Editing Omeprazole (section)

{{Short description|Medication to treat gastroesophageal reflux disease and other conditions}}
{{For|the similarly named medication derived from omeprazole|esomeprazole}}
{{Use dmy dates|date=January 2024}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Infobox drug
| Watchedfields = changed
| verifiedrevid = 462265
| image = Omeprazole enantiomers labelled.svg
| image_class = skin-invert-image
| chirality = [[Racemic mixture]]
| width = 350
| alt = 
| image2 = Omeprazole enantiomers ball-and-stick models from xtal 2015.png
| width2 = 350
| alt2 = 
| caption =

<!-- Clinical data -->
| pronounce = {{IPAc-en|oʊ|ˈ|m|ɛ|p|r|ə|z|oʊ|l|audio=LL-Q1860 (eng)-Naomi Persephone Amethyst (NaomiAmethyst)-omeprazole.wav}}
| tradename = Losec, Prilosec, others<ref name=AHFS2015/><ref name="Drugs.com international" />
| Drugs.com = {{drugs.com|monograph|omeprazole}}
| MedlinePlus = a693050
| DailyMedID = Omeprazole
| pregnancy_AU = B3
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Omeprazole Use During Pregnancy | website=Drugs.com | date=11 April 2019 | url=https://www.drugs.com/pregnancy/omeprazole.html | access-date=15 February 2020 | archive-date=15 February 2020 | archive-url=https://web.archive.org/web/20200215230433/https://www.drugs.com/pregnancy/omeprazole.html | url-status=live }}</ref>
| pregnancy_category= 
| routes_of_administration = [[Oral administration|By mouth]], [[Intravenous therapy|intravenous]]
| class     = [[Proton-pump inhibitor]]
| ATC_prefix = A02
| ATC_suffix = BC01
| ATC_supplemental  = {{ATC|A02|BC51}}

<!-- Legal status -->
| legal_AU = S4
| legal_AU_comment = 
| legal_BR =  <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F-->
| legal_BR_comment = 
| legal_CA = Rx-only
| legal_CA_comment = <ref>{{cite web  | title=Product monograph brand safety updates | website=[[Health Canada]] | date=7 July 2016 | 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=1 April 2024}}</ref>
| legal_DE = <!-- Anlage I, II, III or Unscheduled-->
| legal_DE_comment = 
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment = 
| legal_UK = POM
| legal_UK_comment = 
| legal_US = OTC
| legal_US_comment = /&nbsp;Rx-only
| legal_EU = Rx-only
| legal_EU_comment = <ref name="Omeprazole TriviumVet PI" />
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV-->
| legal_UN_comment = 
| legal_status      = <!--For countries not listed above-->

<!-- Pharmacokinetic data -->
| bioavailability= 35–76%<ref>{{cite web | title=Prilosec- omeprazole magnesium capsule, delayed release Prilosec- omeprazole magnesium granule, delayed release | website=DailyMed | date=22 December 2016 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a1b077e6-b070-43f2-a98e-380cc635419d | access-date=15 February 2020 | archive-date=27 December 2019 | archive-url=https://web.archive.org/web/20191227184048/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a1b077e6-b070-43f2-a98e-380cc635419d | url-status=live }}</ref><ref>{{cite journal | vauthors = Vaz-da-Silva M, Loureiro AI, Nunes T, Maia J, Tavares S, Falcão A, Silveira P, Almeida L, Soares-da-Silva P | title = Bioavailability and bioequivalence of two enteric-coated formulations of omeprazole in fasting and fed conditions | journal = Clinical Drug Investigation | volume = 25 | issue = 6 | pages = 391–399 | year = 2005 | pmid = 17532679 | doi = 10.2165/00044011-200525060-00004 | url = http://www.medscape.com/viewarticle/508018 | url-status = live | access-date = 21 October 2018 | s2cid = 22082780 | archive-url = https://web.archive.org/web/20130313204630/http://www.medscape.com/viewarticle/508018 | archive-date = 13 March 2013 }}</ref>
| protein_bound = 95%
| metabolism = [[Liver]] ([[CYP2C19]], [[CYP3A4]])
| metabolites       = 
| onset             = 
| elimination_half-life= 1–1.2 hours
| duration_of_action = 
| excretion = 80% (urine)<br />20% (bile via feces)

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 73590-58-6
| CAS_supplemental  = 
| PubChem = 4594
| IUPHAR_ligand = 4279
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00338
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4433
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = KG60484QX9
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00455
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 7772
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1503
| NIAID_ChemDB      = 
| PDB_ligand = 1C6
| synonyms          =

<!-- Chemical and physical data -->
| IUPAC_name        = 5-Methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1''H''-benzimidazole
| C = 17 | H = 19 | N = 3 | O = 3 | S = 1
| SMILES            = CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C(N2)C=C(C=C3)OC
| 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)
| StdInChI_comment  = 
| StdInChIKey_Ref   = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SUBDBMMJDZJVOS-UHFFFAOYSA-N
| density           = 1.4±0.1<ref name="chemsrc">{{cite web |url=https://www.chemsrc.com/en/cas/73590-58-6_591579.html |title=Omeprazole MSDS |access-date=21 October 2018 |archive-date=19 April 2017 |archive-url=https://web.archive.org/web/20170419120322/http://www.chemsrc.com/en/cas/73590-58-6_591579.html |url-status=live }}</ref>
| density_notes     = 
| melting_point     = 156
| melting_high      = 
| melting_notes     = 
| boiling_point     = 
| boiling_notes     = 
| solubility        = 
| sol_units         = 
| specific_rotation = 
}}

