amlexanox   Click here for help

GtoPdb Ligand ID: 7113

Synonyms: AA-673 | Amlexanox® | Aphthasol® | CHX-3673
Approved drug PDB Ligand Immunopharmacology Ligand
amlexanox is an approved drug (FDA (1996))
Compound class: Synthetic organic
Comment: Amlexanox has anti-inflammatory [1], antiallergic and immunomodulatory actions [2]. Proposed to inhibit IKKδ and TBK1, albeit with low potency [5].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 106.42
Molecular weight 298.1
XLogP 4.41
No. Lipinski's rules broken 0
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Canonical SMILES CC(c1ccc2c(c1)c(=O)c1c(o2)nc(c(c1)C(=O)O)N)C
Isomeric SMILES CC(c1ccc2c(c1)c(=O)c1c(o2)nc(c(c1)C(=O)O)N)C
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)
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Summary of Clinical Use Click here for help
Used to treat asthma and allergic rhinitis in Japan and was approved in the US to treat aphthous ulcers [1]. Use of this drug is not currently approved in the US (old formulations have been discontinued) or EU. Other national approval agencies may continue to grant marketing authorisation.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Amlexanox's mechanism of action is not well-determined, but likely includes inhibition of histamine and leukotriene release [1], and possibly inhibition of phosphodiesterase [3-4]. Since PDE4 is prevalent in immune cells [6], this may be a target of amlexanox (see the CHEMBL link).
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