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Lansoprazole

April 11, 2024

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]

Lansoprazole
Clinical data
Pronunciation/lænˈsoʊprəzoʊl/ lan-SOH-prə-zohl
Trade namesPrevacid, others
Other namesAG 1749
AHFS/Drugs.comMonograph
MedlinePlusa695020
License data
Pregnancy
category
Routes of
administration		By mouth, intravenous
Drug classProton pump inhibitor
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability80% or more
Protein binding97%
MetabolismLiver (CYP3A4- and CYP2C19-mediated)
Elimination half-life1.0–1.5 hours
ExcretionKidney and fecal
Identifiers
  • (RS)-2-([3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole
CAS Number
  • 103577-45-3 Y
PubChem CID
  • 3883
IUPHAR/BPS
  • 7208
DrugBank
  • DB00448 Y
ChemSpider
  • 3746 Y
UNII
  • 0K5C5T2QPG
KEGG
  • D00355 Y
ChEBI
  • CHEBI:6375 Y
ChEMBL
  • ChEMBL480 Y
CompTox Dashboard (EPA)
  • DTXSID4023200
ECHA InfoCard100.173.220
Chemical and physical data
FormulaC16H14F3N3O2S
Molar mass369.36 g·mol−1
3D model (JSmol)
  • Interactive image
ChiralityRacemic mixture
Melting point178 °C (352 °F) (decomposes)
  • FC(F)(F)COc1ccnc(c1C)CS(=O)c2[nH]c3ccccc3n2
  • InChI=1S/C16H14F3N3O2S/c1-10-13(20-7-6-14(10)24-9-16(17,18)19)8-25(23)15-21-11-4-2-3-5-12(11)22-15/h2-7H,8-9H2,1H3,(H,21,22) Y
  • Key:MJIHNNLFOKEZEW-UHFFFAOYSA-N Y
  (verify)

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]

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]

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]

Lansoprazole possibly interacts with, among other drugs:

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

Main article: Discovery and development of proton pump inhibitors

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

 
Prevacid 30 mg

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 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

  1. ^ a b "Lansoprazole Use During Pregnancy". Drugs.com. Retrieved 3 March 2019.
  2. ^ "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.
  3. ^ 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.
  4. ^ a b c d e f "Lansoprazole Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
  5. ^ a b British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 79–80. ISBN 9780857113382.
  6. ^ 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.
  7. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 445. ISBN 9783527607495.
  8. ^ "The Top 300 of 2021". ClinCalc. from the original on 15 January 2024. Retrieved 14 January 2024.
  9. ^ "Lansoprazole - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  10. ^ 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.
  11. ^ . British National Formulary. Archived from the original on 21 February 2020. Retrieved 1 February 2012.
  12. ^ . British National Formulary. Archived from the original on 21 February 2020. Retrieved 1 February 2012.
  13. ^ "Prevacid (Lansoprazole) Drug Information: Side Effects and Drug Interactions - Prescribing Information". RxList. Retrieved 9 February 2016.
  14. ^ 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.
  15. ^ Sterry W, Assaf C (2007). "Erythroderma". In Bolognia JL (ed.). Dermatology. St. Louis: Mosby. p. 154. ISBN 978-1-4160-2999-1..
  16. ^ . British National Formulary. Archived from the original on 28 August 2021. Retrieved 1 February 2012.
  17. ^ 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.
  18. ^ . Archived from the original on 14 July 2014. Retrieved 2 July 2014.
  19. ^ . RxList.com. 2007. Archived from the original on 16 August 2000. Retrieved 14 April 2007.
  20. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 102. ISBN 9783527607495.
  21. ^ Chorghade MS (2006). Drug Discovery and Development, Volume 1: Drug Discovery. John Wiley & Sons. p. 201. ISBN 9780471780090.
  22. ^ . Mosby's Drug Consult. Archived from the original on 8 February 2009.
  23. ^ "Prevacid Drug Profile". Drugpatentwatch.com. Retrieved 30 April 2020.
  24. ^ Witkowski W (7 November 2008). "Teva to release Prevacid version when patent expires". Market Watch. Dow Jones.
  25. ^ "International availability of lansoprazole". Drugs.com. Retrieved 3 February 2015.
  26. ^ "Generic lansoprazole". Drugs.com. Retrieved 20 November 2023.
  27. ^ "Prevacid 24 HR- lansoprazole capsule, delayed release". DailyMed. U.S. National Library of Medicine. 7 August 2019. Retrieved 31 December 2019.
  28. ^ "Prevacid 24 HR- lansoprazole capsule, delayed release". DailyMed. U.S. National Library of Medicine. 11 December 2019. Retrieved 31 December 2019.
  29. ^ "Lansoprazole 24 HR- lansoprazole capsule, delayed release". DailyMed. U.S. National Library of Medicine. 21 December 2017. Retrieved 31 December 2019.
  30. ^ "Zoton FasTabs". NPS MedicineWise. 2 September 2019. Retrieved 24 April 2022.
  31. ^ 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.

