Prodrugs pp 1335-1346 | Cite as

Case Study: Parecoxib: A Prodrug of Valdecoxib

  • Dirk L. Teagarden
  • Sandeep Nema
Part of the Biotechnology: Pharmaceutical Aspects book series (PHARMASP, volume V)


Parecoxib, a weakly acidic drug (pKa 4.9), was developed as a COX-2 inhibitor for the management and treatment of acute pain. It was designed to be a water-soluble (> 50 mg/mL in normal saline), parenterally safe prodrug form of valdecoxib, or 4-(5-methyl-3-phenyl-4-isoxazolyl) benzenesulfonamide, a diaryl-substituted isoxazole. Valdecoxib is a sparingly water soluble (10 µ/mL), weakly acidic drug with a pKa of 9.8. Valdecoxib is commercially available as Bextra, an oral formulation for the management of acute pain, chronic pain, osteoarthritis (OA), rheumatoid arthritis (RA), and primary dysmenorrhea.


Acidic Drug Primary Dysmenorrhea Sodium Propionate Propionic Anhydride Parecoxib Sodium 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


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Copyright information

© American Association of Pharmaceutical Scientists 2007

Authors and Affiliations

  • Dirk L. Teagarden
    • 1
  • Sandeep Nema
    • 1
  1. 1.Global Research and DevelopmentPfizer Inc.St. LouisUSA

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