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    Lansoprazole (AG 1749)
    Lansoprazole (AG 1749)

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V1632
    CAS #: 103577-45-3Purity ≥98%

    Description: Lansoprazole (also known as A-65006, AG-1749; trade name Prevacid among others), a prescription and OTC drug for treatment for heartburn, is a potent proton-pump inhibitor (PPI) which prevents the stomach from producing gastric acid. Lansoprazole has the same pharmacologic class as omeprazole which inhibits the stomach's production of gastric acids. Research is underway for analogs of lansoprazole to explore their use as potential PET imaging agents for diagnosing tauopathies including Alzheimer's disease. Lansoprazole is also a prodrug that targets the cytochrome bc1 complex of Mycobacterium tuberculosis once converted to lansoprazole sulfide in mycobacterial host cells. 

    References: Ann Pharmacother. 1996 Dec;30(12):1425-36; J Clin Biochem Nutr. 2009 Jul;45(1):9-13.

    Related CAS#:226904-00-3 (Lansoprazole sodium); 131926-98-2 (5-Hydroxylansoprazole); 131927-00-9 ( 5-hydroxylansoprazole); 138530-94-6 (Dexlansoprazole; Dexilant; Kapidex; TAK-390MR; TAK 390MR; TAK390MR); 103577-40-8 (AG-1777, EC 600-451-9, H 225/18, K-1252, Lansoprazole impurity C , Lansoprazole sulfide); 131926-99-3 (Lansoprazole sulfone; AG-1813; AG 1813; AG1813); 138530-95-7 (Levolansoprazole); 700341-80-6 (AG1812 free base; Lansoprazole disulfide active metabolite; UNII-6RI44GB0V9; AC1MIZB6; HE078804); 111712-16-4 (AG 2000); 111712-15-3 (Lansoprazole sulfenamide active metabolite; UNII-7EMR32786O); 1216682-38-0 (Lansoprazole Sulfide D4); 934294-22-1 (Lansoprazole D4)

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    Molecular Weight (MW)369.36
    FormulaC16H14F3N3O2S 
    CAS No.103577-45-3
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 74 mg/mL (200.3 mM)
    Water:<1 mg/mL
    Ethanol: 14 mg/mL (37.9 mM)
    Solubility (In vivo)

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

    InChi Key: MJIHNNLFOKEZEW-UHFFFAOYSA-N

    InChi Code: 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)

    SMILES Code: O=S(C1=NC2=CC=CC=C2N1)CC3=NC=CC(OCC(F)(F)F)=C3C           

    SynonymsA-65006, AG-1749; A65006, AG1749; A 65006, AG 1749; Prevacid, Zoton, Agopton, Bamalite, Opiren


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    In Vitro

    In vitro activity: Lansoprazole inhibits gastric acid secretion via inhibition of gastric hydrogen/potassium adenosine triphosphatase (H+,K(+)-ATPase), an enzyme of the gastric parietal cell membrane that forms part of the proton pump that performs the final step in the acid secretory process. Lansoprazole binds covalently to parietal cell H+,K(+)-ATPase, rendering it nonfunctional and inhibiting the secretion of gastric acid. Lansoprazole is a strong anti-secretory agent that acts on gastric H+/K+-adenosine triphosphatase (H+/K+ ATPase) of parietal cells. Lansoprazole inhibits the increased expression of vascular adhesion molecules, the activation of neutrophils, and the production of pro-inflammatory cytokines from activated endothelial cells. Lansoprazole induces several genes, including phase II detoxifying enzyme (NADPH-ubiquinone oxidoreductase, glutathione S-transferase) and antioxidant stress proteins (HO-1, thioredoxin reductase, and superoxide dismutase) in gastric epithelial cells. Lansoprazole significantly inhibits the production of CINC-1 from stimulated RGM-1 cells with IL-1β. Lansoprazole up-regulates HO-1 expression throughout Nrf2 in rat gastric epithelial cells, and the up-regulated HO-1 has anti-inflammatory effects.

    In VivoLansoprazole inhibits acute inflammatory reactions as well as intestinal mucosal injuries induced by ischemia-reperfusion or indomethacin administration in rats. Lansoprazole significantly inhibits intestinal injuries induced by ischemia-reperfusion or indomethacin. lansoprazole administered exogenously prevents the small intestine against ischemia-reperfusion or indomethacin-induced damage, the action being dependent on its anti-inflammatory and anti-oxidative responses. 
    Animal modelRats
    Formulation & Dosage
    References

    Ann Pharmacother. 1996 Dec;30(12):1425-36; J Clin Biochem Nutr. 2009 Jul;45(1):9-13. 


    These protocols are for reference only. InvivoChem does not independently validate these methods.

    Lansoprazole

    The expression of HO-1 induced by lansoprazole. J Clin Biochem Nutr. 2009 Jul;45(1):9-13.
     

    Lansoprazole

    Lansoprazole induced HO-1 expression throughout the translocation of Nrf2. J Clin Biochem Nutr. 2009 Jul;45(1):9-13.


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