Lansoprazole

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Lansoprazole
Lansoprazole.svg
Lansoprazole 3D.png
Clinical data
Pronunciation/lænˈsprəzl/ 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
Pharmacokinetic data
Bioavailability80% or more
Protein binding97%
MetabolismLiver (CYP3A4- and CYP2C19-mediated)
Elimination half-life1–1.5 hours
ExcretionKidney and fecal
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.173.220 Edit this at Wikidata
Chemical and physical data
FormulaC16H14F3N3O2S
Molar mass369.363 g/mol g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  (verify)

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]

Common side effects include constipation, abdominal pain, and nausea.[1] Serious side effects may include osteoporosis, low blood magnesium, Clostridium difficile infection, and pneumonia.[1] Use in pregnancy and breastfeeding is of unclear safety.[4] 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.[5] It is available as a generic medication.[2] A 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 USD.[6] In 2016 it was the 141st most prescribed medication in the United States with more than 4 million prescriptions.[7]

Medical uses[edit]

Lansoprazole is used for treatment of:

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

Side effects[edit]

Side effects of PPIs in general[9] and lansoprazole in particular[10] may include:

PPIs may be associated with a greater risk of hip fractures and Clostridium difficile-associated diarrhea.[8]:22

Interactions[edit]

Lansoprazole interacts with several other drugs, either due to its own nature or as a PPI.[14]

Lansoprazole possibly interacts with, among other drugs:

Chemistry[edit]

It is a racemic 1:1 mixture of the enantiomers dexlansoprazole and levolansoprazole.[16] 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).[17]

History[edit]

Lansoprazole was originally synthesized at Takeda and was given the development name AG 1749.[18] Takeda patented it in 1984 and the drug launched in 1991.[19] In the United States, it was approved for medical use in 1995.[20]

Society and culture[edit]

Prevacid 30 mg

Patents[edit]

The lansoprazole molecule is off-patent and so generic drugs are available under many brand names in many countries;[21] there are patents covering some formulations in effect as of 2015.[22] Patent protection expired on November 10, 2009.[23][24]

Availability[edit]

Since 2009, lansoprazole has been available over the counter (OTC) in the U.S. in a marketed by Novartis as Prevacid 24HR.[8] In Australia, it is marketed by Pfizer as Zoton.

Research[edit]

In vitro experiments have shown that lansoprazole binds to the pathogenic form of tau protein.[25] 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.[25]

References[edit]

  1. ^ a b c d e f "Lansoprazole Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
  2. ^ a b c British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 79–80. ISBN 9780857113382.
  3. ^ a b "[99] Comparative effectiveness of proton pump inhibitors | Therapeutics Initiative". 28 June 2016. Retrieved 14 July 2016.
  4. ^ "Lansoprazole Use During Pregnancy". Drugs.com. Retrieved 3 March 2019.
  5. ^ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 445. ISBN 9783527607495.
  6. ^ "NADAC as of 2019-02-27". Centers for Medicare and Medicaid Services. Retrieved 3 March 2019.
  7. ^ "The Top 300 of 2019". clincalc.com. Retrieved 22 December 2018.
  8. ^ a b c "Prevacid 24HR Label" (PDF). May 2010. Retrieved November 15, 2014.
  9. ^ British National Formulary (Free registration required) 1.3.5 Proton pump inhibitors
  10. ^ British National Formulary (Free registration required) Lansoprazole
  11. ^ "Prevacid (Lansoprazole) Drug Information: Side Effects and Drug Interactions - Prescribing Information at RxList". RxList. Retrieved 2016-02-09.
  12. ^ K C Singhal & S Z Rahman, Lansoprazole Induced Adverse Effects on the Skin, Indian Medical Gazette, July 2001, Vol. CXXXV. N0. 7: 223-225
  13. ^ Sterry W, Assaf C (2007). "Erythroderma". In Bolognia JL (ed.). Dermatology. St. Louis: Mosby. p. 154. ISBN 1-4160-2999-0..
  14. ^ British National Formulary (Free registration required) Lansoprazole interactions
  15. ^ 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.
  16. ^ "Pharmacy Benefit Update". Retrieved 2 July 2014.
  17. ^ "Prevacid Pharmacology, Pharmacokinetics, Studies, Metabolism". RxList.com. 2007. Retrieved April 14, 2007.
  18. ^ Fischer, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 102. ISBN 9783527607495.
  19. ^ Chorghade, Mukund S. (2006). Drug Discovery and Development, Volume 1: Drug Discovery. John Wiley & Sons. p. 201. ISBN 9780471780090.
  20. ^ Mosby's Drug Consult: Lansoprazole
  21. ^ drugs.com International availability of lansoprazole Page accessed February 3, 2015
  22. ^ drugs.com Generic lansoprazole Page accessed February 3, 2015
  23. ^ Prevacid drug patents
  24. ^ Teva to release Prevacid version when patent expires
  25. ^ 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[edit]