Lansoprazole

Lansoprazole
Clinical data
Pronunciation /lænˈsoʊprəzoʊl/ lan-SOH-prə-zohl
Trade names Prevacid, others
AHFS/Drugs.com Monograph
MedlinePlus a695020
License data
Pregnancy
category
  • AU: B3
  • US: B (No risk in non-human studies)
Routes of
administration		 by mouth, IV
Drug class proton pump inhibitor
ATC code
Legal status
Legal status
  • UK: POM (Prescription only)
  • US: OTC
Pharmacokinetic data
Bioavailability 80% or more
Protein binding 97%
Metabolism Hepatic (CYP3A4- and CYP2C19-mediated)
Biological half-life 1–1.5 hours
Excretion Renal and fecal
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.173.220
Chemical and physical data
Formula C16H14F3N3O2S
Molar mass 369.363 g/mol
3D model (JSmol)
Chirality Racemic mixture
  (verify)

Lansoprazole, sold under the brand name Prevacid among others, is a medication which inhibits the stomach's production of acid. There is no evidence that its effectiveness is different from that of other PPIs.[1] Lansoprazole, given through a nasogatric tube, effectively controls pH inside the stomach and is an alternative to intravenous pantoprazole in people who are unable to swallow solid-dose formulations.[2]

Lansoprazole is a proton-pump inhibitor (PPI) in the same pharmacologic class as omeprazole. Lansoprazole has been marketed for many years and is one of several PPIs available.[3] It is a racemic 1:1 mixture of the enantiomers dexlansoprazole (Dexilant, formerly named Kapidex) and levolansoprazole.[4] 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).[5] The effects of the medication last for over 24 hours after it has been used for a day or more.[6]

It is manufactured by a number of companies worldwide under several brand names. In the United States, it was first approved by the Food and Drug Administration (FDA) in 1995.[7] Prevacid patent protection expired on November 10, 2009.[8][9]

Medical uses

Lansoprazole is used for treatment of:

There is no good evidence that it works better than other PPIs.[1]

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.[6]: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:

History

Lansoprazole was originally synthesized at Takeda and was given the development name AG 1749.[17] Takeda patented it in 1984 and the drug launched in 1991.[18]

Society and culture

Prevacid 30 mg

The lansoprazole molecule is off-patent and so generic drugs are available under many brand names in many countries;[19] there are patents covering some formulations in effect as of 2015.[20]

Since 2009, lansoprazole has been available over the counter (OTC) in the U.S. in a marketed by Novartis as Prevacid 24HR.[21][6][22] 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.[23] 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.[23] Lansoprazole is also a prodrug that targets the cytochrome bc1 complex of Mycobacterium tuberculosis once converted to lansoprazole sulfide in mycobacterial host cells.[24]

References

  1. 1 2 "[99] Comparative effectiveness of proton pump inhibitors | Therapeutics Initiative". 28 June 2016. Retrieved 14 July 2016.
  2. ↑ Freston, James; Chiu, Yi-Lin; Pan, Wei-Jian; Lukasik, Nancy; Taubel, Jorg (2001). "Effects on 24-hour intragastric pH: a comparison of lansoprazole administered nasogastrically in apple juice and pantoprazole administered intravenously". The American Journal of Gastroenterology. 96 (7): 2058–2065. ISSN 0002-9270. PMID 11467632. doi:10.1111/j.1572-0241.2001.03939.x.
  3. ↑ http://www.patient.co.uk/showdoc/30002943/
  4. ↑ "Pharmacy Benefit Update". Retrieved 2 July 2014.
  5. ↑ "Prevacid Pharmacology, Pharmacokinetics, Studies, Metabolism". RxList.com. 2007. Retrieved April 14, 2007.
  6. 1 2 3 4 "Prevacid 24HR Label" (PDF). May 2010. Retrieved November 15, 2014.
  7. ↑ Mosby's Drug Consult: Lansoprazole
  8. ↑ Prevacid drug patents
  9. ↑ Teva to release Prevacid version when patent expires
  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. Dermatology. St. Louis: Mosby. p. 154. ISBN 1-4160-2999-0..
  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. PMC 245265 Freely accessible. PMID 1952845. doi:10.1128/aac.35.9.1765.
  17. ↑ Fischer, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 102. ISBN 9783527607495.
  18. ↑ Chorghade, Mukund S. (2006). Drug Discovery and Development, Volume 1: Drug Discovery. John Wiley & Sons. p. 201. ISBN 9780471780090.
  19. ↑ drugs.com International availability of lansoprazole Page accessed February 3, 2015
  20. ↑ drugs.com Generic lansoprazole Page accessed February 3, 2015
  21. ↑ "Novartis launches Prevacid 24HR over-the-counter for full 24-hour frequent heartburn treatment" (PDF) (Press release). November 12, 2009. Retrieved November 13, 2009.
  22. ↑ "Novartis launches Prevacid 24HR over-the-counter for full 24-hour frequent heartburn treatment" (Press release). November 12, 2009. Retrieved November 13, 2009.
  23. 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. PMID 25496902. doi:10.1016/s1474-4422(14)70252-2.
  24. ↑ Rybniker, Jan; et al. (July 2015). "Lansoprazole is an antituberculous prodrug targeting cytochrome bc1". Nature Communications. 6: 7659. PMC 4510652 Freely accessible. PMID 26158909. doi:10.1038/ncomms8659.
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