Basic information
- CAS
68302-57-8- Standard SMILES
CC(C)c1ccc2oc3nc(N)c(C(=O)O)cc3c(=O)c2c1- InChIKey
SGRYPYWGNKJSDL-UHFFFAOYSA-N- Molecular formula
- C16H14N2O4
- Average molar mass
- 298.29 g/mol
- Monoisotopic mass
- 298.09535693
Overview
Amlexanox is 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. It has a role as a non-steroidal anti-inflammatory drug, an anti-ulcer drug and an anti-allergic agent. It is a monocarboxylic acid and a pyridochromene.
Names & identifiers
- Preferred name
- Amlexanox
- IUPAC
- 2-amino-5-oxo-7-propan-2-ylchromeno[2,3-b]pyridine-3-carboxylic acid
- English name
- Amlexanox
- Molecular formula
- C16H14N2O4
- Molecular weight
- 298.29
Names & synonyms
amlexanox68302-57-8AmoxanoxAphthasolElicsAA-673AmlexanoxoAmlexanoxumaphthealCHX 3673CHX-3673AA 673
Show more names
SolfAmlexanox RSAmlexanox (AA-673)NSC7223
2-amino-5-oxo-7-(propan-2-yl)-5H-chromeno[2,3-b]pyridine-3-carboxylic acid2-Amino-7-isopropyl-5-oxo-5H-(1)benzopyrano(2,3-b)pyridine-3-carboxylic acidBRL1C2459K2-Amino-7-(1-methylethyl)-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylic acidCHEBI:312055H-(1)Benzopyrano(2,3-b)pyridine-3-carboxylic acid, 2-amino-7-(1-methylethyl)-5-oxo-2-Amino-7-isopropyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylic acid2-amino-5-oxo-7-(propan-2-yl)-5H-chromeno(2,3-b)pyridine-3-carboxylic acid
Database identifiers
- CAS
68302-57-8- PubChem CID
- 2161
- DTXSID
DTXSID2022595- ChEMBL
CHEMBL1096- ChEBI
CHEBI:31205- UNII
- BRL1C2459K
- EC Number
- 804-135-3
- Nikkaji
- J22.801J
Properties
Computed structural properties
- XLogP
- 3.1
- Topological polar surface area
- 103 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 467
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP4.1
Solubility1.46e-01 g/L
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 3000 C · >3000C
- Boiling point
- 570 · 570.0±50.0 °C(Predicted)
- Density
- 1.408 · 1.408±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- 10 mg/mL · DMSO: soluble10mg/mL at warmed, clear
- pka
- 3.95 · 3.95±0.20(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- 3
- rtecs
- DJ3102000
- hs_code
- 29349990
- risk_code
- 22-43
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 36/37-37-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
R - Respiratory system
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
QR - Respiratory system
Pharmacodynamics
Amlexanox is a mucoadhesive oral paste which has been clinically proven to abort the onset, accelerate healing and resolve the pain of aphthous ulcers (canker sores). It decreases the time ulcers take to heal. Because amlexanox decreases the healing time, it also decreases the pain you feel. Recent studies have also shown that the majority of ulcers can be prevented by application of the paste during the prodromal (pre-ulcerative) phase of the disease. Recurrent Aphthous Ulcers (RAU) also known as Recurrent Aphthous Stomatitis (RAS) is recognized as the most common oral mucosal disease known to man. Estimates suggest that 20% - 25% of the general population suffer at least one incidence of aphthous ulcers each year. Amlexanox is also being investigated for its anti-allergenic and anti-inflammatory properties.
Mechanism of Action
As a benzopyrano-bipyridine carboxylic acid derivative, amlexanox has anti-inflammatory and antiallergic properties. It inhibits chemical mediatory release of the slow-reacting substance of anaphylaxis (SRS-A) and may have antagonistic effects on interleukin-3. When cells are under stress, they release an inactive form of human fibroblast growth factor 1 (FGF-1), a potent mitogen (entity that causes mitosis). Amlexanox binds to FGF1, increasing its conformational stability, sterically blocking Cu(2+) induced oxidation which normally leads to activation of FGF-1.
Biological Half-LifeElimination half-life is 3.5 ± 1.1 hours.
Metabolism/MetabolitesMetabolized to hydroxylated and conjugated metabolites.
FDA Pharmacological Classification
BRL1C2459K
AMLEXANOX
Physiologic Effects [PE] - Decreased Histamine Release
The physiologic effect of amlexanox is by means of Decreased Histamine Release.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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