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Details

Stereochemistry ACHIRAL
Molecular Formula C16H14N2O4
Molecular Weight 298.2934
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMLEXANOX

SMILES

CC(C)C1=CC2=C(OC3=NC(N)=C(C=C3C2=O)C(O)=O)C=C1

InChI

InChIKey=SGRYPYWGNKJSDL-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description

Amlexanox is an ant allergic 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. The mechanism of action by which amlexanox accelerates healing of aphthous ulcers is unknown. In vitro studies have demonstrated amlexanox to be a potent inhibitor of the formation and/or release of inflammatory mediators (histamine and leukotrienes) from mast cells, neutrophils and mononuclear cells. Given orally to animals, amlexanox has demonstrated anti-allergic and anti-inflammatory activities and has been shown to suppress both immediate and delayed type hypersensitivity reactions. The relevance of these activities of amlexanox to its effects on aphthous ulcers has not been established. Amlexanox 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. This drug has been discontinued in the U.S

Originator

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
APHTHASOL
PubMed

PubMed

TitleDatePubMed
Mechanism of action of an antiallergic agent, amlexanox (AA-673), in inhibiting histamine release from mast cells. Acceleration of cAMP generation and inhibition of phosphodiesterase.
1987
The comparative release of FGF1 by hypoxia and temperature stress.
2001
The precursor but not the mature form of IL1alpha blocks the release of FGF1 in response to heat shock.
2001 Feb 16
Treatment strategies for recurrent oral aphthous ulcers.
2001 Jan 1
Selecting topical and systemic agents for recurrent aphthous stomatitis.
2001 Sep
Interaction of S100 proteins with the antiallergic drugs, olopatadine, amlexanox, and cromolyn: identification of putative drug binding sites on S100A1 protein.
2002 Apr 12
Hsp90 is a direct target of the anti-allergic drugs disodium cromoglycate and amlexanox.
2003 Sep 1
Amlexanox for the treatment of recurrent aphthous ulcers.
2005
A comparative study of the efficacy of Aphtheal in the management of recurrent minor aphthous ulceration.
2005 Aug
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Molecular mechanism of inhibition of nonclassical FGF-1 export.
2005 Nov 29
Olopatadine suppresses the migration of THP-1 monocytes induced by S100A12 protein.
2006
A late cutaneous response in actively sensitized rats: a new method for evaluating the efficacy of antiallergic drugs.
2006 Aug
Evidence for serum-deprivation-induced co-release of FGF-1 and S100A13 from astrocytes.
2006 Aug
The efficacy of amlexanox OraDisc on the prevention of recurrent minor aphthous ulceration.
2006 Feb
Voltage-dependent N-type Ca2+ channel activity regulates the interaction between FGF-1 and S100A13 for stress-induced non-vesicular release.
2006 May
An evaluation on the efficacy and safety of amlexanox oral adhesive tablets in the treatment of recurrent minor aphthous ulceration in a Chinese cohort: a randomized, double-blind, vehicle-controlled, unparallel multicenter clinical trial.
2006 Oct
Mucocutaneous lesions of Behcet's disease.
2007 Aug 31
Effectiveness of two oral pastes for the treatment of recurrent aphthous stomatitis.
2007 Sep
Review of over-the-counter treatments for aphthous ulceration and results from use of a dissolving oral patch containing glycyrrhiza complex herbal extract.
2008 Mar 1
Synergistic Ca2+ and Cu2+ requirements of the FGF1-S100A13 interaction measured by quartz crystal microbalance: an initial step in amlexanox-reversible non-classical release of FGF1.
2008 May
PDE4 inhibitors: current status.
2008 Oct
Treatment of allergic conjunctivitis with olopatadine hydrochloride eye drops.
2008 Sep
[Local Treatment of stomatitis aphthosa].
2008 Sep
Cromoglycate drugs suppress eicosanoid generation in U937 cells by promoting the release of Anx-A1.
2009 Jun 15
RAGE (Receptor for Advanced Glycation Endproducts), RAGE ligands, and their role in cancer and inflammation.
2009 Mar 17
A clinical evaluation of amlexanox oral adhesive pellicles in the treatment of recurrent aphthous stomatitis and comparison with amlexanox oral tablets: a randomized, placebo controlled, blinded, multicenter clinical trial.
2009 May 6
Molecular level interactions of S100A13 with amlexanox: inhibitor for formation of the multiprotein complex in the nonclassical pathway of acidic fibroblast growth factor.
2010 Mar 23
Topical immunomodulators for management of oral mucosal conditions, a systematic review; Part II: miscellaneous agents.
2011 Mar
Patents

