메뉴 건너뛰기




Volumn 20, Issue 8, 2007, Pages 1093-1098

Disproportionation of clozapine radical: A link between one-electron oxidation of clozapine and formation of its nitrenium cation

Author keywords

[No Author keywords available]

Indexed keywords

ANION; AZIDE; CATION; CLOZAPINE; CYSTEINE; GLUTATHIONE; OLANZAPINE; RADICAL;

EID: 34548508871     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx700128c     Document Type: Article
Times cited : (20)

References (35)
  • 1
    • 0035055501 scopus 로고    scopus 로고
    • The pharmacology and toxicology of atypical antipsychotic agents
    • Burns, M. J. (2001) The pharmacology and toxicology of atypical antipsychotic agents. Clin. Toxicol. 39, 1-14.
    • (2001) Clin. Toxicol , vol.39 , pp. 1-14
    • Burns, M.J.1
  • 2
    • 0029775615 scopus 로고    scopus 로고
    • Neutropenia and agranulocytosis in patients receiving clozapine in the UK and Ireland
    • Atkin, K., Kendall, F., Gould, D., Freeman, H., Lieberman, J., and O'Sullivan, D. (1996) Neutropenia and agranulocytosis in patients receiving clozapine in the UK and Ireland. Br. J. Psychiatry 169, 483-488.
    • (1996) Br. J. Psychiatry , vol.169 , pp. 483-488
    • Atkin, K.1    Kendall, F.2    Gould, D.3    Freeman, H.4    Lieberman, J.5    O'Sullivan, D.6
  • 3
    • 0031770078 scopus 로고    scopus 로고
    • Examination of possible toxic and immune mechanisms of clozapine-induced agranulocytosis
    • Guest, I., Sokoluk, B., MacCrimmon, J., and Uetrecht, J. (1998) Examination of possible toxic and immune mechanisms of clozapine-induced agranulocytosis. Toxicology 131, 53-65.
    • (1998) Toxicology , vol.131 , pp. 53-65
    • Guest, I.1    Sokoluk, B.2    MacCrimmon, J.3    Uetrecht, J.4
  • 4
    • 0344043698 scopus 로고
    • Mechanisms of clozapine-induced agranulocytosis
    • Gerson, S. L., and Meltzer, H. (1992) Mechanisms of clozapine-induced agranulocytosis. Drug Saf. 7 (Suppl. 1), 17-25.
    • (1992) Drug Saf , vol.7 , Issue.SUPPL. 1 , pp. 17-25
    • Gerson, S.L.1    Meltzer, H.2
  • 5
    • 0026645711 scopus 로고
    • The role of leukocyte-generated reactive metabolites in the pathogenesis of idiosyncratic drug reactions
    • Uetrecht, J. P. (1992) The role of leukocyte-generated reactive metabolites in the pathogenesis of idiosyncratic drug reactions. Drug Metab. Rev. 24, 299-366.
    • (1992) Drug Metab. Rev , vol.24 , pp. 299-366
    • Uetrecht, J.P.1
  • 9
    • 0031814439 scopus 로고    scopus 로고
    • A comparison of the covalent binding of clozapine and olanzapine to human neutrophils in vitro and in vivo
    • Gardner, I., Leeder, J. S., Chin, T., Zahid, N., and Uetrecht, J. P. (1998) A comparison of the covalent binding of clozapine and olanzapine to human neutrophils in vitro and in vivo. Mol. Pharmacol. 53, 999-1008.
    • (1998) Mol. Pharmacol , vol.53 , pp. 999-1008
    • Gardner, I.1    Leeder, J.S.2    Chin, T.3    Zahid, N.4    Uetrecht, J.P.5
  • 10
    • 0031437166 scopus 로고    scopus 로고
    • Plasma level monitoring of olanzapine in patients with schizophrenia: Determination by high-performance liquid chromatography with electrochemical detection
    • Aravagiri, M., Ames, D., Wirshing, W. C., and Marder, S. R. (1997) Plasma level monitoring of olanzapine in patients with schizophrenia: Determination by high-performance liquid chromatography with electrochemical detection. Ther. Drug Monit. 19, 307-313.
    • (1997) Ther. Drug Monit , vol.19 , pp. 307-313
    • Aravagiri, M.1    Ames, D.2    Wirshing, W.C.3    Marder, S.R.4
  • 11
    • 25444527734 scopus 로고    scopus 로고
    • A comparison of the covalent binding of clozapine, procainamide, and vesnarinone to human neutrophils in vitro and rat tissues in vitro and in vivo
    • Gardner, I., Popovic, M., Zahid, N., and Uetrecht, J. P. (2005) A comparison of the covalent binding of clozapine, procainamide, and vesnarinone to human neutrophils in vitro and rat tissues in vitro and in vivo. Chem. Res. Toxicol. 18, 1384-1394.
    • (2005) Chem. Res. Toxicol , vol.18 , pp. 1384-1394
    • Gardner, I.1    Popovic, M.2    Zahid, N.3    Uetrecht, J.P.4
  • 13
    • 0013677025 scopus 로고
