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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

Profenid     2-[3-(phenylcarbonyl) phenyl]propanoic acid

Synonyms: Alrheumat, Alrheumum, Orudis, ketoprofen, RP-19583, ...
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Disease relevance of Profenid


Psychiatry related information on Profenid


High impact information on Profenid


Chemical compound and disease context of Profenid


Biological context of Profenid


Anatomical context of Profenid

  • Furthermore, the differential response to ketoprofen indicates that the specific antigen-stimulated mediator release profiles of dermal and synovial mast cells are different [22].
  • Total and free ketoprofen in serum and synovial fluid after intramuscular injection [21].
  • Immunoblots of liver microsomes incubated with ketoprofen acylglucuronide and probed with antiketoprofen antibodies revealed the presence of several protein adducts; among those was a major immunoreactive protein at 56 kDa, in the range of the apparent molecular mass of UGTs [23].
  • Addition of ketoprofen in vitro to B cells from patients with CVI resulted in improved proliferation and differentiation in four of five additional patients with CVI studied [24].
  • The presence of these covalent adducts within the endoplasmic reticulum of cells expressing UGT2B1 was demonstrated following addition of ketoprofen to culture medium by immunofluorescence microscopy with antiketoprofen antibodies [23].

Associations of Profenid with other chemical compounds


Gene context of Profenid

  • (S)oxazepam glucuronidation is inhibited by ketoprofen and other substrates of UGT2B7 [29].
  • Therefore, we studied the interaction of the ketoprofen metabolites with the COX enzymes [30].
  • Either M-5011 or ketoprofen potently inhibited prostaglandin (PG) E2 production by cyclooxygenase (COX)-2 from exogenous AA in interleukin-1beta (IL-1beta)-stimulated cells [31].
  • 4. Under these experimental conditions, ketoprofen enantioselectively inhibited the cyclo-oxygenase activity of both PGHS-1 and PGHS-2 with equal potency (IC50 ratio: approx. 0.5 for both enantiomers), while L-745,337 and NS-398 achieved selective inhibition of monocyte PGHS-2 (IC50 ratio: > 150) [32].
  • 4. A cyclo-oxygenase inhibitor, ketoprofen (3 mg kg-1) administered 15 min before either cytokine completely abolished the fever induced by both IL-1 alpha (2500 u kg-1) and IL-1 beta (500 u kg-1) [33].

