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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:53 UTC
HMDB IDHMDB0015160
Secondary Accession Numbers
  • HMDB15160
Metabolite Identification
Common NameAmlexanox
DescriptionAmlexanox, also known as aphthasol or solfa, 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. Amlexanox is a drug which is used as a paste in the mouth to treat aphthous ulcers (canker sores). . Amlexanox is an extremely weak basic (essentially neutral) compound (based on its pKa). A pyridochromene-derived monocarboxylic acid having an amino substituent at the 2-position, an oxo substituent at the 5-position and an isopropyl substituent at the 7-position.
Structure
Thumb
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 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
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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.15 g/LNot Available
LogP4.1Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01025 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01025 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01025
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2076
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmlexanox
METLIN IDNot Available
PubChem Compound2161
PDB IDANW
ChEBI ID31205
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]