Amlexanox | CAS#317183 | D4 antagonist | phosphodiesterase inhibitor

MedKoo Cat#: 317183 | Name: Amlexanox

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Amlexanox, also known as AA-673 and CHX 3673, is an anti-inflammatory antiallergic immunomodulator used to treat recurrent aphthous ulcers (canker sores), and (in Japan) several inflammatory conditions. Amlexanox inhibits the synthesis and release of inflammatory mediators, including leukotrienes and histamine, from mast cells, neutrophils, and mononuclear cells. Amlexanox also acts as a leukotriene D4 antagonist and a phosphodiesterase inhibitor. Amlexanox decreases the time ulcers take to heal as well as the pain associated with the ulcers.

Chemical Structure

Amlexanox

CAS#68302-57-8

Theoretical Analysis

MedKoo Cat#: 317183

Name: Amlexanox

CAS#: 68302-57-8

Chemical Formula: C16H14N2O4

Exact Mass: 298.0954

Molecular Weight: 298.29

Elemental Analysis: C, 64.42; H, 4.73; N, 9.39; O, 21.45

Price and Availability

Size	Price	Availability
200mg	USD 90.00	Ready to ship
500mg	USD 150.00	Ready to ship
1g	USD 250.00	Ready to ship
2g	USD 400.00	Ready to ship
5g	USD 850.00	Ready to ship
10g	USD 1,250.00	2 Weeks

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Related CAS #

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Synonym

AA-673; AA673; AA 673; CHX 3673; CHX-3673; CHX3673; Amoxanox, Brand name: Aphthasol.

IUPAC/Chemical Name

2-amino-5-oxo-7-propan-2-ylchromeno[2,3-b]pyridine-3-carboxylic acid

InChi Key

SGRYPYWGNKJSDL-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

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

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#TCI70510

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Amlexanox (AA673; Amoxanox; CHX3673) is a specific inhibitor of IKKε and TBK1 with an IC50 of approximately 1-2 μM.

In vitro activity:

Based on the anti-inflammatory effects of amlexanox in vitro, this study next evaluated its efficacy in LPS-induced endotoxemia mice. As shown in Fig. 7, an intravenous injection of LPS led to marked increase in TNF-α and IL-6 levels in serum. Single-dose oral administration of amlexanox significantly decreased both TNF-α and IL-6 production, which indicated that amlexanox was able to alleviate systemic inflammation. Reference: Biochim Biophys Acta Mol Cell Res. 2020 Oct;1867(10):118766. https://pubmed.ncbi.nlm.nih.gov/32504661/

In vivo activity:

Based on histopathologic analysis using H&E and Sirius‐red staining, inhibition of TBK1 and IKKε by amlexanox markedly reduced biliary hyperplasia and collagen deposition in the livers of mice fed with DDC diet (Figure 2B,C). Consistent with these findings, this study observed significantly lower serum levels of ALT and AST in amlexanox‐treated mice with fibrosis than those in vehicle‐treated mice with fibrosis (Figure 2D). Additionally, amlexanox‐administered mice showed dose‐dependently reduced IL‐1β and TNFα levels together with reduced NF‐κB activation in fibrotic livers. (Figure 2E,F). In line with histopathologic observation (Figure 2B,C), this study found lower expression levels of pro‐fibrogenic genes such as TGFβ, alpha‐1 type I collagen (Col1α1) and tissue inhibitors of metalloproteinase‐1 (TIMP1) in fibrotic livers of mice treated with amlexanox than those of vehicle‐treated mice (Figure 2G). These findings suggest that suppression of TBK1 and IKKε by using amlexanox can attenuate cholestasis‐induced chronic liver injury and its associated fibro‐inflammatory responses in mice through modulating NF‐κB activation. Reference: J Cell Mol Med. 2020 Jan; 24(2): 1383–1398. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6991653/

	Solvent	mg/mL	mM
Solubility
	DMSO	50.0	167.49
	DMF	14.0	46.93
	DMF:PBS (pH 7.2) (1:1)	0.5	1.68

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 298.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Han Y, Hou R, Zhang X, Liu H, Gao Y, Li X, Qi R, Cai R, Qi Y. Amlexanox exerts anti-inflammatory actions by targeting phosphodiesterase 4B in lipopolysaccharide-activated macrophages. Biochim Biophys Acta Mol Cell Res. 2020 Oct;1867(10):118766. doi: 10.1016/j.bbamcr.2020.118766. Epub 2020 Jun 3. PMID: 32504661. 2. Möller M, Wasel J, Schmetzer J, Weiß U, Meissner M, Schiffmann S, Weigert A, Möser CV, Niederberger E. The Specific IKKε/TBK1 Inhibitor Amlexanox Suppresses Human Melanoma by the Inhibition of Autophagy, NF-κB and MAP Kinase Pathways. Int J Mol Sci. 2020 Jul 2;21(13):4721. doi: 10.3390/ijms21134721. PMID: 32630674; PMCID: PMC7369692. 3. Zhou Z, Qi J, Zhao J, Lim CW, Kim JW, Kim B. Dual TBK1/IKKɛ inhibitor amlexanox attenuates the severity of hepatotoxin-induced liver fibrosis and biliary fibrosis in mice. J Cell Mol Med. 2020 Jan;24(2):1383-1398. doi: 10.1111/jcmm.14817. Epub 2019 Dec 10. PMID: 31821710; PMCID: PMC6991653. 4. Quan MY, Song XJ, Liu HJ, Deng XH, Hou HQ, Chen LP, Ma TZ, Han X, He XX, Jia Z, Guo L. Amlexanox attenuates experimental autoimmune encephalomyelitis by inhibiting dendritic cell maturation and reprogramming effector and regulatory T cell responses. J Neuroinflammation. 2019 Mar 1;16(1):52. doi: 10.1186/s12974-019-1438-z. PMID: 30823934; PMCID: PMC6396467.

