Nicotinic acid N-oxide - CAS 2398-81-4
Catalog number:
2398-81-4
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C6H5NO3
Molecular Weight:
139.11
COA:
Inquire
Targets:
Others
Description:
Nicotinic acid N-oxide is used to treat hyperlipoidemia.
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Purity:
99%
Appearance:
White to pale yellow powder or crystalline powder
Synonyms:
1-oxidopyridin-1-ium-3-carboxylic acid Nicotinic acid N-oxide Oxiniacic acid 2398-81-4 Nicotinic acid 1-oxide Nicotinic acid oxide 3-Pyridinecarboxylic acid, 1-oxide N-Hydroxynicotinic acid 3-Carboxypyridine N-oxide 3-Carboxypyridine 1-oxide 3-Pyridinecar
Solubility:
Soluble in DMSO
Storage:
Store in a cool and dry place and at 0 - 4℃ for short term (days to weeks) or -105℃ for long term (months to years).
MSDS:
Inquire
Shelf Life:
2 years
Boiling Point:
469.0±18.0 °C | Condition: Press: 760 Torr
Melting Point:
254.5 °C (decomp)
Density:
1.34 g/cm3
InChIKey:
FJCFFCXMEXZEIM-UHFFFAOYSA-N
InChI:
1S/C6H5NO3/c8-6(9)5-2-1-3-7(10)4-5/h1-4H,(H,8,9)
Canonical SMILES:
C1=CC(=C[N+](=C1)[O-])C(=O)O
1.Anti-proliferative actions of N'-desmethylsorafenib in human breast cancer cells.
Cui PH1, Rawling T, Gillani TB, Bourget K, Wang XS, Zhou F, Murray M. Biochem Pharmacol. 2013 Aug 1;86(3):419-27. doi: 10.1016/j.bcp.2013.05.014. Epub 2013 May 31.
The multi-kinase inhibitor sorafenib is used for the treatment of renal and hepatic carcinomas and is undergoing evaluation for treatment of breast cancer in combination with other agents. Cytochrome P450 (CYP) 3A4 converts sorafenib to multiple metabolites that have been detected in patient plasma. However, recent clinical findings suggest that combination therapy may elicit inhibitory pharmacokinetic interactions involving sorafenib that increase toxicity. While sorafenib N-oxide is an active metabolite, information on the anti-tumor actions of other metabolites is unavailable. The present study evaluated the actions of sorafenib and its five major metabolites in human breast cancer cell lines. All agents, with the exception of N'-hydroxymethylsorafenib N-oxide, decreased ATP formation in four breast cancer cell lines (MDA-MB-231, MDA-MB-468, MCF-7 and T-47D). Prolonged treatment of MDA-MB-231 cells with N'-desmethylsorafenib, N'-desmethylsorafenib N-oxide and sorafenib (10 μM, 72 h) produced small increases in caspase-3 activity to 128-139% of control.
2.Fibrotic Effects of Arecoline N-Oxide in Oral Potentially Malignant Disorders.
Kuo TM1,2, Luo SY3, Chiang SL1,4, Yeh KT5, Hsu HT5, Wu CT6, Lu CY7, Tsai MH8, Chang JG9,2, Ko YC1,2. J Agric Food Chem. 2015 Jun 24;63(24):5787-94. doi: 10.1021/acs.jafc.5b01351. Epub 2015 Jun 10.
The metabolites of environmental chemicals play key roles in carcinogenesis. Areca nut is strongly associated with the development of oral potentially malignant disorders (OPMD) or cancer. The main alkaloid in the areca nut is arecoline, which is highly cytotoxic and genotoxic. Arecoline N-oxide, a metabolite of areca nut alkaloids, which has been identified in animal urine, has been shown to induce mutagenicity in bacteria. In this study, it was found that its protein adduct could be detected in oral keratinocytes treated with areca nut extract. Increased collagen expression and severity of squamous hyperplasia were observed in arecoline N-oxide treated mice. In cultured oral fibroblasts, arecoline N-oxide showed stronger effects on the increase of fibrotic related genes including TGF-beta1, S100A4, MMP-9, IL-6, and fibronectin and a decrease of E-cadherin as compared with arecoline. Finally, arecoline N-oxide stimulation effectively increased the DNA damage marker, gamma-H2A.
3.Simultaneous measurement of nicotinamide and its catabolites, nicotinamide N-oxide, N(1)-methyl-2-pyridone-5-carboxamide, and N(1)-methyl-4-pyridone-3-carboxamide, in mice urine.
Maeta A1, Sano M, Fukuwatari T, Shibata K. Biosci Biotechnol Biochem. 2014;78(8):1306-9. doi: 10.1080/09168451.2014.918495. Epub 2014 Jun 17.
Nicotinamide N-oxide is a major nicotinamide catabolite in mice but not in humans and rats. A high-performance liquid chromatographic method for the simultaneous measurement of nicotinamide, nicotinamide N-oxide, N(1)-methyl-2-pyridone-5-carboxamide, and N(1)-methyl-4-pyridone-3-carboxamide in mice urine was developed by modifying the mobile phase of a reported method for measurement of nicotinamide N-oxide.
4.Contribution of OATP1B1 and OATP1B3 to the disposition of sorafenib and sorafenib-glucuronide.
Zimmerman EI1, Hu S, Roberts JL, Gibson AA, Orwick SJ, Li L, Sparreboom A, Baker SD. Clin Cancer Res. 2013 Mar 15;19(6):1458-66. doi: 10.1158/1078-0432.CCR-12-3306. Epub 2013 Jan 22.
PURPOSE: Many tyrosine kinase inhibitors (TKI) undergo extensive hepatic metabolism, but mechanisms of their hepatocellular uptake remain poorly understood. We hypothesized that liver uptake of TKIs is mediated by the solute carriers OATP1B1 and OATP1B3.
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CAS 2398-81-4 Nicotinic acid N-oxide

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