<!-- Definition and medical uses -->
'''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]].<ref name="AHFS2015">{{cite web |title=Omeprazole |url=https://www.drugs.com/monograph/omeprazole.html |publisher=The American Society of Health-System Pharmacists |access-date=21 October 2018 |archive-date=19 February 2011 |archive-url=https://web.archive.org/web/20110219135631/http://www.drugs.com/monograph/omeprazole.html |url-status=live }}</ref> It is also used to prevent [[upper gastrointestinal bleeding]] in people who are at high risk.<ref name=AHFS2015/> Omeprazole is a [[proton-pump inhibitor]] (PPI) and its effectiveness is similar to that of other 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|archive-date=30 October 2020|archive-url=https://web.archive.org/web/20201030063031/https://www.ti.ubc.ca/2016/06/28/99-comparative-effectiveness-proton-pump-inhibitors/|url-status=live}}</ref> It can be taken by mouth or by [[intravenous|injection into a vein]].<ref name=AHFS2015/><ref name=UK2016>{{cite web |title=Omeprazole 40 mg Powder for Solution for Infusion |url=https://www.medicines.org.uk/emc/medicine/25259 |website=EMC |access-date=21 October 2018 |date=10 February 2016 |url-status=live |archive-url=https://web.archive.org/web/20160407193540/https://www.medicines.org.uk/emc/medicine/25259 |archive-date=7 April 2016}}</ref> It is also available in the fixed-dose [[combination medication]] omeprazole/sodium bicarbonate as Zegerid<ref name="Zegerid FDA label">{{cite web | title=Zegerid- omeprazole and sodium bicarbonate powder, for suspension Zegerid- omeprazole and sodium bicarbonate capsule | website=DailyMed | date=4 March 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=cd6868b9-5824-442b-8d65-4db29ecb70a4 | access-date=16 December 2022}}</ref><ref name="Zegerid OTC FDA label">{{cite web | title=Zegerid OTC- omeprazole and sodium bicarbonate capsule, gelatin coated | website=DailyMed | date=5 December 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=5ad1ca2b-3119-b8c2-e053-2a91aa0a2f77 | access-date=16 December 2022}}</ref> and as Konvomep.<ref>{{cite web | title=Konvomep- omeprazole and sodium bicarbonate kit | website=DailyMed | date=30 August 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=688ed6f1-d78a-4006-a682-57021cb38a3e | access-date=21 January 2023}}</ref>

<!-- Side effects and mechanism -->
Common side effects include nausea, vomiting, headaches, abdominal pain, and [[flatulence|increased intestinal gas]].<ref name=AHFS2015/><ref name=Dav2015 /> Serious side effects may include [[Clostridioides difficile infection|''Clostridioides difficile'' colitis]], an increased risk of [[pneumonia]], an increased risk of [[bone fractures]], and the potential of masking [[stomach cancer]].<ref name=AHFS2015/> Whether it is safe for use in [[pregnancy]] is unclear.<ref name=AHFS2015/> It works by blocking the release of [[stomach acid]].<ref name=AHFS2015/>

<!-- History, society and culture -->
Omeprazole was patented in 1978 and approved for medical use in 1988.<ref>{{cite web | title=Drug Approval Package: Prilosec (Omeprazole) NDA# 019-810s38s50s5 | website=U.S. [[Food and Drug Administration]] (FDA) | date=30 March 2001 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/019810s38s50s56.cfm | access-date=5 October 2022 | archive-date=1 April 2021 | archive-url=https://web.archive.org/web/20210401151454/https://www.accessdata.fda.gov/drugsatfda_docs/nda/98/019810s38s50s56.cfm | url-status=dead }}</ref><ref>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=445 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA445 |access-date=29 June 2020 |archive-date=3 August 2020 |archive-url=https://web.archive.org/web/20200803230101/https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA445 |url-status=live }}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO23rd">{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) | year = 2023 | hdl = 10665/371090 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2023.02 | hdl-access=free }}</ref> It is available as a [[generic medication]].<ref name=AHFS2015/> In 2022, it was the ninth most commonly prescribed medication in the United States, with more than 52{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Omeprazole Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Omeprazole | access-date = 30 August 2024 }}</ref> It is also available without a prescription in the United States.<ref>{{cite web |title=Questions and Answers on Prilosec OTC (omeprazole) |url=https://www.fda.gov/about-fda/center-drug-evaluation-and-research-cder/questions-and-answers-prilosec-otc-omeprazole |website=U.S. [[Food and Drug Administration]] (FDA) |access-date=2 March 2020 |date=3 November 2018 |archive-date=28 August 2021 |archive-url=https://web.archive.org/web/20210828195503/https://www.fda.gov/about-fda/center-drug-evaluation-and-research-cder/questions-and-answers-prilosec-otc-omeprazole |url-status=dead }}</ref><ref>{{cite web | title=Drug Approval Package: Prilosec (Omeprazole Magnesium) NDA #021229 | website=U.S. [[Food and Drug Administration]] (FDA) | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-229_Prilosec.cfm | access-date=6 October 2022 | archive-date=24 January 2022 | archive-url=https://web.archive.org/web/20220124210732/https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-229_Prilosec.cfm | url-status=live }}</ref>