Analytical, diagnostic and therapeutic context of Profenid


  1. Ketoprofen causing pseudotumor cerebri in Bartter's syndrome. Larizza, D., Colombo, A., Lorini, R., Severi, F. N. Engl. J. Med. (1979) [Pubmed]
  2. Clinical and pharmacokinetic evidence of a life-threatening interaction between methotrexate and ketoprofen. Thyss, A., Milano, G., Kubar, J., Namer, M., Schneider, M. Lancet (1986) [Pubmed]
  3. Life-threatening asthma, urticaria, and angiooedema after ketoprofen. Frith, P., Dolovich, J., Hargreave, F.E. Lancet (1978) [Pubmed]
  4. Conjunctivitis due to ketoprofen. Umez-Eronini, E.M. Lancet (1978) [Pubmed]
  5. Interferon-alpha 2b combined with daily ketoprofen administration improves virological response in chronic hepatitis C: a prospective and randomised trial. Muñoz, A.E., Levi, D., Podestá, A., Gorín, J.M., González, J., Bartellini, M.A., Munne, M.S., Cabanne, A., Flichman, D., Terg, R. Gut (2000) [Pubmed]
  6. Protein binding and stereoselectivity of nonsteroidal anti-inflammatory drugs. Lapicque, F., Muller, N., Payan, E., Dubois, N., Netter, P. Clinical pharmacokinetics. (1993) [Pubmed]
  7. Improved brain delivery of a nonsteroidal anti-inflammatory drug with a synthetic glyceride ester: a preliminary attempt at a CNS drug delivery system for the therapy of Alzheimer's disease. Deguchi, Y., Hayashi, H., Fujii, S., Naito, T., Yokoyama, Y., Yamada, S., Kimura, R. Journal of drug targeting. (2000) [Pubmed]
  8. Ketoprofen ion-selective electrode and its application to pharmaceutical analysis. Lenik, J., Wardak, C., Marczewska, B. Acta poloniae pharmaceutica (2006) [Pubmed]
  9. Involvement of opioidergic and alpha2-adrenergic mechanisms in the central analgesic effects of non-steroidal anti-inflammatory drugs in sheep. Lizarraga, I., Chambers, J.P. Res. Vet. Sci. (2006) [Pubmed]
  10. Risk of upper gastrointestinal bleeding and perforation associated with individual non-steroidal anti-inflammatory drugs. García Rodríguez, L.A., Jick, H. Lancet (1994) [Pubmed]
  11. Cyclooxygenase-2-selective nonsteroidal anti-inflammatory drugs inhibit hepatocyte growth factor/scatter factor-induced angiogenesis. Sengupta, S., Sellers, L.A., Cindrova, T., Skepper, J., Gherardi, E., Sasisekharan, R., Fan, T.P. Cancer Res. (2003) [Pubmed]
  12. Lipopolysaccharide-induced increase of prostaglandin E(2) is mediated by inducible nitric oxide synthase activation of the constitutive cyclooxygenase and induction of membrane-associated prostaglandin E synthase. Devaux, Y., Seguin, C., Grosjean, S., de Talancé, N., Camaeti, V., Burlet, A., Zannad, F., Meistelman, C., Mertes, P.M., Longrois, D. J. Immunol. (2001) [Pubmed]
  13. Arginine 120 of prostaglandin G/H synthase-1 is required for the inhibition by nonsteroidal anti-inflammatory drugs containing a carboxylic acid moiety. Mancini, J.A., Riendeau, D., Falgueyret, J.P., Vickers, P.J., O'Neill, G.P. J. Biol. Chem. (1995) [Pubmed]
  14. Double-blind evaluation of short-term analgesic efficacy of orally administered dexketoprofen trometamol and ketorolac in bone cancer pain. Rodríguez, M.J., Contreras, D., Gálvez, R., Castro, A., Camba, M.A., Busquets, C., Herrera, J. Pain (2003) [Pubmed]
  15. Clinical experiences with the intramuscular injection of tiaprofenic acid in rheumatic diseases, with particular emphasis on time of onset and duration of the analgesic effect. Katona, G., Burgos-Vargas, R. Drugs (1988) [Pubmed]
  16. Effects of ketoprofen and indomethacin on leukocyte migration in two models of pleurisy induced by carrageenan or zymosan-activated serum in rats. Vannier, E., Roch-Arveiller, M., Molinie, B., Terlain, B., Giroud, J.P. J. Pharmacol. Exp. Ther. (1989) [Pubmed]
  17. Adverse drug reactions related to the use of NSAIDs with a focus on nimesulide: results of spontaneous reporting from a Northern Italian area. Conforti, A., Leone, R., Moretti, U., Mozzo, F., Velo, G. Drug safety : an international journal of medical toxicology and drug experience. (2001) [Pubmed]
  18. Studies in laboratory animals to assess the safety of anti-inflammatory agents in acute porphyria. McColl, K.E., Thompson, G.G., Moore, M.R. Ann. Rheum. Dis. (1987) [Pubmed]
