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
Licence data	US FDA:link
Pregnancy cat.	B3(AU) B(US)
Legal status	OTC (US) Rx Only
Routes	Oral, IV
Pharmacokinetic data
Bioavailability	80% or more
Protein binding	97%
Metabolism	Hepatic (CYP3A4- and CYP2C19-mediated)
Half-life	1–1.5 hours
Excretion	Renal and fecal
Identifiers
CAS number	103577-45-3 Y
ATC code	A02BC03
PubChem	CID 3883
DrugBank	APRD00077
ChemSpider	3746 Y
UNII	0K5C5T2QPG Y
KEGG	D00355 Y
ChEBI	CHEBI:6375 Y
ChEMBL	CHEMBL480 Y
Chemical data
Formula	C16H14F3N3O2S
Mol. mass	369.363 g/mol
SMILES	eMolecules & PubChem
InChI 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) Y Key:MJIHNNLFOKEZEW-UHFFFAOYSA-N Y
N(what is this?)  (verify)

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]

Lansoprazole has been available as a generic drug since 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]

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] Lansoprazole is a racemate [1:1-mixture of the enantiomers dexlansoprazole (Kapidex) and levolansoprazole].^[8] Dexlanprantazole is an enantiomerically pure active ingredient of a commercial drug as a result of the 'enantiomeric shift'.

Lansoprazole's plasma elimination half-life is not proportional to the duration of the drug's effects to the person (i.e. gastric acid suppression). The mean plasma elimination half-life is 1.5 hours,^[9] and the effects of the drug last for over 24 hours after it has been used for 1 day or more.^[10] Lansoprazole, 30 mg administered nasogastrically, effectively controls intragastric pH and is an alternative to i.v. pantoprazole in patients who are unable to swallow solid dosage formulations.^[11]

Indications

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Lansoprazole is indicated for:

• Treatment of ulcers of the stomach and duodenum, and NSAID-induced ulcers.
• Adjunctive treatment of Helicobacter pylori infection, alongside antibiotics. Treatment to kill Helicobacter pylori (H. pylori) causing ulcers or other problems involves using two other drugs besides lansoprazole. This treatment is known as "triple therapy", and involves taking twice daily for 10 or 14 days lansoprazole 30 mg, amoxicillin 1,000 mg, and clarithromycin 500 mg.
• Treatment of gastroesophageal reflux disease (GERD) (also known as acid reflux disease).
• Treatment of Zollinger-Ellison Syndrome.

Drug interactions

Lansoprazole interacts with several other drugs, either due to its own nature or as a proton pump inhibitor^[12].

• PPIs reduce absorption of antifungals (itraconazole and ketoconazole) ^[13] and possibly increase Digoxin in plasma
• Increases plasma concentrations of Cilostazol (risk of toxicity)
• Lansoprazole possibly interacts with, amongst other drugs:
  • sucralfate
  • ampicillin
  • bisacodyl
  • clopidogrel
  • delavirdine
  • fluvoxamine
  • iron salts
  • voriconazole
  • aminophylline and theophylline
  • astemizole

Side effects

Side effects of proton pump inhibitors in general^[14] and lansoprazole in particular^[15] may include:

• Infrequent: dry mouth, insomnia, drowsiness, blurred vision, rash, pruritus
• Rarely and very rarely: taste disturbance, liver dysfunction, peripheral oedema, hypersensitivity reactions (including bronchospasm, urinary, angioedema, anaphylaxis), photosensitivity, fever, sweating, depression, interstitial nephritis, blood disorders (including leukopenia, leukocytosis, pancytopenia, thrombocytopenia), arthralgia, myalgia, skin reactions^[16] including (erythroderma^[17] Stevens–Johnson syndrome, toxic epidermal necrolysis, bullous eruption)
• Severe: Gastro-intestinal disturbances (such as nausea 1.3%, abdominal pain 2.1%, diarrhea 3.8%).^[9]

Proton-pump inhibitors may be associated with a greater risk of hip fractures^[18] and Clostridium difficile-associated diarrhea.^[19] Patients are frequently administered the drugs in intensive care as a protective measure against ulcers, but this use is also associated with a 30% increase in occurrence of pneumonia.^[20]

Brand names

Prevacid 30 mg

Lansoprazole is available as a generic drug in the US, UK, Canada, Belgium, Finland,^[21] France, Colombia, Italy, Sweden,^[22] and Mexico.^{[citation needed]}

The drug is also sold under several brand names, including:^[1]

• Agopton (Germany)
• Digest (Indonesia)
• Duogast (Syria)
• Gastrolan (Indonesia)
• Lanciprol (Greece)
• Lansazol (Jordan)
• Lansobene (Austria)
• Lansoloc (South Africa)
• Lansoprazol (Denmark)
• Lansoptol (Hungary)
• Lansor (Turkey)
• Lansox (Italy)
• Lanston LFDT (South Korea)
• Lenzo (India)
• Lanzol (India, Ireland)
• Lanzotec (Jordan)
• Lanzul (Slovenia)
• Lanton (Israel)
• Lanzo (Sweden)
• Lanzopral (Argentina, Chile, Peru, Venezuela[2])
• Lanzor (France, South Africa)
• Lanzostad (Lithuania, Latvia, Estonia)
• Laprazol (Greece)
• Limpidex (Italy)
• Monolitum (Spain)
• Ogast and OgastORO (France)
• Ogastro (Mexico)
• Prevacid (U.S. and Canada)
• Prosogan and Prosogan FD (Indonesia)
• pro-ulco (Spain)
• Refluxon (Hungary)
• Sabax (Serbia)
• SOLOX (New Zealand)
• Takepron (Japan)
• Zolt (Finland)
• Zoton (Italy, Ireland, Australia, UK)
• ZOMEL (Ireland)

References

External links

• Prevacid official website Takeda Pharmaceuticals North America
• Prevacid 24HR official website Novartis Consumer Health
• Prevpac official website Takeda Pharmaceuticals North America
• U.S. National Library of Medicine: Drug Information Portal - Lansoprazole