Loxoprofen sodium
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Loxoprofen sodium
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CAS No:
80382-23-6
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Formula:
C15H18O3.Na
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Chemical Name:
Loxoprofen sodium
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Synonyms:
Benzeneacetic acid,α-methyl-4-[(2-oxocyclopentyl)methyl]-,sodium salt (1:1);Benzeneacetic acid,α-methyl-4-[(2-oxocyclopentyl)methyl]-,sodium salt;CS 600 (antiinflammatory);Loxoprofen sodium;Sodium loxoprofen;CS 600;Loxonin;Sodium 2-[4-[(2-Oxocyclopentyl)methyl]phenyl]propionate;Lobu
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CAS No:
Description
ChEBI: A hydrate that is the dihydrate form of loxoprofen sodium. The parent acid, loxoprofen, is a prodrug that is rapidly converted to its active trans-alcohol metabolite following oral administration.
Loxoprofen sodium Use and Manufacturing
Compound 9 and methanol were charged into a round bottom reaction flask, To the above solution was added 1 equivalent of sodium hydroxide solution, Stirred for 1 hour, Distilled at 50-55 ° C under reduced pressure, 5percent aqueous ethyl acetate was added, Heated, then cooled to room temperature, Seed crystals were added to the solution, Stirred at 0-5 ° C for 5-6 hours to obtain turbid liquid, Filtered to obtain loxoprofen sodium dihydrate, Yield 95percent, HPLC purity 99.1percent.The reaction formula is as follows: The losoprofen acid d 12.3g was added to 30 ml of acetone and stirred to dissolve, and the temperature was raised appropriately, and the maximum temperature did not exceed 30 °C. After the completion of the dissolution, 6.5 g of a 30percent NaOH solution was added dropwise to the solution at 30 ° C until the pH of the system reached 7.2, and the reaction was completed.The temperature was raised to 45 ° C, the formed solid was dissolved, 0.3 g of activated carbon was added for decolorization for 15 min, hot filtered, and the filtrate was slowly cooled and cooled to 2°C, maintained for 2h, filtered, the filter cake was washed with a small amount of acetone, and the wet product was dried under vacuum at 30 ° C to obtain 13.4 g of white flake crystals, the yield was 88.6percent, the HPLC content was 99.95percent, the single impurity was 0.02percent, and the total impurities were 0.05percent.Methyl 2-(4-((2-oxocyclopentyl)methyl)phenyl) propionate (compound 6, 38 g, 154.28 mmol) was introduced into a 500 ml three-necked flask, ethanol (200 ml) was added, refluxed, and sodium hydroxide solution (20.9 g, 30percent by mass) was dropped to the resulting mixture for 1 hour. After completion of dripping, the material was concentrated to dryness. The residue was recrystallized from ethanol-methyl tert-butyl ether to give a white powdery solid (35.36 g, 131.80 mmol). Molar yield 85.43percent, HPLC purity 99.7percent
Anti-inflammatory.Loxoprofen sodium is a new type of NSAIDs. The drug is a prodrug and has no activity itself. It needs to be metabolized by the liver after oral administration to transform it into a trans-OH body before it can exert its therapeutic effect. It has a wide range of applications. , Can be used for osteoarthritis, rheumatoid arthritis, periarthritis, low back pain, neck, shoulder and wrist syndrome, etc. It is also commonly used in surgery, pain after tooth extraction and acute upper respiratory tract inflammation and other diseases.
Drug Function and Efficacy
After being absorbed by the digestive tract, it is converted into active metabolites in the body. Its active metabolites exert analgesic, anti-inflammatory and antipyretic effects by inhibiting the synthesis of prostaglandins.
Registered Holders
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METROCHEM API PRIVATE LTD
Active
United States
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KOLON LIFE SCIENCE,INC.
Active
Japan
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Dijia Pharmaceutical Group Co.,Ltd.
Active
Japan
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