The possible role of an active metabolite derived from the neuroleptic agent haloperidol in drug-induced parkinsonism

Journal of Toxicology - Toxin Reviews

Volumn 17, Issue 1, 1998, Pages 27-38

  Igarashi, Kazuo ^a  

^a KOBE GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 METHYL 4 PHENYLPYRIDINIUM; CYTOCHROME P450; DRUG METABOLITE; HALOPERIDOL; NEUROLEPTIC AGENT; NEUROTOXIN;

BLOOD BRAIN BARRIER; CHEMICAL STRUCTURE; CONFERENCE PAPER; DOPAMINERGIC NERVE CELL; DRUG BRAIN LEVEL; EXTRAPYRAMIDAL SYMPTOM; LIVER MICROSOME; LONG TERM CARE; MICRODIALYSIS; NERVE CELL CULTURE; PARKINSONISM; SEROTONINERGIC NERVE CELL; TARDIVE DYSKINESIA;

ANIMALIA;

EID: 0031892391     PISSN: 07313837     EISSN: None     Source Type: Journal    
DOI: 10.3109/15569549809006488     Document Type: Conference Paper

References (57)

1. Barbeau, A., Roy, M., Cloutier, T. and Bernier, G., Environmental and genetic factors in aetiology of Parkinson's disease. Adv. Neurol., 45: 299-306, 1986.
2. Bloomquist, J., King, E.Y., Wright, A., Mytilineou, C., Kimura, K., Castagnoli, K. and Castagnoli, N.Jr.., 1-Methyl-4-phenylpyridinium-like neurotoxicity of a pyridinium metabolite derived from haloperidol: cell culture and neurotransmitter uptake studies. J. Pharmacol. Exp. Ther., 270: 822-830, 1994.
3. +. Neurosci. Lett., 100: 306-312, 1989.
4. Calne, D.B. and Langston, J.w., Aetiology of Parkinson's disease. Lancet, ii: 1457-1459, 1983.
5. Chan, P., Ellanney, L.E., Irwin, I., Langston, J.W. and Dimonte, D., MPTP-induced ATP loss in mouse brain. Ann. N.Y. Acad. Sci., 648: 306-308, 1992.
6. Chiba, K., Trevor, A.J. and Castagnoli, N.Jr., Metabolism of the neurotoxic ternary amine, MPTP, by brain monoamine oxidase. Biochem. Biophys. Res. Commun., 120: 574-578, 1984.
7. +, a metabolite of MPTP, by brain synaptosomes. Biochem. Biophys. Res. Commun., 128: 1228-1232, 1985.
8. Chouza, C., Scaramelli, A., Caamano, J.L., DeMedina, O., Ailanati, R. and Romero, S., Parkinsonism, tardive dyskinesia, akathisia and depression induced by flunarizine. Lancet, I: 1303-1305, 1986.
9. Davis, G.C., Williams, A.C., Markey, S.P., Ebert, M.H., Caine, E.D., Reichert, C.M. and Kopin, I.J., Chronic parkinsonism secondary to intravenous injection of meperidine analoges. Psychiatry Res., 1: 249-254, 1979.
10. +) cause rapid ATP depletion in isolated hepatocytes. Biochem. Biophys. Res. Commun., 137: 310-315. 1986.
11. Eyles, D.W., McLennan, H.R., Jones, A., McGrath, J.J., Stedman, T.J. and Pond, S.M., Quantitative analysis of one pyridinium metabolite of haloperidol and identification of another in schizophrenic patients. Clin. Pharmacol. Ther., 56: 512-520, 1994.
12. Eyles, D.W., Avent, K.M., Stedman, T.J. and Pond, S.M., Two pyridinium metabolites of haloperidol are present in the brain of patients at post-mortem. Life Sci., 60: 529-534, 1997.
13. Fang, J. and Gorrod, J.W., Dehydration in the first step in the bioactivation of haloperidol to its pyridinium metabolite. Toxicol. Lett., 59: 117-123, 1991.
14. +) towards cultured dopaminergic neuroblastoma cell. Psychopharmacology, 121: 373-378, 1995.
15. Glazer, W.M., Moore, D.C, Schooler, N.R., Brenner, L.M. and Morgenstern, H., Tardive dyskinesia. Arch. Gen. Psychiatry, 42: 623-627, 1984.
16. Gorrod, J.W. and Fang, J., On the metabolism of haloperidol. Xenobiotica, 23: 495-508, 1993.
17. Heikkila, R.E., Youngster, S.K., Manzino, L., Cabbat, F.S. and Duvoisin, R.C., Effects of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine and related compounds on the uptake of [3H]-3,4-dihydroxyphenylethylamine and [3H]-5-hydroxytryptamine in neostriatal synaptosomal preparations. J. Neurochem., 44: 310-314, 1985.
18. Igarashi, K. and Castagnoli, N.Jr., Determination of the pyridinium metabolite derived from haloperidol in brain tissue, plasma and urine by high-performance liquid chromatography with fluorescence detection. J. Chromatogr. B, 579: 277-283, 1992.
19. + found in rat brain following ip administration of HP. Life Sci., 57: 2439-2446, 1995.
