View source for Esomeprazole

{{Short description|Medication which reduces stomach acid}}
{{Redirect|Nexium|the defunct cult with the same pronunciation|NXIVM}}
{{For|the similarly named medication esomeprazole is derived from|omeprazole}}
{{Use dmy dates|date=October 2022}}
{{Infobox drug
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477167063
| image = Esomeprazole.svg
| width = 245
| alt = 
| image2 = Esomeprazole ball-and-stick model.png
| width2 = 250
| alt2 =

<!--Clinical data-->
| pronounce = {{IPAc-en|ˌ|ɛ|s|oʊ|ˈ|m|ɛ|p|r|ə|ˌ|z|oʊ|l|,_|-|ˈ|m|iː|-|,_|-|ˌ|z|ɒ|l}}{{refn|{{MerriamWebsterDictionary|access-date=21 January 2016|Esomeprazole}}
}}
| tradename = Nexium, others<ref name=brands>{{cite web | title = Esomeprazole Brand Names | date = 2011 | work = BDdrugs.com | location = Bangladesh | url = http://www.bddrugs.com/product5.php?idn=5&prev=&prev1=&prev2= | url-status = usurped | archive-url = https://web.archive.org/web/20120207193751/http://www.bddrugs.com/product5.php?idn=5&prev=&prev1=&prev2= | archive-date = 7 February 2012 }}</ref>
| Drugs.com = {{drugs.com|monograph|esomeprazole-magnesium}}
| MedlinePlus = a699054
| DailyMedID = Esomeprazole
| pregnancy_AU = B3
| pregnancy_AU_comment = <ref name=Preg2019 />
| routes_of_administration = [[Oral administration|By mouth]], [[Intravenous therapy|intravenous]]
| class            = [[Proton pump inhibitor]]
| ATC_prefix = A02
| ATC_suffix = BC05

| legal_AU = S2
| legal_AU_comment = / &nbsp;S4 (Prescription Only Medicine)<ref>{{cite web | title=Esomeprazole | website=Therapeutic Goods Administration (TGA) | date=15 September 2017 | url=https://www.tga.gov.au/book-page/14-esomeprazole | access-date=19 July 2020}}</ref><ref>{{cite web | title=Toreso/Esocolam/Meprator/Esotor/Nesed/Esome/Esotrack (Torrent Australasia Pty Ltd) | website=Therapeutic Goods Administration (TGA) | date=16 February 2023 | url=https://www.tga.gov.au/resources/prescription-medicines-registrations/toresoesocolammepratoresotornesedesomeesotrack-torrent-australasia-pty-ltd | access-date=9 April 2023}}</ref>
| legal_CA          = Rx-only
| legal_CA_comment  = <ref>{{cite web | title=Product monograph brand safety updates | website=[[Health Canada]] | date=February 2024 | url=https://www.canada.ca/en/health-canada/services/drugs-health-products/drug-products/drug-product-database/label-safety-assessment-update/product-monograph-brand-safety-updates.html | access-date=24 March 2024}}</ref>
| legal_UK = GSL
| legal_US = OTC
| legal_US_comment = /&nbsp;Rx-only<ref>{{cite web | title=Nexium- esomeprazole magnesium capsule, delayed release Nexium- esomeprazole magnesium granule, delayed release | work = DailyMed | publisher = U.S. Library of Medicine | date=7 June 2018 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f4853677-1622-4037-688b-fdf533a11d96 | access-date=7 December 2020}}</ref><ref>{{cite web | title=Nexium 24HR- esomeprazole magnesium capsule, delayed release Nexium 24HR ClearMinis- esomeprazole magnesium capsule, delayed release | website=DailyMed | date=26 May 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4513934d-0cf0-40fc-a348-b4e75a33b094 | access-date=7 December 2020}}</ref><ref name="Nexium I.V. FDA label">{{cite web | title=Nexium I.V.- esomeprazole sodium injection| work = DailyMed | publisher = U.S. Library of Medicine | date=27 November 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c325bbfc-46f3-471e-7bbc-ed0d6965d13b | access-date=7 December 2020}}</ref>
| legal_EU = OTC
| legal_EU_comment = <ref>{{cite web | title=Nexium Control EPAR | website=[[European Medicines Agency]] (EMA) | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/nexium-control | access-date=14 January 2021}}</ref>
| legal_status =

