Amlexanox Chemical Properties

Melting point:

>3000C

Boiling point:

570.0±50.0 °C(Predicted)

Density 

1.408±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

DMSO: soluble10mg/mL at warmed, clear

pka

3.95±0.20(Predicted)

form 

powder

color 

white to beige

Merck 

14,490

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.

CAS DataBase Reference

68302-57-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-43

Safety Statements 

36/37-37-36

WGK Germany 

3

RTECS 

DJ3102000

HS Code 

29349990

MSDS

• Language:English Provider:2-Amino-7-isopropyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylic acid

Amlexanox Usage And Synthesis

Description

Amlexanox is an orally-active antiasthmatic agent useful in the treatment of bronchial asthma and allergy-related sinus disorders. The therapeutic effect of amlexanox appears to be attributed to its inhibitory actions on leukohiene D₄, PAF and histamine.

Chemical Properties

White Crystalline Solid

Originator

Takeda (Japan)

Uses

Inhibits release of allergic mediators from mast cells. Antiallergic; antiasthmatic

Definition

ChEBI: A pyridochromene-derived monocarboxylic acid having an amino substituent at the 2-position, an oxo substituent at the 5-position and an isopropyl substituent at the 7-position.

Manufacturing Process

A mixture of 2 ml of morpholine, 3 ml of dimethylformamide and 10 ml of water was heated to 60°C and under stirring the equal molecular quantity of 6-isopropyl-4-oxo-4H-1-benzopyran-3-carbonitrile was added for 5 minutes. The mixture was heated at that temperature for one hour and the resultant precipitate was filtered, rained with water recrystallized from acetic acid and washed with chloroform. By the above procedure was obtained 2-amino-6- isopropyl-4-oxo-4H-1-benzopyran-3-carboxaldehyde melting at 206°-208°C. A mixture of 4 ml ethyl cyanoacetate, 50 ml of ethanol, 5 ml of piperidine and the equal molecular quantity of 2-amino-6-isopropyl-4-oxo-4H-1-benzopyran- 3-carboxaldehyde was refluxed for 30 minutes and, after cooling, the crystalline precipitate was filtered and washed with chloroform. By above procedure was obtained ethyl-2-amino-7-isopropyl-1-azaxanthone-3- carboxylate, melting after recrystallization from ethanol at 243°-244°C. A mixture of 10 ml of acetic acid and 10 ml of 55% sulfuric acid the equal molecular quantity and 2-ethyl-amino-7-isopropyl-1-azaxanthone-3- carboxylate was stirred at 130°C for 4 hours and, after water was added, the precipitate was collected by filtration and recrystalllized from dimethylformamide to give the 2-amino-7-(1-methylethyl)-5-oxo-5H- [1]benzopyrano[2,3-b]pyridine-3-carboxylic acid, melting point 300°C.

brand name

Aphthasol (Uluru);Solfa.

Therapeutic Function

Antiulcer (topical)

General Description

Amlexanox is an anti-allergic drug with anti-inflammatory properties.

Biochem/physiol Actions

Amlexanox elevates the amount of nonsense-containing mRNAs in treated cells and helps to generate full-length proteins effectively.

storage

Store at -20°C

References

1) Koch et al. (2013), Obesity: Teaching an old drug new tricks – amlexanox targets inflammation to improve metabolic dysfunction; Nat. Rev. Endocrinol., 9 185 2) Reilly et al. (2013), An inhibitor of the protein kinases TBK1 and IKK-ε improves obesity-related metabolic dysfunctions in mice; Nat. Med., 19 313 3) Nasry et al. (2016), Different modalities for treatment of recurrent aphthous stromatitis. A Randomized clinical trial; J. Clin. Exp. Dent. 8 e517 4) Cheng et al. (2018), Aphthous ulcer drug inhibits prostate tumor metastasis by targeting IKKε/TBK1/NFκB signaling; Theranostics 8 4633

Amlexanox(68302-57-8)Related Product Information

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