20. Igarashi, K., Kasuya, F., Fukui, M., Abe, T. and Castagnoli, N.Jr., Simultaneous determination of haloperidol and its neurotoxic metabolite in plasma and brain tissue from schizophrenic patients treated with haloperidol using HPLC and solid-phase extraction. Jpn. J. Forensic Toxicol., 13: 31-38, 1995.
21. Igarashi, K., Matsubara, K., Kasuya, F., Fukui, M., Idzu, T. and Castagnoli, N.Jr., Effect of a pyridinium metabolite derived from haloperidol on the activities of striatal tyrosine hydroxylase in freely moving rats. Neurosci. Lett., 214: 183-186, 1996.
22. Indo, T. and Ando, K., Metoclopramide-induced parkinsonism-clinical characteristics of ten cases. Arch. Neurol., 39: 494-500, 1982.
23. Javitch, J.A., D'Amato, R.J., Strittmatter, S.M. and Snyder, S.H., Parkinsonism-inducing neurotoxin N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine: uptake of the metabolite N-methyl-4-phenylpyridine by dopamine neurons explains selective toxicity. Proc. Natl. Acad. Sci. USA, 82: 2173-2177, 1985.
24. Koike, K., Takayanagi, I., Wani, S., Ohta, S. and Hirobe, M., Effect of tetrahydroisoquinoline (TIQ), one of endogenous substances indicating parkinsonism, on isolated rat vas deferens. Gen. Pharmacol., 20: 259-260, 1989.
25. Langston, J.W., Ballard, P., Tetrud, J.W. and Irwin, I., Chronic parkinsonism in human due to a product of meperidine-analog. Science, 219: 979-980, 1983.
26. Langston, J.W., Mechanisms underlying neuronal degeneration in Parkinson's disease: an experimantal and theoretical treatise. Movement Disord., Suppl. 1: S15-S25, 1989.
27. Markey, S.P., Johannessen, J.N., Chiuch, C.C., Burns, R.S. and Herkenham, M.A., Intra-neuronal generation of a pyridinium metabolite may cause drug-induced parkinsonism. Nature, 311: 464-466, 1984.
28. Maruyama, W., Nakahara, D., Ota, M., Takahashi, T., Nagatsu, T. and Naoi, M., N-Methylation of dopamine-derived 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, (R)-salsolinol, in rat brain; in vivo microdialysis. J. Neurochem., 59: 395-400, 1992.
29. Matsubara, K., Collins, M.A., Akane, A., Ikebuchi, J., Neafsey, E.J., Kagawa, M. and Shiono, H., Potential bioactivated neurotoxin, N-methylated β-carbolinium ions, are present in human brain. Brain Res., 610: 90-96, 1993.
30. Matsubara, K., Idzu, T., Kobayashi, Y., Nakahara, D., Maruyama, W., Kobayashi, S., Kimura, K. and Naoi, M., N-Methyl-4-phenylpyridinium and an endogenously formed analog, N-methylated β-carbolinium, inhibit striatal tyrosine hydroxylation in freely moving rats. Neurosci. Lett., 199: 199-202, 1995.
31. Micheli, F., Flunarizine- and cinnarizine-induced extrapyramidal reactions. Neurology, 37: 881-886, 1987.
32. Nagatsu, T., Naoi, M., Niwa, T. and Yoshida, M., Endogenous MPTP-like amines in the brain: isoquinolines. In Advances in Research on Neurodegeneration Vol. 2 Etiopathogenesis, edited by Y. Mizuno, O.B. Caline and R. Horowski, pp. 149-159, Birkhauser, Boston, 1993.
33. Naoi, M., Matsuura, S., Takahashi, T. and Nagatsu, T., An N-methyltransferase in human brain catalyzes N-methylation of 1,2,3,4-tetrahydroisoquinoline into N-methyl-1,2,3,4-tetrahydroisoquinoline, a precursor of a dopaminergic neurotoxin, N-methylisoquinolinium ion. Biochem. Biophys. Res. Commun., 161: 1213-1219, 1989.
34. Nicklas, W.J., Vyas, I. and Heikkila, R.E., Inhibition of NADH-linked oxidation in brain mitochondria by 1-methyl-4-phenylpyridinium, a metabolite of the neurotoxin 1-methyl-1,2,3,6-tetrahydropyridine. Life Sci., 36: 2503-2508, 1985.
35. Niwa, T., Takeda, N., Kaneda, N., Hashizume, Y. and Nagatsu, T., Presence of tetrahydroisoquinoline and 2-methyl-tetrahydroquinoline in parkinsonian and normal human brain. Biochem. Biophys. Res. Commun., 144: 1084-1089, 1987.
36. Ohta, S., Kohno, M., Makino, Y., Tachikawa, O. and Hirobe, M., Tetrahydroisoquinoline and 1-methyl-tetrahydroisoquinoline are present in the human brain: relation to Parkinson's disease. Biomed. Res., 8: 453-456, 1987.
