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Lansoprazole

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
  • 2-{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methanesulfinyl}-1H-benzimidazole
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.173.220 Edit this at Wikidata
Chemical and physical data
FormulaC16H14F3N3O2S
Molar mass369.36 g·mol−1
3D model (JSmol)
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) checkY
  • Key:MJIHNNLFOKEZEW-UHFFFAOYSA-N checkY
  (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, Clostridioides 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

Lansoprazole is used for treatment of:[3]

There is no good evidence that it works better than other PPIs.[6]

Side effects

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 Clostridioides difficile-associated diarrhea.[3]: 22 

Interactions

Lansoprazole interacts with several other drugs, either due to its nature or as a PPI.[16]

Lansoprazole possibly interacts with, among other drugs:

Chemistry

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

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

Prevacid 30 mg

Patents

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

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

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

  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. Archived 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. ^ "1.3.5 Proton pump inhibitors". British National Formulary. Archived from the original on 21 February 2020. Retrieved 1 February 2012.
  12. ^ "Lansoprazole". 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. ^ "Lansoprazole interactions". 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. ^ "Pharmacy Benefit Update". Archived from the original on 14 July 2014. Retrieved 2 July 2014.
  19. ^ "Prevacid Pharmacology, Pharmacokinetics, Studies, Metabolism". 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. ^ "Lansoprazole". 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.
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