Lansoprazole Explained

Watchedfields:changed
Verifiedrevid:458267412
Width:245
Chirality:Racemic mixture
Tradename:Prevacid, others
Dailymedid:Lansoprazole
Pregnancy Au:B3
Routes Of Administration:By mouth, intravenous
Class:Proton pump inhibitor
Atc Prefix:A02
Atc Suffix:BC03
Legal Au:S2, S3, & S4
Legal Uk:POM
Legal Us:OTC
Legal Us Comment:/Rx-only
Bioavailability:80% or more
Protein Bound:97%
Metabolism:Liver (CYP3A4- and CYP2C19-mediated)
Elimination Half-Life:1.0–1.5 hours
Excretion:Kidney and fecal
Cas Number:103577-45-3
Pubchem:3883
Iuphar Ligand:7208
Drugbank:DB00448
Chemspiderid:3746
Unii:0K5C5T2QPG
Kegg:D00355
Chebi:6375
Chembl:480
Synonyms:AG 1749
Iupac Name:(RS)-2-([3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole
C:16
H:14
F:3
N:3
O:2
S:1
Smiles:FC(F)(F)COc1ccnc(c1C)CS(=O)c2[nH]c3ccccc3n2
Stdinchi: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)
Stdinchikey:MJIHNNLFOKEZEW-UHFFFAOYSA-N
Melting Point:178
Melting Notes:(decomposes)

Lansoprazole, sold under the brand name Prevacid among others, is a medication which reduces stomach acid. It is a proton pump inhibitor (PPI), used to treat peptic ulcer disease, gastroesophageal reflux disease, and Zollinger–Ellison syndrome. Its effectiveness is similar to that of other PPIs.[1] It is taken by mouth. Onset is over a few hours and effects last up to a couple of days.

Common side effects include constipation, abdominal pain, and nausea. Serious side effects may include osteoporosis, low blood magnesium, Clostridium difficile infection, and pneumonia. Use in pregnancy and breastfeeding is of unclear safety.[2] It works by blocking H+/K+-ATPase in the parietal cells of the stomach.[3]

Lansoprazole was patented in 1984 and came into medical use in 1992.[4] 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 1million prescriptions.[6] [7]

Medical uses

Lansoprazole is used for treatment of:[8]

There is no good evidence that it works better than other PPIs.[1]

Side effects

Side effects of PPIs in general[10] and lansoprazole in particular[11] may include:

PPIs may be associated with a greater risk of hip fractures and Clostridium difficile-associated diarrhea.

Interactions

Lansoprazole interacts with several other drugs, either due to its own nature or as a PPI.[15]

Lansoprazole possibly interacts with, among other drugs:

Chemistry

It is a racemic 1:1 mixture of the enantiomers dexlansoprazole and levolansoprazole.[17] 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).[18]

History

See main article: Discovery and development of proton pump inhibitors. Lansoprazole was originally synthesized at Takeda and was given the development name AG 1749.[19] Takeda patented it in 1984 and the drug launched in 1991.[20] In the United States, it was approved for medical use in 1995.[21]

Society and culture

Patents

Patent protection of the lansoprazole molecule expired on 10 November 2009,[22] [23] and generic formulations became available under many brand names in many countries.[24] Some formulations may not be available in generic form.[25]

Availability

Since 2009, lansoprazole has been available over the counter (OTC) in the U.S. as Prevacid 24HR[26] [27] and as Lansoprazole 24HR.[28] In Australia, it is marketed by Pfizer as Zoton.[29]

Research

In vitro experiments have shown that lansoprazole binds to the pathogenic form of tau protein. laboratory studies were underway on analogs of lansoprazole to explore their use as potential PET imaging agents for diagnosing tauopathies including Alzheimer's disease.[30]

