2-METHYL-8-(PHENYLMETHOXY)IMIDAZO[1,2-A]PYRIDINE-3-ACETONITRILE Chemical Properties

Density 

1.16±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

DMSO: >10 mg/mL, soluble

form 

solid

pka

5.85±0.10(Predicted)

color 

white to light tan

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

2-METHYL-8-(PHENYLMETHOXY)IMIDAZO[1,2-A]PYRIDINE-3-ACETONITRILE Usage And Synthesis

Description

SCH 28080 is a reversible K⁺-competitive inhibitor of H⁺/K⁺-ATPases that is best known for its ability to block acid secretion through its action against the gastric H⁺/K⁺-ATPase (IC₅₀ = 1.3 μM). It is effective against gastric H⁺/K⁺-ATPases from a variety of species and can inhibit colonic H⁺/K⁺-ATPases, but this activity appears to be species-dependent. SCH 28080 is also used to investigate the role of H⁺/K⁺-ATPases in non-mammalian organisms and to distinguish the actions of H⁺/K⁺-ATPases from other ATP-dependent transporters.

Uses

SCH 28080 is a potent inhibitor of H+,K+-ATPase.

Definition

ChEBI: 2-(2-methyl-8-phenylmethoxy-3-imidazo[1,2-a]pyridinyl)acetonitrile is an imidazopyridine.

Biological Activity

Potent inhibitor of H + ,K + -ATPase (IC 50 = 20 nM); binds to the K + recognition site and is competitive with respect to K + . Inhibits gastric acid secretion in vitro and in vivo .

Biochem/physiol Actions

SCH-28080 is a potent inhibitor of gastric H+ and K+-ATPase. The novel antiulcer agents, SCH-28080 and SCH-32651 were examined for their ability to inhibit the H+K+ ATPase enzyme activity in a preparation of microsomal membranes from rabbit fundic mucosa. SCH- 28080 inhibited the isolated enzyme activity with a potency similar to omeprazole, IC50s of 2.5 and 4.0 μM respectively. SCH 32651 was less potent exhibiting an IC50 of 200.0 μM. Both compounds may therefore exert their antisecretory activity via a direct inhibition of the parietal cell H+K+ ATPase.

storage

Room temperature

References

[1] W. BEIL  K. Fr S  I Hackbarth. Mechanism of gastric antisecretory effect of SCH 28080[J]. British Journal of Pharmacology, 1986, 88 1: 19-23. DOI: 10.1111/j.1476-5381.1986.tb09466.x
[2] B WALLMARK. Inhibition of gastric H+,K+-ATPase and acid secretion by SCH 28080, a substituted pyridyl(1,2a)imidazole.[J]. The Journal of Biological Chemistry, 1987, 262 5: 2077-2084.
[3] H G SWARTS. Conformation-dependent inhibition of gastric H+,K+-ATPase by SCH 28080 demonstrated by mutagenesis of glutamic acid 820.[J]. Molecular Pharmacology, 1999, 55 3: 541-547.
[4] JIAHONG SHAO . Pharmacological profiles of the murine gastric and colonic H,K-ATPases[J]. Biochimica et biophysica acta. General subjects, 2010, 1800 9: Pages 906-911. DOI: 10.1016/j.bbagen.2010.05.002
[5] WENDY S BEANE. A chemical genetics approach reveals H,K-ATPase-mediated membrane voltage is required for planarian head regeneration.[J]. Chemistry & biology, 2011, 18 1: 77-89. DOI: 10.1016/j.chembiol.2010.11.012
[6] SARAH A. SALYER . Vacuolar ATPase driven potassium transport in highly metastatic breast cancer cells[J]. Biochimica et biophysica acta. Molecular basis of disease, 2013, 1832 10: Pages 1734-1743. DOI: 10.1016/j.bbadis.2013.04.023

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