Inhibition of cyclooxygenases by dipyrone

British Journal of Pharmacology

Volumn 151, Issue 4, 2007, Pages 494-503

  Pierre, S C ^a   Schmidt, R ^a   Brenneis, C ^a   Michaelis, M ^b   Geisslinger, G ^a   Scholich, K ^a  

^a UNIVERSITY HOSPITAL FRANKFURT   (Germany)

^b SANOFI AVENTIS DEUTSCHLAND GMBH   (Germany)

Author keywords

Cyclooxygenase; Dipyrone; Haem; Prostaglandin E2; Prostaglandin H 2 synthase; Radical

Indexed keywords

4 ACETYL AMINO ANTIPYRINE; 4 FORMYL AMINO ANTIPYRINE; 4 METHYL AMINO ANTIPYRINE; AMINO ANTIPYRINE; DIPYRONE; DRUG METABOLITE; FERROUS ION; HEME; PROSTAGLANDIN SYNTHASE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG BINDING; DRUG EFFECT; ENZYME ACTIVE SITE; ENZYME INHIBITION; HUMAN; HUMAN CELL; LIPID PEROXIDATION; MALE; MASS SPECTROMETRY; MOUSE; NONHUMAN; NORMAL HUMAN; PHOTOMETRY; PRIORITY JOURNAL; PROSTAGLANDIN SYNTHESIS; PROTEIN EXPRESSION; RAT; ULTRAVIOLET SPECTROSCOPY; WESTERN BLOTTING;

AMPYRONE; ANIMALS; CYCLOOXYGENASE INHIBITORS; DIPYRONE; HEME; HYDROGEN PEROXIDE; IRON; MALE; RATS; RATS, SPRAGUE-DAWLEY;

EID: 34250156372     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1038/sj.bjp.0707239     Document Type: Article

References (42)