Notes and References

  1. Web site: Comparative effectiveness of proton pump inhibitors . Therapeutics Initiative . Dept of Anesthesiology, Pharmacology & Therapeutics, Faculty of Medicine, University of British Columbia . 14 July 2016. 28 June 2016.
  2. Web site: Lansoprazole Use During Pregnancy. Drugs.com . 3 March 2019 .
  3. Web site: Lansoprazole Monograph for Professionals . Drugs.com . American Society of Health-System Pharmacists . 3 March 2019 .
  4. Book: Fischer J, Ganellin CR . Analogue-based Drug Discovery . 2006 . John Wiley & Sons . 9783527607495 . 445 .
  5. Book: British national formulary : BNF 76. 2018. Pharmaceutical Press. 9780857113382. 79–80. 76.
  6. Web site: The Top 300 of 2021 . ClinCalc . 14 January 2024 . 15 January 2024 . https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx . live .
  7. Web site: Lansoprazole - Drug Usage Statistics . ClinCalc . 14 January 2024.
  8. Web site: Lansoprazole capsule, delayed release pellets . DailyMed . U.S. National Library of Medicine . 11 October 2016 . 31 December 2019.
  9. Hirschowitz BI, Mohnen J, Shaw S . Long-term treatment with lansoprazole for patients with Zollinger-Ellison syndrome . Alimentary Pharmacology & Therapeutics . 10 . 4 . 507–522 . August 1996 . 8853754 . 10.1046/j.1365-2036.1996.10152000.x . 10668517 .
  10. Web site: 1.3.5 Proton pump inhibitors . British National Formulary . registration . 1 February 2012 . 21 February 2020 . https://web.archive.org/web/20200221070446/https://about.medicinescomplete.com/#_200909 . dead .
  11. Web site: Lansoprazole . British National Formulary . registration . 1 February 2012 . 21 February 2020 . https://web.archive.org/web/20200221070438/https://about.medicinescomplete.com/#_129429 . dead .
  12. Web site: Prevacid (Lansoprazole) Drug Information: Side Effects and Drug Interactions - Prescribing Information . RxList. 9 February 2016.
  13. Salloum A, Nasr D, Maalouf D . Dermatologic adverse reactions to proton-pump inhibitors: A synthetized review . Journal of Cosmetic Dermatology . 20 . 4 . 1073–1079 . April 2021 . 33031621 . 10.1111/jocd.13763 . 222236157 .
  14. Book: Sterry W, Assaf C . Erythroderma . Bolognia JL . Dermatology . Mosby . St. Louis . 2007 . 154 . 978-1-4160-2999-1. .
  15. Web site: Lansoprazole interactions . British National Formulary . registration . 1 February 2012 . 28 August 2021 . https://web.archive.org/web/20210828140753/https://about.medicinescomplete.com/wp-content/themes/mc-marketing/assets/images/favicons-tiles/favicon.ico . dead .
  16. Piscitelli SC, Goss TF, Wilton JH, D'Andrea DT, Goldstein H, Schentag JJ . Effects of ranitidine and sucralfate on ketoconazole bioavailability . Antimicrobial Agents and Chemotherapy . 35 . 9 . 1765–1771 . September 1991 . 1952845 . 245265 . 10.1128/aac.35.9.1765 .
  17. Web site: Pharmacy Benefit Update. 2 July 2014. 14 July 2014. https://web.archive.org/web/20140714200303/http://epharmacytechnicanschools.com/pharmacy-benefit-update/. dead.
  18. Web site: Prevacid Pharmacology, Pharmacokinetics, Studies, Metabolism . 2007 . 14 April 2007 . RxList.com . https://web.archive.org/web/20000816224850/http://www.rxlist.com/cgi/generic/lansop_cp.htm . 16 August 2000 . dead .
  19. Book: Fischer J, Ganellin CR . Analogue-based Drug Discovery. 2006. John Wiley & Sons. 9783527607495. 102.
  20. Book: Chorghade MS . Drug Discovery and Development, Volume 1: Drug Discovery. 2006. John Wiley & Sons. 9780471780090. 201.
  21. Web site: Lansoprazole . https://web.archive.org/web/20090208113930/http://www.mosbysdrugconsult.com/DrugConsult/Top_200/Drugs/e3230.html . 8 February 2009 . Mosby's Drug Consult .
  22. Web site: Prevacid Drug Profile . Drugpatentwatch.com . 30 April 2020 .
  23. Web site: Witkowski W . 7 November 2008 . Market Watch . Dow Jones . Teva to release Prevacid version when patent expires .
  24. Web site: International availability of lansoprazole . Drugs.com . 3 February 2015 .
  25. Web site: Generic lansoprazole . Drugs.com . 20 November 2023.
  26. Web site: Prevacid 24 HR- lansoprazole capsule, delayed release . DailyMed . U.S. National Library of Medicine. 7 August 2019 . 31 December 2019.
  27. Web site: Prevacid 24 HR- lansoprazole capsule, delayed release . DailyMed . U.S. National Library of Medicine . 11 December 2019 . 31 December 2019.
  28. Web site: Lansoprazole 24 HR- lansoprazole capsule, delayed release . DailyMed . U.S. National Library of Medicine . 21 December 2017 . 31 December 2019.
  29. Web site: Zoton FasTabs . NPS MedicineWise . 2 September 2019 . 24 April 2022 . en.
  30. Villemagne VL, Fodero-Tavoletti MT, Masters CL, Rowe CC . Tau imaging: early progress and future directions . The Lancet. Neurology . 14 . 1 . 114–124 . January 2015 . 25496902 . 10.1016/s1474-4422(14)70252-2 . 10502833 .

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