Name | 1-oxidopyridin-1-ium-3-carboxamide |
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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 |
Description | Nicotinamide N-oxide, an in vivo nicotinamide metabolite, is a potent, and selective antagonist of the CXCR2 receptor. |
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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 |
Density | 1.34 g/cm3 |
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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 |
Symbol |
![]() GHS07 |
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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 |
~95% 1986-81-8 |
Literature: Rout, Laxmidhar; Punniyamurthy, Tharmalingam Advanced Synthesis and Catalysis, 2005 , vol. 347, # 15 p. 1958 - 1960 |
~55% 1986-81-8 |
Literature: Moehrle, Hans; Niessen, Robert Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2000 , vol. 55, # 5 p. 434 - 442 |
~% 1986-81-8 |
Literature: Dissertationes Pharmaceuticae, , vol. 9, p. 197,203 Chem.Abstr., , p. 6337 |
~% 1986-81-8 |
Literature: Yakugaku Zasshi, , vol. 72, p. 1474,1476 Chem.Abstr., , p. 8077 |
~% 1986-81-8 |
Literature: Yakugaku Zasshi, , vol. 72, p. 1474,1476 Chem.Abstr., , p. 8077 |