<!--Pharmacokinetic data-->
| bioavailability = 50 to 90%
| metabolism = [[Liver]] ([[CYP2C19]], [[CYP3A4]])
| elimination_half-life = 1–1.5 hours
| excretion = 80% [[Kidney]]<br />20% [[Feces]]

<!--Identifiers-->
| index2_label = as salt
| CAS_number_Ref = {{cascite|changed|CAS}}
| CAS_number = 119141-88-7
| PubChem = 9579578
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00736
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 7843323
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = N3PA6559FT
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07917
| KEGG2_Ref = {{keggcite|correct|kegg}}
| KEGG2 = D01984
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 50275
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1201320

<!--Chemical data-->
| IUPAC_name = (''S'')-(−)-5-Methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-3''H''-benzoimidazole
 | C=17 | H=19 | N=3 | O=3 | S=1
| smiles = COc1ccc2nc([nH]c2c1)[S@](=O)Cc1ncc(C)c(OC)c1C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SUBDBMMJDZJVOS-XMMPIXPASA-N
}}

<!-- Definition and medical uses -->
'''Esomeprazole''', sold under the brand name '''Nexium''' [or '''Neksium'''] among others,<ref name=brands/> is a medication which reduces [[gastric acid|stomach acid]].<ref name=AHFS2019/> It is used to treat [[gastroesophageal reflux disease]], [[peptic ulcer|peptic ulcer disease]], and [[Zollinger–Ellison syndrome]].<ref name=AHFS2019/><ref name=BNF76>{{cite book|title=British national formulary: BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=978-0-85711-338-2 |page=78|edition=76}}</ref> Its effectiveness is similar to that of other [[proton pump inhibitors]] (PPIs).<ref name=TI2016>{{cite web|title=[99] Comparative effectiveness of proton pump inhibitors {{!}} Therapeutics Initiative|url=http://www.ti.ubc.ca/2016/06/28/99-comparative-effectiveness-proton-pump-inhibitors/|access-date=14 July 2016|date=28 June 2016}}</ref> It is taken by mouth or [[intravenous|injection into a vein]].<ref name=AHFS2019/>

<!-- Side effects and mechanisms -->
Common side effects include headache, constipation, dry mouth, and abdominal pain.<ref name=AHFS2019/> Serious side effects may include [[angioedema]], [[Clostridioides difficile infection]], and [[pneumonia]].<ref name=AHFS2019/> Use in [[pregnancy]] appears to be safe, while safety during [[breastfeeding]] is unclear.<ref name=Preg2019>{{cite web |title=Esomeprazole Pregnancy and Breastfeeding Warnings |url=https://www.drugs.com/pregnancy/esomeprazole.html |website=Drugs.com |access-date=3 March 2019 }}</ref> Esomeprazole is the (''S'')-(−)-[[enantiomer]] (or less specifically the S-[[isomer]]) of [[omeprazole]].<ref name=AHFS2019/> It works by blocking [[Hydrogen potassium ATPase|H<sup>+</sup>/K<sup>+</sup>-ATPase]] in the [[parietal cell]]s of the stomach.<ref name=AHFS2019>{{cite web |title=Esomeprazole Magnesium Monograph for Professionals |url=https://www.drugs.com/monograph/esomeprazole-magnesium.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=3 March 2019 }}</ref>

