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Lansoprazole

Lansoprazole is a proton pump (H+/K+ ATPase) inhibitor (PPI) that exhibits antacid and anti-inflammatory activities. Lansoprazole is clinically used to treat gastroesophageal reflux disease (GERD). Lansoprazole inhibits indomethacin-induced gastric damage by preventing activation of mitochondria- and Fas-mediated apoptosis signaling pathways. Lansoprazole also inhibits PMA-induced activation of ERK1/2 and LPS-induced activation of p38 MAPK in neutrophils and decreases levels of pro-inflammatory cytokines in macrophages.

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18937521/

Cas No.

103577-45-3

Purity

≥98%

Formula

C16H14F3N3O2S

Formula Wt.

369.36

Chemical Name

1H-Benzimidazole, 2-(((3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl)methyl)sulfinyl)-

IUPAC Name

2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]-1H-benzimidazole

Synonym

AG-1749; Agopton; Lansox; Lanzor; Limpidex.

Melting Point

178-182°C (dec)

Solubility

Insoluble in water. Soluble in methanol and DMF.

Appearance

A white to off white powder

Koshio O, Tansho S, Ubagai T, et al. Suppression of phosphorylation of extracellular-signal-regulated kinase and p38 mitogen-activated protein kinase in polymorphonuclear leukocytes by the proton pump inhibitor lansoprazole. J Infect Chemother. 2010 Apr;16(2):100-6. PMID: 20094750.

Maity P, Bindu S, Choubey V, et al. Lansoprazole protects and heals gastric mucosa from non-steroidal anti-inflammatory drug (NSAID)-induced gastropathy by inhibiting mitochondrial as well as Fas-mediated death pathways with concurrent induction of mucosal cell renewal. J Biol Chem. 2008 May 23;283(21):14391-401. PMID: 18375387.

Hinoki A, Yoshimura K, Fujita K, et al. Suppression of proinflammatory cytokine production in macrophages by lansoprazole. Pediatr Surg Int. 2006 Nov;22(11):915-23. PMID: 16932910.

Shin JM, Cho YM, Sachs G. Chemistry of covalent inhibition of the gastric (H+, K+)-ATPase by proton pump inhibitors. J Am Chem Soc. 2004 Jun 30;126(25):7800-11. PMID: 15212527.

ICG-002