    • Metabolism of clozapine by neutrophils. Possible implications for clozapine-induced agranulocytosis
    • Uetrecht, J. P. (1992) Metabolism of clozapine by neutrophils. Possible implications for clozapine-induced agranulocytosis. Drug Saf. 7 (Suppl. 1), 51-56.
    • (1992) Drug Saf , vol.7 , Issue.SUPPL. 1 , pp. 51-56
    • Uetrecht, J.P.1
  • 14
    • 0029555342 scopus 로고
    • Clozapine is oxidized by activated human neutrophils to a reactive nitrenium ion that irreversibly binds to the cells
    • Liu, C. Z., and Uetrecht, J. P. (1995) Clozapine is oxidized by activated human neutrophils to a reactive nitrenium ion that irreversibly binds to the cells. J. Pharmacol. Exp. Ther. 275, 1476-1483.
    • (1995) J. Pharmacol. Exp. Ther , vol.275 , pp. 1476-1483
    • Liu, C.Z.1    Uetrecht, J.P.2
  • 15
    • 0031842867 scopus 로고    scopus 로고
    • A comparison of the oxidation of clozapine and olanzapine to reactive metabolites and the toxicity of these metabolites to human leukocytes
    • Gardner, I., Zahid, N., MacCrimmon, D., and Uetrecht, J. P. (1998) A comparison of the oxidation of clozapine and olanzapine to reactive metabolites and the toxicity of these metabolites to human leukocytes. Mol. Pharmacol. 53, 991-998.
    • (1998) Mol. Pharmacol , vol.53 , pp. 991-998
    • Gardner, I.1    Zahid, N.2    MacCrimmon, D.3    Uetrecht, J.P.4
  • 16
    • 0029416850 scopus 로고
    • The metabolic formation of reactive intermediates from clozapine, a drug associated with agranulocytosis in man
    • Maggs, J. L., Williams, D., Pirmohamed, M., and Park, B. K. (1995) The metabolic formation of reactive intermediates from clozapine, a drug associated with agranulocytosis in man. J. Pharmacol. Exp. Ther. 275, 1463-1475.
    • (1995) J. Pharmacol. Exp. Ther , vol.275 , pp. 1463-1475
    • Maggs, J.L.1    Williams, D.2    Pirmohamed, M.3    Park, B.K.4
  • 17
    • 0025746640 scopus 로고
    • Possible role of free radical formation in clozapine (clozaril)-induced agranulocytosis
    • Fischer, V., Haar, J. A., Greiner, L., Lloyd, R. V., and Mason, R. P. (1991) Possible role of free radical formation in clozapine (clozaril)-induced agranulocytosis. Mol. Pharmacol. 40, 846-853.
    • (1991) Mol. Pharmacol , vol.40 , pp. 846-853
    • Fischer, V.1    Haar, J.A.2    Greiner, L.3    Lloyd, R.V.4    Mason, R.P.5
  • 18
    • 0026493448 scopus 로고
    • Possible role of free radical formation in drug-induced agranulocytosis
    • Mason, R. P., and Fischer, V. (1992) Possible role of free radical formation in drug-induced agranulocytosis. Drug Saf. 7 (Suppl. 1), 45-50.
    • (1992) Drug Saf , vol.7 , Issue.SUPPL. 1 , pp. 45-50
    • Mason, R.P.1    Fischer, V.2
  • 19
    • 33947384478 scopus 로고    scopus 로고
    • Mechanistic aspects of the oxidative and reductive fragmentation of N-nitrosoamines: A new method for generating nitrenium cations, amide anions and aminyl radicals
    • Piech, K., Bally, T., Sikora, A., and Marcinek, A. (2007) Mechanistic aspects of the oxidative and reductive fragmentation of N-nitrosoamines: A new method for generating nitrenium cations, amide anions and aminyl radicals. J. Am. Chem. Soc. 129, 3211-3217.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 3211-3217
    • Piech, K.1    Bally, T.2    Sikora, A.3    Marcinek, A.4
  • 21
    • 0013442632 scopus 로고    scopus 로고
    • Radical ions: Generation, characterization and reactions
    • Alfassi, Z. B, Ed, pp, Wiley, Chichester, U.K
    • Gêbicki, J., and Marcinek, A. (1999) Radical ions: Generation, characterization and reactions. In General Aspects of the Chemistry of Radicals (Alfassi, Z. B., Ed.) pp 175-208, Wiley, Chichester, U.K.
    • (1999) General Aspects of the Chemistry of Radicals , pp. 175-208
    • Gêbicki, J.1    Marcinek, A.2
  • 22
    • 33847087730 scopus 로고
    • Yield for the scavenging of hydroxyl radicals in the radiolysis of nitrous oxide-saturated aqueous solutions
    • Schuler, R. H., Patterson, L. K., and Janata, E. (1980) Yield for the scavenging of hydroxyl radicals in the radiolysis of nitrous oxide-saturated aqueous solutions. J. Phys. Chem. 84, 2088-2089.