April 11, 2024
lansoprazole, sold, under, brand, name, prevacid, among, others, medication, which, reduces, stomach, acid, proton, pump, inhibitor, used, treat, peptic, ulcer, disease, gastroesophageal, reflux, disease, zollinger, ellison, syndrome, effectiveness, similar, t. 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 LansoprazoleClinical dataPronunciation l ae n ˈ s oʊ p r e z oʊ l lan SOH pre zohlTrade namesPrevacid othersOther namesAG 1749AHFS Drugs comMonographMedlinePlusa695020License dataUS DailyMed LansoprazolePregnancycategoryAU B3 1 Routes ofadministrationBy mouth intravenousDrug classProton pump inhibitorATC codeA02BC03 WHO Legal statusLegal statusAU S2 S3 amp S4 UK POM Prescription only US WARNING 2 OTC Rx only 3 Pharmacokinetic dataBioavailability80 or moreProtein binding97 MetabolismLiver CYP3A4 and CYP2C19 mediated Elimination half life1 0 1 5 hoursExcretionKidney and fecalIdentifiersIUPAC name RS 2 3 methyl 4 2 2 2 trifluoroethoxy pyridin 2 yl methylsulfinyl 1H benzo d imidazoleCAS Number103577 45 3 YPubChem CID3883IUPHAR BPS7208DrugBankDB00448 YChemSpider3746 YUNII0K5C5T2QPGKEGGD00355 YChEBICHEBI 6375 YChEMBLChEMBL480 YCompTox Dashboard EPA DTXSID4023200ECHA InfoCard100 173 220Chemical and physical dataFormulaC 16H 14F 3N 3O 2SMolar mass369 36 g mol 13D model JSmol Interactive imageChiralityRacemic mixtureMelting point178 C 352 F decomposes SMILES FC F F COc1ccnc c1C CS O c2 nH c3ccccc3n2InChI InChI 1S C16H14F3N3O2S c1 10 13 20 7 6 14 10 24 9 16 17 18 19 8 25 23 15 21 11 4 2 3 5 12 11 22 15 h2 7H 8 9H2 1H3 H 21 22 YKey MJIHNNLFOKEZEW UHFFFAOYSA N Y verify 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 Contents 1 Medical uses 2 Side effects 3 Interactions 4 Chemistry 5 History 6 Society and culture 6 1 Patents 6 2 Availability 7 Research 8 ReferencesMedical uses editLansoprazole 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 editSide 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 editLansoprazole 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 astemizoleChemistry editIt 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 editMain article Discovery and development of proton pump inhibitors 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 nbsp Prevacid 30 mgPatents 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 editIn 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 amp 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 amp 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 amp 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 amp Sons p 102 ISBN 9783527607495 Chorghade MS 2006 Drug Discovery and Development Volume 1 Drug Discovery John Wiley amp 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 Portal nbsp Medicine Retrieved from https en wikipedia org w index php title Lansoprazole amp oldid 1212582961, wikipedia, wiki, book, books, library,

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