Lansoprazole: Difference between revisions
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{{Short description|Stomach acid suppressing medication}} |
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{{cs1 config|name-list-style=vanc|display-authors=6}} |
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{{Infobox drug |
{{Infobox drug |
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| Watchedfields = changed |
| Watchedfields = changed |
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| verifiedrevid = 458267412 |
| verifiedrevid = 458267412 |
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| drug_name = Selanz SR |
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| INN = |
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| type = <!-- empty --> |
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| image = Lansoprazole.svg |
| image = Lansoprazole.svg |
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| width = 245 |
| width = 245 |
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| Drugs.com = {{drugs.com|monograph|lansoprazole}} |
| Drugs.com = {{drugs.com|monograph|lansoprazole}} |
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| MedlinePlus = a695020 |
| MedlinePlus = a695020 |
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| licence_EU = yes |
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| DailyMedID = Lansoprazole |
| DailyMedID = Lansoprazole |
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| licence_US = Lansoprazole |
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| pregnancy_AU = B3 |
| pregnancy_AU = B3 |
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| pregnancy_AU_comment = <ref name=Preg2019 /> |
| pregnancy_AU_comment = <ref name=Preg2019 /> |
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| pregnancy_US = B |
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| pregnancy_US_comment = <ref name=Preg2019 /> |
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| pregnancy_category= |
| pregnancy_category= |
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| dependency_liability = |
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| addiction_liability = |
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| class = [[Proton pump inhibitor]] |
| class = [[Proton pump inhibitor]] |
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| ATCvet = |
| ATCvet = |
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| legal_UK_comment = |
| legal_UK_comment = |
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| legal_US = OTC |
| legal_US = OTC |
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| legal_US_comment = / |
| legal_US_comment = /{{nbsp}}Rx-only<ref name="Lansoprazole label" /> |
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| legal_EU = |
| legal_EU = |
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| legal_EU_comment = |
| legal_EU_comment = |
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| NIAID_ChemDB = |
| NIAID_ChemDB = |
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| PDB_ligand = |
| PDB_ligand = |
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| synonyms = |
| synonyms = AG 1749 |
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<!-- Chemical and physical data --> |
<!-- Chemical and physical data --> |
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| density = |
| density = |
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| density_notes = |
| density_notes = |
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| melting_point = |
| melting_point = 178 |
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| melting_high = |
| melting_high = |
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| melting_notes = |
| melting_notes = (decomposes) |
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| boiling_point = |
| boiling_point = |
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| boiling_notes = |
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<!-- Definition and medical uses --> |
<!-- Definition and medical uses --> |
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'''Lansoprazole''', sold under the brand name |
