Amlenanox (CHEM016563)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:37:09 UTC
Update Date2016-11-09 01:15:25 UTC
Accession NumberCHEM016563
Identification
Common NameAmlenanox
ClassSmall Molecule
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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Amino-7-isopropyl-5-oxo-5H-(1)benzopyrano(2,3-b)pyridine-3-carboxylic acidChEBI
AmlexanoxoChEBI
AmlexanoxumChEBI
AphthasolKegg
SolfaKegg
2-Amino-7-isopropyl-5-oxo-5H-(1)benzopyrano(2,3-b)pyridine-3-carboxylateGenerator
2-Amino-7-isopropyl-5-oxo-5H-(1)benzopyrano(2,3b)pyridine-3-carboxylic acidHMDB
GlaxoSmithKline brand OF amlexanoxHMDB
AmoxanoxHMDB
Chemical FormulaC16H14N2O4
Average Molecular Mass298.293 g/mol
Monoisotopic Mass298.095 g/mol
CAS Registry Number68302-57-8
IUPAC Name2-amino-5-oxo-7-(propan-2-yl)-5H-chromeno[2,3-b]pyridine-3-carboxylic acid
Traditional Nameaphthasol
SMILESCC(C)C1=CC2=C(OC3=NC(N)=C(C=C3C2=O)C(O)=O)C=C1
InChI IdentifierInChI=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
Description belongs to the class of organic compounds known as chromeno[2,3-b]pyridine-5-ones. Chromeno[2,3-b]pyridine-5-ones are compounds containing a Chromeno[2,3-b]pyridine moiety that carries an oxo group at the 5-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentChromeno[2,3-b]pyridine-5-ones
Alternative Parents
Substituents
  • Chromeno[2,3-b]pyridine-5-one
  • Chromenopyridine
  • Pyranopyridine
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Aminopyridine
  • Pyranone
  • Pyran
  • Pyridine
  • Benzenoid
  • Imidolactam
  • Heteroaromatic compound
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-0390000000-7ee61efa9635374d2e64Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9456000000-b9624d4096b63a87688aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0091000000-00993cade43b41e35544Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0udi-0090000000-b3b8517df7b9224b9b0fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000t-0090000000-8e4fc4d5f71fd828eec7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-6251cf97e8c45ca915cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zgi-0090000000-4e3a6005c4c7903e8304Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2290000000-4ce7d5b38aec871db123Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-0090000000-363c3c4f6b29bd793e36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-4242451c12a02c097cfcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ktr-2290000000-fe4c8daf1591c12dffa9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-298901b9b72f633ddf1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-0090000000-7ae2b8d3206733616bb9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0290000000-23dd9de629c968ef59aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-977fc6f1952ba1618211Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-d126c3ae8460a1113700Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01p9-0590000000-299584979cf6ca2fac81Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01025
HMDB IDHMDB0015160
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDANW
Wikipedia LinkAmlexanox
Chemspider ID2076
ChEBI ID31205
PubChem Compound ID2161
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Bell J: Amlexanox for the treatment of recurrent aphthous ulcers. Clin Drug Investig. 2005;25(9):555-66.
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12873507
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=3989816