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Identification
Name Amlexanox
Accession Number DB01025 (APRD00795)
Type small molecule
Groups approved
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 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Amlexanox [USAN:INN:JAN]
Amlexanoxo [Spanish]
Amlexanoxum [Latin]
Salts Not Available
Brand names
Name Company
Amlenanox
Amoxanox
Aphthasol
Elics
OraDisc
Solfa
Brand mixtures Not Available
Categories
  • Anti-Allergic Agents
  • Antiulcer agent (topical)
  • Anti-inflammatory Agents, Locally Applied
CAS number 68302-57-8
Weight Average: 298.2934
Monoisotopic: 298.095356946
Chemical Formula C16H14N2O4
InChI Key InChIKey=SGRYPYWGNKJSDL-UHFFFAOYSA-N
InChI
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)
Plain Text
IUPAC Name
2-amino-5-oxo-7-(propan-2-yl)-5H-chromeno[2,3-b]pyridine-3-carboxylic acid
SMILES
CC(C)C1=CC2=C(OC3=NC(N)=C(C=C3C2=O)C(O)=O)C=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Chromones
Substructures
  • Hydroxy Compounds
  • Acetates
  • Pyridines and Derivatives
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Chromones
  • Carboxylic Acids and Derivatives
  • Aminopyridines and Derivatives
  • Heterocyclic compounds
  • Aromatic compounds
Pharmacology
Indication Used as a paste in the mouth to treat aphthous ulcers (canker sores).
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.
Absorption No significant absorption directly through the active ulcer. Most of the systemic absorption is via the gastrointestinal tract.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Metabolized to hydroxylated and conjugated metabolites.
Route of elimination Not Available
Half life Elimination half-life is 3.5 ± 1.1 hours.
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Uluru inc
Packagers
Dosage forms Not Available
Prices
Unit description Cost Unit
Aphthasol 5% Paste 3 gm Tube 29.99 USD tube
Aphthasol 5% paste 7.36 USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Country Patent Number Approved Expires (estimated)
United States 5362737 1994-11-08 2011-11-08
Properties
State solid
Experimental Properties
Property Value Source
logP 4.1 Not Available
Predicted Properties
Property Value Source
water solubility 1.46e-01 g/l ALOGPS
logP 2.76 ALOGPS
logP 3.65 ChemAxon
logS -3.3 ALOGPS
pKa (strongest acidic) 4.3 ChemAxon
pKa (strongest basic) 0.87 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 102.51 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 81.43 ChemAxon
polarizability 30.82 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Bell J: Amlexanox for the treatment of recurrent aphthous ulcers. Clin Drug Investig. 2005;25(9):555-66. Pubmed
External Links
Resource Link
KEGG Drug D01828 Link_out
PubChem Compound 2161 Link_out
PubChem Substance 46504508 Link_out
ChemSpider 2076 Link_out
ChEBI 31205 Link_out
ChEMBL 31205 Link_out
Therapeutic Targets Database DAP000321 Link_out
PharmGKB PA164745310 Link_out
Drugs.com http://www.drugs.com/cdi/amlexanox.html Link_out
ATC Codes
  • A01AD07
  • R03DX01
AHFS Codes Not Available
PDB Entries Not Available
FDA label show (129 KB)
MSDS show (79.7 KB)
Interactions
Drug Interactions Searched, but no interactions found.
Food Interactions Not Available
Targets

1. Protein S100-A12

Pharmacological action: unknown
Actions: antagonist

Calcitermin possesses antifungal activity against C.albicans and is also active against E.coli and P.aeruginosa but not L.monocytogenes and S.aureus

Organism class: human
UniProt ID: P80511 Link_out
Gene: S100A12 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Shishibori T, Oyama Y, Matsushita O, Yamashita K, Furuichi H, Okabe A, Maeta H, Hata Y, Kobayashi R: Three distinct anti-allergic drugs, amlexanox, cromolyn and tranilast, bind to S100A12 and S100A13 of the S100 protein family. Biochem J. 1999 Mar 15;338 ( Pt 3):583-9. Pubmed
  2. Okada M, Tokumitsu H, Kubota Y, Kobayashi R: Interaction of S100 proteins with the antiallergic drugs, olopatadine, amlexanox, and cromolyn: identification of putative drug binding sites on S100A1 protein. Biochem Biophys Res Commun. 2002 Apr 12;292(4):1023-30. Pubmed
  3. Kishimoto K, Kaneko S, Ohmori K, Tamura T, Hasegawa K: Olopatadine suppresses the migration of THP-1 monocytes induced by S100A12 protein. Mediators Inflamm. 2006;2006(1):42726. Pubmed

2. Protein S100-A13

Pharmacological action: unknown
Actions: antagonist
Organism class: human
UniProt ID: Q99584 Link_out
Gene: S100A13 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Shishibori T, Oyama Y, Matsushita O, Yamashita K, Furuichi H, Okabe A, Maeta H, Hata Y, Kobayashi R: Three distinct anti-allergic drugs, amlexanox, cromolyn and tranilast, bind to S100A12 and S100A13 of the S100 protein family. Biochem J. 1999 Mar 15;338 ( Pt 3):583-9. Pubmed
  2. Landriscina M, Prudovsky I, Mouta Carreira C, Soldi R, Tarantini F, Maciag T: Amlexanox reversibly inhibits cell migration and proliferation and induces the Src-dependent disassembly of actin stress fibers in vitro. J Biol Chem. 2000 Oct 20;275(42):32753-62. Pubmed
  3. Okada M, Tokumitsu H, Kubota Y, Kobayashi R: Interaction of S100 proteins with the antiallergic drugs, olopatadine, amlexanox, and cromolyn: identification of putative drug binding sites on S100A1 protein. Biochem Biophys Res Commun. 2002 Apr 12;292(4):1023-30. Pubmed
  4. Matsunaga H, Ueda H: Evidence for serum-deprivation-induced co-release of FGF-1 and S100A13 from astrocytes. Neurochem Int. 2006 Aug;49(3):294-303. Epub 2006 Mar 7. Pubmed
  5. Mouta Carreira C, LaVallee TM, Tarantini F, Jackson A, Lathrop JT, Hampton B, Burgess WH, Maciag T: S100A13 is involved in the regulation of fibroblast growth factor-1 and p40 synaptotagmin-1 release in vitro. J Biol Chem. 1998 Aug 28;273(35):22224-31. Pubmed

3. Interleukin-3

Pharmacological action: unknown
Actions: antagonist

This CSF induces granulocytes, macrophages, mast cells, stem cells, erythroid cells, eosinophils and megakaryocytes

Organism class: human
UniProt ID: P08700 Link_out
Gene: IL3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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

4. Fibroblast growth factor 1

Pharmacological action: unknown
Actions: inhibitor

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

Organism class: human
UniProt ID: P05230 Link_out
Gene: FGF1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19