycin) will be absorbed to a greater extent than normal.[33]

Pharmacokinetics

Single 20 to 40 mg oral doses generally give rise to peak plasma esomeprazole concentrations of 0.5-1.0 mg/L within 1–4 hours, but after several days of once-daily administration, these levels may increase by about 50%. A 30-minute intravenous infusion of a similar dose usually produces peak plasma levels on the order of 1–3 mg/L. The drug is rapidly cleared from the body, largely by urinary excretion of pharmacologically inactive metabolites such as 5-hydroxymethylesomeprazole and 5-carboxyesomeprazole. Esomeprazole and its metabolites are analytically indistinguishable from omeprazole and the corresponding omeprazole metabolites unless chiral techniques are employed.[36]

Dosage forms

Esomeprazole strontium delayed-release capsules, 49.3 mg
40 mg Nexium (esomeprazole magnesium) capsules

Esomeprazole is available as delayed-release capsules in the United States or as delayed-release tablets in Australia, the United Kingdom, and Canada (containing esomeprazole magnesium) in strengths of 20 and 40 mg, as delayed-release capsules in the United States (containing esomeprazole strontium) in a 49.3 mg strength (delivering the equivalent of 40 mg of esomeprazole,

intravenous injection/infusion. Oral esomeprazole preparations are enteric-coated, due to the rapid degradation of the drug in the acidic conditions of the stomach
. This is achieved by formulating capsules using the multiple-unit pellet system.

The combination

acute interstitial nephritis and risk of kidney problems in some patients.[39]

Multiple-unit pellet system

Esomeprazole capsules, as well as Losec/Prilosec tablets, are formulated as a "multiple-unit pellet system" (MUPS). Essentially, the

nasogastric tube feeding and those with difficulty swallowing (dysphagia).[40][41][42][43]

Society and culture

Global distribution

In 2010, AstraZeneca announced a co-promotion agreement with Daiichi Sankyo to distribute Nexium in Japan.[44] In September 2011, Nexium was approved for sale and was launched by Daiichi Sankyo in Japan.[45] Esomeprazole was approved for use in the United States in February 2001.[46][47]

Economics

Between the launch of esomeprazole in 2001 and 2005, the drug netted AstraZeneca about $14.4 billion.[48]

Controversy

Main article: AstraZeneca's marketing of Nexium

There has been some controversy about AstraZeneca's behaviour in creating, patenting, and marketing the drug. Esomeprazole's successful predecessor, omeprazole, is a mixture of two mirror-imaged molecules (esomeprazole which is the S-enantiomer, and R-omeprazole); critics said the company was trying to "evergreen" its omeprazole patent by patenting the pure esomeprazole and aggressively marketing to doctors that it is more effective than the mixture.[49]

Brand names

Generic versions of esomeprazole magnesium are available worldwide.

over-the-counter under the brand name Nexium in the United States[18][50] and the UK.[51]

Veterinary use

Injection formulations of esomeprazole are used for gastroprotection in veterinary medicine. In goats administered the drug by intravenous or subcutaneous injection rapid elimination was noted.[52] In that study the sulfone metabolite was detectable for several hours after injection of the parent drug.

Other uses

Esomeprazole can be used as a

parasiticide.[53] Gokmen et al., 2016 screen for efficacy against Trichomonas vaginalis isolates from horses.[53] They found esomeprazole to be effective as a veterinary antiparasitic.[53]

Footnotes

  1. ^ The name thus is an onomatopoeia, as it can also be read as Es + omeprazole

References

  1. ^ "Esomeprazole". Merriam-Webster.com Dictionary. Retrieved 21 January 2016.
  2. ^ a b c "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. ^ a b "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. ^
    ISBN 978-0-85711-338-2
    .
  13. ^ "[99] Comparative effectiveness of proton pump inhibitors | Therapeutics Initiative". 28 June 2016. Retrieved 14 July 2016.
  14. ISBN 978-3-527-60749-5
    .
  15. 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. ^ a b "Esomeprazole". MedlinePlus. United States National Library of Medicine. Retrieved 2 March 2020.
  19. ^ "About esomeprazole". 13 January 2022.
  20. ^ "Australian TGA Scheduling of Esomeprazole". 15 September 2017. Retrieved 1 August 2023.
  21. ^ "Esomeprazole Magnesium". The American Society of Health-System Pharmacists. Retrieved 3 April 2011.
  22. PMID 16750456
    .
  23. ^ "Gastroesophageal Reflux Disease". The Lecturio Medical Concept Library. Retrieved 23 July 2021.
  24. ^ "Barrett's Esophagus". The Mayo Clinic. 8 February 2023. Retrieved 1 August 2023.
  25. PMID 17162239
    .
  26. S2CID 23189853
    .
  27. PMID 28953640
    .
  28. ^ "Nexium side effects". Drug information online. Drugs.com. Retrieved 23 June 2009.
  29. PMID 17190895
    .
  30. ^ "Proton pump inhibitors and Clostridium difficile". Bandolier. 2003. Archived from the original on 23 December 2012. Retrieved 13 July 2007.
  31. PMID 19470989
    .
  32. PMID 29089382
    .
  33. ^
    S2CID 45337685
    .
  34. PMID 19332744
    .
  35. S2CID 13227312
    .
  36. ISBN 978-0-9626523-7-0
    .
  37. ^ "esomeprazole strontium capsule, delayed release". DailyMed. U.S. Library of Medicine.
  38. ^ "VIMOVO (naproxen and esomeprazole magnesium) delayed release tablets, for oral use" (PDF). Horizon Pharma USA. U.S. Food and Drug Administration. December 2014.
  39. ^ "Vimovo (naproxen/esomeprazole magnesium) tablets". U.S. Food and Drug Administration. December 2014. Archived from the original on 11 February 2015. Safety Labeling Changes Approved By FDA Center for Drug Evaluation and Research (CDER)
  40. PMID 20678688
    .
  41. PMID 29292694
    .
  42. PMID 15704615
    .
  43. S2CID 3596776
    .
  44. ^ "AstraZeneca announces co-promotion agreement with Daiichi Sankyo for NEXIUM in Japan" (Press release). AstraZeneca. 29 October 2010. Retrieved 15 July 2019.
  45. ^ "Daiichi Sankyo and AstraZeneca Launch NEXIUM 10mg and 20mg Capsules in Japan" (Press release). Daiichi Sankyo. 15 September 2011. Retrieved 15 July 2019.
  46. ^ "Drug Approval Package: Nexium (Esomeprazole Magnesium) NDA #21-153 & 21-154". U.S. Food and Drug Administration (FDA). 24 December 1999. Retrieved 4 April 2020.
  47. ^ "Nexium: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 4 April 2020.
  48. ^ Financial impact information:
  49. ^ Gladwell M (25 October 2004). "High Prices: How to think about prescription drugs". The New Yorker. Retrieved 23 June 2006.
  50. ^ "Nonprescription Nexium Heartburn Medicine Launches". ABC News. 27 May 2014.
  51. ^ "Esomeprazole: medicine to lower stomach acid". nhs.uk. 29 August 2018. Retrieved 9 December 2019.
  52. PMID 36590808
    .
  53. ^
    OCLC 1104533040
    .

Further reading
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