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].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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)
1. Bell J. (2005)
Amlexanox for the treatment of recurrent aphthous ulcers.
Clin Drug Investig, 25 (9): 555-66. [PMID:17532700]
2. Elad S, Epstein JB, von Bültzingslöwen I, Drucker S, Tzach R, Yarom N. (2011)
Topical immunomodulators for management of oral mucosal conditions, a systematic review; Part II: miscellaneous agents.
Expert Opin Emerg Drugs, 16 (1): 183-202. [PMID:21244328]
3. Makino H, Saijo T, Ashida Y, Kuriki H, Maki Y. (1987)
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.
Int Arch Allergy Appl Immunol, 82 (1): 66-71. [PMID:2433225]
4. Mowers J, Uhm M, Reilly SM, Simon J, Leto D, Chiang SH, Chang L, Saltiel AR. (2013)
Inflammation produces catecholamine resistance in obesity via activation of PDE3B by the protein kinases IKKε and TBK1.
Elife, 2: e01119. DOI: 10.7554/eLife.01119 [PMID:24368730]
5. Reilly SM, Chiang SH, Decker SJ, Chang L, Uhm M, Larsen MJ, Rubin JR, Mowers J, White NM, Hochberg I et al.. (2013)
An inhibitor of the protein kinases TBK1 and IKK-ɛ improves obesity-related metabolic dysfunctions in mice.
Nat Med, 19 (3): 313-21. [PMID:23396211]
6. Spina D. (2008)
PDE4 inhibitors: current status.
Br J Pharmacol, 155 (3): 308-15. [PMID:18660825]