<!-- Society and culture -->
It was patented in 1993 and approved for medical use in 2000.<ref>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=978-3-527-60749-5 |page=445 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA445 }}</ref> It is available as a [[generic medication]] and sold [[over the counter]] in several countries.<ref>{{cite book | vauthors = ((Jones & Bartlett Learning)) |title=2018 Nurse's Drug Handbook |date=2017 |publisher=Jones & Bartlett Learning |isbn=978-1-284-12134-6 |page=394 |url=https://books.google.com/books?id=rD1DDwAAQBAJ&pg=PA394 }}</ref><ref name=BNF76/> In 2023, it was the 147th most commonly prescribed medication in the United States, with more than 3{{nbsp}}million prescriptions.<ref name="Top 300">{{cite web | title=Top 300 of 2023 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=12 August 2025 | archive-date=12 August 2025 | archive-url=https://web.archive.org/web/20250812130026/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Esomeprazole Drug Usage Statistics, United States, 2013 - 2023 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Esomeprazole | access-date = 18 August 2025 }}</ref> In Australia, it was one of the top ten most-prescribed medications between 2017 and 2023.<ref>{{cite web | title=Medicines in the health system | website=Australian Institute of Health and Welfare | date=2 July 2024 | url=https://www.aihw.gov.au/reports/medicines/medicines-in-the-health-system | access-date=30 September 2024}}</ref> It is also available in lower dose formulations without a prescription in the United States,<ref name=USA2020OTC/> the United Kingdom<ref>{{cite web | url=https://www.nhs.uk/medicines/esomeprazole/about-esomeprazole/ | title=About esomeprazole | date=13 January 2022 }}</ref> as well as Australia, Canada, and New Zealand.<ref>{{cite web | url=
https://www.tga.gov.au/resources/publication/scheduling-decisions-interim/scheduling-delegates-interim-decisions-and-invitation-further-comment-accsacms-march-and-july-2017/14-esomeprazole/ | title=Australian TGA Scheduling of Esomeprazole | date=15 September 2017 | access-date=1 August 2023 }}</ref>

==Medical use==
The primary uses of esomeprazole are gastroesophageal reflux disease, treatment and maintenance of [[erosive esophagitis]], treatment of [[duodenal ulcers]] caused by ''H. pylori'', prevention of [[gastric ulcers]] in those on chronic [[NSAID]] therapy, and treatment of gastrointestinal ulcers associated with [[Crohn's disease]].<ref name=AHFS>{{cite web | title = Esomeprazole Magnesium | url = https://www.drugs.com/monograph/esomeprazole-magnesium.html | work = The American Society of Health-System Pharmacists | access-date = 3 April 2011 }}</ref><ref>{{cite journal | vauthors = Li J, Zhao J, Hamer-Maansson JE, Andersson T, Fulmer R, Illueca M, Lundborg P | title = Pharmacokinetic properties of esomeprazole in adolescent patients aged 12 to 17 years with symptoms of gastroesophageal reflux disease: A randomized, open-label study | journal = Clin Ther | volume = 28 | issue = 3 | pages = 419–27 | date = March 2006 | pmid = 16750456 | doi = 10.1016/j.clinthera.2006.03.010 }}</ref>

===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]].<ref>{{cite web |url=https://www.lecturio.com/concepts/gastroesophageal-reflux-disease/| title=Gastroesophageal Reflux Disease|website=The Lecturio Medical Concept Library |access-date= 23 July 2021}}</ref> Long-term contact between gastric acids and the esophagus can cause permanent damage to the esophagus and is associated with [[Barrett's esophagus]].<ref>{{cite web |url=https://www.mayoclinic.org/diseases-conditions/barretts-esophagus/symptoms-causes/syc-20352841/| date=8 February 2023 | title=Barrett's Esophagus|website=The Mayo Clinic |access-date= 1 August 2023}}</ref> Esomeprazole reduces the production of digestive acids, thus reducing their effect on the esophagus.