    • (1980) J. Phys. Chem , vol.84 , pp. 2088-2089
    • Schuler, R.H.1    Patterson, L.K.2    Janata, E.3
  • 24
    • 0026797203 scopus 로고
    • Pulse radiolysis system based on ELU-6e linac. II. Development and upgrading the system
    • Karolczak, S., Hodyr, K., and Połowiński, M. (1992) Pulse radiolysis system based on ELU-6e linac. II. Development and upgrading the system. Radiat. Phys. Chem. 39, 1-5.
    • (1992) Radiat. Phys. Chem , vol.39 , pp. 1-5
    • Karolczak, S.1    Hodyr, K.2    Połowiński, M.3
  • 25
    • 84889557831 scopus 로고
    • Rate constants for reactions of inorganic radicals in aqueous solutions
    • Neta, P., Huie, R. E., and Ross, A. B. (1988) Rate constants for reactions of inorganic radicals in aqueous solutions. J. Phys. Chem. Ref. Data 17, 1027-1284.
    • (1988) J. Phys. Chem. Ref. Data , vol.17 , pp. 1027-1284
    • Neta, P.1    Huie, R.E.2    Ross, A.B.3
  • 26
    • 84872846883 scopus 로고
    • Reduction potentials of one-electron couples involving free radicals in aqueous solution
    • Wardman, P. (1989) Reduction potentials of one-electron couples involving free radicals in aqueous solution. J. Phys. Chem. Ref. Data 18, 1637-1755.
    • (1989) J. Phys. Chem. Ref. Data , vol.18 , pp. 1637-1755
    • Wardman, P.1
  • 27
    • 33947335189 scopus 로고
    • The pulse radiolysis of deaerated aqueous bromide solutions
    • Matheson, M. S., Mulac, W. A., Weeks, J. L., and Rabani, J. (1966) The pulse radiolysis of deaerated aqueous bromide solutions. J. Phys. Chem. 70, 2092-2099.
    • (1966) J. Phys. Chem , vol.70 , pp. 2092-2099
    • Matheson, M.S.1    Mulac, W.A.2    Weeks, J.L.3    Rabani, J.4
  • 28
    • 0000189651 scopus 로고
    • Density-functional thermochemistry. III. The role of exact exchange
    • Becke, A. D. (1993) Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98, 5648-5652.
    • (1993) J. Chem. Phys , vol.98 , pp. 5648-5652
    • Becke, A.D.1
  • 29
    • 0345491105 scopus 로고
    • Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
    • Lee, C., Yang, W., and Parr, R. G. (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 37, 785-789.
    • (1988) Phys. Rev. B , vol.37 , pp. 785-789
    • Lee, C.1    Yang, W.2    Parr, R.G.3
  • 30
    • 34548487282 scopus 로고    scopus 로고
    • Frisch, M. J., et al. (2003) Gaussian 03, revision B.01, Gaussian, Inc., Pittsburgh, PA.
    • Frisch, M. J., et al. (2003) Gaussian 03, revision B.01, Gaussian, Inc., Pittsburgh, PA.
  • 31
    • 0001157659 scopus 로고
    • Time-Dependent Density Functional Response Theory for Molecules
    • Chong, D. P, Ed, pp, World Scientific, Singapore
    • Casida, M. E. (1995) Time-Dependent Density Functional Response Theory for Molecules. In Recent Advances in Density Functional Methods, Part I (Chong, D. P., Ed.) pp 155, World Scientific, Singapore.
    • (1995) Recent Advances in Density Functional Methods, Part I , pp. 155
    • Casida, M.E.1
  • 33
    • 30344475058 scopus 로고
    • Cation radicals: Tris-(p-bromophenyl)aminium perchlorate and hexachloroantimonate
    • Bell, F. A., Ledwith, A., and Sherrington, D. C. (1969) Cation radicals: Tris-(p-bromophenyl)aminium perchlorate and hexachloroantimonate. J. Chem. Soc. C 2719-2720.
    • (1969) J. Chem. Soc , vol.100 , pp. 2719-2720
    • Bell, F.A.1    Ledwith, A.2    Sherrington, D.C.3
  • 34
    • 0025881949 scopus 로고
    • One-electron oxidation of glutathione by azide radicals in neutral medium: A gamma and pulse radiolysis study
    • Abedinzadeh, Z., Gardes-Albert, M., and Ferradini, C. (1991) One-electron oxidation of glutathione by azide radicals in neutral medium: A gamma and pulse radiolysis study. Radiat. Phys. Chem. 38, 1-5.
    • (1991) Radiat. Phys. Chem , vol.38 , pp. 1-5
    • Abedinzadeh, Z.1    Gardes-Albert, M.2    Ferradini, C.3
  • 35
    • 0018647380 scopus 로고
    • Reaction of azide radicals with amino acids and proteins
    • Land, E. J., and Prütz, W. A. (1979) Reaction of azide radicals with amino acids and proteins. Int. J. Radiat. Biol. 36, 75-83.
    • (1979) Int. J. Radiat. Biol , vol.36 , pp. 75-83
    • Land, E.J.1    Prütz, W.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.