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68302-57-8

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68302-57-8 Usage

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.

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)

68302-57-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (A2401)  Amlexanox  >98.0%(HPLC)(T)

  • 68302-57-8

  • 1g

  • 590.00CNY

  • Detail
  • TCI America

  • (A2401)  Amlexanox  >98.0%(HPLC)(T)

  • 68302-57-8

  • 5g

  • 1,650.00CNY

  • Detail

68302-57-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

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

1.2 Other means of identification

Product number -
Other names 2-amino-7-isopropyl-5-oxo-5H-chromeno[2,3-b]pyridine-3-carboxylic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:68302-57-8 SDS

68302-57-8Synthetic route

ethyl 2-amino-7-isopropyl-5-oxo-5H-<1>benzopyrano<2,3-b>pyridine-3-carboxylate
68301-99-5

ethyl 2-amino-7-isopropyl-5-oxo-5H-<1>benzopyrano<2,3-b>pyridine-3-carboxylate

amlexanox
68302-57-8

amlexanox

Conditions
ConditionsYield
With sulfuric acid; acetic acid at 130℃; for 3h;88%
6-isopropyl-4-oxo-4H-1-benzopyran-3-carbonitrile
50743-32-3

6-isopropyl-4-oxo-4H-1-benzopyran-3-carbonitrile

amlexanox
68302-57-8

amlexanox

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / piperidine / ethanol / 5 h / Heating
2: 88 percent / 50percent aq. H2SO4, AcOH / 3 h / 130 °C
View Scheme

68302-57-8Relevant articles and documents

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.

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