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Record Information
Version4.0
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-09-27 08:27:50 UTC
HMDB IDHMDB0015160
Secondary Accession Numbers
  • HMDB15160
Metabolite Identification
Common NameAmlexanox
DescriptionAmlexanox 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 ulcers. Recurrent aphthous ulcer (RAU) is the most prevalent oral mucosal disease in humans, estimated to affect between 5% and 50% of the general population.
Structure
Thumb
Synonyms
ValueSource
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 FormulaC16H14N2O4
Average Molecular Weight298.2934
Monoisotopic Molecular Weight298.095356946
IUPAC Name2-amino-5-oxo-7-(propan-2-yl)-5H-chromeno[2,3-b]pyridine-3-carboxylic acid
Traditional Nameaphthasol
CAS Registry Number68302-57-8
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 KeySGRYPYWGNKJSDL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzopyrans
Direct ParentChromeno[2,3-b]pyridine-5-ones
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.15 g/LNot Available
LogP4.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity81.43 m³·mol⁻¹ChemAxon
Polarizability30.82 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0091000000-00993cade43b41e35544View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-6251cf97e8c45ca915cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zgi-0090000000-4e3a6005c4c7903e8304View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2290000000-4ce7d5b38aec871db123View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-0090000000-363c3c4f6b29bd793e36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-4242451c12a02c097cfcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ktr-2290000000-fe4c8daf1591c12dffa9View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01025 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01025 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01025
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2076
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2161
PDB IDANW
ChEBI ID31205
References
Synthesis ReferenceNot 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 ]