'''Lansoprazole''', sold under the brand name '''Prevacid''' among others, is a [[medication]] which reduces [[stomach acid]].<ref name=AHFS2019/> It is a [[proton pump inhibitor]] (PPI), used to treat [[peptic ulcer disease]], [[gastroesophageal reflux disease]], and [[Zollinger–Ellison syndrome]].<ref name=BNF76/> Its effectiveness is similar to that of other PPIs.<ref name=TI2016>{{cite web|title= Comparative effectiveness of proton pump inhibitors | work = Therapeutics Initiative | publisher = Dept of Anesthesiology, Pharmacology & Therapeutics, Faculty of Medicine, University of British Columbia |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 [[Oral administration|by mouth]].<ref name=AHFS2019/> Onset is over a few hours and effects last up to a couple of days.<ref name=AHFS2019/> |
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<!-- Side effects and mechanisms --> |
<!-- Side effects and mechanisms --> |
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<!-- History and culture --> |
<!-- History and culture --> |
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Lansoprazole was patented in 1984 and came into medical use in 1992.<ref>{{cite book | |
Lansoprazole was patented in 1984 and came into medical use in 1992.<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 }}</ref> It is available as a [[generic medication]].<ref name=BNF76>{{cite book|title=British national formulary : BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=79–80|edition=76}}</ref> In 2021, it was the 216th most commonly prescribed medication in the United States, with more than 1{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2021 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=14 January 2024 | archive-date=15 January 2024 | archive-url=https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Lansoprazole - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Lansoprazole | access-date = 14 January 2024}}</ref> |
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==Medical uses== |
==Medical uses== |
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Lansoprazole is used for treatment of:<ref name="Lansoprazole label">{{cite web | title=Lansoprazole capsule, delayed release pellets | |
Lansoprazole is used for treatment of:<ref name="Lansoprazole label">{{cite web | title=Lansoprazole capsule, delayed release pellets | work = DailyMed | publisher = U.S. National Library of Medicine | date=11 October 2016 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c8fa7401-907f-41b6-a2e1-f4bc214f2cdf | access-date=31 December 2019}}</ref> |
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* [[Peptic ulcer|Ulcers]] of the stomach and [[duodenum]], and [[NSAID]]-induced ulcers |
* [[Peptic ulcer|Ulcers]] of the stomach and [[duodenum]], and [[NSAID]]-induced ulcers |
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* ''[[Helicobacter pylori]]'' infection, alongside [[antibiotics]] (adjunctive treatment), treatment to kill ''H. pylori'' causing ulcers or other problems involves using two other drugs besides lansoprazole known as "[[Helicobacter pylori eradication protocols|triple therapy]]", and involves taking twice daily for 10 or 14 days lansoprazole, [[amoxicillin]], and [[clarithromycin]] |
* ''[[Helicobacter pylori]]'' infection, alongside [[antibiotics]] (adjunctive treatment), treatment to kill ''H. pylori'' causing ulcers or other problems involves using two other drugs besides lansoprazole known as "[[Helicobacter pylori eradication protocols|triple therapy]]", and involves taking twice daily for 10 or 14 days lansoprazole, [[amoxicillin]], and [[clarithromycin]] |
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* [[Gastroesophageal reflux disease]] |
* [[Gastroesophageal reflux disease]] |
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* [[Zollinger-Ellison syndrome|Zollinger–Ellison syndrome]]<ref>{{cite journal |vauthors=Hirschowitz BI, Mohnen J, Shaw S |title=Long-term treatment with lansoprazole for patients with Zollinger-Ellison syndrome |journal= |
* [[Zollinger-Ellison syndrome|Zollinger–Ellison syndrome]]<ref>{{cite journal | vauthors = Hirschowitz BI, Mohnen J, Shaw S | title = Long-term treatment with lansoprazole for patients with Zollinger-Ellison syndrome | journal = Alimentary Pharmacology & Therapeutics | volume = 10 | issue = 4 | pages = 507–522 | date = August 1996 | pmid = 8853754 | doi = 10.1046/j.1365-2036.1996.10152000.x | s2cid = 10668517 }}</ref> |
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There is no good evidence that it works better than other PPIs.<ref name=TI2016/> |
There is no good evidence that it works better than other PPIs.<ref name=TI2016/> |
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==Side effects== |
