Lansoprazole

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Lansoprazole
Clinical data
Pronunciation/lænˈsoʊprəzoʊl/ lan-SOH-prə-zohl
Trade namesPrevacid, others
AHFS/Drugs.comMonograph
MedlinePlusa695020
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth, IV
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
  • (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 Edit this at Wikidata
Chemical and physical data
FormulaC16H14F3N3O2S
Molar mass369.363 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • 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.[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]

Common side effects include constipation, abdominal pain, and nausea.[2] Serious side effects may include osteoporosis, low blood magnesium, Clostridium difficile infection, and pneumonia.[2] Use in pregnancy and breastfeeding is of unclear safety.[5] 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] A one month supply, in the United Kingdom, costs the NHS less than £5, as of 2019.[3] In the United States, the wholesale cost of this amount is about $5.40, as of 2019.[7] In 2016, it was the 141st most prescribed medication in the United States, with more than 4 million prescriptions.[8]

Medical uses

Lansoprazole is used for treatment of:

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:

PPIs may be associated with a greater risk of hip fractures and Clostridium difficile-associated diarrhea.[9]: 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 November 10, 2009.[24][25]

Availability

Since 2009, lansoprazole has been available over the counter (OTC) in the U.S. in a marketed by Novartis as Prevacid 24HR.[9] 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.[26] 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.[26]

References

  1. ^ "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 Oct 2023.
  2. ^ a b c d e f "Lansoprazole Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
  3. ^ a b c British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 79–80. ISBN 9780857113382.
  4. ^ a b "[99] Comparative effectiveness of proton pump inhibitors | Therapeutics Initiative". 28 June 2016. Retrieved 14 July 2016.
  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 2019". clincalc.com. Retrieved 22 December 2018.
  9. ^ a b c "Prevacid 24HR Label" (PDF). May 2010. Retrieved November 15, 2014.
  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 2016-02-09.
  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. Retrieved April 14, 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 February 3, 2015
  23. ^ drugs.com Generic lansoprazole Page accessed February 3, 2015
  24. ^ Prevacid drug patents
  25. ^ Teva to release Prevacid version when patent expires
  26. ^ 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): 114–24. doi:10.1016/s1474-4422(14)70252-2. PMID 25496902.

External links

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