Lansoprazole

Stomach acid suppressing medication From Wikipedia, the free encyclopedia

Lansoprazole, sold under the brand name Prevacid among others, is a medication which reduces stomach acid.[3] It is a proton pump inhibitor (PPI), used to treat peptic ulcer disease, gastroesophageal reflux disease, and Zollinger–Ellison syndrome.[4] Its effectiveness is similar to that of other PPIs.[5] It is taken by mouth.[3] Onset is over a few hours and effects last up to a couple of days.[3]

Trade namesPrevacid, others
Other namesAG 1749
Quick facts Clinical data, Pronunciation ...
Lansoprazole
Clinical data
Pronunciation/lænˈsprəzl/ lan-SOH-prə-zohl
Trade namesPrevacid, others
Other namesAG 1749
AHFS/Drugs.comMonograph
MedlinePlusa695020
License data
Pregnancy
category
Routes of
administration
By mouth, intravenous
Drug classProton pump inhibitor
ATC code
Legal status
Legal status
  • AU: S2, S3, & S4
  • UK: POM (Prescription only)
  • US: OTC / Rx-only[2]
Pharmacokinetic data
Bioavailability80% or more
Protein binding97%
MetabolismLiver (CYP3A4- and CYP2C19-mediated)
Elimination half-life1.0–1.5 hours
ExcretionKidney and fecal
Identifiers
  • 2-{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methanesulfinyl}-1H-benzimidazole
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 mass369.36 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
Melting point178 °C (352 °F) (decomposes)
  • 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)
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Common side effects include constipation, abdominal pain, and nausea.[3][2] Serious side effects may include osteoporosis, low blood magnesium, Clostridioides difficile infection, and pneumonia.[3][2] Use in pregnancy and breastfeeding is of unclear safety.[1] It works by blocking H+/K+-ATPase in the parietal cells of the stomach.[3]

Lansoprazole was patented in 1984 and came into medical use in 1992.[6] It is available as a generic medication.[4] In 2022, it was the 224th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[7][8]

Medical uses

Lansoprazole is used for treatment of:[2]

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

Side effects

Side effects of PPIs in general[10] and lansoprazole in particular[11] may include:[2]

PPIs may be associated with a greater risk of hip fractures and Clostridioides difficile-associated diarrhea.[2]:22

Interactions

Lansoprazole interacts with several other drugs, either due to its 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

Lansoprazole was originally synthesized at Takeda and was given the development name AG 1749.[19] Takeda patented it in 1984 and the drug was launched in 1991.[20] In the United States, it was approved for medical use in 1995.[21]

Society and culture

Prevacid 30 mg

Patents

Patent protection of the lansoprazole molecule expired on 10 November 2009,[22][23] and generic formulations became available under many brand names in many countries.[24] Some formulations may not be available in generic form.[25]

Availability

Since 2009, lansoprazole has been available over the counter (OTC) in the U.S. as Prevacid 24HR[26][27] and as Lansoprazole 24HR.[28] In Australia, it is marketed by Pfizer as Zoton.[29]

Research

In vitro experiments have shown that lansoprazole binds to the pathogenic form of tau protein.[30] 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.[30]

References

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