Amlexanox

Base Information

• Chemical Name: Amlexanox
• CAS No.: 68302-57-8
• Molecular Formula: C16H14N2O4
• Molecular Weight: 298.298
• Hs Code.: 29349990
• European Community (EC) Number: 804-135-3
• UNII: BRL1C2459K
• DSSTox Substance ID: DTXSID2022595
• Nikkaji Number: J22.801J
• Wikipedia: Amlexanox
• Wikidata: Q695611
• NCI Thesaurus Code: C47395
• Pharos Ligand ID: BQU5D4ZF972P
• Metabolomics Workbench ID: 43268
• ChEMBL ID: CHEMBL1096
• Mol file: 68302-57-8.mol

Synonyms:2-Amino-7-isopropyl-5-oxo-5H-(1)benzopyrano(2,3-b)pyridine-3-carboxylic acid;5H-(1)Benzopyrano(2,3-b)pyridine-3-carboxylic acid, 2-amino-7-(1-methylethyl)-5-oxo-;Aphtheal;Elics;Solfa;

Chemical Property of Amlexanox

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 7.86E-14mmHg at 25°C
• Melting Point: >300 °C
• Refractive Index: 1.668
• Boiling Point: 570 °C at 760 mmHg
• PKA: 3.95±0.20(Predicted)
• Flash Point: 298.5 °C
• PSA: 106.42000
• Density: 1.408 g/cm³
• LogP: 3.32620
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: soluble10mg/mL at warmed, clear
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 298.09535693
• Heavy Atom Count: 22
• Complexity: 467

Purity/Quality:

99% ^*data from raw suppliers

Amlexanox ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36/37-37-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=CC2=C(C=C1)OC3=NC(=C(C=C3C2=O)C(=O)O)N
• Recent ClinicalTrials: Amlexanox for Type 2 Diabetes and Obesity
• Description: Amlexanox is an orally-active antiasthmatic agent useful in the treatment of bronchial asthma and allergy-related sinus disorders. The therapeutic effect of amlexanox appears to be attributed to its inhibitory actions on leukohiene D4, PAF and histamine.
• Uses: Inhibits release of allergic mediators from mast cells. Antiallergic; antiasthmatic
• Therapeutic Function: Antiulcer (topical)

Technology Process of Amlexanox

There total 4 articles about Amlexanox which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

ethyl 2-amino-7-isopropyl-5-oxo-5H-<1>benzopyrano<2,3-b>pyridine-3-carboxylate (68301-99-5) → amlexanox (68302-57-8)

Guidance literature:

With sulfuric acid; acetic acid; at 130 ℃; for 3h;

DOI:10.1021/jm50001a005

Reference yield:

6-isopropyl-4-oxo-4H-1-benzopyran-3-carbonitrile (50743-32-3) → amlexanox (68302-57-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / piperidine / ethanol / 5 h / Heating

2: 88 percent / 50percent aq. H₂SO₄, AcOH / 3 h / 130 °C

With piperidine; sulfuric acid; acetic acid; In ethanol;

DOI:10.1021/jm50001a005

Reference yield:

→ amlexanox (68302-57-8) + hydroxypropylmethylcellulose

Guidance literature:

upstream raw materials:

ethyl 2-amino-7-isopropyl-5-oxo-5H-<1>benzopyrano<2,3-b>pyridine-3-carboxylate

6-isopropyl-4-oxo-4H-1-benzopyran-3-carbonitrile

Downstream raw materials:

2-amino-6-hydroxy-5-(2-hydroxy-5-isopropylbenzoyl)pyridine-3-carboxylic acid

ethyl 2-amino-7-isopropyl-5-oxo-5H-<1>benzopyrano<2,3-b>pyridine-3-carboxylate

Refernces

• 1、 Nohara,Ishiguro,Ukawa,Sugihara,Maki,Sanno. "Studies on antianaphylactic agents. 7. Synthesis of antiallergic 5-oxo-5H-[1]benzopyrano[2,3-b]pyridines". . p. 559 - 586. Retrieved 2007/10/02.