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Chemical Compound Review

zomepirac     2-[5-(4- chlorophenyl)carbonyl-1,4- dimethyl...

Synonyms: Zomepiracum, CHEMBL19490, SureCN25735, AGN-PC-005DDV, AG-J-61452, ...
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Disease relevance of ZOMEPIRAC SODIUM


Psychiatry related information on ZOMEPIRAC SODIUM


High impact information on ZOMEPIRAC SODIUM


Chemical compound and disease context of ZOMEPIRAC SODIUM


Biological context of ZOMEPIRAC SODIUM


Anatomical context of ZOMEPIRAC SODIUM


Associations of ZOMEPIRAC SODIUM with other chemical compounds

  • In vitro drug binding was also observed for the isomers of zomepirac glucuronide which were formed by intramolecular acyl migration [11].
  • Probenecid decreased total plasma clearance of zomepirac by 64%, which resulted in an increase in bioavailability from 0.55 without probenecid to 0.84 when given concurrently [16].
  • In contrast, zomepirac did not inhibit [cAMP]i generation or stimulate cell migration but weakly antagonized the effects of indomethacin on [cAMP]i. Together, these results reveal structural features of arylacetic acid NSAIDs that may be exploited for the development of selective CRTH2 ligands [22].
  • Human serum albumins modified by covalently bound tolmetin or zomepirac were synthesized as models for similar products formed in vivo from acyl glucuronides [23].
  • When acyl glucuronide metabolites of two previously marketed acidic drugs, zomepirac and suprofen, were incubated with albumin at a concentration of 2.5 mM, more fluorescent product was formed than by 500 mM glucose [24].

Gene context of ZOMEPIRAC SODIUM

  • Clinical comparison of zomepirac with APC/codeine combination in the treatment of pain following oral surgery [25].
  • Bovine brain microtubular protein (MTP) was purified by assembly-disassembly cycles and incubated with the nonsteroidal anti-inflammatory drug (NSAID) zomepirac (ZP), its acyl glucuronide (ZAG) and rearrangement isomers (iso-ZAG) at various concentrations for 2 h at room temperature and pH 7 [26].
  • Nonsteroidal anti-inflammatory agents, Part IV - A new analgesic: zomepirac [27].
  • Zomepirac failed to displace tritiated etorphine significantly at concentrations up to 200 mumol/l. It was active (3-7 X 10(-5) mol/l) on both the electrically stimulated guinea pig ileum and mouse vas deferens but was less efficacious than morphine; these effects were not reversed by narcotic antagonists [7].