==Side effects== |
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Side effects of PPIs in general<ref> |
Side effects of PPIs in general<ref>{{cite web | url = http://bnf.org/bnf/bnf/current/2137.htm#_200909 | work = British National Formulary | url-access = registration | title = 1.3.5 Proton pump inhibitors | access-date = 1 February 2012 | archive-date = 21 February 2020 | archive-url = https://web.archive.org/web/20200221070446/https://about.medicinescomplete.com/#_200909 | url-status = dead }}</ref> and lansoprazole in particular<ref>{{cite web | url = http://bnf.org/bnf/bnf/current/129429.htm#_129429 | work = British National Formulary | url-access = registration | title = Lansoprazole | access-date = 1 February 2012 | archive-date = 21 February 2020 | archive-url = https://web.archive.org/web/20200221070438/https://about.medicinescomplete.com/#_129429 | url-status = dead }}</ref> may include:<ref name="Lansoprazole label" /> |
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*Common: diarrhea, abdominal pain<ref>{{Cite web|title = Prevacid (Lansoprazole) Drug Information: Side Effects and Drug Interactions - Prescribing Information |
*Common: diarrhea, abdominal pain<ref>{{Cite web|title = Prevacid (Lansoprazole) Drug Information: Side Effects and Drug Interactions - Prescribing Information |url = http://www.rxlist.com/prevacid-drug/side-effects-interactions.htm|website = RxList|access-date = 9 February 2016}}</ref> |
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*Infrequent: [[dry mouth]], [[insomnia]], [[drowsiness]], blurred [[Visual perception|vision]], [[rash]], [[pruritus]] |
*Infrequent: [[dry mouth]], [[insomnia]], [[drowsiness]], blurred [[Visual perception|vision]], [[rash]], [[pruritus]] |
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*Rarely and very rarely: [[taste]] disturbance, [[liver]] dysfunction, [[oedema|peripheral oedema]], hypersensitivity reactions (including [[bronchospasm]], urinary, [[angioedema]], [[anaphylaxis]]), [[photosensitivity]], [[fever]], [[sweating]], [[clinical depression|depression]], [[interstitial nephritis]], blood disorders (including [[leukopenia]], [[leukocytosis]], [[pancytopenia]], [[thrombocytopenia]]), [[arthralgia]], [[myalgia]], skin reactions<ref> |
*Rarely and very rarely: [[taste]] disturbance, [[liver]] dysfunction, [[oedema|peripheral oedema]], hypersensitivity reactions (including [[bronchospasm]], urinary, [[angioedema]], [[anaphylaxis]]), [[photosensitivity]], [[fever]], [[sweating]], [[clinical depression|depression]], [[interstitial nephritis]], blood disorders (including [[leukopenia]], [[leukocytosis]], [[pancytopenia]], [[thrombocytopenia]]), [[arthralgia]], [[myalgia]], skin reactions<ref>{{cite journal | vauthors = Salloum A, Nasr D, Maalouf D | title = Dermatologic adverse reactions to proton-pump inhibitors: A synthetized review | journal = Journal of Cosmetic Dermatology | volume = 20 | issue = 4 | pages = 1073–1079 | date = April 2021 | pmid = 33031621 | doi = 10.1111/jocd.13763 | s2cid = 222236157 }}</ref> including ([[erythroderma]],<ref name="bolognia">{{cite book |vauthors=Sterry W, Assaf C |chapter=Erythroderma | veditors = Bolognia JL |title=Dermatology |publisher=Mosby |location=St. Louis |year=2007 |page=154 |isbn=978-1-4160-2999-1}}.</ref> [[Stevens–Johnson syndrome]], [[toxic epidermal necrolysis]], [[blister|bullous eruption]]) |
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PPIs may be associated with a greater risk of hip fractures and ''[[Clostridium difficile colitis|Clostridium difficile]]''-associated [[diarrhea]].<ref name="Lansoprazole label" />{{rp|22}} |
PPIs may be associated with a greater risk of hip fractures and ''[[Clostridium difficile colitis|Clostridium difficile]]''-associated [[diarrhea]].<ref name="Lansoprazole label" />{{rp|22}} |
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==Interactions== |
== Interactions == |
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Lansoprazole interacts with several other drugs, either due to its own nature or as a PPI.<ref> |
Lansoprazole interacts with several other drugs, either due to its own nature or as a PPI.<ref>{{cite web | url = http://bnf.org/bnf/bnf/current/41001i753.htm | work = British National Formulary | url-access = registration | title = Lansoprazole interactions | access-date = 1 February 2012 | archive-date = 28 August 2021 | archive-url = https://web.archive.org/web/20210828140753/https://about.medicinescomplete.com/wp-content/themes/mc-marketing/assets/images/favicons-tiles/favicon.ico | url-status = dead }}</ref> |
