Lansoprazole

Lansoprazole
Systematic (IUPAC) name
(RS)-2-([3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole
Clinical data
Trade names Prevacid
AHFS/Drugs.com monograph
MedlinePlus a695020
License data
Pregnancy
category
  • AU: B3
  • US: B (No risk in non-human studies)
Routes of
administration		 Oral, IV
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 103577-45-3 YesY
ATC code A02BC03 (WHO)
PubChem CID 3883
IUPHAR/BPS 7208
DrugBank DB00448 YesY
ChemSpider 3746 YesY
UNII 0K5C5T2QPG YesY
KEGG D00355 YesY
ChEBI CHEBI:6375 YesY
ChEMBL CHEMBL480 YesY
Chemical data
Formula C16H14F3N3O2S
Molar mass 369.363 g/mol
Chirality Racemic mixture
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Lansoprazole (/lænˈsoʊprəzoʊl/ lan-SOH-prə-zohl; INN) is a proton-pump inhibitor (PPI) which inhibits the stomach's production of gastric acids. 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.[1] Prevacid patent protection expired on November 10, 2009.[2][3] Since 2009, lansoprazole has been available over the counter (OTC) in the U.S. in a 15-mg dose marketed by Novartis as Prevacid 24HR.[4][5][6] In Australia, it is marketed by Pfizer as Zoton.

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.[7] It is a racemic 1:1 mixture of the enantiomers dexlansoprazole (Dexilant, formerly named Kapidex) and levolansoprazole.[8] 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).[9] and the effects of the drug last for over 24 hours after it has been used for a day or more.[5] Lansoprazole, 30-mg administered nasogastrically, effectively controls intragastric pH and is an alternative to intravenous pantoprazole in patients who are unable to swallow solid-dose formulations.[10]

Indications

Lansoprazole is indicated for treatment of:

Drug interactions

Lansoprazole interacts with several other drugs, either due to its own nature or as a PPI.[11]

Lansoprazole possibly interacts with, amongst other drugs:

Side effects

Side effects of PPIs in general[13] and lansoprazole in particular[14] may include:

PPIs may be associated with a greater risk of hip fractures and Clostridium difficile-associated diarrhea.[5]:22

Availability

Prevacid 30 mg

The lansoprazole molecule is off-patent and so generic drugs are available under many brand names in many countries;[18] there are patents covering some formulations in effect as of 2015.[19]

Research

In vitro experiments have shown that lansoprazole binds to the pathogenic form of tau protein.[20] 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.[20] Lansoprazole is also a prodrug that targets the cytochrome bc1 complex of Mycobacterium tuberculosis once converted to lansoprazole sulfide in mycobacterial host cells.[21]

References

  1. ↑ Mosby's Drug Consult: Lansoprazole
  2. ↑ Prevacid drug patents
  3. ↑ Teva to release Prevacid version when patent expires
  4. ↑ "Novartis launches Prevacid 24HR over-the-counter for full 24-hour frequent heartburn treatment" (PDF) (Press release). November 12, 2009. Retrieved November 13, 2009.
  5. 1 2 3 4 "Prevacid 24HR Label" (PDF). May 2010. Retrieved November 15, 2014.
  6. ↑ "Novartis launches Prevacid 24HR over-the-counter for full 24-hour frequent heartburn treatment" (Press release). November 12, 2009. Retrieved November 13, 2009.
  7. ↑ http://www.patient.co.uk/showdoc/30002943/
  8. ↑ "Pharmacy Benefit Update". Retrieved 2 July 2014.
  9. ↑ "Prevacid Pharmacology, Pharmacokinetics, Studies, Metabolism". RxList.com. 2007. Retrieved April 14, 2007.
  10. ↑ 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. doi:10.1111/j.1572-0241.2001.03939.x. ISSN 0002-9270. PMID 11467632.
  11. ↑ British National Formulary (Free registration required) Lansoprazole interactions
  12. ↑ Antimicrob Agents Chemother. 1991 September; 35(9): 1765–1771. Effects of ranitidine and sucralfate on ketoconazole bioavailability. S C Piscitelli, T F Goss, J H Wilton, D T D'Andrea, H Goldstein, and J J Schentag
  13. ↑ British National Formulary (Free registration required) 1.3.5 Proton pump inhibitors
  14. ↑ British National Formulary (Free registration required) Lansoprazole
  15. ↑ "Prevacid (Lansoprazole) Drug Information: Side Effects and Drug Interactions - Prescribing Information at RxList". RxList. Retrieved 2016-02-09.
  16. ↑ K C Singhal & S Z Rahman, Lansoprazole Induced Adverse Effects on the Skin, Indian Medical Gazette, July 2001, Vol. CXXXV. N0. 7: 223-225
  17. ↑ Sterry W, Assaf C (2007). "Erythroderma". In Bolognia JL. Dermatology. St. Louis: Mosby. p. 154. ISBN 1-4160-2999-0..
  18. ↑ drugs.com International availability of lansoprazole Page accessed February 3, 2015
  19. ↑ drugs.com Generic lansoprazole Page accessed February 3, 2015
  20. 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.
  21. ↑ Rybniker, Jan; et al. (July 2015). "Lansoprazole is an antituberculous prodrug targeting cytochrome bc1". Nature Communications 6: 7659. doi:10.1038/ncomms8659.

External links

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