Nicotinamide N-oxide

ALK-0139

Nicotinamide N-oxide

1986-81-8

Nicotinamide N-oxide, an in vivo nicotinamide metabolite, is a potent, and selective antagonist of the CXCR2 receptor.

Nicotinamide N-oxide

138.12

C6H6N2O2

0.9985

Solid

H2O : 20 mg/mL(144.80 mM;Need ultrasonic) DMSO : 10 mg/mL(72.40 mM;Need ultrasonic)

-20℃ for 3 years

Room temperature in continental US; may vary elsewhere.

O=C(C1=C[N+]([O-])=CC=C1)N

Nicotinamide is one of the forms of vitamin B3. It is a precursor for nicotinamide adenine dinucleotide, which is best known as an electron carrier in oxidative phosphorylation and as a cofactor for many dehydrogenases. It is metabolized through two enzymatic systems. The first system starts with the methylation of nicotinamide by nicotinamide N-methyltransferase, which can subsequently be oxidized by aldehyde oxidase. The second enzymatic system oxidizes nicotinamide to nicotinamide N-oxide. A series of nicotinamide N-oxides is synthesized and shown to be novel, potent, and selective antagonists of the CXCR2 receptor. Compound 1 has demonstrated potent inhibition of neutrophil chemotaxis (IC50=10 nM). Compound 2 is a selective antagonist of IL-8 binding (IC50=110 nM) and potent inhibitor of neutrophil chemotaxis (IC50=170 nM).