Structural contributions of antipsychotic drugs to their therapeutic profiles and metabolic side effects

Journal of Neurochemistry

Volumn 120, Issue 3, 2012, Pages 371-384

  Jafari, Somayeh ^a   Fernandez Enright, Francesca ^a,b   Huang, Xu Feng ^a,b  

^a UNIVERSITY OF WOLLONGONG   (Australia)

^b SCHIZOPHRENIA RESEARCH INSTITUTE   (Australia)

Author keywords

antipsychotics; dibenzodiazepines; metabolic side effect; SAR; structural modification; thienobenzodiazepines

Indexed keywords

AMISULPRIDE; ARIPIPRAZOLE; ATYPICAL ANTIPSYCHOTIC AGENT; BENZAMIDE DERIVATIVE; BUTYROPHENONE DERIVATIVE; CHLORPROMAZINE; CLOZAPINE; DIPHENYLBUTYLPIPERIDINE DERIVATIVE; DOPAMINE 2 RECEPTOR; FLUPENTIXOL; HALOPERIDOL; HISTAMINE H1 RECEPTOR; ILOPERIDONE; LOXAPINE; LURASIDONE; NEUROLEPTIC AGENT; OLANZAPINE; PALIPERIDONE; PHENOTHIAZINE DERIVATIVE; PIMOZIDE; PROMETHAZINE; QUETIAPINE; REMOXIPRIDE; RISPERIDONE; SERTINDOLE; SULPIRIDE; THIOXANTHENE DERIVATIVE; TIOTIXENE; UNINDEXED DRUG; ZIPRASIDONE;

AGRANULOCYTOSIS; AKATHISIA; CARDIOVASCULAR DISEASE; COGNITIVE DEFECT; CONGESTIVE CARDIOMYOPATHY; DRUG EFFICACY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DYSLIPIDEMIA; EMOTIONAL DISORDER; EXTRAPYRAMIDAL SYMPTOM; GLUCOSE METABOLISM; HUMAN; HYPERGLYCEMIA; HYPERPROLACTINEMIA; HYPERTENSION; INSULIN RESISTANCE; LIPID METABOLISM; METABOLIC DISORDER; MOTOR DYSFUNCTION; NEUROLEPTIC MALIGNANT SYNDROME; NON INSULIN DEPENDENT DIABETES MELLITUS; PRIORITY JOURNAL; PSYCHOSIS; QT INTERVAL; RECEPTOR AFFINITY; RECEPTOR BLOCKING; RECEPTOR OCCUPANCY; REVIEW; SCHIZOPHRENIA; SIDE EFFECT; STRUCTURE ACTIVITY RELATION; TARDIVE DYSKINESIA; UNSPECIFIED SIDE EFFECT; WEIGHT GAIN;

ANIMALS; ANTIPSYCHOTIC AGENTS; BASAL GANGLIA DISEASES; HUMANS; MENTAL DISORDERS; MOVEMENT DISORDERS; SEROTONIN; STRUCTURE-ACTIVITY RELATIONSHIP; WEIGHT GAIN;

EID: 84855701701     PISSN: 00223042     EISSN: 14714159     Source Type: Journal    
DOI: 10.1111/j.1471-4159.2011.07590.x     Document Type: Review

References (102)

