Lansoprazole

Lansoprazole

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Systematic (IUPAC) name
(RS)-2-([3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole
Clinical data
[[Regulation of therapeutic goods |Template:Engvar data]]	US FDA: Lansoprazole
Pregnancy category	AU: B3 US: B (No risk in non-human studies)
Routes of administration	Oral, IV
Legal status
Legal status	US: OTC ℞ (Prescription only)
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
ATC code	A02BC03 (WHO)
PubChem	CID 3883
DrugBank	APRD00077
ChemSpider	3746
Chemical data
Formula	C16H14F3N3O2S
Molar mass	369.363 g/mol[[]]
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Lansoprazole (pronounced /lænˈsoʊprəzoʊl/, lan-SOE-pra-zole, INN) is a proton-pump inhibitor (PPI) which prevents the stomach from producing gastric acid. It is manufactured by a number of companies worldwide under several brand names (some brand names include: Prevacid, Helicid, Zoton, Inhibitol). It was first approved by the U.S. Food and Drug Administration (FDA) in 1995.

Prevacid patent protection expired on November 10, 2009. As a result, prescription Lansoprazole is now available in the form of a generic drug. As of November 12, 2009 (2009 -11-12), Lansoprazole is available over-the-counter (OTC) in the U.S. in a 15 mg dose marketed by Novartis as Prevacid 24HR.

Currently (November 25, 2009), prescription Lansoprazole and OTC Prevacid sell for about 50% and 25% of the cost of prescription Prevacid, respectively, in the U.S.

Pharmacology

Main article: Proton-pump inhibitor

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. Lansoprazole is a racemate [1:1-mixture of the enantiomers dexlansoprazole (Kapidex) and levolansoprazole]. 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 (i.e. gastric acid suppression). The mean plasma elimination half-life is 1.5 hours, and the effects of the drug last for over 24 hours after it has been used for 1 day or more.

Indications

Lansoprazole is indicated for:

• Treatment of ulcers of the stomach and duodenum, and NSAID-induced ulcers
• Treatment of gastroesophageal reflux disease (GERD) (also known as acid reflux disease)
• Treatment of Zollinger-Ellison Syndrome
• Adjunctive treatment of Helicobacter pylori infection, alongside antibiotics

Drug interactions

• PPIs reduce absorption of antifungals (itraconazole and ketoconazole) and possibly increase Digoxin in plasma
• Increases plasma concentrations of Cilostazol (risk of toxicity)
• Absorption of lansoprazole possibly reduced by:
  • sucralfate
  • ampicillin
  • bisacodyl
  • delavirdine
  • fluvoxamine
  • iron salts
  • theophylline
  • voriconazole
  • aminophylline and theophylline
  • astemizole

Side effects

• 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 including (erythroderma Stevens-Johnson syndrome, toxic epidermal necrolysis, bullous eruption)
• Severe: Gastro-intestinal disturbances (such as nausea 1.3%, abdominal pain 2.1%, diarrhea 3.8%).

Proton-pump inhibitors may be associated with a greater risk of hip fractures, clostridium difficile-associated diarrhea. 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.

Brand names

File:Prevacid30mg.png

Prevacid 30 mg

The drug is sold under several brand names, including:

• Agopton (Germany)
• Lansor (Turkey)
• Digest (Indonesia)
• Duogast (Syria)
• Gastrolan (Indonesia)
• Lanpro (India)
• Lanzol (India)
• Lanzul (Slovenia)
• Lansoptol (Hungary)
• Lansox (Italy)
• Lansoloc (South Africa)
• Lanston LFDT (South Korea)
• Lanton (Israel)
• Lanzo (Sweden)
• Lanzor (France, South Africa)
• Lanzostad (Lithuania, Latvia, Estonia)
• Laprazol (Greece)
• Lanciprol (Greece)
• Limpidex (Italy)
• Monolitum (Spain)
• Ogast and OgastORO (France)
• Ogastro (Mexico)
• Prevacid (U.S. and Canada) Prevacid is a product of Takeda Pharmaceuticals.
• Prevacid 24HR (U.S.)
• pro-ulco (Spain)
• Prosogan and Prosogan FD (Indonesia)
• Refluxon (Hungary)
• SOLOX (New Zealand)
• Takepron (Japan)
• Zolt (Finland)
• Zoton (Italy, Ireland, Australia, UK)
• ZOMEL (Ireland)

Lansoprazole is also available as a generic drug in the US, UK, Canada, Belgium, Finland, France, Colombia, Italy, Sweden, and Mexico.

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

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