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* PPIs reduce absorption of [[Antifungal drug|antifungals]] ([[itraconazole]] and [[ketoconazole]]) <ref>{{cite journal| |
* PPIs reduce absorption of [[Antifungal drug|antifungals]] ([[itraconazole]] and [[ketoconazole]]) <ref>{{cite journal | vauthors = Piscitelli SC, Goss TF, Wilton JH, D'Andrea DT, Goldstein H, Schentag JJ | title = Effects of ranitidine and sucralfate on ketoconazole bioavailability | journal = Antimicrobial Agents and Chemotherapy | volume = 35 | issue = 9 | pages = 1765–1771 | date = September 1991 | pmid = 1952845 | pmc = 245265 | doi = 10.1128/aac.35.9.1765 }}</ref> and possibly increase [[digoxin]] in plasma |
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* Increases plasma concentrations of [[cilostazol]] (risk of toxicity) |
* Increases plasma concentrations of [[cilostazol]] (risk of toxicity) |
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==Chemistry== |
==Chemistry== |
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It is a [[racemate|racemic]] 1:1 mixture of the [[enantiomer]]s [[dexlansoprazole]] and levolansoprazole.<ref>{{cite web|title=Pharmacy Benefit Update|url=http://epharmacytechnicanschools.com/pharmacy-benefit-update/|access-date=2 July 2014}}</ref> Dexlansoprazole is an enantiomerically pure active ingredient of a commercial drug as a result of the ''[[Chiral derivatizing agent|enantiomeric shift]]''. Lansoprazole's plasma elimination half-life (1.5 h) is not proportional to the duration of the drug's effects to the person (i.e. [[gastric acid]] suppression).<ref name="RxList">{{cite web | url = http://www.rxlist.com/cgi/generic/lansop_cp.htm | title = Prevacid Pharmacology, Pharmacokinetics, Studies, Metabolism | year = 2007 | access-date = 14 April 2007 | publisher = RxList.com | archive-url = https://web.archive.org/web/20000816224850/http://www.rxlist.com/cgi/generic/lansop_cp.htm | archive-date = 16 August 2000 | url-status = dead }}</ref> |
It is a [[racemate|racemic]] 1:1 mixture of the [[enantiomer]]s [[dexlansoprazole]] and levolansoprazole.<ref>{{cite web|title=Pharmacy Benefit Update|url=http://epharmacytechnicanschools.com/pharmacy-benefit-update/|access-date=2 July 2014|archive-date=14 July 2014|archive-url=https://web.archive.org/web/20140714200303/http://epharmacytechnicanschools.com/pharmacy-benefit-update/|url-status=dead}}</ref> Dexlansoprazole is an enantiomerically pure active ingredient of a commercial drug as a result of the ''[[Chiral derivatizing agent|enantiomeric shift]]''. Lansoprazole's plasma elimination half-life (1.5 h) is not proportional to the duration of the drug's effects to the person (i.e. [[gastric acid]] suppression).<ref name="RxList">{{cite web | url = http://www.rxlist.com/cgi/generic/lansop_cp.htm | title = Prevacid Pharmacology, Pharmacokinetics, Studies, Metabolism | year = 2007 | access-date = 14 April 2007 | publisher = RxList.com | archive-url = https://web.archive.org/web/20000816224850/http://www.rxlist.com/cgi/generic/lansop_cp.htm | archive-date = 16 August 2000 | url-status = dead }}</ref> |
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==History== |
==History== |
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{{main|Discovery and development of proton pump inhibitors}} |
{{main|Discovery and development of proton pump inhibitors}} |
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Lansoprazole |
Lansoprazole was originally synthesized at [[Takeda Pharmaceutical Company|Takeda]] and was given the development name AG 1749.<ref>{{cite book| vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery|date=2006|publisher=John Wiley & Sons|isbn=9783527607495|page=102|url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA102}}</ref> Takeda patented it in 1984 and the drug launched in 1991.<ref>{{cite book| vauthors = Chorghade MS |title=Drug Discovery and Development, Volume 1: Drug Discovery|date=2006|publisher=John Wiley & Sons|isbn=9780471780090|page=201|url=https://books.google.com/books?id=Bu5IHnBxjxwC&pg=PA201}}</ref> In the United States, it was approved for medical use in 1995.<ref name="Mosby's">{{cite web | url = http://www.mosbysdrugconsult.com/DrugConsult/Top_200/Drugs/e3230.html | archive-url = https://web.archive.org/web/20090208113930/http://www.mosbysdrugconsult.com/DrugConsult/Top_200/Drugs/e3230.html | archive-date = 8 February 2009 | work = Mosby's Drug Consult | title = Lansoprazole }}</ref> |