1. Abdelmawla N., and, Mitchell A. J., (2006) Sudden cardiac death and antipsychotics part 2: Monitoring and prevention. Adv. Psychiatr. Treat. 12, 100-109. (Pubitemid 43338103)
2. Aicher T. D., Chen Z., Le H. Y., Martin F. M., Pineiro-Nunez M. M., Rocco V. P., Ruley K. M., Schaus J. M., Spinazze P. G., and, Tupper D. E., (2004) Preparation of Piperazine-Substituted Aryl-Fused Benzodiazepines as Dopamine D2 Receptor Antagonists for Treating Psychosis and Bipolar Disorders. WO 2004014895 A1 20040219. Eli Lilly and Company, USA.
3. Allison D. B., Mentore J. L., Heo M., Chandler L. P., and, Cappelleri J. C., (1999) Antipsychotic-induced weight gain: a comprehensive research synthesis. Am. J. Psychiatry 156, 1686-1696. (Pubitemid 29517559)
4. Apiquian R., Ulloa E., Fresan A., Loyzaga C., Nicolini H., and, Kapur S., (2003) Amoxapine shows atypical antipsychotic effects in patients with schizophrenia: results from a prospective open-label study. Schizophr. Res. 59, 35-39. (Pubitemid 35284491)
5. Ashby C. R., and, Wang R. Y., (1996) Pharmacological action of the atypical antipsychotic drug clozapine: a review. Synapse 24, 349-394. (Pubitemid 26418687)
6. Bai Y. M., Chen T. T., Yang W. S., Chi Y. C., Lin C. C., Liou Y. J., Wang Y. C., Su U. P., Chou P., and, Chen J. Y., (2009) Association of adiponectin and metabolic syndrome among patients taking atypical antipsychotics for schizophrenia: A cohort study. Schizophr. Res. 111, 1-8.
7. Baldwin C. M., and, Scott L. J., (2009) Quetiapine extended release. In schizophrenia. CNS Drugs 23, 261-269.
8. Battaglia J., (2005) Pharmacological management of acute agitation. Drugs 65, 1207-1222. (Pubitemid 41032047)
9. Bishara D., and, Taylor D., (2008) Upcoming agents for the treatment of schizophrenia: Mechanism of action, efficacy and tolerability. Drugs 68, 2269-2292.
10. Bloomgarden Z. T., (2005) Atypical antipsychotic agents, retinopathy, nephropathy, and cardiovascular disease. Diabetes Care 29, 1439-1446.
11. Bobo W. V., Jayathilake K., Lee M. A., and, Meltzer H. Y., (2010) Changes in weight and body mass index during treatment with melperone, clozapine and typical neuroleptics. Psychiatry Res. 176, 114-119.
12. Breden E. L., Liu M. T., and, Dean S. R., (2009) Metabolic and cardiacs side effects of second -generation antipsychotics: What every clinician should known. J. Pharm. Prac. 22, 478-488.
13. 123I]epidepride spet study of amisulpride-treated patients. Am. J. Psychiatry 160, 1413-1420. (Pubitemid 41070915)
14. 2A receptors in afferents of the rat striatum. Synapse 39, 297-304. (Pubitemid 32128651)
15. Buckley P., (2005) Olanzapine: A critical review of recent literature. Expert Opin. Pharmacother. 6, 2077-2089. (Pubitemid 41600584)
16. Campiani G., Butini S., Fattorusso C., et al. (2004) Pyrrolo[1,3] benzothiazepine-based serotonin and dopamine receptor antagonists. Molecular modeling, further structure-activity relationship studies, and identification of novel atypical antipsychotic agents. J. Med. Chem. 47, 143-157. (Pubitemid 38040498)
17. Campiani G., Butini S., Fattorusso C., et al. (2005) Novel atypical antipsychotic agents: rational design, an efficient palladium-catalyzed route, and pharmacological studies. J. Med. Chem. 48, 1705-1708. (Pubitemid 40396301)
18. Chakrabarti J. k., Horsman L., Hotten T. M., Pullar I. A., Tupper D. E., and, Wright F. C., (1980) 4-piperazinyl-10H-thieno[2,3-b][1,5]benzodiazepines as potential neuroleptics. J. Med. Chem. 23, 878-884. (Pubitemid 10091531)
