Parecoxib sodium

Celecoxib, rofecoxib, valdecoxib, parecoxib sodium, and etoricoxib all belong to this chemical class. 

Synthesis The acylation of 4-(5-methyl-3-phenylisoxazol-4-yl)benzenesulfonamide (valdecoxib), with propionic anhydride in a solution of TEA and DMAP in tetrahydrofurane gives A/-(4-(5-methyl-3-phenylisoxazol-4-yl)phenylsulfonyl)propionamide, which is treated with NaOH in ethanol to give parecoxib sodium salt (Talley (Parmacia Corp.), 1996 2000b Sorbera, 2001b). 

Talley, J. J., Bertenshaw, S. R., Brown, D. L., Carter, J. S., Graneto, M. J., Kellogg, M. S., Koboldt, C. M., Yuan. J., Zhang, Y. Y., Seibert, K. N-[[(5-methyl-3-phenylisoxazol-4-yl)-phenyl]sulfonyl]propanamide, sodium salt, parecoxib sodium A potent and selective inhibitor of COX-2 for parenteral administration, J. Med. Chem. 2000b, 43, 1661-1663. 

Similarly, the sodium salt of the poorly soluble COX-2 inhibitor pare-coxib, parecoxib sodium (Dynastat ), was designed as a parenteral analgesic for the management of acute pain to improve solubility of the parent compound. On administration, parecoxib sodium is converted rapidly and essentially completely to the pharmacologically active... 

Noveck, R. J., and Hubbard, R. C. Parecoxib sodium, an injectable COX-2-specific inhibitor, does not affect unfractionated heparin-regulated blood coagulation parameters. J. Clin. Pharmacol. 44 474—480, 2004. 

Parecoxib sodium is an injectable COX-2 inhibitor developed for the treatment of acnte pain. It is a prodrug of a sulfonamide-based COX-2 inhibitor, valdecoxib, a potent anti-inflammatory and analgesic dmg. The published information on this componnd is inadequate to draw any conclusion about its tolerability. Single-dose and mnlti-ple-dose studies have not shown any safety problems compared with placebo (1 ). In small short-term endoscopic studies parecoxib was much better tolerated than the non-selective NSAID ketorolac (5,6). However, it shonld be noted that valdecoxib was withdrawn in 2005 (7). 

Sorbera LA, Leeson PA, Castaner J, Castaner RM. Valdecoxib and parecoxib sodium. Analgesic, antiarthritic, cyclooxygenase inhibitor. Drugs Future 2001 26 133 0. 

Karim A, Laurent A, Slater ME, Kuss ME, Qian J, Crosby-Sessoms SL, Hubbard RC. A pharmacokinetic study of intramuscular (i.m.) parecoxib sodium in normal subjects J Clin Pharmacol 2001 41(10) 1111-19. 

Daniels SE, Grossman EH, Kuss ME, Talwalker S, Hubbard RC. A double-blind, randomized comparison of intramuscularly and intravenously administered parecoxib sodium versus ketorolac and placebo in a post-oral surgery pain model. Clin Ther 2001 23(7) 1018-31. 

Stoltz RR, Harris SI, Kuss ME, LeComte D, Talwalker S, Dhadda S, Hubbard RC. Upper GI mucosal effects of parecoxib sodium in healthy elderly subjects. Am J Gastroenterol 2002 97(1) 65-71. 

Harris SI, Kuss M, Hubbard RC, Goldstein JL. Upper gastrointestinal safety evaluation of parecoxib sodium, a new parenteral cyclooxygenase-2-specific inhibitor, compared with ketorolac, naproxen, and placebo. Clin Ther 2001 23(9) 1422-8. 

Dynastat Injection (Parecoxib sodium). Pfizer Ltd. UK Summary of product characteristics, April 2007. 

Noveck RJ, Kuss ME, Qian J, North J, Hubbard RC. Parecoxib sodium, injectable COX-2 specific inhibitor, does not affect aspirin-mediated platelet function. RegAnes t Penn Med (2001)26(Suppl), 19. 

Karim A Bradford D, Qian J, Hubbard R. The COX-2-specific inhibitor parecoxib sodium does not affect warfarin pharmacokinetic and pharmacodynamic parameters. American College of Emergency Physicians. Scientific Assembly, Chicago, Illinois, 15-18 October 2001. Abstract 130. 

Parecoxib sodium in a syringe administered intramusculary or intravenously as a bolus... 

Parecoxib sodium, reconstituted with the solvent indicated in the SmPC, diluted in an infusion bag/bottle 100 mL, administered intravenously... 

Noveck RJ, Laurent A, Kuss M, Talwalker S, Hubbard, RG. Parecoxib sodium does not impair platelet function in healthy elderly and non-elderly individuals two randomized, controlled tirals. Clin DrugInvestig2001 2 A6S-A76. 

Harris SI, Stoltz RR, LeComte D, Hubbard RC. Parecoxib sodium demonstrates gastrointestinal safety comparable to placebo in healthy subjects. / Clin... 

Malan TP Jr, Marsh G, Hakki SI, Grossman E, Traylor L, Hubbard RC. Parecoxib sodium, a parenteral cyclooxygenase 2 selective inhibitor, improves morphine analgesia and is opioid-sparing following total hip arthroplasty. Anesthesiology 2003 98 ... 

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