Lansoprazole

Lansoprazole
Names
Pronunciation/lænˈsoʊprəzoʊl/ lan-SOH-prə-zohl
Trade namesPrevacid, others
IUPAC name
  • (RS)-2-([3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole
Clinical data
Drug classProton pump inhibitor
Main usesPeptic ulcer disease, gastroesophageal reflux disease, Zollinger–Ellison syndrome[1]
Side effectsConstipation, abdominal pain, nausea[2][3]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • AU: B3
  • US: B (No risk in non-human studies)
    Routes of
    use    		By mouth, IV
    Defined daily dose30 mg[4]
    External links
    AHFS/Drugs.comMonograph
    MedlinePlusa695020
    Legal
    License data
    Legal status
    • UK: POM (Prescription only)
    • US: OTC / Rx-only
    Pharmacokinetics
    Bioavailability80% or more
    Protein binding97%
    MetabolismLiver (CYP3A4- and CYP2C19-mediated)
    Elimination half-life1.0–1.5 hours
    ExcretionKidney and fecal
    Chemical and physical data
    FormulaC16H14F3N3O2S
    Molar mass369.363 g·mol−1
    3D model (JSmol)
    ChiralityRacemic mixture
    SMILES
    • FC(F)(F)COc1ccnc(c1C)CS(=O)c2[nH]c3ccccc3n2
    InChI
    • 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

    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.[1] Effectiveness is similar to other proton pump inhibitors (PPIs).[5] It is taken by mouth.[2] Onset is over a few hours and effects last up to a couple of days.[2]

    Common side effects include constipation, abdominal pain, and nausea.[2][3] Serious side effects may include osteoporosis, low blood magnesium, Clostridium difficile infection, and pneumonia.[2][3] Use in pregnancy and breastfeeding is of unclear safety.[6] 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.[7] It is available as a generic medication.[1] A one-month supply, in the United Kingdom, costs the NHS less than £5, as of 2019.[1] In the United States, the wholesale cost of this amount is about $5.40, as of 2019.[8] In 2017, it was the 188th most commonly prescribed medication in the United States, with more than three million prescriptions.[9][10]

    Medical uses

    Healing of an ulcer with lansoprazole, with the second image on day 8 and the third on day 28

    Lansoprazole is used for treatment of:[3]

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

    Dosage

    The defined daily dose is 30 mg by mouth.[4]

    Side effects

    Side effects of PPIs in general[12] and lansoprazole in particular[13] may include:[3]

    PPIs may be associated with a greater risk of hip fractures and Clostridium difficile-associated diarrhea.[3]: 22 

    Interactions

    Lansoprazole interacts with several other drugs, either due to its own nature or as a PPI.[17]

    Lansoprazole possibly interacts with, among other drugs:

    Chemistry

    It is a racemic 1:1 mixture of the enantiomers dexlansoprazole and levolansoprazole.[19] 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).[20]

    History

    Main article: Discovery and development of proton pump inhibitors

    Lansoprazole was originally synthesized at Takeda and was given the development name AG 1749.[21] Takeda patented it in 1984 and the drug launched in 1991.[22] In the United States, it was approved for medical use in 1995.[23]

    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;[24] there are patents covering some formulations in effect as of 2015.[25] Patent protection expired on 10 November 2009.[26][27]

    Availability

    Since 2009, lansoprazole has been available over the counter (OTC) in the U.S. as Prevacid 24HR[28][29] and as Lansoprazole 24HR.[30] In Australia, it is marketed by Pfizer as Zoton.

    Cost

    A one-month supply, in the United Kingdom, costs the NHS less than £5, as of 2019.[1] In the United States, the wholesale cost of this amount is about $5.40, as of 2019.[8] In 2017, it was the 188th most commonly prescribed medication in the United States, with more than three million prescriptions.[9][10]

    • Lansoprazole costs (US)
      Lansoprazole costs (US)
    • Lansoprazole prescriptions (US)
      Lansoprazole prescriptions (US)

