| Identification | More | [Name]
Amlexanox | [CAS]
68302-57-8 | [Synonyms]
2-amino-7-isopropyl-5-oxo-5h-[1]benzopyrano[2,3-b]pyridine-3-carboxylic acid
AMLEXANOX
RARECHEM AL BO 1376
5h-(1)benzopyrano(2,3-b)pyridine-3-carboxylicacid,2-amino-7-(1-methylethyl)-5
aa-673
amoxanox
2-Amino-7-(1-methylethyl)-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylic Acid
Aphthasol
CHX-3673
Elics
Solf
2-Amino-7-(1-methylethyl)-5-oxo-5H-[1]benzopyrano[2,3-β]pyridine-3-carboxylic Acid
2-Amino-7-(1-methylethyl)-5-oxo-5H-[1]benzopyrano[2，3-b J pyridine-3-carboxylic acid
2-Amino-5-oxo-7-propan-2-ylchromeno[3,2-e]pyridine-3-carboxylic acid
5H-(1)Benzopyrano(2,3-b)pyridine-3-carboxylic acid, 2-amino-7-(1-methylethyl)-5-oxo-
3-Amino-7-isopropyl-9-oxo-4-aza-9H-xanthene-2-carboxylic acid | [EINECS(EC#)]
804-135-3 | [Molecular Formula]
C16H14N2O4 | [MDL Number]
MFCD00864790 | [Molecular Weight]
298.29 | [MOL File]
68302-57-8.mol |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [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 | [form ]
powder | [pka]
3.95±0.20(Predicted) | [color ]
white to beige | [Usage]
Inhibits release of allergic mediators from mast cells. Antiallergic; antiasthmatic | [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) |
| Hazard Information | Back Directory | [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 |
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