Nicotinamide N-oxide

Modify Date: 2024-01-02 12:49:06

Nicotinamide N-oxide Structure
Nicotinamide N-oxide structure
Common Name Nicotinamide N-oxide
CAS Number 1986-81-8 Molecular Weight 138.12400
Density 1.34 g/cm3 Boiling Point 514.7ºC at 760 mmHg
Molecular Formula C6H6N2O2 Melting Point 291-293 °C (dec.)(lit.)
MSDS Chinese USA Flash Point 265.1ºC
Symbol GHS07
GHS07
Signal Word Warning

 Use of Nicotinamide N-oxide


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

 Names

Name 1-oxidopyridin-1-ium-3-carboxamide
Synonym More Synonyms

 Nicotinamide N-oxide Biological Activity

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

 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

 Safety Information

Symbol GHS07
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

~95%

Nicotinamide N-oxide Structure

Nicotinamide N-oxide

CAS#:1986-81-8

Literature: Rout, Laxmidhar; Punniyamurthy, Tharmalingam Advanced Synthesis and Catalysis, 2005 , vol. 347, # 15 p. 1958 - 1960

~55%

Nicotinamide N-oxide Structure

Nicotinamide N-oxide

CAS#:1986-81-8

Literature: Moehrle, Hans; Niessen, Robert Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2000 , vol. 55, # 5 p. 434 - 442

~%

Nicotinamide N-oxide Structure

Nicotinamide N-oxide

CAS#:1986-81-8

Literature: Dissertationes Pharmaceuticae, , vol. 9, p. 197,203 Chem.Abstr., , p. 6337

~%

Nicotinamide N-oxide Structure

Nicotinamide N-oxide

CAS#:1986-81-8

Literature: Yakugaku Zasshi, , vol. 72, p. 1474,1476 Chem.Abstr., , p. 8077

~%

Nicotinamide N-oxide Structure

Nicotinamide N-oxide

CAS#:1986-81-8

Literature: Yakugaku Zasshi, , vol. 72, p. 1474,1476 Chem.Abstr., , p. 8077

 Articles21

More 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...

 Synonyms

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
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