===Duodenal ulcers===
Esomeprazole is combined with the antibiotics [[clarithromycin]] and [[amoxicillin]] (or [[metronidazole]] instead of amoxicillin in penicillin-hypersensitive patients) in a 10-day eradication triple therapy for ''[[Helicobacter pylori]]''. Infection by ''H. pylori'' is a causative factor in the majority of [[Peptic ulcer|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{{clarify|date=October 2021}}), but appeared more in those with severe disease (number needed to treat 8{{clarify|date=October 2021}}).<ref>{{cite journal | vauthors = Gralnek IM, Dulai GS, Fennerty MB, Spiegel BM | title = Esomeprazole versus other proton pump inhibitors in erosive esophagitis: a meta-analysis of randomized clinical trials | journal = Clin. Gastroenterol. Hepatol. | volume = 4 | issue = 12 | pages = 1452–8 | date = December 2006 | pmid = 17162239 | doi = 10.1016/j.cgh.2006.09.013 }}</ref> A second meta analysis also found increases in erosive esophageal healing (>95% healing rate) when compared to standardized doses in broadly selected patient populations.<ref>{{cite journal | vauthors = Edwards SJ, Lind T, Lundell L | title = Systematic review: proton pump inhibitors (PPIs) for the healing of reflux oesophagitis - a comparison of esomeprazole with other PPIs | journal = Aliment. Pharmacol. Ther. | volume = 24 | issue = 5 | pages = 743–50 | date = September 2006 | pmid = 16918878 | doi = 10.1111/j.1365-2036.2006.03074.x | s2cid = 23189853 | doi-access = free }}</ref> A 2017 study found esomeprazole to be among a number of effective PPIs.<ref>{{cite journal | vauthors = Li MJ, Li Q, Sun M, Liu LQ | title=Comparative effectiveness and acceptability of the FDA-licensed proton pump inhibitors for erosive esophagitis | journal=Medicine | volume=96 | issue=39 | year=2017 | issn=0025-7974 | pmid=28953640 | pmc=5626283 | doi=10.1097/md.0000000000008120 | article-number=e8120}}</ref>

==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.<ref>{{cite web | title = Nexium side effects | url = https://www.drugs.com/sfx/nexium-side-effects.html | work = Drug information online | publisher = Drugs.com | access-date = 23 June 2009 }}</ref>

Proton pump inhibitors may be associated with a greater risk of hip fractures<ref name="JAMA">{{cite journal | vauthors = Yang YX, Lewis JD, Epstein S, Metz DC | title = Long-term proton pump inhibitor therapy and risk of hip fracture | journal = JAMA | volume = 296 | issue = 24 | pages = 2947–53 | year = 2006 | pmid = 17190895 | doi = 10.1001/jama.296.24.2947 | doi-access = free }}</ref> and ''[[Clostridioides difficile infection|Clostridioides difficile]]''-associated [[diarrhoea]].<ref name="Bandolier">{{cite web | url = http://www.medicine.ox.ac.uk/bandolier/booth/Pharmacy/PPIcdiff.html | archive-url = https://archive.today/20121223071436/http://www.medicine.ox.ac.uk/bandolier/booth/Pharmacy/PPIcdiff.html | archive-date = 23 December 2012 | title = Proton pump inhibitors and Clostridium difficile | year = 2003 | access-date = 13 July 2007 | publisher = Bandolier }}</ref> 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]].<ref name="JAMA2">{{cite journal | vauthors = Herzig SJ, Howell MD, Ngo LH, Marcantonio ER | title = Acid-suppressive medication use and the risk for hospital-acquired pneumonia | journal = JAMA | volume = 301 | issue = 20 | pages = 2120–8 | year = 2009 | pmid = 19470989 | doi = 10.1001/jama.2009.722 | doi-access =  }}</ref>

Long-term use of proton pump inhibitors in patients treated for ''[[Helicobacter pylori]]'' has been shown to dramatically increase the risk of gastric cancer.<ref>{{cite journal | vauthors = Cheung KS, Chan EW, Wong AY, Chen L, Wong IC, Leung WK | title = Long-term proton pump inhibitors and risk of gastric cancer development after treatment for ''Helicobacter pylori'': a population-based study | journal = Gut | volume = 67 | issue = 1 | pages = 28–35 | date = January 2018 | pmid = 29089382 | doi = 10.1136/gutjnl-2017-314605 | doi-access = free }}</ref>