Sample Use Guides

In Vivo Use Guide
Four times daily, preferably following oral hygiene after breakfast, lunch, dinner, and at bedtime. Squeeze a dab of paste approximately 1/4 inch (0.5 cm) onto a finger tip. With gentle pressure, dab the paste onto each ulcer in the mouth. Use of the medication should be continued until the ulcer heals.
Route of Administration: Dental
In Vitro Use Guide
Amlexanox at concentrations of 10(-7)-10(-4) M showed an inhibition of histamine, LTB4, LTC4, LTD4 and LTE4 release from passively sensitized human lung fragments in a concentration-dependent fashion.
Name Type Language
AMLEXANOX
INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
AMOXANOX
Common Name English
AMLEXANOX [VANDF]
Common Name English
AMLEXANOX [MI]
Common Name English
AMLEXANOX [JAN]
Common Name English
AMLEXANOX [WHO-DD]
Common Name English
CHX-3673
Code English
AMLEXANOX [INN]
Common Name English
5H-(1)BENZOPYRANO(2,3-.BETA.)PYRIDINE-3-CARBOXYLIC ACID, 2-AMINO-7-(1-METHYLETHYL)-5-OXO-
Systematic Name English
CHX 3673
Code English
AMLEXANOX [USP-RS]
Common Name English
APHTHASOL
Brand Name English
AMLEXANOX [USAN]
Common Name English
AMLEXANOX [ORANGE BOOK]
Common Name English
2-AMINO-7-ISOPROPYL-5-OXO-5H-(1)BENZOPYRANO(2,3-B)PYRIDINE-3-CARBOXYLIC ACID
Systematic Name English
APHTHEAL
Common Name English
SOLFA
Brand Name English
ELICS
Common Name English
AA-673
Code English
AMLEXANOX [MART.]
Common Name English
Classification Tree Code System Code
WHO-ATC A01AD07
Created by admin on Tue Oct 22 00:17:40 UTC 2019 , Edited by admin on Tue Oct 22 00:17:40 UTC 2019
NCI_THESAURUS C29578
Created by admin on Tue Oct 22 00:17:40 UTC 2019 , Edited by admin on Tue Oct 22 00:17:40 UTC 2019
WHO-VATC QR03DX01
Created by admin on Tue Oct 22 00:17:40 UTC 2019 , Edited by admin on Tue Oct 22 00:17:40 UTC 2019
NDF-RT N0000175628
Created by admin on Tue Oct 22 00:17:40 UTC 2019 , Edited by admin on Tue Oct 22 00:17:40 UTC 2019
WHO-ATC R03DX01
Created by admin on Tue Oct 22 00:17:40 UTC 2019 , Edited by admin on Tue Oct 22 00:17:40 UTC 2019
WHO-VATC QA01AD07
Created by admin on Tue Oct 22 00:17:40 UTC 2019 , Edited by admin on Tue Oct 22 00:17:40 UTC 2019
Code System Code Type Description
WIKIPEDIA
AMLEXANOX
Created by admin on Tue Oct 22 00:17:40 UTC 2019 , Edited by admin on Tue Oct 22 00:17:40 UTC 2019
PRIMARY
EVMPD
SUB05465MIG
Created by admin on Tue Oct 22 00:17:40 UTC 2019 , Edited by admin on Tue Oct 22 00:17:40 UTC 2019
PRIMARY
CAS
68302-57-8
Created by admin on Tue Oct 22 00:17:40 UTC 2019 , Edited by admin on Tue Oct 22 00:17:40 UTC 2019
PRIMARY
MERCK INDEX
M1756
Created by admin on Tue Oct 22 00:17:40 UTC 2019 , Edited by admin on Tue Oct 22 00:17:40 UTC 2019
PRIMARY Merck Index
EPA CompTox
68302-57-8
Created by admin on Tue Oct 22 00:17:40 UTC 2019 , Edited by admin on Tue Oct 22 00:17:40 UTC 2019
PRIMARY
NCI_THESAURUS
C47395
Created by admin on Tue Oct 22 00:17:40 UTC 2019 , Edited by admin on Tue Oct 22 00:17:40 UTC 2019
PRIMARY
MESH
C045742
Created by admin on Tue Oct 22 00:17:40 UTC 2019 , Edited by admin on Tue Oct 22 00:17:40 UTC 2019
PRIMARY
RXCUI
46307
Created by admin on Tue Oct 22 00:17:40 UTC 2019 , Edited by admin on Tue Oct 22 00:17:40 UTC 2019
PRIMARY RxNorm
IUPHAR
7113
Created by admin on Tue Oct 22 00:17:40 UTC 2019 , Edited by admin on Tue Oct 22 00:17:40 UTC 2019
PRIMARY
INN
5950
Created by admin on Tue Oct 22 00:17:40 UTC 2019 , Edited by admin on Tue Oct 22 00:17:40 UTC 2019
PRIMARY
DRUG BANK
DB01025
Created by admin on Tue Oct 22 00:17:40 UTC 2019 , Edited by admin on Tue Oct 22 00:17:40 UTC 2019
PRIMARY
ChEMBL
CHEMBL1096
Created by admin on Tue Oct 22 00:17:40 UTC 2019 , Edited by admin on Tue Oct 22 00:17:40 UTC 2019
PRIMARY
PUBCHEM
2161
Created by admin on Tue Oct 22 00:17:40 UTC 2019 , Edited by admin on Tue Oct 22 00:17:40 UTC 2019
PRIMARY