68302-57-8 Usage
Uses
Used in Pharmaceutical Industry:
Amlexanox is used as an antiallergic and antiasthmatic agent for inhibiting the release of allergic mediators from mast cells. It is particularly effective in treating bronchial asthma and allergy-related sinus disorders due to its inhibitory actions on leukohiene D4, PAF, and histamine.
Originator
Takeda (Japan)
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.
Therapeutic Function
Antiulcer (topical)
Biochem/physiol Actions
Amlexanox elevates the amount of nonsense-containing mRNAs in treated cells and helps to generate full-length proteins effectively.
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
Check Digit Verification of cas no
The CAS Registry Mumber 68302-57-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,8,3,0 and 2 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 68302-57:
(7*6)+(6*8)+(5*3)+(4*0)+(3*2)+(2*5)+(1*7)=128
128 % 10 = 8
So 68302-57-8 is a valid CAS Registry Number.
InChI:InChI=1/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)
68302-57-8Relevant academic research and scientific papers
Spherical granules having core and their production
-
, (2008/06/13)
The spherical granules having a core coated with spraying powder containing a drug and low substituted hydroxypropylcellulose, because of their excellent hardness, can be coated further evenly, (e.g. sustained release coating, gastric coating, enteric coating), and at the time the granules are excellent in disintegration.
Studies on antianaphylactic agents. 7. Synthesis of antiallergic 5-oxo-5H-[1]benzopyrano[2,3-b]pyridines
Nohara,Ishiguro,Ukawa,Sugihara,Maki,Sanno
, p. 559 - 586 (2007/10/02)
5-Oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylic acids 23 and their tetrazole analogues 24 were synthesized from 4-oxo-4H-1-benzopyran-3-carbonitriles or 2-amino-4-oxo-4H-1-benzopyran-3-carboxaldehydes. When administered intravenously, they exhibited antiallergic activity in a reaginic PCA test in rats. In the carboxylic acid series, the activity was influenced by the substituents at the 2-position and increased substantially in the following order: Me, OMe 2 OH, H NHOMe. On the other hand, in the tetrazole series, 2-unsubsitituted derivatives showed the highest activity. Regardless of the kinds of substituents at positions 2 and 3, compounds bearing an alkyl group, especially an isopropyl group at the 7-position, were superior in activity to the corresponding unsubstituted compounds. Among these alkyl derivatives, 3-carboxylic acid derivatives, i.e., 23c (7-ethyl), 23g (2-amino-7-isopropyl), 23r [2-(methoxyamino)-7-isopropyl], and a 3-tetrazole derivative 24c (7-isopropyl), were 41-184 times as potent as disodium cromoglycate. They also exhibited remarkable activity when administered orally; clinical studies on 23g (AA-673) are in progress.
