Lansoprazole

Lansoprazole, sold under the brand name Prevacid among others, is a medication which reduces stomach acid.[2] It is used to treat peptic ulcer disease, gastroesophageal reflux disease, and Zollinger–Ellison syndrome.[3] Effectiveness is similar to other proton pump inhibitors (PPIs).[4] It is taken by mouth.[2] Onset is over a few hours and effects last up to a couple of days.[2]

Selanz SR
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 (IV)
Drug classProton pump inhibitor
ATC code
Legal status
Legal status
  • AU: S2, S3, & S4
  • UK: POM (Prescription only)
  • US: OTC / Rx-only
Pharmacokinetic data
Bioavailability80% or more
Protein binding97%
MetabolismLiver (CYP3A4- and CYP2C19-mediated)
Elimination half-life1.0–1.5 hours
ExcretionKidney and fecal
Identifiers
IUPAC name
  • (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) Y
  • Key:MJIHNNLFOKEZEW-UHFFFAOYSA-N Y
  (verify)

Common side effects include constipation, abdominal pain, and nausea.[2][5] Serious side effects may include osteoporosis, low blood magnesium, Clostridium difficile infection, and pneumonia.[2][5] Use in pregnancy and breastfeeding is of unclear safety.[1] It works by blocking H+/K+-ATPase in the parietal cells of the stomach.[2]

Lansoprazole was patented in 1984 and came into medical use in 1992.[6] It is available as a generic medication.[3] In 2017, it was the 188th most commonly prescribed medication in the United States, with more than three million prescriptions.[7][8]

Medical uses

Lansoprazole is used for treatment of:[5]

There is no good evidence that it works better than other PPIs.[4]

Side effects

Side effects of PPIs in general[10] and lansoprazole in particular[11] may include:[5]

PPIs may be associated with a greater risk of hip fractures and Clostridium difficile-associated diarrhea.[5]: 22 

Interactions

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

  • PPIs reduce absorption of antifungals (itraconazole and ketoconazole) [16] and possibly increase digoxin in plasma
  • Increases plasma concentrations of cilostazol (risk of toxicity)

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

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 Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
  3. British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 79–80. ISBN 9780857113382.
  4. "[99] Comparative effectiveness of proton pump inhibitors | Therapeutics Initiative". 28 June 2016. Retrieved 14 July 2016.
  5. "Lansoprazole capsule, delayed release pellets". DailyMed. 11 October 2016. Retrieved 31 December 2019.
  6. Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 445. ISBN 9783527607495.
  7. "The Top 300 of 2020". ClinCalc. Retrieved 11 April 2020.
  8. "Lansoprazole - Drug Usage Statistics". ClinCalc. Retrieved 11 April 2020.
  9. Hirschowitz BI, Mohnen J, Shaw S (August 1996). "Long-term treatment with lansoprazole for patients with Zollinger-Ellison syndrome". Aliment. Pharmacol. Ther. 10 (4): 507–22. doi:10.1046/j.1365-2036.1996.10152000.x. PMID 8853754. S2CID 10668517.
  10. British National Formulary (Free registration required) 1.3.5 Proton pump inhibitors
  11. British National Formulary (Free registration required) Lansoprazole
  12. "Prevacid (Lansoprazole) Drug Information: Side Effects and Drug Interactions - Prescribing Information at RxList". 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. British National Formulary (Free registration required) Lansoprazole interactions
  16. Piscitelli, S. C.; Goss, T. F.; Wilton, J. H.; d'Andrea, D. T.; Goldstein, H; Schentag, J. J. (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, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 102. ISBN 9783527607495.
  20. Chorghade, Mukund S. (2006). Drug Discovery and Development, Volume 1: Drug Discovery. John Wiley & Sons. p. 201. ISBN 9780471780090.
  21. Mosby's Drug Consult: Lansoprazole
  22. drugs.com International availability of lansoprazole Page accessed 3 February 2015
  23. drugs.com Generic lansoprazole Page accessed 3 February 2015
  24. "Prevacid Drug Profile". Drugpatentwatch.com. Retrieved 30 April 2020.
  25. Teva to release Prevacid version when patent expires
  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. 11 December 2019. Retrieved 31 December 2019.
  28. "Lansoprazole 24 HR- lansoprazole capsule, delayed release". DailyMed. 21 December 2017. Retrieved 31 December 2019.
  29. "Zoton FasTabs". NPS MedicineWise. 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): 114–24. 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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