In vitro protocol:

In vivo protocol:

1. Zhou Z, Qi J, Zhao J, Lim CW, Kim JW, Kim B. Dual TBK1/IKKɛ inhibitor amlexanox attenuates the severity of hepatotoxin-induced liver fibrosis and biliary fibrosis in mice. J Cell Mol Med. 2020 Jan;24(2):1383-1398. doi: 10.1111/jcmm.14817. Epub 2019 Dec 10. PMID: 31821710; PMCID: PMC6991653. 2. Quan MY, Song XJ, Liu HJ, Deng XH, Hou HQ, Chen LP, Ma TZ, Han X, He XX, Jia Z, Guo L. Amlexanox attenuates experimental autoimmune encephalomyelitis by inhibiting dendritic cell maturation and reprogramming effector and regulatory T cell responses. J Neuroinflammation. 2019 Mar 1;16(1):52. doi: 10.1186/s12974-019-1438-z. PMID: 30823934; PMCID: PMC6396467.

1: Zhang Y, Guan H, Li J, Fang Z, Chen W, Li F. Amlexanox Suppresses Osteoclastogenesis and Prevents Ovariectomy-Induced Bone Loss. Sci Rep. 2015 Sep 4;5:13575. doi: 10.1038/srep13575. PubMed PMID: 26338477; PubMed Central PMCID: PMC4559750. 2: Walash MI, Belal F, Tolba MM, Halawa MI. Micelle-enhanced spectrofluorimetric determination of amlexanox in bioadhesive buccal tablets: application to content uniformity testing. Luminescence. 2015 Sep;30(6):823-9. doi: 10.1002/bio.2828. Epub 2015 Jan 21. PubMed PMID: 25611457. 3: Homan KT, Wu E, Cannavo A, Koch WJ, Tesmer JJ. Identification and characterization of amlexanox as a G protein-coupled receptor kinase 5 inhibitor. Molecules. 2014 Oct 22;19(10):16937-49. doi: 10.3390/molecules191016937. PubMed PMID: 25340299; PubMed Central PMCID: PMC4621012. 4: Ballal V, V J. Oral medicine: amlexanox. Br Dent J. 2014 Sep;217(5):208. doi: 10.1038/sj.bdj.2014.770. PubMed PMID: 25213502. 5: Darshan DD, Kumar CN, Kumar AD, Manikantan NS, Balakrishnan D, Uthkal MP. Clinical study to know the efficacy of Amlexanox 5% with other topical Antiseptic, Analgesic and Anesthetic agents in treating minor RAS. J Int Oral Health. 2014 Feb;6(1):5-11. Epub 2014 Feb 26. PubMed PMID: 24653596; PubMed Central PMCID: PMC3959130. 6: Bhat S, Sujatha D. A clinical evaluation of 5% amlexanox oral paste in the treatment of minor recurrent aphthous ulcers and comparison with the placebo paste: a randomized, vehicle controlled, parallel, single center clinical trial. Indian J Dent Res. 2013 Sep-Oct;24(5):593-8. doi: 10.4103/0970-9290.123382. PubMed PMID: 24355961. 7: Koch L. Obesity: Teaching an old drug new tricks--amlexanox targets inflammation to improve metabolic dysfunction. Nat Rev Endocrinol. 2013 Apr;9(4):185. doi: 10.1038/nrendo.2013.42. Epub 2013 Feb 26. PubMed PMID: 23438840. 8: Gonzalez-Hilarion S, Beghyn T, Jia J, Debreuck N, Berte G, Mamchaoui K, Mouly V, Gruenert DC, Déprez B, Lejeune F. Rescue of nonsense mutations by amlexanox in human cells. Orphanet J Rare Dis. 2012 Aug 31;7:58. doi: 10.1186/1750-1172-7-58. PubMed PMID: 22938201; PubMed Central PMCID: PMC3562214. 9: Fu J, Zhu X, Dan H, Zhou Y, Liu C, Wang F, Li Y, Liu N, Chen Q, Xu Y, Zeng X, Jiang L. Amlexanox is as effective as dexamethasone in topical treatment of erosive oral lichen planus: a short-term pilot study. Oral Surg Oral Med Oral Pathol Oral Radiol. 2012 May;113(5):638-43. doi: 10.1016/j.oooo.2011.10.013. Epub 2012 Mar 3. PubMed PMID: 22668622. 10: Rani SG, Mohan SK, Yu C. Molecular level interactions of S100A13 with amlexanox: inhibitor for formation of the multiprotein complex in the nonclassical pathway of acidic fibroblast growth factor. Biochemistry. 2010 Mar 23;49(11):2585-92. doi: 10.1021/bi9019077. PubMed PMID: 20178375.