Acute [[tubulointerstitial nephritis]] is a possible adverse reaction when using proton pump inhibitors.<ref name="Nexium I.V. FDA label" />

== Interactions ==
Esomeprazole is a [[enzyme inhibitor|competitive inhibitor]] of the enzyme [[CYP2C19]], and may therefore [[drug interaction|interact]] with drugs that depend on it for [[drug metabolism|metabolism]], such as [[diazepam]] and [[warfarin]]; the concentrations of these drugs may increase if they are used concomitantly with esomeprazole.<ref name=Stedman>{{cite journal | vauthors = Stedman CA, Barclay ML | title = Review article: comparison of the pharmacokinetics, acid suppression and efficacy of proton pump inhibitors | journal = Aliment. Pharmacol. Ther. | volume = 14 | issue = 8 | pages = 963–78 | date = August 2000 | pmid = 10930890 | doi = 10.1046/j.1365-2036.2000.00788.x | s2cid = 45337685 }}</ref> 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.<ref>{{cite journal | vauthors = Lau WC, Gurbel PA | title = The drug-drug interaction between proton pump inhibitors and clopidogrel | journal = CMAJ | volume = 180 | issue = 7 | pages = 699–700 | date = March 2009 | pmid = 19332744 | pmc = 2659824 | doi = 10.1503/cmaj.090251 }}</ref><ref>{{cite journal | vauthors = Norgard NB, Mathews KD, Wall GC | title = Drug-drug interaction between clopidogrel and the proton pump inhibitors | journal = Ann Pharmacother | volume = 43 | issue = 7 | pages = 1266–74 | date = July 2009 | pmid = 19470853 | doi = 10.1345/aph.1M051 | s2cid = 13227312 }}</ref>

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.<ref name=Stedman/>

== Pharmacokinetics ==
Single 20 to 40{{nbsp}}mg oral doses generally give rise to peak plasma esomeprazole concentrations of 0.5-1.0{{nbsp}}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{{nbsp}}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.<ref>{{cite book |last1=Baselt RC |title=Disposition of toxic drugs and chemicals in man |date=2008 |publisher=Biomedical Publications |location=Foster City, Ca |isbn=978-0-9626523-7-0 |edition=8th | pages = 388–389 }}</ref>

== Dosage forms ==
[[File:Esomeprazole Strontium 49.3 mg Delayed-Release Capsules.jpg|thumb|Esomeprazole strontium delayed-release capsules, 49.3 mg]]
[[Image:Nexium (esomeprazole magnesium) pills.JPG|thumb|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{{nbsp}}mg, as delayed-release capsules in the United States (containing esomeprazole strontium) in a 49.3{{nbsp}}mg strength (delivering the equivalent of 40{{nbsp}}mg of esomeprazole,<ref name="urlDailyMed">{{cite web | url = https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=61a5a84e-0194-4f11-91f8-83d7ac404932 | title = esomeprazole strontium capsule, delayed release | work = DailyMed | publisher = U.S. Library of Medicine }}</ref> and as esomeprazole sodium for [[intravenous]] injection/infusion. Oral esomeprazole preparations are [[enteric coating|enteric-coated]], due to the rapid degradation of the drug in the [[acid]]ic conditions of the [[stomach]]. This is achieved by formulating capsules using the multiple-unit pellet system.

