Nicotinamide N-oxide

Names

[ CAS No. ]:
1986-81-8

[ Name ]:
Nicotinamide N-oxide

[Synonym ]:
3-carbamoylpyridine 1-oxide
Nicotinamide,1-oxide
nicotinamide N1-oxide
EINECS 217-859-4
3-Pyridinecarboxamide,1-oxide
1-Oxy-nicotinamide
Nicotinic acid amide N-oxide
3-Pyridincarboxamid-1-oxid
Nicotinamide N-oxide
3-Pyridinecarboxamide,Oxynicotinamide
MFCD00006202

Biological Activity

[Description]:

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

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Natural Products >> Others

[Target]

Human Endogenous Metabolite

[In Vitro]

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[1]. 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)[2].

[References]

[1]. Real AM, et al. Nicotinamide N-oxidation by CYP2E1 in human liver microsomes. Drug Metab Dispos. 2013 Mar;41(3):550-3.

[2]. Cutshall NS, et al. Nicotinamide N-oxides as CXCR2 antagonists. Bioorg Med Chem Lett. 2001 Jul 23;11(14):1951-4.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.34 g/cm3

[ Boiling Point ]:
514.7ºC at 760 mmHg

[ Melting Point ]:
291-293 °C (dec.)(lit.)

[ Molecular Formula ]:
C₆H₆N₂O₂

[ Molecular Weight ]:
138.12400

[ Flash Point ]:
265.1ºC

[ Exact Mass ]:
138.04300

[ PSA ]:
68.55000

[ LogP ]:
0.91430

[ Vapour Pressure ]:
1.05E-10mmHg at 25°C

[ Index of Refraction ]:
1.602

[ Storage condition ]:
Refrigerator

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Articles

Effects of excess nicotinamide administration on the urinary excretion of nicotinamide N-oxide and nicotinuric acid by rats.

Biosci. Biotechnol. Biochem. 68(1) , 44-50, (2004)

We investigated a useful chemical index for an excessive nicotinamide intake and how this excessive nicotinamide intake affects the tryptophan-nicotinamide metabolism in rats. Weaning rats were fed on...

Pharmacokinetics and biochemistry studies on nicotinamide in the mouse.

Cancer Chemother. Pharmacol. 34(5) , 399-404, (1994)

Nicotinamide sensitizes murine tumours to the effect of radiation, but the pharmacokinetics are not well characterized at doses that are achievable in humans. In the mouse, nicotinamide given i.p. at ...

Plasma and urine pharmacokinetics of niacin and its metabolites from an extended-release niacin formulation.

Int. J. Clin. Pharmacol. Ther. 45(8) , 448-54, (2007)

To characterize plasma and urine pharmacokinetics of niacin and its metabolites after oral administration of 2,000 mg of extended-release (ER) niacin in healthy male volunteers.Niacin ER was administe...

Related Compounds

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