Lansoprazole

Lansoprazole, sold under the brand name Prevacid among others, is a medication which reduces stomach acid.[3] It is a proton pump inhibitor (PPI), used to treat peptic ulcer disease, gastroesophageal reflux disease, and Zollinger–Ellison syndrome.[4] Its effectiveness is similar to that of other PPIs.[5] It is taken by mouth.[3] Onset is over a few hours and effects last up to a couple of days.[3]

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
  • AU: S2, S3, & S4
  • UK: POM (Prescription only)
  • US: OTC / Rx-only[2]
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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.173.220
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)

Common side effects include constipation, abdominal pain, and nausea.[3][2] Serious side effects may include osteoporosis, low blood magnesium, Clostridium difficile infection, and pneumonia.[3][2] Use in pregnancy and breastfeeding is of unclear safety.[1] 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.[6] It is available as a generic medication.[4] In 2020, it was the 191st most commonly prescribed medication in the United States, with more than 2 million prescriptions.[7][8]

Medical uses

Lansoprazole is used for treatment of:[2]

There is no good evidence that it works better than other PPIs.[5]

Side effects

Side effects of PPIs in general[10] and lansoprazole in particular[11] may include:[2]

PPIs may be associated with a greater risk of hip fractures and Clostridium difficile-associated diarrhea.[2]: 22 

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
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
Prevacid 30 mg

Patents

The lansoprazole molecule is off-patent and so generic drugs are available under many brand names in many countries;[22] there are patents covering some formulations in effect as of 2015.[23] Patent protection expired on 10 November 2009.[24][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.[30] 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.[30]

References
  1. "Lansoprazole Use During Pregnancy". Drugs.com. Retrieved 3 March 2019.
  2. "Lansoprazole capsule, delayed release pellets". DailyMed. U.S. National Library of Medicine. 11 October 2016. Retrieved 31 December 2019.
  3. "Lansoprazole Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
  4. British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 79–80. ISBN 9780857113382.
  5. "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.
  6. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 445. ISBN 9783527607495.
  7. "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
  8. "Lansoprazole - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.
  9. 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.
  10. "1.3.5 Proton pump inhibitors". British National Formulary.
  11. "Lansoprazole". British National Formulary.
  12. "Prevacid (Lansoprazole) Drug Information: Side Effects and Drug Interactions - Prescribing Information". RxList. Retrieved 9 February 2016.
  13. K C Singhal & S Z Rahman, Lansoprazole Induced Adverse Effects on the Skin, Indian Medical Gazette, July 2001, Vol. CXXXV. N0. 7: 223-225
  14. Sterry W, Assaf C (2007). "Erythroderma". In Bolognia JL (ed.). Dermatology. St. Louis: Mosby. p. 154. ISBN 978-1-4160-2999-1..
  15. "Lansoprazole interactions". British National Formulary.
  16. 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.
  17. "Pharmacy Benefit Update". Retrieved 2 July 2014.
  18. "Prevacid Pharmacology, Pharmacokinetics, Studies, Metabolism". RxList.com. 2007. Archived from the original on 16 August 2000. Retrieved 14 April 2007.
  19. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 102. ISBN 9783527607495.
  20. Chorghade MS (2006). Drug Discovery and Development, Volume 1: Drug Discovery. John Wiley & Sons. p. 201. ISBN 9780471780090.
  21. "Lansoprazole". Mosby's Drug Consult. Archived from the original on 8 February 2009.
  22. "International availability of lansoprazole". Drugs.com. Retrieved 3 February 2015.
  23. "Generic lansoprazole". Retrieved 3 February 2015.
  24. "Prevacid Drug Profile". Drugpatentwatch.com. Retrieved 30 April 2020.
  25. Witkowski W (7 November 2008). "Teva to release Prevacid version when patent expires". Market Watch. Dow Jones.
  26. "Prevacid 24 HR- lansoprazole capsule, delayed release". DailyMed. 7 August 2019. Retrieved 31 December 2019.
  27. "Prevacid 24 HR- lansoprazole capsule, delayed release". DailyMed. U.S. National Library of Medicine. 11 December 2019. Retrieved 31 December 2019.
  28. "Lansoprazole 24 HR- lansoprazole capsule, delayed release". DailyMed. U.S. National Library of Medicine. 21 December 2017. Retrieved 31 December 2019.
  29. "Zoton FasTabs". NPS MedicineWise. 2 September 2019. Retrieved 24 April 2022.
  30. 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.
  • "Lansoprazole". Drug Information Portal. U.S. National Library of Medicine.
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