An electronic study of pyrazolones drugs on agranulocytosis

Medicinal Chemistry Research

Volumn 21, Issue 7, 2012, Pages 1389-1394

  Silva, J Rodrigues ^a   Queiroz, A Noronha ^a   Fontes Jr , E A ^a   Silva, M V Santos ^a   Herculano, A Manoel ^a   Neto, A M J Chaves ^a   Borges, R Santos ^a  

^a FEDERAL UNIVERSITY OF PARÁ   (Brazil)

Author keywords

Agranulocytosis; Antioxidant; MEPs; Pyrazolones derivatives; Stereoelectronic properties; Theoretical study

Indexed keywords

AMINOPHENAZONE; DIPYRONE; PHENAZONE; PROPYPHENAZONE; PYRAZOLONE DERIVATIVE;

AGRANULOCYTOSIS; ARTICLE; DENSITY; DRUG SAFETY; DRUG STRUCTURE; ELECTRONICS; OXIDATION; TOXICOLOGY;

EID: 84861872065     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-011-9652-y     Document Type: Article

References (32)

1. Alves CN, Borges RS, Silva ABF (2006) Density functional theory study of metabolic derivatives of the oxidation of paracetamol. Int J Quant Chem 106:2617-2623
2. Becke AD (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648-5652
3. Bentur Y, Cohen O (2004) Dipyrone overdose. J Toxicol Clin Toxicol 42:261-265
4. Borges RS, Mendes APS, Silva BHS, Alves CN, Nascimento JLM (2011) A theoretical study of salicylate oxidation for ADME prediction. Med Chem Res 20:269-273
5. Brogden RN (1986) Pyrazolone derivatives. Drugs 32:60-70
6. ChemOffice (2005) CambridgeSoft Corporation, User's Manual Revision .0.1
7. Coersmeier C, Wittenberg HR, Aehringhaus U et al (1986) Effect of anti-inflammatory and analgesic pyrazoles on arachidonic acid metabolism in isolated heart and gastric mucosa preparations. Agents Actions Suppl 19:137-153
8. Costa D, Marques AP, Lima JLFC, Fernandes E (2006) Inhibition of human neutrophil oxidative burst by pyrazolone derivatives. Free Radic Biol Med 40:632-640
9. Diniz JEM, Borges RS, Alves CN (2004) A DFT study for paracetamol and 3,5-disubstituted analogues. J Mol Struct Theochem 673:93-97
10. 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
11. Freire ADT, Landivar LMC, Queiroz AN, Borges RS (2009) A theoretical study for oxidative metabolism of salicylates. J Comp Theor Nanosci 6:1140-1142
12. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Aust in AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2003) Gaussian 03, Revision B.03, Gaussian, Inc. Wallingford, CT
13. Gomes BAQ, Queiroz AN, Borges RS (2009) A theoretical study of resveratrol oxidation. J Comp Theor Nanosci 6:1637-1639
14. Graham GG, Scott KF (2003) Mechanisms of action of paracetamol and related analgesics. Inflammopharmacol 11:401-413
15. Griffin BW (1977) Free radical intermediate in the N-demethylation of aminopyrine by horseradish peroxidase-hydrogen peroxide. FEBS Lett 74:139-143
16. Griffin BW, Ting PL (1978) Mechanism of N-de-methylation of aminopyrine by hydrogen peroxide catalyzed by horseradish peroxidase, methemoglobin, and protohemin. Biochemistry 17:2206-2211
17. Gursoy A, Demirayak S, Capan G et al (2000) Synthesis and preliminary evaluation of new 5-pyrazolinone derivatives as analgesic agents. Eur J Med Chem 35:359-364
18. Hehre WJ, Radom L, Schleyer PVR, Pople JA (1986) Ab initio molecular orbital theory. Wiley, New York
19. Ibáñez L, Vidal X, Ballarín E et al (2005) Agranulocytosis associated with dipyrone (metamizol). Eur J Clin Pharmacol 60:821-829
20. Kalyanaraman B, Sohnle PG (1985) Generation of free radical intermediates from foreign compounds by neutrophil-derived oxidants. J Clin Investig 75:1618-1622
21. Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785-789
22. Levy M (2000) Hypersensitivity to pyrazolones. Thorax 55:S72-S74
23. Patton W, Dufful S (1994) Idiosyncratic drug-induced haematological abnormalities. Drug Saf 11:445-462
24. Pérez-Gilabert M, Sanchez-Ferrer A, Garcia-Carmona F (1997) Oxidation of aminopyrine by the hydroperoxidase activity of lipoxygenase: a new proposed mechanism of N-demethylation. Free Radic Biol Med 23:548-555
25. Portmann S, Lüthi HP (2000) Molekel: an interactive molecular graphics. Chimia 54:766-770
26. Queiroz AN, Bruno AQ, Moraes WMJ, Borges RS (2009) A theoretical antioxidant pharmacophore for resveratrol. Eur J Med Chem 44:1644-1649
27. Queiroz AN, Mendes APS, Leal MRS, Chaves Neto AMJ, Borges RS (2010) Tautomerism and radical-scavenging activity of edaravone by DFT methods. J Comp Theor Nanosci 7:153-156
28. Sayo H, Saito M (1990) The mechanism of myeloperoxidasecatalysed oxidation of aminopyrine. Xenobiotica 9:957-965
29. Silva ER, Queiroz AN, Almeida ED, Borges RS (2009) A DFT study of aminophenol stability. J Comp Theor Nanosci 6:1694-1696
30. Stewart JJP (1989) Optimization of parameters for semiempirical methods I. Method. J Comput Chem 10:209-220
31. 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
32. Xia Y, Zweier JL (1997) Measurement of myeloperoxidase in leukocyte-containing tissues. Anal Biochem 245:193-196