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== Society and culture == |
== Society and culture == |
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===Patents=== |
===Patents=== |
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The lansoprazole molecule is off-patent and so [[generic drugs]] are available under many brand names in many countries;<ref>drugs.com [https://www.drugs.com/international/lansoprazole.html International availability of lansoprazole] Page accessed 3 February 2015</ref> there are patents covering some [[formulations]] in effect {{as of|2015|lc=yes}}.<ref>drugs.com [https://www.drugs.com/availability/generic-prevacid.html Generic lansoprazole] Page accessed 3 February 2015</ref> Patent protection expired on 10 November 2009.<ref>{{cite web | url=https://www.drugpatentwatch.com/p/tradename/index.php?query=PREVACID&archive=2008 | title=Prevacid Drug Profile | publisher=Drugpatentwatch.com | access-date=30 April 2020 }}</ref><ref name="Teva">[http://www.marketwatch.com/story/teva-to-release-prevacid-version-when-patent-expires Teva to release Prevacid version when patent expires]</ref> |
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Patent protection of the lansoprazole molecule expired on 10 November 2009,<ref>{{cite web | url=https://www.drugpatentwatch.com/p/tradename/index.php?query=PREVACID&archive=2008 | title=Prevacid Drug Profile | publisher=Drugpatentwatch.com | access-date=30 April 2020 }}</ref><ref name="Teva">{{cite web | vauthors = Witkowski W | date = 7 November 2008 | work = Market Watch | publisher = Dow Jones | url = http://www.marketwatch.com/story/teva-to-release-prevacid-version-when-patent-expires | title = Teva to release Prevacid version when patent expires }}</ref> and [[Generic drugs|generic formulations]] became available under many brand names in many countries.<ref>{{cite web | url = https://www.drugs.com/international/lansoprazole.html | title = International availability of lansoprazole | work = Drugs.com | access-date = 3 February 2015 }}</ref> Some [[formulations]] may not be available in generic form.<ref>{{cite web | url = https://www.drugs.com/availability/generic-prevacid.html | title = Generic lansoprazole | work = Drugs.com | access-date = 20 November 2023}}</ref> |
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===Availability=== |
===Availability=== |
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Since 2009, lansoprazole has been available [[Over-the-counter drug|over the counter]] (OTC) in the U.S. as Prevacid 24HR<ref>{{cite web | title=Prevacid 24 HR- lansoprazole capsule, delayed release | website=DailyMed | date=7 August 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=fd4629d5-b876-4ae9-bb32-c3560ad416a9 | access-date=31 December 2019}}</ref><ref>{{cite web | title=Prevacid 24 HR- lansoprazole capsule, delayed release | |
Since 2009, lansoprazole has been available [[Over-the-counter drug|over the counter]] (OTC) in the U.S. as Prevacid 24HR<ref>{{cite web | title=Prevacid 24 HR- lansoprazole capsule, delayed release | website=DailyMed | publisher = U.S. National Library of Medicine| date=7 August 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=fd4629d5-b876-4ae9-bb32-c3560ad416a9 | access-date=31 December 2019}}</ref><ref>{{cite web | title=Prevacid 24 HR- lansoprazole capsule, delayed release | work = DailyMed | publisher = U.S. National Library of Medicine | date=11 December 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=99a97004-e247-4f4d-a38c-f28f521de1c4 | access-date=31 December 2019}}</ref> and as Lansoprazole 24HR.<ref>{{cite web | title=Lansoprazole 24 HR- lansoprazole capsule, delayed release | work = DailyMed | publisher = U.S. National Library of Medicine | date=21 December 2017 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=b5b4e61e-91c5-41bd-a16d-e25d9be2c87e | access-date=31 December 2019}}</ref> In Australia, it is marketed by [[Pfizer]] as Zoton.<ref>{{cite web |title=Zoton FasTabs |url=https://www.nps.org.au/medicine-finder/zoton-fas-tabs-orally-disintegrating-tablets |website=NPS MedicineWise |date=2 September 2019 |access-date=24 April 2022 |language=en}}</ref> |
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==Research== |
==Research== |