19. Chakrabarti J. K., Hotten T. M., Morgan S. E., Pullar I. A., Rackham D. M., Risius F. C., Wedley S., Chaney M. O., and, Jones N. D., (1982) Effects of conformationally restricted 4-piperazinyl-10H-thienobenzodiazepine neuroleptics on central dopaminergic and cholinergic systems. J. Med. Chem. 25, 1133-1140. (Pubitemid 13241894)
20. Chodorowski Z., Anand J. S., and, Rutkowski P., (2003) Neuroleptic malignant syndrome. Przegl. Lek. 60, 299-301.
21. Coccurello R., and, Moles A., (2010) Potential mechanism of atypical antipsychotic-induced metabolic derangement: Clues for understanding obesity and novel drug design. Pharmacol. Ther. 127, 210-251.
22. Coccurello R., Caprioli A., Conti R., Ghirardi O., Borsini F., Carminati P., and, Moles A., (2008) Olanzapine (ly17053, 2-methyl-4-(4-methyl-1- piperazinyl)-10H-thieno[2,3-b] benzodiazepine), but not the novel atypical antipsychotic ST2472 (9-piperazin-1-ylpyrrolo[2,1-b][1,3]benzothiazepine), chronic administration induces weight gain, hyperphagia, and metabolic dysregulation in mice. J. Pharmacol. Exp. Ther. 326, 905-911.
23. Cohen L. J., (1994) Risperidone. Pharmacotherapy 14, 253-265. (Pubitemid 24161030)
24. Conley R. R., and, Kelly D. L., (2005) Second generation antipsychotics for schizophrenia: a review of clinical pharmacology and medication-associated side effects. J. Psychiatr. Relat. Sci. 42, 51-60. (Pubitemid 41159764)
25. Dargham A., and, Laruelle M., (2005) Mechanisms of action of second generation antipsychotic drugs in schizophrenia: Insights from brain imaging studies. Eur. Psychiatry 20, 15-27. (Pubitemid 40092387)
26. Demler T. L., and, Trigoboff E., (2011) Are clozapine blood dyscrasias associated with concomitant medications? Innov. Clin. Neurosci. 8, 35-41.
27. Deshmukh R., and, Franco K., (2003) Managing weight gain as a side effect of antidepressant therapy. Cleve. Clin. J. Med. 70, 614-623. (Pubitemid 36939961)
28. 2-dopamine receptor occupancy in schizophrenia patients treated with antipsychotic drugs. Arch. Gen. Psychiatry 45, 71-76. (Pubitemid 18018572)
29. Gardner D. M., Baldessarini R. J., and, Waraich P., (2005) Modern antipsychotic drugs: a critical overview. Synthèse 172, 1703-1711. (Pubitemid 40896865)
30. Glassman A. H., and, Bigger J. T. J., (2001) Antipsychotic drugs: Prolonged qtc interval, torsade de pointes, and sudden death. Am. J. Psychiatry 158, 1774-1782. (Pubitemid 33054769)
31. 1 receptor expression. Psychoneuroendocrinology 33, 569-580.
32. 2 receptors. Int. Clin. Psychopharmacol. 10, 19-30.
33. Holt R. I., (2006) Severe mental illness, antipsychotic drugs and the metabolic syndrome. BJDVD 6, 199-204. (Pubitemid 44823422)
34. Howes O. D., and, Kapur S., (2009) The dopamine hypothesis of schizophrenia: version III-The final common pathway. Schizophr. Bull. 35, 549-562.
35. Huf G., Coutinho E. S., and, Adams C. E., (2009) Haloperidol plus promethazine for agitated patients-a systematic review. Rev. Bras. Psychiatry 31, 265-270.
36. Jain K. K., (2000) An assessment of iloperidone for the treatment of schizophrenia. Expert. Opin. Investig. Drugs 9, 2935-2943.
37. Jones B., Basson B. R., Walker D. J., Crawford M. K., and, Kinon B. J., (2001) Weight change and atypical antipsychotic treatment in patients with schizophrenia. J. Clin. Psychiatry 62, 41-44. (Pubitemid 32154141)
38. 2 receptor explain the action of atypical antipsychotics? A new hypothesis. Am. J. Psychiatry 158, 360-369. (Pubitemid 32205190)
39. 2 receptor occupancy of clozapine, risperidone, and olanzapine in schizophrenia. Am. J. Psychiatry 156, 286-293. (Pubitemid 29077120)
40. Kapur S., Zipursky R., Jones C., Shammi C. S., Remington G., and, Seeman P., (2000) A positron emission temography study of quetiapin in schizophrenia. Arch. Gen. Psychiatry 57, 553-559.