The combination [[naproxen/esomeprazole magnesium]] (brand name Vimovo) is used for the prevention of gastric ulcers associated with chronic [[NSAID]] therapy. Vimovo is available in two dosage strengths: 500/20{{nbsp}}mg and 375/20{{nbsp}}mg. Clinical trials of naproxen/esomeprazole demonstrated an incidence of GI ulcer in 24% of patients on naproxen (alone) versus 7% on naproxen/esomeprazole.<ref name=VimovoLabel>{{cite web | url = http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022511s017lbl.pdf | title = VIMOVO (naproxen and esomeprazole magnesium) delayed release tablets, for oral use | work = Horizon Pharma USA | publisher = U.S. Food and Drug Administration | date = December 2014 }}{{dead link|date=May 2025|bot=medic}}{{cbignore|bot=medic}}</ref> The FDA has added warnings to the label for Vimovo concerning [[acute interstitial nephritis]] and risk of [[kidney]] problems in some patients.<ref>{{cite web | url = https://www.fda.gov/Safety/MedWatch/SafetyInformation/ucm262248.htm | archive-url = https://web.archive.org/web/20150211053608/https://www.fda.gov/Safety/MedWatch/SafetyInformation/ucm262248.htm | archive-date = 11 February 2015 | title = Vimovo (naproxen/esomeprazole magnesium) tablets | quote = Safety Labeling Changes Approved By FDA Center for Drug Evaluation and Research (CDER) | publisher = U.S. Food and Drug Administration | date = December 2014 }}</ref>

=== Multiple-unit pellet system ===
Esomeprazole capsules, as well as Losec/Prilosec tablets, are formulated as a "multiple-unit pellet system" (MUPS). Essentially, the [[Capsule (pharmacy)|capsule]] consists of extremely small enteric-coated granules (pellets) of the esomeprazole formulation inside an outer shell. When the capsule is immersed in an aqueous solution, as happens when the capsule reaches the stomach, water enters the capsule by [[osmosis]]. The contents swell from water absorption, causing the shell to burst, and releasing the enteric-coated granules. For most patients, the multiple-unit pellet system is of no advantage over conventional enteric-coated preparations. Patients for whom the formulation is of benefit include those requiring [[nasogastric tube]] feeding and those with difficulty swallowing ([[dysphagia]]).<ref>{{cite journal | vauthors = Ullah MA, Maruf AA, Azad MA, Shohag MH, Sultana R, Latif AH, Hasnat A | title = Relative bioavailability and pharmacokinetic properties of two different enteric formulations of esomeprazole in healthy Bangladeshi male volunteers: An open-label, single-dose, randomized-sequence, two-way crossover study | journal = Clinical Therapeutics | volume = 32 | issue = 7 | pages = 1419–1426 | date = July 2010 | pmid = 20678688 | doi = 10.1016/j.clinthera.2010.07.007 }}</ref><ref>{{cite journal | vauthors = Vegesna V, Li J, Pollack C, Moreira S | title = Assessing the bioequivalence of over-the-counter esomeprazole banded capsules and multiple-unit pellet system tablets | journal = International Journal of Clinical Pharmacology and Therapeutics | volume = 56 | issue = 2 | pages = 92–99 | date = February 2018 | pmid = 29292694 | doi = 10.5414/CP203075 }}</ref><ref>{{cite journal | vauthors = Talpes S, Knoerzer D, Huber R, Pfaffenberger B | title = Esomeprazole MUPS 40 mg tablets and esomeprazole MUPS 40 mg tablets encapsulated in hard gelatine are bioequivalent | journal = International Journal of Clinical Pharmacology and Therapeutics | volume = 43 | issue = 1 | pages = 51–56 | date = January 2005 | pmid = 15704615 | doi = 10.5414/CPP43051 }}</ref><ref>{{cite journal | vauthors = Hamman H, Hamman J, Wessels A, Scholtz J, Steenekamp J | title = Development of multiple-unit pellet system tablets by employing the SeDeM expert diagram system II: pellets containing different active pharmaceutical ingredients | journal = Pharmaceutical Development and Technology | volume = 24 | issue = 2 | pages = 145–156 | date = February 2019 | pmid = 29394129 | doi = 10.1080/10837450.2018.1435691 | s2cid = 3596776 }}</ref>