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''In vitro'' experiments have shown that lansoprazole binds to [[Hyperphosphorylation|the pathogenic form]] of [[tau protein]].<ref name=Lancetrev2015/> {{As of|2015}} laboratory studies were underway on analogs of lansoprazole to explore their use as potential [[Positron emission tomography|PET imaging]] [[radiotracers|agents]] for diagnosing [[Tauopathy|tauopathies]] including [[Alzheimer's disease]].<ref name=Lancetrev2015>{{cite journal| |
''[[In vitro]]'' experiments have shown that lansoprazole binds to [[Hyperphosphorylation|the pathogenic form]] of [[tau protein]].<ref name=Lancetrev2015/> {{As of|2015}} laboratory studies were underway on analogs of lansoprazole to explore their use as potential [[Positron emission tomography|PET imaging]] [[radiotracers|agents]] for diagnosing [[Tauopathy|tauopathies]] including [[Alzheimer's disease]].<ref name=Lancetrev2015>{{cite journal | vauthors = Villemagne VL, Fodero-Tavoletti MT, Masters CL, Rowe CC | title = Tau imaging: early progress and future directions | journal = The Lancet. Neurology | volume = 14 | issue = 1 | pages = 114–124 | date = January 2015 | pmid = 25496902 | doi = 10.1016/s1474-4422(14)70252-2 | s2cid = 10502833 }}</ref> |
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== References == |
== References == |
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{{reflist}} |
{{reflist}} |
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== External links == |
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* {{cite web| url = https://druginfo.nlm.nih.gov/drugportal/name/lansoprazole | publisher = U.S. National Library of Medicine| work = Drug Information Portal| title = Lansoprazole }} |
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{{Proton-Pump Inhibitors}} |
{{Proton-Pump Inhibitors}} |
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[[Category:Benzimidazoles]] |
[[Category:Benzimidazoles]] |
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[[Category: |
[[Category:Drugs developed by GSK plc]] |
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[[Category: |
[[Category:Drugs developed by Novartis]] |
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[[Category:Organofluorides]] |
[[Category:Organofluorides]] |
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[[Category:Phenol ethers]] |
[[Category:Phenol ethers]] |
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[[Category:Sanofi]] |
[[Category:Sanofi]] |
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[[Category:Sulfoxides]] |
[[Category:Sulfoxides]] |
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[[Category: |
[[Category:Drugs developed by AbbVie]] |
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[[Category:Takeda Pharmaceutical Company |
[[Category:Drugs developed by Takeda Pharmaceutical Company]] |
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[[Category:Trifluoromethyl compounds]] |
[[Category:Trifluoromethyl compounds]] |
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[[Category:Wikipedia medicine articles ready to translate]] |
[[Category:Wikipedia medicine articles ready to translate]] |
Latest revision as of 16:13, 8 March 2024
Clinical data | |
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Pronunciation | /lænˈsoʊprəzoʊl/ lan-SOH-prə-zohl |
Trade names | Prevacid, others |
Other names | AG 1749 |
AHFS/Drugs.com | Monograph |
MedlinePlus | a695020 |
License data |
|
Pregnancy category |
|
Routes of administration | By mouth, intravenous |
Drug class | Proton pump inhibitor |
ATC code | |
Legal status | |
Legal status | |
Pharmacokinetic data | |
Bioavailability | 80% or more |
Protein binding | 97% |
Metabolism | Liver (CYP3A4- and CYP2C19-mediated) |
Elimination half-life | 1.0–1.5 hours |
Excretion | Kidney and fecal |
Identifiers | |
| |
CAS Number | |
PubChem CID | |
IUPHAR/BPS | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEBI | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.173.220 |
Chemical and physical data | |
Formula | C16H14F3N3O2S |
Molar mass | 369.36 g·mol−1 |
3D model (JSmol) | |
Chirality | Racemic mixture |
Melting point | 178 °C (352 °F) (decomposes) |
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(verify) |
Lansoprazole, sold under the brand name Prevacid among others, is a medication which reduces stomach acid.[4] It is a proton pump inhibitor (PPI), used to treat peptic ulcer disease, gastroesophageal reflux disease, and Zollinger–Ellison syndrome.[5] Its effectiveness is similar to that of other PPIs.[6] It is taken by mouth.[4] Onset is over a few hours and effects last up to a couple of days.[4]