41. 1 receptor-linked activation of hypothalamic AMP-kinase. Proc. Natl Acad. Sci. USA 104, 3456-3459. (Pubitemid 46364180)
42. Kohara T., Tanaka H., Kimura K., Horiuchi H., Seio K., Arita M., Fujimoto T. Y., and, Yamamoto I., (2002) Synthesis of thieno[2,3-b][1,5]benzoxazepine derivatives. J. Heterocyclic Chem. 39, 163-171. (Pubitemid 34194152)
43. 1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs. Neuropsychopharmacology 28, 519-526.
44. Lieberman J. A., (2006) Comprative effectiveness of antipsychotic drugs. Arch. Gen. Psychiatry 63, 1069-1072.
45. Lieberman J. A., Stroup T. S., McEvoy J. P., et al. (2005) Effectiveness of antipsychotic drugs in patients with chronic schizophrenia. N. Engl. J. Med. 353, 1209-1223. (Pubitemid 41345943)
46. Llorente M. D., and, Urrutia V., (2006) Diabetes, psychiatric disorders, and the metabolic effects of antipsychotic medications. Clin. Diabetes 24, 18-24. (Pubitemid 43276936)
47. Maloney A. E., and, Linmarie S., (2010) Olanzapine approved for the acute treatment of schizophrenia or manic/mixed episodes associated with bipolar I disorder in adolescent patients. Neuropsychiatr. Dis. Treat. 6, 749-766.
48. Mardera S. R., McQuadeb R. D., Stockc E., Kaplitac S., Marcusc R., Saffermanc A. Z., Sahad A., Alid M., and, Iwamotoe T., (2003) Aripiprazole in the treatment of schizophrenia: Safety and tolerability in short-term, placebo-controlled trials. Schizophr. Res. 61, 123-136.
49. Marino J., and, Caballero J., (2010) Iloperidone for the treatment of schizophrenia. Ann. Pharmacol. Ther. 44, 863-870.
50. 1 receptor: a novel therapeutic target for disrupting diurnal feeding rhythm and obesity. Trends Pharmacol. Sci. 27, 279-284.
51. 1 receptor in the regulation of feeding rhythm and obesity. Diabetes 53, 2250-2260. (Pubitemid 39145578)
52. Mathews M., and, Muzina J. D., (2007) Atypical antipsychotics: new drugs, new challenges. Cleve. Clin. J. Med. 74, 597-606.
53. McIntyre R. S., McCann S. M., and, Kennedy S. H., (2001) Antipsychotic metabolic effects: weight gain, diabetes mellitus, and lipid abnormalities. Can. J. Psychiatry 46, 273-281. (Pubitemid 32423994)
54. Melkersson K., (2004) Clozapine and olanzapine, but not conventional antipsychotics, increase insulin release in vitro. Eur. Neuropsychopharmacol. 14, 115-119. (Pubitemid 38175428)
55. Meltzer H. Y., (1999) The role of seretonin in antipsychotic drug action. Neuropsychopharmacology 21, 106-115S.
56. Meltzer H. Y., Sommers A. A., and, Luchins D. J., (1986) The effect of neuroleptics and other psychotropic drugs on negative symptoms in schizophrenia. J. Clin. Psychopharmacol. 6, 329-338. (Pubitemid 17217503)
57. i values. J. Pharmacol. Exp. Ther. 251, 238-246.
58. Meltzer H. Y., Matsubara S., and, Lee J. C., (1989b) The ratios of seretonin2 and dopamine2 affinities differentiate atypical and typical antipsychotic drugs. Psychopharmacol. Bull. 25, 390-392. (Pubitemid 20260244)
59. Mercer L. P., (1997) Histamine and the neuroregulation of food intake. Nutrition 13, 581-582. (Pubitemid 27360312)
60. Mercer L. P., Kelley D. S., Haq A. U., and, Humphries L. L., (1996) Dietary induced anorexia: a review of involvement of the histaminergic system. J. Am. Coll. Nutr. 15, 223-230. (Pubitemid 26170856)
61. Miceli J. J., Tensfeldt G., Shiovitz T., Anziano R., O'Gorman C., and, Harrigan R. H., (2010) Effects of oral ziprasidone and oral haloperidol on QTc interval in patients with schizophrenia or schizoaffective disorder. Pharmacotherapy 30, 127-135.