  19. Effects of food and sucralfate on the pharmacokinetics of naproxen and ketoprofen in humans. Caillé, G., du Souich, P., Besner, J.G., Gervais, P., Vézina, M. Am. J. Med. (1989) [Pubmed]
  20. Effects of probenecid on ketoprofen kinetics. Upton, R.A., Williams, R.L., Buskin, J.N., Jones, R.M. Clin. Pharmacol. Ther. (1982) [Pubmed]
  21. Total and free ketoprofen in serum and synovial fluid after intramuscular injection. Netter, P., Bannwarth, B., Lapicque, F., Harrewyn, J.M., Frydman, A., Tamisier, J.N., Gaucher, A., Royer, R.J. Clin. Pharmacol. Ther. (1987) [Pubmed]
  22. In vivo effects of nonsteroidal antiinflammatory drugs on rat skin and synovial mast cell-induced vasopermeability. Malone, D.G., Vikingsson, A., Seebruch, J.S., Verbsky, J.W., Dolan, P.W. Arthritis Rheum. (1991) [Pubmed]
  23. Human and rat liver UDP-glucuronosyltransferases are targets of ketoprofen acylglucuronide. Terrier, N., Benoit, E., Senay, C., Lapicque, F., Radominska-Pandya, A., Magdalou, J., Fournel-Gigleux, S. Mol. Pharmacol. (1999) [Pubmed]
  24. Improved in vitro antigen-specific antibody synthesis in two patients with common variable immunodeficiency taking an oral cyclooxygenase and lipoxygenase inhibitor (ketoprofen). Ambrus, J.L., Haneiwich, S., Chesky, L., McFarland, P., Engler, R.J. J. Allergy Clin. Immunol. (1991) [Pubmed]
  25. Variability in risk of gastrointestinal complications with different nonsteroidal anti-inflammatory drugs. García Rodríguez, L.A. Am. J. Med. (1998) [Pubmed]
  26. Liquid-phase microextraction and capillary electrophoresis of acidic drugs. Pedersen-Bjergaard, S., Rasmussen, K.E. Electrophoresis (2000) [Pubmed]
  27. Preclinical and clinical development of dexketoprofen. Mauleón, D., Artigas, R., García, M.L., Carganico, G. Drugs (1996) [Pubmed]
  28. Double-blind parallel comparison of multiple doses of ketorolac, ketoprofen and placebo administered orally to patients with postoperative dental pain. Olmedo, M.V., Gálvez, R., Vallecillo, M. Pain (2001) [Pubmed]
  29. (S)oxazepam glucuronidation is inhibited by ketoprofen and other substrates of UGT2B7. Patel, M., Tang, B.K., Kalow, W. Pharmacogenetics (1995) [Pubmed]
  30. Elucidation of the mechanism of inhibition of cyclooxygenases by acyl-coenzyme A and acylglucuronic conjugates of ketoprofen. Levoin, N., Blondeau, C., Guillaume, C., Grandcolas, L., Chretien, F., Jouzeau, J.Y., Benoit, E., Chapleur, Y., Netter, P., Lapicque, F. Biochem. Pharmacol. (2004) [Pubmed]
  31. The effects of a newly developed nonsteroidal anti-inflammatory drug (M-5011) on arachidonic acid metabolism in rheumatoid synovial fibroblasts. Tobetto, K., Yamamoto, Y., Kataoka, M., Ando, T., Sugimoto, K., Himeno, M. Jpn. J. Pharmacol. (1997) [Pubmed]
  32. Effects of the novel anti-inflammatory compounds, N-[2-(cyclohexyloxy)-4-nitrophenyl] methanesulphonamide (NS-398) and 5-methanesulphonamido-6-(2,4-difluorothio-phenyl)-1-inda none (L-745,337), on the cyclo-oxygenase activity of human blood prostaglandin endoperoxide synthases. Panara, M.R., Greco, A., Santini, G., Sciulli, M.G., Rotondo, M.T., Padovano, R., di Giamberardino, M., Cipollone, F., Cuccurullo, F., Patrono, C. Br. J. Pharmacol. (1995) [Pubmed]
  33. A study of the pyrogenic actions of interleukin-1 alpha and interleukin-1 beta: interactions with a steroidal and a non-steroidal anti-inflammatory agent. Davidson, J., Milton, A.S., Rotondo, D. Br. J. Pharmacol. (1990) [Pubmed]
  34. Ketoprofen, acetaminophen plus oxycodone, and acetaminophen in the relief of postoperative pain. Sunshine, A., Olson, N.Z., Zighelboim, I., De Castro, A. Clin. Pharmacol. Ther. (1993) [Pubmed]
  35. Clinical pharmacokinetics of ketoprofen after single intravenous administration as a bolus or infusion. Debruyne, D., Hurault de Ligny, B., Ryckelynck, J.P., Albessard, F., Moulin, M. Clinical pharmacokinetics. (1987) [Pubmed]
  36. Pharmacokinetics of intravenous and rectal ketoprofen in young children. Kokki, H., Karvinen, M., Suhonen, P. Clinical pharmacokinetics. (2003) [Pubmed]
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