Nicotinamide N-oxide, an in vivo nicotinamide metabolite, is a potent, and selective antagonist of the CXCR2 receptor.Human Endogenous Metabolite 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). . Real AM, et al. Nicotinamide N-oxidation by CYP2E1 in human liver microsomes. Drug Metab Dispos. 2013 Mar;41(3):550-3.. Cutshall NS, et al. Nicotinamide N-oxides as CXCR2 antagonists. Bioorg Med Chem Lett. 2001 Jul 23;11(14):1951-4.

Product information

CAS Number: 1986-81-8

Molecular Weight: 138.12

Formula: C6H6N2O2

Chemical Name: 3-carbamoylpyridin-1-ium-1-olate

Smiles: NC(=O)C1C=CC=[N+]([O-])C=1

InChiKey: USSFUVKEHXDAPM-UHFFFAOYSA-N

InChi: InChI=1S/C6H6N2O2/c7-6(9)5-2-1-3-8(10)4-5/h1-4H,(H2,7,9)

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

Products are for research use only. Not for human use.