62. Minchin S. A., and, Csernansky J. G., (1996) Classification schemes for antipsychotic drugs, in Antipsychotics (, Csernansky J. G. E., ed.), pp. 1-21. Springer, Berlin.
63. Mitterschiffthaler G., Hackl J. M., and, Neumann R., (1989) The malignant neuroleptic syndrome and malignant hyperthermia. Anaesthesist 38, 210-213.
64. Muench J., and, Hamer A. M., (2010) Adverse effects of antipsychotic medications. Am. Fam. Physician 81, 617-622.
65. Nasrallah H. N., (2008) Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles. Mol. Psychiatry 13, 27-35.
66. 1A receptor agonism in antipsychotic drug action: Rationale and perspectives. Curr. Opin. Invest. Drugs 11, 802-812.
67. Nielsen J., Skadhede S., and, Correll C. U., (2010) Antipsychotics associated with the development of type 2 diabetes in antipsychotic-naïve schizophrenia patients. Neuropsychopharmacology 35, 1997-2004.
68. Normala I., and, Hamidin A., (2009) The use of aripiprazole in early onset schizophrenia: safety and efficacy. Med. J. Malaysia 64, 240-241.
69. Nuss P., and, Tessier C., (2010) Antipsychotic medication, functional outcome and quality of life in schizophrenia: Focus on amisulpride. Curr. Med. Res. Opin. 26, 787-801.
70. Oakley N. R., Hayes A. G., and, Sheehan M. J., (1991) Effect of typical and atypical neuroleptics on the behavioural consequences of activation by muscimol of mesolimbic and nigro-striatal dopaminergic pathways in the rat. Psychopharmacology 105, 204-208.
71. Parsons B., David B. A., Loebel A., Williams K., Giller E., Romano S., and, Siu C., (2009) Weight effects associated with antipsychotics: a comprehensive database analysis. Schizophr. Res. 110, 103-110.
72. Petit M., and, Dollfus S., (1991) Chemotherapies of negative schizophrenia. Encephale 17, 241-245.
73. Pijl H., and, Meinders A. E., (1996) Body weight change and adverse effect of drug treatment. Echansm and management. Drug Saf. 14, 329-342.
74. Porsolt R. D., Moser P. C., and, Castagné V., (2010) Behavioral indices in antipsychotic drug discovery. J. Pharmacol. Exp. Ther. 333, 632-638.
75. 1 receptor affinity than olanzapine. J. Pharmacol. Exp. Ther. 315, 1265-1277. (Pubitemid 41635415)
76. Ravanic D. B., Dejanovic S. M., Janjic V., Jovic S. D., Milovanovic D. R., Jakovljevic V., Pantovic V., Ravanic B., Pantovic M., and, Pantovic M. M., (2009) Effectiveness of clozapine, haloperidol and chlorpromazine in schizophrenia during a five-year period. Arq. Neuropsiquiatr. 67, 195-202.
77. Recasens C., (2001) Body weight changes and psychotropic drug treatment: neuroleptics. Encephale 27, 269-276. (Pubitemid 32678136)
78. Reimold M., Solbach C., Noda S., Schaefer J. E., Bartels M., Beneke M., Machulla H. J., Bares R., Glaser T., and, Wormstall H., (2007) Occupancy of dopamine D(1), D(2) and serotonin (2A) receptors in schizophrenic patients treated with flupentixol in comparison with risperidone and haloperidol. Psychopharmacology (Berl) 190, 241-249. (Pubitemid 46011184)
79. Reynolds G. P., and, Kirk S. L., (2010) Metabolic side effect of antipsychotic treatment-pharmacological mechanism. Pharmacol. Ther. 125, 169-179.
80. 2C receptor gene polymorphism. Lancet 359, 2086-2087. (Pubitemid 34680975)
81. Roerig J. L., Steffen K. J., Mitchell J. E., Crosby R. D., and, Gosnell B. A., (2009) An exploration of the effect of modafinil on olanzapine associated weight gain in normal human subject. Biol. Psychiatry 65, 607-613.
82. Roth B. L., Craigo S. C., Choudhary M. S., Uluer A., Monsma F. J., Jr, Shen Y., Meltzer H. Y., and, Sibley D. R., (1994) Binding of typical and atypical antipsychotic agents to 5-hydroxytryptamine-6 and 5-hydroxytryptamine-7 rceptors. J. Pharmacol. Exp. Ther. 268, 1403-1410. (Pubitemid 24100360)