37. Pi, E.H. and Simpson, G.M., Central nervous system toxicity of psychopharmacological agents. In Neurotoxicology, edited by K. Blum and L. Manzo, pp. 219-23, Marcel Dekker, New York, 1985.
38. Ramsay, R.R. and Singer, T.P., Energy dependent uptake of N-methyl-4-phenylpyridinium, the neurotoxic metabolite of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, by mitochondria. J. Biol. Chem., 261: 7585-7587, 1986.
39. Reynolds, G.P., Development in the drug treatment of schizophrenia, Trends Pharmacol. Sci., 13: 116-121, 1992.
40. + analogs and related charged species. J. Med. Chem., 33: 2221-2230, 1990.
41. +-like neurotoxicity of a pyridinium metabolite derived from haloperidol: In vivo microdialysis and in vitro mitochondrial studies. J. Pharmacol. Exp. Ther., 268: 380-387, 1994.
42. + in both electron transport particles and intact mitochondria. Biochem. Biophys. Res. Commun., 161: 809-818, 1989.
43. Singer, T.P., Ramsay, R.R., Sonsalla, P.K., Nicklas, W.J. and Heikkila, R.E., Biochemical mechanism underlying MPTP-induced and idiopathic parkinsonism-New vistas. Adv. Neurol., 60: 300-305, 1993.
44. Singer, T.P., Castagnoli, N.Jr., Ramsay, R.R. and Trevor, A.J., Bochemical events in the development of parkinsonism induced by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine. J. Neurochem., 49: 1-8, 1987.
45. Sjöquist, B., Eriksson, A. and Winblad, B., Brain salsolinol level in alcholism. Lancet, i: 675-676, 1982.
46. Stacy, M. and Jankovic, J., Clinical and neurobiological aspects of Parkinson's disease. In Parkinson's disease: Neurobehavioral Aspects, edited by Huber, S.E. and Cummings, J.L., pp. 10-31, Oxford Univ. Press., New york, 1992.
47. Subramanyam, B., Rollema, H., Wolf, T. and Castagnoli, N.Jr., Identification of apotentially neurotoxic pyridinium metabolite of haloperidol in rats. Biochem. Biophys. Res. Commun., 166: 238-244, 1990.
48. Subramanyam, B., Pond, S.M., Eyles, D.W., Whiteford, H.A., Fouda, H.G. and Castagnoli, N.Jr., Identification of a potentially neurotoxic pyridinium metabolite in the urine of schizophrenic patients treated with haloperidol. Biochem. Biophys. Res. Commun., 181: 573-578, 1991.
49. Subramanyam, B., Wolf, T. and Castagnoli, N.Jr., Studies on the in vitro conversion of haloperidol to apotentially neurotoxic pyridinim metabolite. Chem. Res. Toxicol., 4: 123-128, 1991.
50. Tanner, C.M., Epidemiology of Parkinson's disease. Neurol. Clin., 10: 317-329, 1992.
51. Tanner, C.M., The role of the environmental toxins in the etiology of Parkinson's disease. TINS, 12: 49-54, 1989.
52. Tanner, C.M. and Langston, J.W., Do environmental toxins cause Parkinson's disease ? A critical review. Neurology, 40: 17-30, 1990.
53. Usuki, E., Pearce, R., Parkinson, A. and Castagnol, N.Jr., Studies on the conversion of haloperidol and its tetrahydropyridine dehydration product to potentially neurotoxic pyridinium metabolite by human liver microsomes. Chem. Res. Toxicol., 9: 800-806, 1996.
54. Vyas, I., Heikkila, R.E. and Nicklas, W.J., Studies on the neurotoxicity of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine: Inhibition of NAD-linked substrate oxidation by its metabolite, 1-methyl-4-phenylpyridinium. J. Neurochem., 46: 1501-1507, 1986.
55. Youngster, S.K., Sonsalla, P.K. and Heikkila, R.E., Evaluation of the biological activity of several analogs of the dopaminergic neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine. J. Neurochem., 48: 929-934, 1987.
56. Youngster, S.K., Sonsalla, P.K., Sieber, B.E. and Heikkila, R.E., Structure-activity study of the mechanism of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced neurotoxicity. I. Evaluation of the biological acyivity of MPTP analogs. J. Pharmacol. Exp. Ther., 248: 820-828, 1989a.
57. Youngster, S.K., Nicklas, W.J. and Heikkila, R.E., Structure-activity study of the mechanism of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) -induced neurotoxicity. II. Evaluation of the biological activity of the pyridinium metabolites formed from the monoamine oxidase-catalyzed oxidation of MPTP analogs. J. Pharmacol. Exp. Ther., 248: 828-835, 1989b.