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SML0517 Sigma

Amlexanox

≥98% (HPLC)

Synonym: 2-Amino-7-(1-methylethyl)-5-oxo-5H-[1]Benzopyrano[2,3-b]pyridine-3-carboxylic acid, AA 673, Amoxanox, CHX 3673

  • CAS Number 68302-57-8

  • Empirical Formula (Hill Notation) C16H14N2O4

  • Molecular Weight 298.29

  •  MDL number MFCD00864790

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Properties

Related Categories A-AM, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience,
assay   ≥98% (HPLC)
form   powder
color   white to beige
solubility   DMSO: soluble10 mg/mL at warmed, clear
shipped in   wet ice
storage temp.   −20°C

Description

Biochem/physiol Actions

Amlexanox is an anti-allergy and anti-asthma drug that blocks histamine and leukotriene release from leukocytes and mast cells. Amlexanox has also been shown to inhibit cahaperone activity of Hsp90, and S100A13, which is involved in transport of proteins devoid of signal peptide sequences.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®,1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Hazard Codes (Europe) 
Xn
Risk Statements (Europe) 
Safety Statements (Europe) 
36/37
WGK Germany 
3

Documents

Certificate of Analysis

Protocols & Articles

Peer-Reviewed Papers

References

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An inhibitor of the protein kinases TBK1 and IKK-ɛ improves obesity-related metabolic dysfunctions in mice. Reilly SM, Chiang SH, Decker SJ, et al. Nat. Med. 19(3), 313-21, (2013)

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Neuron-specific non-classical release of prothymosin alpha, a novel neuroprotective DAMPs. Halder, S.K., et al. J. Neurochem. Jul 31, (2012)

Turning off the inflammatory, but not the metabolic, flames. Calay ES and Hotamisligil GS Nat. Med. 19(3), 265-7, (2013)

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Clinical inquiry. What is the most effective way to treat recurrent canker sores? Bailey J, McCarthy C, and Smith RF J. Fam. Pract. 60(10), 621-32, (2011)

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[Local Treatment of stomatitis aphthosa]. Höger P Med. Monatsschr. Pharm. 31(9), 356, (2008)

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Review of over-the-counter treatments for aphthous ulceration and results from use of a dissolving oral patch containing glycyrrhiza complex herbal extract. Burgess JA, van der Ven PF, Martin M, et al. J. Contemp. Dent. Pract. 9(3), 88-98, (2008)

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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. Matsunaga, H., and Ueda, H. Neurochem. Int. 52, 1076-1085, (2008)

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Hsp90 is a direct target of the anti-allergic drugs disodium cromoglycate and amlexanox. Okada, M., et al. Biochem. J. 374, 433-441, (2003)

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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. Meng W, Dong Y, Liu J, et al. Trials 10, 30, (2009)

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A comparative study of the efficacy of Aphtheal in the management of recurrent minor aphthous ulceration. Murray B, McGuinness N, Biagioni P, et al. J. Oral. Pathol. Med. 34(7), 413-9, (2005)

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The efficacy of amlexanox OraDisc on the prevention of recurrent minor aphthous ulceration. Murray B, Biagioni PA, and Lamey PJ J. Oral. Pathol. Med. 35(2), 117-22, (2006)

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Amlexanox is as effective as dexamethasone in topical treatment of erosive oral lichen planus: a short-term pilot study. Fu J, Zhu X, Dan H, et al. Oral Surg. Oral Med. Oral Pathol. Oral Radiol. 113(5), 638-43, (2012)

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Effectiveness of two oral pastes for the treatment of recurrent aphthous stomatitis. Rodríguez M, Rubio JA, and Sanchez R Oral Dis. 13(5), 490-4, (2007)

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Treatment strategies for recurrent oral aphthous ulcers. Barrons RW Am. J. Health Syst. Pharm. 58(1), 41-50; quiz 51-3, (2001)

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The precursor but not the mature form of IL1alpha blocks the release of FGF1 in response to heat shock. Tarantini F, Micucci I, Bellum S, et al. J. Biol. Chem. 276(7), 5147-51, (2001)

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Rescue of nonsense mutations by amlexanox in human cells. Gonzalez-Hilarion S, Beghyn T, Jia J, et al. Orphanet J. Rare Dis. 7, 58, (2012)

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Interaction of S100 proteins with the antiallergic drugs, olopatadine, amlexanox, and cromolyn: identification of putative drug binding sites on S100A1 protein. Okada M, Tokumitsu H, Kubota Y, et al. Biochem. Biophys. Res. Commun. 292(4), 1023-30, (2002)

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Molecular mechanism of inhibition of nonclassical FGF-1 export. Rajalingam D, Kumar TK, Soldi R, et al. Biochemistry 44(47), 15472-9, (2005)

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Molecular level interactions of S100A13 with amlexanox: inhibitor for formation of the multiprotein complex in the nonclassical pathway of acidic fibroblast growth factor. Rani SG, Mohan SK, and Yu C Biochemistry 49(11), 2585-92, (2010)

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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. Liu J, Zeng X, Chen Q, et al. Oral Surg. Oral Med. Oral Pathol. Oral Radiol. Endod. 102(4), 475-81, (2006)

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Voltage-dependent N-type Ca2+ channel activity regulates the interaction between FGF-1 and S100A13 for stress-induced non-vesicular release. Matsunaga H and Ueda H Cell. Mol. Neurobiol. 26(3), 237-46, (2006)

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Selecting topical and systemic agents for recurrent aphthous stomatitis. Eisen D and Lynch DP Cutis. 68(3), 201-6, (2001)

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A late cutaneous response in actively sensitized rats: a new method for evaluating the efficacy of antiallergic drugs. Shishikura T, Shito K, Uchida M, et al. J. Pharmacol. Sci. 101(4), 350-5, (2006)

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Fixed drug eruption due to amlexanox. Sugiura M, Hayakawa R, and Osada T Contact Dermatitis 38(2), 65-7, (1998)

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Inhibitory effects of amlexanox on carbachol-induced contractions of rabbit ciliary muscle and guinea-pig taenia caecum. Watanabe N, Tominaga Y, Mizutani K, et al. J. Pharm. Pharmacol. 52(11), 1377-85, (2000)

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The comparative release of FGF1 by hypoxia and temperature stress. Mouta Carreira C, Landriscina M, Bellum S, et al. Growth Factors 18(4), 277-85, (2001)

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Olopatadine suppresses the migration of THP-1 monocytes induced by S100A12 protein. Kishimoto K, Kaneko S, Ohmori K, et al. Mediators Inflamm. 2006(1), 42726, (2006)

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