83. Ruhrmann S., Kissling W., Lesch O. M., Schmauss M. S., Eemann U., and, Philipp M., (2007) Efficacy of flupentixol and risperidone in chronic schizophrenia with predominantly negative symptoms. Prog. Neuropsychopharmacol. Biol. Psychiatry 31, 1012-1022. (Pubitemid 46810092)
84. Schotte A., Janssen P. F., Gommeren W., Luyten W. H., Van Gompel P., Lesage A. S., De Loore K., and, Leysen J. E., (1996) Risperidone compared with new and reference antipsychotic drugs: in vitro and in vivo receptor binding. Psychopharmacology 124, 57-73. (Pubitemid 26112775)
85. Seeman P., (2002) Atypical antipsychotics: mechanism of action. Can. J. Psychiatry 47, 27-38. (Pubitemid 34302921)
86. 2 receptor in schizophrenia. Expert. Opin. Ther. Target. 10, 515-531. (Pubitemid 44165124)
87. 2 receptors as treatment target in schizophrenia. Clin. Schizophr. Relat. Psychoses 4, 56-73.
88. 2 receptors: An explanation for low receptor occupancy and early clinical relapse upon withdrawal of clozapine and quetiapine. Am. J. Psychiatry 156, 876-884. (Pubitemid 29260342)
89. Seeman P., Lee T., Chau-Wong M., and, Wong K., (1976) Antipsychotic drug doses and neuroleptic/dopamine receptors. Nature 261, 717-719.
90. Sernyak M. J., Leslie D. L., Alarcon R. D., Losonczy M. F., and, Rosenheck R., (2002) Association of diabetes mellitus with use of atypical neuroleptics in the treatment of schizophrenia. Am. J. Clin. Psychiatry 159, 561-566. (Pubitemid 34274937)
91. Serretti A., Ronchi D. D., Lorenzi C., and, Berardi D., (2004) New antipsychotics and schizophrenia: a review on efficacy and side effects. Curr. Med. Chem. 11, 343-358. (Pubitemid 38240211)
92. Stahl S. M., (1998) Psychosis and schisophrenia, in Essentional Psychopharmacology (, Stahl S. M., ed.), pp. 249-262. Cambridge University Press, Cambridge.
93. Stip E., and, Tourjman V., (2010) Aripiprazole in schizophrenia and schizoaffective disorder: a review. Clin. Ther. 32, S3-S20.
94. Sussman N., (2003) The implications of weight changes with antipsychotic treatment. J. Clin. Psychopharmacol. 23, S21-S26. (Pubitemid 36807784)
95. Tandon R., and, Jibson M. D., (2002) Extrapyramidal side effects of antipsychotic treatment: scope of problem and impact on outcome. Ann. Clin. Psychiatry 14, 123-129. (Pubitemid 35006794)
96. Tehan B. G., Lioyd E. J., and, Wong M. G., (2001) Molecular field analysis of clozapine analogs in the development of a pharmacophore model of antipsychotic drug action. J. Mol. Graphics. Modell. 19, 418-426.
97. Tolosa-Vilella C., Ruiz-Ripoll A., Mari-Alfonso B., and, Naval-Sendra E., (2002) Olanzapine-induced agranulocytosis-a case report and review of the literature. Prog. Neuro-Psychopharmacol. Biol. Psychiatry 26, 411-414. (Pubitemid 34038075)
98. Volkov V. P., (2009) Phenothiazine-induced dilatation cardiomyopathy: selected aspects of clinical course and morphology. Klin. Med (Mosk). 87, 13-16.
99. Wang J., Omori I. M., Fenton M., and, Soares B., (2010) Sulpiride augmentation for schizophrenia. Cochrane Database Syst. Rev. 20, CD008125.
100. Wetterling T., (2001) Body weight gain with atypical antipsychotics. A comparative review. Drug Saf. 24, 59-73. (Pubitemid 32113367)
101. Worrel J. A., Marken P. A., Beckman S. E., and, Ruehter V. L., (2000) Atypical antipsychotic agents: a critical review. Am. J. Health-Syst. Pharm. 57, 238-255.
102. Zhang Y., Xu H., He J., Yan B., Jiang W., and, Li X., (2007) Quetiapine reverses altered locomotor activity and tyrosine hydroxylase immunoreactivity in rat caudate putamen following long-term haloperidol treatment. Neurosci. Lett. 420, 66-71. (Pubitemid 46777105)