Parecoxib sodium

Parecoxib sodium 화학적 특성, 용도, 생산

• 개요

  Parecoxib sodium (19) is a cyclooxygenase 2 (COX-2) inhibitor and was introduced by Pharmacia (now Pfizer) as an injectable formulation for short-term treatment of postoperative pain. Parecoxib is a water-soluble prodrug of valdecoxib (27) that undergoes biotransformation in vivo to release valdecoxib (27).

• 용도

  Anti-inflammatory; analgesic (cyclooxygenase).

• Synthesis

  The synthesis of parecoxib sodium (19) started from commercially available deoxybenzoin (165). Deoxybenzoin (165) was treated with hydroxylamine in EtOH/H2O (3:1) to give deoxybenzoin oxime 166 in 95% yield. Deprotonation of oxime 166 with two equivalents of n-hexyllithium followed by condensation with ethyl acetate afforded isoxazoline 167 in 59% yield. Treatment of isoxazoline 167 with chlorosulfonic acid followed by reaction of the incipient sulfonyl chloride with aqueous ammonia furnished valdecoxib (27). Acylation of isoxazole sulfonamide 27 with propionic anhydride afforded parecoxib, which was converted to its sodium salt by titration with aqueous sodium hydroxide (64%).

  

Parecoxib sodium 공급 업체

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