Common side effects include constipation, abdominal pain, and nausea.[4][3] Serious side effects may include osteoporosis, low blood magnesium, Clostridium difficile infection, and pneumonia.[4][3] Use in pregnancy and breastfeeding is of unclear safety.[1] It works by blocking H+/K+-ATPase in the parietal cells of the stomach.[4]
Lansoprazole was patented in 1984 and came into medical use in 1992.[7] It is available as a generic medication.[5] In 2021, it was the 216th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[8][9]
Medical uses
[edit]Lansoprazole is used for treatment of:[3]
- Ulcers of the stomach and duodenum, and NSAID-induced ulcers
- Helicobacter pylori infection, alongside antibiotics (adjunctive treatment), treatment to kill H. pylori causing ulcers or other problems involves using two other drugs besides lansoprazole known as "triple therapy", and involves taking twice daily for 10 or 14 days lansoprazole, amoxicillin, and clarithromycin
- Gastroesophageal reflux disease
- Zollinger–Ellison syndrome[10]
There is no good evidence that it works better than other PPIs.[6]
Side effects
[edit]Side effects of PPIs in general[11] and lansoprazole in particular[12] may include:[3]
- Common: diarrhea, abdominal pain[13]
- Infrequent: dry mouth, insomnia, drowsiness, blurred vision, rash, pruritus
- Rarely and very rarely: taste disturbance, liver dysfunction, peripheral oedema, hypersensitivity reactions (including bronchospasm, urinary, angioedema, anaphylaxis), photosensitivity, fever, sweating, depression, interstitial nephritis, blood disorders (including leukopenia, leukocytosis, pancytopenia, thrombocytopenia), arthralgia, myalgia, skin reactions[14] including (erythroderma,[15] Stevens–Johnson syndrome, toxic epidermal necrolysis, bullous eruption)
PPIs may be associated with a greater risk of hip fractures and Clostridium difficile-associated diarrhea.[3]: 22
Interactions
[edit]Lansoprazole interacts with several other drugs, either due to its own nature or as a PPI.[16]
- PPIs reduce absorption of antifungals (itraconazole and ketoconazole) [17] and possibly increase digoxin in plasma
- Increases plasma concentrations of cilostazol (risk of toxicity)
Lansoprazole possibly interacts with, among other drugs:
- sucralfate
- ampicillin
- bisacodyl
- clopidogrel
- delavirdine
- fluvoxamine
- iron salts
- voriconazole
- aminophylline and theophylline
- astemizole
Chemistry
[edit]It is a racemic 1:1 mixture of the enantiomers dexlansoprazole and levolansoprazole.[18] Dexlansoprazole is an enantiomerically pure active ingredient of a commercial drug as a result of the enantiomeric shift. Lansoprazole's plasma elimination half-life (1.5 h) is not proportional to the duration of the drug's effects to the person (i.e. gastric acid suppression).[19]
History
[edit]Lansoprazole was originally synthesized at Takeda and was given the development name AG 1749.[20] Takeda patented it in 1984 and the drug launched in 1991.[21] In the United States, it was approved for medical use in 1995.[22]
Society and culture
[edit]Patents
[edit]Patent protection of the lansoprazole molecule expired on 10 November 2009,[23][24] and generic formulations became available under many brand names in many countries.[25] Some formulations may not be available in generic form.[26]
Availability
[edit]Since 2009, lansoprazole has been available over the counter (OTC) in the U.S. as Prevacid 24HR[27][28] and as Lansoprazole 24HR.[29] In Australia, it is marketed by Pfizer as Zoton.[30]
Research
[edit]In vitro experiments have shown that lansoprazole binds to the pathogenic form of tau protein.[31] As of 2015[update] laboratory studies were underway on analogs of lansoprazole to explore their use as potential PET imaging agents for diagnosing tauopathies including Alzheimer's disease.[31]
References
[edit]- ^ a b "Lansoprazole Use During Pregnancy". Drugs.com. Retrieved 3 March 2019.
- ^ "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.
- ^ a b c d e f "Lansoprazole capsule, delayed release pellets". DailyMed. U.S. National Library of Medicine. 11 October 2016. Retrieved 31 December 2019.
- ^ a b c d e f "Lansoprazole Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
- ^ a b British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 79–80. ISBN 9780857113382.