    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. 1 2 3 4 5 British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 79–80. ISBN 9780857113382.
    2. 1 2 3 4 5 6 7 "Lansoprazole Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 27 March 2019. Retrieved 3 March 2019.
    3. 1 2 3 4 5 6 "Lansoprazole capsule, delayed release pellets". DailyMed. 11 October 2016. Archived from the original on 24 July 2021. Retrieved 31 December 2019.
    4. 1 2 "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 26 September 2020. Retrieved 7 September 2020.
    5. 1 2 "[99] Comparative effectiveness of proton pump inhibitors | Therapeutics Initiative". 28 June 2016. Archived from the original on 30 October 2020. Retrieved 14 July 2016.
    6. ↑ "Lansoprazole Use During Pregnancy". Drugs.com. Archived from the original on 20 June 2020. Retrieved 3 March 2019.
    7. ↑ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 445. ISBN 9783527607495. Archived from the original on 28 February 2019. Retrieved 28 February 2019.
    8. 1 2 "NADAC as of 2019-02-27". Centers for Medicare and Medicaid Services. Archived from the original on 6 March 2019. Retrieved 3 March 2019.
    9. 1 2 "The Top 300 of 2020". ClinCalc. Archived from the original on 12 February 2021. Retrieved 11 April 2020.
    10. 1 2 "Lansoprazole - Drug Usage Statistics". ClinCalc. Archived from the original on 28 August 2021. Retrieved 11 April 2020.
    11. ↑ 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.
    12. ↑ British National Formulary Archived 21 February 2020 at the Wayback Machine (Free registration required) 1.3.5 Proton pump inhibitors
    13. ↑ British National Formulary Archived 21 February 2020 at the Wayback Machine (Free registration required) Lansoprazole
    14. ↑ "Prevacid (Lansoprazole) Drug Information: Side Effects and Drug Interactions - Prescribing Information at RxList". RxList. Archived from the original on 15 February 2016. Retrieved 9 February 2016.
    15. ↑ K C Singhal & S Z Rahman, Lansoprazole Induced Adverse Effects on the Skin, Indian Medical Gazette, July 2001, Vol. CXXXV. N0. 7: 223-225
    16. ↑ Sterry W, Assaf C (2007). "Erythroderma". In Bolognia JL (ed.). Dermatology. St. Louis: Mosby. p. 154. ISBN 978-1-4160-2999-1..
    17. ↑ British National Formulary Archived 28 August 2021 at the Wayback Machine (Free registration required) Lansoprazole interactions
    18. ↑ 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.
    19. ↑ "Pharmacy Benefit Update". Archived from the original on 14 July 2014. Retrieved 2 July 2014.
    20. ↑ "Prevacid Pharmacology, Pharmacokinetics, Studies, Metabolism". RxList.com. 2007. Archived from the original on 16 August 2000. Retrieved 14 April 2007.
    21. ↑ Fischer, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 102. ISBN 9783527607495.
    22. ↑ Chorghade, Mukund S. (2006). Drug Discovery and Development, Volume 1: Drug Discovery. John Wiley & Sons. p. 201. ISBN 9780471780090.
    23. ↑ "Mosby's Drug Consult: Lansoprazole". Archived from the original on 8 February 2009. Retrieved 6 May 2008.
    24. ↑ drugs.com International availability of lansoprazole Archived 29 March 2016 at the Wayback Machine Page accessed 3 February 2015
    25. ↑ drugs.com Generic lansoprazole Archived 17 March 2017 at the Wayback Machine Page accessed 3 February 2015
    26. ↑ "Prevacid Drug Profile". Drugpatentwatch.com. Archived from the original on 1 March 2012. Retrieved 30 April 2020.
    27. ↑ "Teva to release Prevacid version when patent expires". Archived from the original on 6 February 2016. Retrieved 3 November 2009.
    28. ↑ "Prevacid 24 HR- lansoprazole capsule, delayed release". DailyMed. 7 August 2019. Archived from the original on 24 July 2021. Retrieved 31 December 2019.
    29. ↑ "Prevacid 24 HR- lansoprazole capsule, delayed release". DailyMed. 11 December 2019. Archived from the original on 24 July 2021. Retrieved 31 December 2019.
    30. ↑ "Lansoprazole 24 HR- lansoprazole capsule, delayed release". DailyMed. 21 December 2017. Archived from the original on 10 August 2020. Retrieved 31 December 2019.
    31. 1 2 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.
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