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2-Nicotinamidoethyl Acetate (SG-209) Is a Potassium Channel Opener: Structure Activity Relationship Among Nicorandil Derivatives

2-Nicotinamidoethyl Acetate (SG-209) Is a Potassium Channel Opener: Structure Activity Relationship Among Nicorandil Derivatives

T Ishibashi, M Hamaguchi, S Imai

Naunyn Schmiedebergs Arch Pharmacol. 1991 Aug;344(2):235-9.

PMID: 1658666

Abstract:

The mechanism of the vasodilating action of 2-nicotinamidoethyl acetate (SG-209), a derivative of nicorandil, was examined in the isolated rabbit aorta. Comparison was made using 2-nicotinamidoethyl alcohol (SG-86) and 2-nicotinamidoethyl nitrate (nicorandil; SG-75) to reveal any structure-activity relationships. SG-209 and nicorandil caused concentration-dependent relaxation in preparations precontracted with phenylephrine (10(-7) mol/l), while SG-86 produced a relaxation only at very high concentrations. The pD2 values (-log[EC50]) of SG-209 and nicorandil were 3.59 +/- 0.07 and 5.95 +/- 0.10, respectively. The vasorelaxant activity of nicorandil was associated with significant increases in cyclic GMP content, while that of SG-209 was not. Methylene blue (10(-5) mol/l) attenuated the relaxant effect of nicorandil, but had no effect on that of SG-209. Furthermore, the relaxant effect of nicorandil was not affected by glibenclamide (10(-5) mol/l), whilst the relaxant effect of SG-209 was abolished by this compound. In the presence of methylene blue (10(-5) mol/l), however, glibenclamide (10(-5) mol/l) attenuated the relaxant effect of higher concentrations of nicorandil (greater than or equal to 10(-5) mol/l). These results indicate that the relaxant effect of SG-209 is mostly if not exclusively due to the activation of potassium channels, while this action contributes to the vasodilating action of nicorandil only at higher concentrations.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP83440033	SG-209		83440-03-3	Price

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