== Society and culture ==

=== Global distribution ===
In 2010, AstraZeneca announced a co-promotion agreement with [[Daiichi Sankyo]] to distribute Nexium in Japan.<ref>{{cite press release | title=AstraZeneca announces co-promotion agreement with Daiichi Sankyo for NEXIUM in Japan | publisher=AstraZeneca | date=29 October 2010 | url=https://www.astrazeneca.com/media-centre/press-releases/2010/AstraZeneca-announces-copromotion-agreement-with-Daiichi-Sankyo-29102010.html | access-date=15 July 2019}}</ref> In September 2011, Nexium was approved for sale and was launched by Daiichi Sankyo in Japan.<ref>{{cite press release | url = http://www.daiichisankyo.com/media_investors/media_relations/press_releases/detail/005767.html | title = Daiichi Sankyo and AstraZeneca Launch NEXIUM 10mg and 20mg Capsules in Japan | publisher = Daiichi Sankyo | date=15 September 2011 | access-date=15 July 2019}}</ref> Esomeprazole was approved for use in the United States in February 2001.<ref>{{cite web | title=Drug Approval Package: Nexium (Esomeprazole Magnesium) NDA #21-153 & 21-154 | website=U.S. [[Food and Drug Administration]] (FDA) | date=24 December 1999 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21154_Nexium.cfm | archive-url=https://web.archive.org/web/20150712000405/http://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21154_Nexium.cfm | archive-date=12 July 2015 | access-date=4 April 2020}}</ref><ref>{{cite web | title=Nexium: FDA-Approved Drugs | website=U.S. [[Food and Drug Administration]] (FDA) | url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=021153 | archive-url=https://web.archive.org/web/20170430075658/https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=021153 | archive-date=30 April 2017 | access-date=4 April 2020}}</ref>

===Economics===
Between the launch of esomeprazole in 2001 and 2005, the drug netted AstraZeneca about $14.4{{nbsp}}billion.<ref>Financial impact information: 
*{{cite web | title = Annual Review 2005 | publisher = AstraZeneca | quote = $4.6 billion| url = http://www.astrazeneca.com/sites/7/imagebank/typeArticleparam511672/astrazeneca-2005-annual-review.pdf | archive-url = https://web.archive.org/web/20060312000637/http://www.astrazeneca.com/sites/7/imagebank/typeArticleparam511672/astrazeneca-2005-annual-review.pdf | archive-date = 12 March 2006 }}; 
*{{cite web | title = Annual Review 2004 | publisher = AstraZeneca | quote = $3.9 billion | url = http://www.astrazeneca.com/sites/7/imagebank/typearticleparam511562/astrazeneca-2004-annual-report.pdf | archive-url = https://web.archive.org/web/20070202143327/http://www.astrazeneca.com/sites/7/imagebank/typeArticleparam511562/astrazeneca-2004-annual-report.pdf | archive-date=2 February 2007 }}; 
*{{cite web | title = Annual Review 2003 | publisher = AstraZeneca | quote = $3.3 billion | url =  http://www.astrazeneca.com/sites/7/imagebank/typearticleparam503063/AstraZeneca%20Annual%20Report%202003.pdf | archive-url = https://web.archive.org/web/20040728120928/http://www.astrazeneca.com/sites/7/imagebank/typearticleparam503063/AstraZeneca%20Annual%20Report%202003.pdf | archive-date=28 July 2004 }}; 
*{{cite web | title = Annual Review 2002 | publisher = AstraZeneca | quote = $2 billion | url = http://www2.astrazeneca.com/annualrep2002/pdf/694617_Report_front.pdf | archive-url = https://web.archive.org/web/20030608161027/http://www.astrazeneca.com/annualrep2002/pdf/694617_Report_front.pdf | archive-date=8 June 2003 }}; 
*{{cite web | title = Annual Review 2001 | publisher = AstraZeneca | quote = launch and $580 million | url = http://www2.astrazeneca.com/annualrep2001/pdf/first.pdf }} {{dead link|date=February 2018|bot=medic}}{{cbignore|bot=medic}}</ref>

