Lansoprazole

Lansoprazole

Clinical data
Pronunciation	/lænˈsoʊprəzoʊl/ lan-SOH-prə-zohl
Trade names	Prevacid, others
AHFS/Drugs.com	Monograph
MedlinePlus	a695020
License data	US FDA: Lansoprazole
Pregnancy category	AU: B3 US: B (No risk in non-human studies)
Routes of administration	Oral, IV
ATC code	A02BC03 (WHO)
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
IUPAC name (RS)-2-([3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole
CAS Number	103577-45-3 Y
PubChem CID	3883
IUPHAR/BPS	7208
DrugBank	DB00448 Y
ChemSpider	3746 Y
UNII	0K5C5T2QPG
KEGG	D00355 Y
ChEBI	CHEBI:6375 Y
ChEMBL	CHEMBL480 Y
ECHA InfoCard	100.173.220
Chemical and physical data
Formula	C16H14F3N3O2S
Molar mass	369.363 g/mol
3D model (Jmol)	Interactive image
Chirality	Racemic mixture
SMILES FC(F)(F)COc1ccnc(c1C)CS(=O)c2[nH]c3ccccc3n2
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

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. 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.

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. It is a racemic 1:1 mixture of the enantiomers dexlansoprazole (Dexilant, formerly named Kapidex) and levolansoprazole. 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). The effects of the medication last for over 24 hours after it has been used for a day or more.

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. Prevacid patent protection expired on November 10, 2009.

Lansoprazole is used for treatment of:

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

Side effects of PPIs in general and lansoprazole in particular may include:

PPIs may be associated with a greater risk of hip fractures and Clostridium difficile-associated diarrhea.