77837-08-2

Basic information

• Product Name: 5-CARBOXY-N-PHENYL-2-1H-PYRIDONE
• Synonyms: 1,6-Dihydro-6-oxo-1-phenyl-3-pyridinecarboxylic Acid;5-Carboxy Pirfenidone;6-Oxo-1-phenyl-1,6-dihydropyridine-3-carboxylic Acid;5-carboxy-N-phenyl-2-pyridone
• CAS NO: 77837-08-2
• Molecular Formula: C₁₂H₉NO₃
• Molecular Weight: 215.2
• Product Categories: Aromatics;Metabolites;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 77837-08-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 282-284°C
• Boiling Point: 382.807°C at 760 mmHg
• Flash Point: 185.315°C
• Appearance: /
• Density: 1.388g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.649
• Storage Temp.: -20°C Freezer
• CAS DataBase Reference: 5-CARBOXY-N-PHENYL-2-1H-PYRIDONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CARBOXY-N-PHENYL-2-1H-PYRIDONE(77837-08-2)
• EPA Substance Registry System: 5-CARBOXY-N-PHENYL-2-1H-PYRIDONE(77837-08-2)

Safety Data

• Hazardous Substances Data: 77837-08-2(Hazardous Substances Data)

Usage

Description

5-CARBOXY-N-PHENYL-2-1H-PYRIDONE is a chemical compound derived from the metabolism of Pirfenidone, a medication used to treat patients with kidney disease who also have diabetes. 5-CARBOXY-N-PHENYL-2-1H-PYRIDONE has potential applications in the medical field due to its association with the therapeutic effects of Pirfenidone.

Uses

Used in Pharmaceutical Applications:
5-CARBOXY-N-PHENYL-2-1H-PYRIDONE is used as a metabolite in the treatment of patients with kidney disease who have diabetes. Its role in the metabolism of Pirfenidone suggests that it may contribute to the drug's therapeutic effects, potentially offering benefits in managing kidney function and overall health for these patients.
Used in Research and Development:
As a metabolite of Pirfenidone, 5-CARBOXY-N-PHENYL-2-1H-PYRIDONE may also be used in research and development to better understand the mechanisms of action of the parent drug. This could lead to the development of new treatments or improved drug formulations for patients with kidney disease and diabetes.
Used in Drug Metabolism Studies:
5-CARBOXY-N-PHENYL-2-1H-PYRIDONE can be utilized in drug metabolism studies to investigate how the body processes and eliminates Pirfenidone. This information can be valuable for optimizing dosing regimens, assessing potential drug interactions, and understanding the compound's pharmacokinetics and pharmacodynamics.

InChI:InChI=1/C12H9NO3/c14-11-7-6-9(12(15)16)8-13(11)10-4-2-1-3-5-10/h1-8H,(H,15,16)

Upstream product

• 6018-41-3 methyl coumalate 
• 62-53-3 aniline 
• 66171-50-4 6-oxo-1,6-dihydropyridin-3-carboxylic acid methyl ester 
• 77837-09-3 methyl 6-oxo-1-phenyl-1,6-dihydropyridine-3-carboxylate 
• 500-05-0 2H-pyran-2-one-5-carboxylic acid 

Downstream Products

• 1392219-90-7 N-(1-azabicyclo[2.2.2]octan-3-yl)-6-oxo-1-phenyl-3-pyridinecarboxamide 
• 1392221-19-0 6-oxo-1-phenyl-1,6-dihydro-pyridine-3-carbonyl chloride 
• 1392221-04-3 (1-azabicyclo[2.2.2]octan-3-yl)-6-oxo-1-phenyl-3-pyridinecarboxylate 
• 1093952-03-4 5-(hydroxy(methyl-d2))-1-phenylpyridin-2(1H)-one 
• 1093951-85-9 5-(methyl-d3)-1-phenylpyridin-2(1H)-one 
• 1228275-03-3 6-oxo-1-phenyl-1,6-dihydropyridine-3-deuterocarboxylic acid 

Relevant articles and documents

Discovery of dap-3 polymyxin analogues for the treatment of multidrug-resistant gram-negative nosocomial infections

We report novel polymyxin analogues with improved antibacterial in vitro potency against polymyxin resistant recent clinical isolates of Acinetobacter baumannii and Pseudomonas aeruginosa. In addition, a human renal cell in vitro assay (hRPTEC) was used to inform structure-toxicity relationships and further differentiate analogues. Replacement of the Dab-3 residue with a Dap-3 in combination with a relatively polar 6-oxo-1-phenyl-1,6-dihydropyridine-3- carbonyl side chain as a fatty acyl replacement yielded analogue 5x, which demonstrated an improved in vitro antimicrobial and renal cytotoxicity profiles relative to polymyxin B (PMB). However, in vivo PK/PD comparison of 5x and PMB in a murine neutropenic thigh model against P. aeruginosa strains with matched MICs showed that 5x was inferior to PMB in vivo, suggesting a lack of improved therapeutic index in spite of apparent in vitro advantages.

Synthesis, pharmacophores, and mechanism study of pyridin-2(1H)-one derivatives as regulators of translation initiation factor 3A

Twenty-seven 1,5-disubstituted-pyridin-2(1H)-one derivatives were synthesized and evaluated for their anti-cancer and anti-fibrosis activity by A549 and NIH3T3 cell viability assays, respectively. To study the selectivity between the cancer and fibrosis cell lines, pharmacophore models (F 1-F4) were built in advance for compounds with pyridin-2(1H)-one scaffold, which revealed the relationship between the occupation of the aromatic sub-site F4 and potent anti-cancer activity. The relationship between structure and anti-cancer activity for all target compounds is also reported herein: 1-Phenyl-5-((m-tolylamino)methyl) pyridine-2(1H)-one (22) displayed both potency and selectivity (IC50 = 0.13 mM) toward the A549 cell line through the inhibition of translation initiation, especially by eIF3a suppression, and can be treated as a lead for the design of novel eIF3a regulators and anti-lung cancer agents. A series of pyridin-2(1H)-one derivatives were synthesized. Elucidation of their pharmacophores and mechanism of action suggested that structures with F 4 occupation displayed more selective anti-cancer than anti-fibrosis activity and that they interrupt the initiation phase of translation by acting on the eukaryotic translation initiation factor 3, subunit A.

PHARMACEUTICAL COMPOSITION COMPRISING PYRIDONE DERIVATIVES

A pyridone derivative compound and a pharmaceutically acceptable salt, isomer, solvate or hydrate thereof, and a preventive or therapeutic pharmaceutical composition for cognitive disorders that includes the pyridone derivative compound or a pharmaceutically acceptable salt, isomer, solvate or hydrate thereof.