=== Controversy ===
{{main|AstraZeneca#Nexium|l1=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 [[Chirality (chemistry)|mirror-imaged molecules]] (esomeprazole which is the S-enantiomer, and R-omeprazole); critics said the company was trying to "[[Evergreening|evergreen]]" its omeprazole patent by patenting the pure esomeprazole and aggressively marketing to doctors that it is more effective than the mixture.<ref>{{cite magazine | title = High Prices: How to think about prescription drugs | vauthors = Gladwell M | author-link = Malcolm Gladwell | url = http://www.newyorker.com/archive/2004/10/25/041025crat_atlarge | magazine = [[The New Yorker]] | date = 25 October 2004 | access-date = 23 June 2006 }}</ref>

=== Brand names ===
Generic versions of esomeprazole magnesium are available worldwide.<ref name=brands/> It is available [[over-the-counter]] under the brand name Nexium in the United States<ref name=USA2020OTC>{{cite web |url=https://medlineplus.gov/druginfo/meds/a699054.html |website=[[MedlinePlus]] |publisher=[[United States National Library of Medicine]] |access-date=2 March 2020 |title=Esomeprazole}}</ref><ref>{{Cite web | url =https://abcnews.go.com/Health/wireStory/nonprescription-nexium-heartburn-medicine-launches-23883946 | title = Nonprescription Nexium Heartburn Medicine Launches | date = 27 May 2014 | work = ABC News}}</ref> and the UK.<ref>{{cite web |title=Esomeprazole: medicine to lower stomach acid |url=https://www.nhs.uk/medicines/esomeprazole/ |website=nhs.uk |access-date=9 December 2019 |date=29 August 2018}}</ref>

=== 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.<ref>{{cite journal | vauthors = Fladung R, Smith JS, Hines M, Soto-Gonzalez WM, Fayne B, Rahn RR, Escher OG, Harvill L, Garcia JD, Kreuder AJ, Cox S | display-authors = 6 | title = Pharmacokinetics of esomeprazole in goats (Capra aegagrus hircus) after intravenous and subcutaneous administration. | journal = Frontiers in Veterinary Science | date = December 2022 | volume = 9| article-number = 968973| doi = 10.3389/fvets.2022.968973 | pmid = 36590808 | pmc = 9797722 | doi-access = free }}</ref> 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]].<ref name="Drug-Efficacy-Screening" /> Gokmen ''et al.'', 2016 screen for efficacy against ''[[Trichomonas vaginalis]]'' isolates from [[horse]]s.<ref name="Drug-Efficacy-Screening" /> They found esomeprazole to be effective as a veterinary antiparasitic.<ref name="Drug-Efficacy-Screening">{{cite book | veditors = Marchiondo AA, Cruthers LR, Fourie JJ | year=2019 | volume=1 | pages=xxxi+576 | publication-place=[[London]] | publisher=[[Academic Press]] | title=Parasiticide screening - In Vitro and in Vivo Tests with Relevant Parasite Rearing and Host Infection/Infestation Methods | isbn=978-0-12-813890-8 | oclc=1104533040}}</ref>

== References ==
{{reflist}}

== Further reading ==
{{refbegin}}
* {{cite book | vauthors = Dean L | chapter=Esomeprazole Therapy and CYP2C19 Genotype | chapter-url=https://www.ncbi.nlm.nih.gov/books/NBK100896/ | veditors=Pratt VM, McLeod HL, Rubinstein WS, Scott SA, Dean LC, Kattman BL, Malheiro AJ | title=Medical Genetics Summaries  | display-editors=6 | location = Bethesda (MD) | publisher=[[National Center for Biotechnology Information]] (NCBI) | year=2012 | pmid=28520354 | id=Bookshelf ID: NBK100896 | url=https://www.ncbi.nlm.nih.gov/books/NBK61999/ }}
{{refend}}

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