Lansoprazole

Lansoprazole, sold under the brand name Prevacid among others, is a medication which reduces stomach acid.[1] It is used to treat peptic ulcer disease, gastroesophageal reflux disease, and Zollinger–Ellison syndrome.[2] Effectiveness is similar to other proton pump inhibitors (PPIs).[3] It is taken by mouth.[1] Onset is over a few hours and effects last up to a couple of days.[1]

Lansoprazole
Clinical data
Pronunciation/lænˈsoʊprəzoʊl/ lan-SOH-prə-zohl
Trade namesPrevacid, others
AHFS/Drugs.comMonograph
MedlinePlusa695020
License data
Pregnancy
category
  • AU: B3
  • US: B (No risk in non-human studies)
    Routes of
    administration    		By mouth, IV
    Drug classProton pump inhibitor
    ATC code
    Legal status
    Legal status
    • 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
    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 mass369.363 g·mol−1
    3D model (JSmol)
    ChiralityRacemic mixture
      (verify)

    Common side effects include constipation, abdominal pain, and nausea.[1][4] Serious side effects may include osteoporosis, low blood magnesium, Clostridium difficile infection, and pneumonia.[1][4] Use in pregnancy and breastfeeding is of unclear safety.[5] It works by blocking H+/K+-ATPase in the parietal cells of the stomach.[1]

    Lansoprazole was patented in 1984 and came into medical use in 1992.[6] It is available as a generic medication.[2] A one month supply, in the United Kingdom, costs the NHS less than £5, as of 2019.[2] In the United States, the wholesale cost of this amount is about $5.40, as of 2019.[7] In 2017, it was the 188th most commonly prescribed medication in the United States, with more than three million prescriptions.[8][9]

    Medical uses

    Lansoprazole is used for treatment of:[4]

    There is no good evidence that it works better than other PPIs.[3]

    Side effects

    Side effects of PPIs in general[11] and lansoprazole in particular[12] may include:[4]

    PPIs may be associated with a greater risk of hip fractures and Clostridium difficile-associated diarrhea.[4]:22

    Interactions

    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

    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

    The lansoprazole molecule is off-patent and so generic drugs are available under many brand names in many countries;[23] there are patents covering some formulations in effect as of 2015.[24] Patent protection expired on 10 November 2009.[25][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.

    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 Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
    2. British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 79–80. ISBN 9780857113382.
    3. "[99] Comparative effectiveness of proton pump inhibitors | Therapeutics Initiative". 28 June 2016. Retrieved 14 July 2016.
    4. "Lansoprazole capsule, delayed release pellets". DailyMed. 11 October 2016. Retrieved 31 December 2019.
    5. "Lansoprazole Use During Pregnancy". Drugs.com. Retrieved 3 March 2019.
    6. Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 445. ISBN 9783527607495.
    7. "NADAC as of 2019-02-27". Centers for Medicare and Medicaid Services. Retrieved 3 March 2019.
    8. "The Top 300 of 2020". ClinCalc. Retrieved 11 April 2020.
    9. "Lansoprazole - Drug Usage Statistics". ClinCalc. Retrieved 11 April 2020.
    10. 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.
    11. British National Formulary (Free registration required) 1.3.5 Proton pump inhibitors
    12. British National Formulary (Free registration required) Lansoprazole
    13. "Prevacid (Lansoprazole) Drug Information: Side Effects and Drug Interactions - Prescribing Information at RxList". RxList. Retrieved 9 February 2016.
    14. K C Singhal & S Z Rahman, Lansoprazole Induced Adverse Effects on the Skin, Indian Medical Gazette, July 2001, Vol. CXXXV. N0. 7: 223-225
    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 (Free registration required) Lansoprazole interactions
    17. 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.
    18. "Pharmacy Benefit Update". 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, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 102. ISBN 9783527607495.
    21. Chorghade, Mukund S. (2006). Drug Discovery and Development, Volume 1: Drug Discovery. John Wiley & Sons. p. 201. ISBN 9780471780090.
    22. Mosby's Drug Consult: Lansoprazole
    23. drugs.com International availability of lansoprazole Page accessed 3 February 2015
    24. drugs.com Generic lansoprazole Page accessed 3 February 2015
    25. "Prevacid Drug Profile". Drugpatentwatch.com. Retrieved 30 April 2020.
    26. Teva to release Prevacid version when patent expires
    27. "Prevacid 24 HR- lansoprazole capsule, delayed release". DailyMed. 7 August 2019. Retrieved 31 December 2019.
    28. "Prevacid 24 HR- lansoprazole capsule, delayed release". DailyMed. 11 December 2019. Retrieved 31 December 2019.
    29. "Lansoprazole 24 HR- lansoprazole capsule, delayed release". DailyMed. 21 December 2017. Retrieved 31 December 2019.
    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.
    • "Lansoprazole". Drug Information Portal. U.S. National Library of Medicine.
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