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Amlexanox

July 24, 2017
Common Name

Amlexanox Description

Amlexanox is an antiallergic drug, clinically effective for atopic diseases, especially allergic asthma and rhinitis. Amlexanox as a topical paste is a well tolerated treatment of recurrent aphthous licers. Recurrent aphthous licer (RAU) is the most prevalent oral mucosal disease in humans, estimated to affect between 5% and 50% of the general popliation. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 2-amino-7-Isopropyl-5-oxo-5H-(1)benzopyrano(2,3-b)pyridine-3-carboxylic acidChEBI AmlexanoxoChEBI AmlexanoxumChEBI 2-amino-7-Isopropyl-5-oxo-5H-(1)benzopyrano(2,3-b)pyridine-3-carboxylateGenerator AphthasolMeSH 2-amino-7-Isopropyl-5-oxo-5H-(1)benzopyrano(2,3b)pyridine-3-carboxylic acidMeSH GlaxoSmithKline brand OF amlexanoxMeSH AmoxanoxMeSH

Chemical Formlia

C16H14N2O4 Average Molecliar Weight

298.2934 Monoisotopic Molecliar Weight

298.095356946 IUPAC Name

2-amino-5-oxo-7-(propan-2-yl)-5H-chromeno[2,3-b]pyridine-3-carboxylic acid Traditional Name

aphthasol CAS Registry Number

68302-57-8 SMILES

CC(C)C1=CC2=C(OC3=NC(N)=C(C=C3C2=O)C(O)=O)C=C1

InChI Identifier

InChI=1S/C16H14N2O4/c1-7(2)8-3-4-12-9(5-8)13(19)10-6-11(16(20)21)14(17)18-15(10)22-12/h3-7H,1-2H3,(H2,17,18)(H,20,21)

InChI Key

SGRYPYWGNKJSDL-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as chromeno[2,3-b]pyridine-5-ones. These are compounds containing a Chromeno[2,3-b]pyridine moiety that carries an oxo group at the 5-position. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Benzopyrans Direct Parent

Chromeno[2,3-b]pyridine-5-ones Alternative Parents

  • Chromenopyridines
  • Pyranopyridines
  • Pyridinecarboxylic acids
  • Cumenes
  • Pyranones and derivatives
  • Aminopyridines and derivatives
  • Primary aromatic amines
  • Imidolactams
  • Vinylogous amides
  • Heteroaromatic compounds
  • Amino acids
  • Oxacyclic compounds
  • Azacyclic compounds
  • Carboxylic acids
  • Monocarboxylic acids and derivatives
  • Organooxygen compounds
  • Organic oxides
  • Organopnictogen compounds
  • Hydrocarbon derivatives

    • Substituents

  • Chromeno[2,3-b]pyridine-5-one
  • Chromenopyridine
  • Pyranopyridine
  • Cumene
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Aminopyridine
  • Pyranone
  • Primary aromatic amine
  • Pyran
  • Pyridine
  • Imidolactam
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Primary amine
  • Organic oxide
  • Amine
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • monocarboxylic acid (CHEBI:31205 )
  • pyridochromene (CHEBI:31205 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Allergic Agents
  • Anti-inflammatory Agents, Locally Applied
  • Antilicer agent (topical)

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Extracellliar

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility1.46e-01 g/LNot Available LogP4.1Not Available

    Predicted Properties

    Property Value Source Water Solubility0.15 mg/mLALOGPS logP2.76ALOGPS logP3.65ChemAxon logS-3.3ALOGPS pKa (Strongest Acidic)4.3ChemAxon pKa (Strongest Basic)0.87ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area102.51 Å2ChemAxon Rotatable Bond Count2ChemAxon Refractivity81.43 m3·mol-1ChemAxon Polarizability30.82 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-0002-0091000000-00993cade43b41e35544View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Extracellliar

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01025

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01025

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01025 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    2076 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB15160 Metagene Link

    HMDB15160 METLIN ID

    Not Available PubChem Compound

    2161 PDB ID

    ANW ChEBI ID

    31205

    Product: INH2

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Bell J: Amlexanox for the treatment of recurrent aphthous ulcers. Clin Drug Investig. 2005;25(9):555-66. [PubMed:17532700 ]

    Enzymes

    General function:
    Not Available
    Specific function:
    This CSF induces granulocytes, macrophages, mast cells, stem cells, erythroid cells, eosinophils and megakaryocytes
    Gene Name:
    IL3
    Uniprot ID:
    P08700
    Molecular weight:
    17233.0
    References
    1. Urisu A, Iimi K, Kondo Y, Horiba F, Masuda S, Tsuruta M, Yazaki T, Torii S: [Inhibitory action amlexanox on interleukin-3-induced enhancement of histamine releasability of human leukocytes]. Arerugi. 1990 Oct;39(10):1448-54. [PubMed:1701989 ]
    2. Nagai H, Suda H, Iwama T, Daikoku M, Yanagihara Y, Koda A: Effect of NZ-107, a newly synthesized pyridazinone derivative, on antigen-induced contraction of human bronchial strips and histamine release from human lung fragments or leukocytes. Int Arch Allergy Immunol. 1992;98(1):57-63. [PubMed:1378042 ]
    General function:
    Involved in fibroblast growth factor receptor binding
    Specific function:
    The heparin-binding growth factors are angiogenic agents in vivo and are potent mitogens for a variety of cell types in vitro. There are differences in the tissue distribution and concentration of these 2 growth factors
    Gene Name:
    FGF1
    Uniprot ID:
    P05230
    Molecular weight:
    17459.6
    References
    1. Rajalingam D, Kumar TK, Soldi R, Graziani I, Prudovsky I, Yu C: Molecular mechanism of inhibition of nonclassical FGF-1 export. Biochemistry. 2005 Nov 29;44(47):15472-9. [PubMed:16300395 ]

    PMID: 15072922

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