Analytical, diagnostic and therapeutic context of ZOMEPIRAC SODIUM


  1. Apparent anaphylactic reaction to zomepirac (Zomax). Samuel, S.A. N. Engl. J. Med. (1981) [Pubmed]
  2. Zomepirac sodium in the treatment of primary dysmenorrhea syndrome. Budoff, P.W. N. Engl. J. Med. (1982) [Pubmed]
  3. Orally administered zomepirac and parenterally administered morphine. Comparison for the treatment of postoperative pain. Forrest, W.H. JAMA (1980) [Pubmed]
  4. Nonoliguric renal failure associated with zomepirac. Lisker, W.H. JAMA (1983) [Pubmed]
  5. Anaphylactic shock, acute renal failure, and disseminated intravascular coagulation. Suspected complications of zomepirac. Smith, V.T. JAMA (1982) [Pubmed]
  6. Evaluation for withdrawal symptoms following chronic zomepirac administration. O'Brien, C.P., Minn, F.L. Journal of clinical pharmacology. (1980) [Pubmed]
  7. Zomepirac: preclinical narcotic abuse liability evaluation. Woods, J.H., Young, A.M., Medzihradsky, F., Smith, C.B., Aceto, M.D., Harris, L.S., Jacobson, A.E. Arzneimittel-Forschung. (1983) [Pubmed]
  8. Zomepirac-induced serum sickness. A report of two cases. Kiani, R., Kushner, M. JAMA (1983) [Pubmed]
  9. Stomatitis associated with zomepirac. Bates, L.H., Triplett, W.C., Berry, E.R., Weddle, R.A. JAMA (1982) [Pubmed]
  10. Zomepirac sodium. A new nonaddicting analgesic. Lewis, J.R. JAMA (1981) [Pubmed]
  11. Irreversible binding of zomepirac to plasma protein in vitro and in vivo. Smith, P.C., McDonagh, A.F., Benet, L.Z. J. Clin. Invest. (1986) [Pubmed]
  12. Abnormal glucuronidation of zomepirac in patients with cirrhosis of the liver. Witassek, F., Bircher, J., Huguenin, P., Preisig, R. Hepatology (1983) [Pubmed]
  13. Evidence for the bioactivation of zomepirac and tolmetin by an oxidative pathway: identification of glutathione adducts in vitro in human liver microsomes and in vivo in rats. Chen, Q., Doss, G.A., Tung, E.C., Liu, W., Tang, Y.S., Braun, M.P., Didolkar, V., Strauss, J.R., Wang, R.W., Stearns, R.A., Evans, D.C., Baillie, T.A., Tang, W. Drug Metab. Dispos. (2006) [Pubmed]
  14. Zomepirac-related acute renal failure. Boike, S.C., Rybak, M.J., Tintinalli, J.E., Veneri, R. Drug intelligence & clinical pharmacy. (1983) [Pubmed]
  15. Zomepirac kinetics in healthy males. Nayak, R.K., Ng, K.T., Gottlieb, S., Plostnieks, J. Clin. Pharmacol. Ther. (1980) [Pubmed]
  16. Effect of probenecid on the formation and elimination of acyl glucuronides: studies with zomepirac. Smith, P.C., Langendijk, P.N., Bosso, J.A., Benet, L.Z. Clin. Pharmacol. Ther. (1985) [Pubmed]
  17. Focal renal cortical necrosis associated with zomepirac. Darwish, R., Vaziri, N.D., Gupta, S., Novey, H., Spear, G.S., Licorish, K., Powers, D., Cesario, T. Am. J. Med. (1984) [Pubmed]
  18. The effect of zomepirac on red blood cell survival and immune system. Johnson, P.C. Journal of clinical pharmacology. (1980) [Pubmed]
  19. Effect of zomepirac on experimental coronary artery thrombosis and ischemic myocardial injury in the conscious dog. Hook, B.G., Romson, J.L., Jolly, S.R., Bailie, M.B., Lucchesi, B.R. J. Cardiovasc. Pharmacol. (1983) [Pubmed]
  20. Bile duct ligation promotes covalent drug-protein adduct formation in plasma but not in liver of rats given zomepirac. Wang, M., Dickinson, R.G. Life Sci. (2000) [Pubmed]
  21. Inhibition of proliferation of HT-29 colon adenocarcinoma cells by carboxylate NSAIDs and their acyl glucuronides. Cannell, G.R., Vesey, D.A., Dickinson, R.G. Life Sci. (2001) [Pubmed]
  22. Structural determinants of arylacetic acid nonsteroidal anti-inflammatory drugs necessary for binding and activation of the prostaglandin D2 receptor CRTH2. Hata, A.N., Lybrand, T.P., Marnett, L.J., Breyer, R.M. Mol. Pharmacol. (2005) [Pubmed]
  23. Synthesis and mass-spectrometric characterization of human serum albumins modified by covalent binding of two non-steroidal anti-inflammatory drugs: tolmetin and zomepirac. Zia-Amirhosseini, P., Ding, A., Burlingame, A.L., McDonagh, A.F., Benet, L.Z. Biochem. J. (1995) [Pubmed]
  24. Nonenzymic glycation of albumin by acyl glucuronides in vitro. Comparison of reactions with reducing sugars. Smith, P.C., Wang, C. Biochem. Pharmacol. (1992) [Pubmed]
  25. Clinical comparison of zomepirac with APC/codeine combination in the treatment of pain following oral surgery. Mehlisch, D.R., Joy, E.D., Moore, T.E., Porter, K., Stumpf, A.J., Wolfe, S.H. Journal of clinical pharmacology. (1980) [Pubmed]
  26. Zomepirac acyl glucuronide covalently modifies tubulin in vitro and in vivo and inhibits its assembly in an in vitro system. Bailey, M.J., Worrall, S., de Jersey, J., Dickinson, R.G. Chem. Biol. Interact. (1998) [Pubmed]
  27. Nonsteroidal anti-inflammatory agents, Part IV - A new analgesic: zomepirac. Romankiewicz, J.A. The Journal of practical nursing. (1982) [Pubmed]
  28. Influence of uremia, hemodialysis, and nonesterified fatty acids on zomepirac plasma protein binding. Pritchard, J.F., O'Neill, P.J., Affrime, M.B., Lowenthal, D.T. Clin. Pharmacol. Ther. (1983) [Pubmed]
  29. Abuse potential of zomepirac. Johnson, R.E., Jasinski, D.R., Kocher, T.R. Clin. Pharmacol. Ther. (1983) [Pubmed]
  30. Analgesic activity of diflunisal [MK-647; 5-(2,4-difluorophenyl)salicylic acid] in rats with hyperalgesia induced by Freund's adjuvant. Winter, C.A., Kling, P.J., Tocco, D.J., Tanabe, K. J. Pharmacol. Exp. Ther. (1979) [Pubmed]
  31. Renal handling of zomepirac sodium (McN-2783-21-98) in the rat. O'Neill, P.J., Yorgey, K.A., Migdalof, B.H., Gussin, R.Z. J. Pharmacol. Exp. Ther. (1979) [Pubmed]
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