- ^ a b "Comparative effectiveness of proton pump inhibitors". Therapeutics Initiative. Dept of Anesthesiology, Pharmacology & Therapeutics, Faculty of Medicine, University of British Columbia. 28 June 2016. Retrieved 14 July 2016.
- ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 445. ISBN 9783527607495.
- ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
- ^ "Lansoprazole - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
- ^ Hirschowitz BI, Mohnen J, Shaw S (August 1996). "Long-term treatment with lansoprazole for patients with Zollinger-Ellison syndrome". Alimentary Pharmacology & Therapeutics. 10 (4): 507–522. doi:10.1046/j.1365-2036.1996.10152000.x. PMID 8853754. S2CID 10668517.
- ^ "1.3.5 Proton pump inhibitors". British National Formulary. Archived from the original on 21 February 2020. Retrieved 1 February 2012.
- ^ "Lansoprazole". British National Formulary. Archived from the original on 21 February 2020. Retrieved 1 February 2012.
- ^ "Prevacid (Lansoprazole) Drug Information: Side Effects and Drug Interactions - Prescribing Information". RxList. Retrieved 9 February 2016.
- ^ Salloum A, Nasr D, Maalouf D (April 2021). "Dermatologic adverse reactions to proton-pump inhibitors: A synthetized review". Journal of Cosmetic Dermatology. 20 (4): 1073–1079. doi:10.1111/jocd.13763. PMID 33031621. S2CID 222236157.
- ^ Sterry W, Assaf C (2007). "Erythroderma". In Bolognia JL (ed.). Dermatology. St. Louis: Mosby. p. 154. ISBN 978-1-4160-2999-1..
- ^ "Lansoprazole interactions". British National Formulary. Archived from the original on 28 August 2021. Retrieved 1 February 2012.
- ^ Piscitelli SC, Goss TF, Wilton JH, D'Andrea DT, Goldstein H, Schentag JJ (September 1991). "Effects of ranitidine and sucralfate on ketoconazole bioavailability". Antimicrobial Agents and Chemotherapy. 35 (9): 1765–1771. doi:10.1128/aac.35.9.1765. PMC 245265. PMID 1952845.
- ^ "Pharmacy Benefit Update". Archived from the original on 14 July 2014. Retrieved 2 July 2014.
- ^ "Prevacid Pharmacology, Pharmacokinetics, Studies, Metabolism". RxList.com. 2007. Archived from the original on 16 August 2000. Retrieved 14 April 2007.
- ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 102. ISBN 9783527607495.
- ^ Chorghade MS (2006). Drug Discovery and Development, Volume 1: Drug Discovery. John Wiley & Sons. p. 201. ISBN 9780471780090.
- ^ "Lansoprazole". Mosby's Drug Consult. Archived from the original on 8 February 2009.
- ^ "Prevacid Drug Profile". Drugpatentwatch.com. Retrieved 30 April 2020.
- ^ Witkowski W (7 November 2008). "Teva to release Prevacid version when patent expires". Market Watch. Dow Jones.
- ^ "International availability of lansoprazole". Drugs.com. Retrieved 3 February 2015.
- ^ "Generic lansoprazole". Drugs.com. Retrieved 20 November 2023.
- ^ "Prevacid 24 HR- lansoprazole capsule, delayed release". DailyMed. U.S. National Library of Medicine. 7 August 2019. Retrieved 31 December 2019.
- ^ "Prevacid 24 HR- lansoprazole capsule, delayed release". DailyMed. U.S. National Library of Medicine. 11 December 2019. Retrieved 31 December 2019.
- ^ "Lansoprazole 24 HR- lansoprazole capsule, delayed release". DailyMed. U.S. National Library of Medicine. 21 December 2017. Retrieved 31 December 2019.
- ^ "Zoton FasTabs". NPS MedicineWise. 2 September 2019. Retrieved 24 April 2022.
- ^ a b Villemagne VL, Fodero-Tavoletti MT, Masters CL, Rowe CC (January 2015). "Tau imaging: early progress and future directions". The Lancet. Neurology. 14 (1): 114–124. doi:10.1016/s1474-4422(14)70252-2. PMID 25496902. S2CID 10502833.