1. Abbate R, Gori AM, Pinto S, Attanasio M, Paniccia R, Coppo M et al. (1990). Cyclooxygenase and lipoxygenase metabolite synthesis by polymorphonuclear neutrophils: in vitro effect of dipyrone. Prostaglandins Leukot Essent Fatty Acids 41: 89-93.
2. Aronoff DM, Boutaud O, Marnett LJ, Oates JA (2003). Inhibition of prostaglandin H2 synthases by salicylate is dependent on the oxidative state of the enzymes. J Pharmacol Exp Ther 304: 589-595.
3. Ayoub SS, Botting RM, Goorha S, Colville-Nash PR, Willoughby DA, Ballou LR (2004). Acetaminophen-induced hypothermia in mice is mediated by a prostaglandin endoperoxide synthase 1 gene-derived protein. Proc Natl Acad Sci USA 101: 11165-11169.
4. Boutaud O, Aronoff DM, Richardson JH, Marnett LJ, Oates JA (2002). Determinants of the cellular specificity of acetaminophen as an inhibitor of prostaglandin H(2) synthases. Proc Natl Acad Sci USA 99: 7130-7135.
5. Brenneis C, Maier TJ, Schmidt R, Hofacker A, Zulauf L, Jakobsson PJ et al. (2006). Inhibition of prostaglandin E2 synthesis by SC-560 is independent of cyclooxygenase 1 inhibition. FASEB J 20: 1352-1360.
6. Campos C, de Gregorio R, Garcia-Nieto R, Gago F, Ortiz P, Alemany S (1999). Regulation of cyclooxygenase activity by metamizol. Eur J Pharmacol 378: 339-347.
7. Carlsson KH, Helmreich J, Jurna I (1986). Activation of inhibition from the periaqueductal grey matter mediates central analgesic effect of metamizol (dipyrone). Pain 27: 373-390.
8. Chandrasekharan NV, Dai H, Roos KL, Evanson NK, Tomsik J, Elton TS et al. (2002). COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: cloning, structure, and expression. Proc Natl Acad Sci USA 99: 13926-13931.
9. Costa D, Marques AP, Reis RL, Lima JL, Fernandes E (2006a). Inhibition of human neutrophil oxidative burst by pyrazolone derivatives. Free Radic Biol Med 40: 632-640.
10. Costa D, Vieira A, Fernandes E (2006b). Dipyrone and aminopyrine are effective scavengers of reactive nitrogen species. Redox Rep 11: 136-142.
11. Damm D (1989). Simultaneous determination of the main metabolites of dipyrone by high-pressure liquid chromatography. Arzneimittelforschung 39: 1415-1417.
12. Eldor A, Polliack G, Vlodavsky I, Levy M (1983). Effects of dipyrone on prostaglandin production by human platelets and cultured bovine aortic endothelial cells. Thromb Haemost 49: 132-137.
13. Eldor A, Zylber-Katz E, Levy M (1984). The effect of oral administration of dipyrone on the capacity of blood platelets to synthesize thromboxane A2 in man. Eur J Clin Pharmacol 26: 171-176.
14. Eling TE, Mason RP, Sivarajah K (1985). The formation of aminopyrine cation radical by the peroxidase activity of prostaglandin H synthase and subsequent reactions of the radical. J Biol Chem 260: 1601-1607.
15. Geisslinger G, Peskar BA, Pallapies D, Sittl R, Levy M, Brune K (1996). The effects on platelet aggregation and prostanoid biosynthesis of two parenteral analgesics: ketorolac tromethamine and dipyrone. Thromb Haemost 76: 592-597.
16. Gelgor L, Cartmell S, Mitchell D (1992). Intracerebroventricular micro-injections of non-steroidal anti-inflammatory drugs abolish reperfusion hyperalgesia in the rat's tail. Pain 50: 323-329.
17. Huang X, Moir RD, Tanzi RE, Bush AI, Rogers JT (2004). Redox-active metals, oxidative stress, and Alzheimer's disease pathology. Ann N Y Acad Sci 1012: 153-163.
18. Imlay JA (2003). Pathways of oxidative damage. Annu Rev Microbiol 57: 395-418.
19. Iogannsen MG, Petrov AS, Kachurin AM (1993). Aminopyrazolone free radicals in the hydrogen peroxide oxidation reaction. Vopr Med Khim 39: 9-13.
20. Lambeir AM, Markey CM, Dunford HB, Marnett LJ (1985). Spectral properties of the higher oxidation states of prostaglandin H synthase. J Biol Chem 260: 14894-14896.
21. Lasker JM, Sivarajah K, Mason RP, Kalyanaraman B, Abou-Donia MB, Eling TE (1981). A free radical mechanism of prostaglandin synthase-dependent aminopyrine demethylation. J Biol Chem 256: 7764-7767.
22. Levy M, Brune K, Zylber-Katz E, Cohen O, Caraco Y, Geisslinger G (1998). Cerebrospinal fluid prostaglandins after systemic dipyrone intake. Clin Pharmacol Ther 64: 117-122.
23. Levy M, Zylber-Katz E, Rosenkranz B (1995). Clinical pharmacokinetics of dipyrone and its metabolites. Clin Pharmacokinet 28: 216-234.
24. Lipinski P, Drapier J.C, Oliveira L, Retmanska H, Sochanowicz B, Kruszewski M (2000). Intracellular iron status as a hallmark of mammalian cell susceptibility to oxidative stress: a study of L5178Y mouse lymphoma cell lines differentially sensitive to H(2)O(2). Blood 95: 2960-2966.
25. Lucas R, Warner TD, Vojnovic I, Mitchell JA (2005). Cellular mechanisms of acetaminophen: role of cyclo-oxygenase. FASEB J 19: 635-637.
26. Marnett LJ (2000). Cyclooxygenase mechanisms. Curr Opin Chem Biol 4: 545-552.
27. Marnett LJ, Rowlinson SW, Goodwin DC, Kalgutkar AS, Lanzo CA (1999). Arachidonic acid oxygenation by COX-1 and COX-2. Mechanisms of catalysis and inhibition. J Biol Chem 274: 22903-22906.
28. Smith WL, Dewitt DL (1996). Prostaglandin endoperoxide H synthases-1 and -2. Adv Immunol 62: 167-215.
29. Smith WL, DeWitt DL, Garavito RM (2000). Cyclooxygenases: structural, cellular, and molecular biology. Annu Rev Biochem 69: 145-182.
30. Tegeder I, Geisslinger G (2006). Cardiovascular risk with cyclooxygenase inhibitors: general problem with substance specific differences? Naunyn Schmiedebergs Arch Pharmacol 12: 1269-1277.
31. Tortorici V, Vanegas H (1995). Anti-nociception induced by systemic or PAG-microinjected lysine-acetylsalicylate in rats. Effects on tailflick related activity of medullary off- and on-cells. Eur J Neurosci 7: 1857-1865.
32. Tsai A, Palmer G, Xiao G, Swinney DC, Kulmacz RJ (1998). Structural characterization of arachidonyl radicals formed by prostaglandin H synthase-2 and prostaglandin H synthase-1 reconstituted with mangano protoporphyrin IX. J Biol Chem 273: 3888-3894.
33. Uetrecht JP, Ma HM, MacKnight E, McClelland R (1995). Oxidation of aminopyrine by hypochlorite to a reactive dication: possible implications for aminopyrine-induced agranulocytosis. Chem Res Toxicol 8: 226-233.
34. Van Eps N, Szundi I, Einarsdottir O (2003). pH dependence of the reduction of dioxygen to water by cytochrome c oxidase. 1. The P(R) state is a pH-dependent mixture of three intermediates, A, P, and F. Biochemistry 42: 5065-5073.
35. Vanegas H, Schaible HG (2001). Prostaglandins and cyclooxygenases in the spinal cord. Prog Neurobiol 64: 327-363.
36. Vlahov V, Badian M, Verho M, Bacracheva N (1990). Pharmacokinetics of metamizol metabolites in healthy subjects after a single oral dose of metamizol sodium. Eur J Clin Pharmacol 38: 61-65.
37. Voegtle HL, Sono M, Adak S, Pond AE, Tomita T, Perera R et al. (2003). Spectroscopic characterization of five- and six-coordinate ferrous-NO heme complexes. Evidence for heme Fe-proximal cysteinate bond cleavage in the ferrous-NO adducts of the Trp-409Tyr/Phe proximal environment mutants of neuronal nitric oxide synthase. Biochemistry 42: 2475-2484.
38. Wang MX, Wei A, Yuan J, Trickett A, Knoops B, Murrell GA (2002). Expression and regulation of peroxiredoxin 5 in human osteoarthritis. FEBS Lett 531: 359-362.
39. Warner TD, Mitchell JA (2002). Cyclooxygenase-3 (COX-3): filling in the gaps toward a COX continuum? Proc Natl Acad Sci USA 99: 13371-13373.
40. Wickelgren I (2002). Pain research. Enzyme might relieve research headache. Science 297: 1976.
41. Wong BS, Brown DR, Pan T, Whiteman M, Liu T, Bu X et al. (2001). Oxidative impairment in scrapie-infected mice is associated with brain metals perturbations and altered antioxidant activities. J Neurochem 79: 689-698.
42. Woolf CJ, Costigan M (1999). Transcriptional and posttranslational plasticity and the generation of inflammatory pain. Proc Natl Acad Sci USA 96: 7723-7730.