Norclozapine (BioDeep_00000397502)
代谢物信息卡片
N-Desmethylclozapine
化学式: C17H17ClN4 (312.1141672)
中文名称: N-去甲基氯氮平
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1CN(CCN1)C2=C3C=CC=CC3=NC4=C(N2)C=C(C=C4)Cl
InChI: InChI=1S/C17H17ClN4/c18-12-5-6-15-16(11-12)21-17(22-9-7-19-8-10-22)13-3-1-2-4-14(13)20-15/h1-6,11,19,21H,7-10H2
描述信息
D002492 - Central Nervous System Depressants > D014149 - Tranquilizing Agents > D014150 - Antipsychotic Agents
D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D014149 - Tranquilizing Agents
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants
CONFIDENCE standard compound; INTERNAL_ID 1563
INTERNAL_ID 1563; CONFIDENCE standard compound
CONFIDENCE standard compound; EAWAG_UCHEM_ID 3607
N-Desmethylclozapine is a major active metabolite of the atypical antipsychotic agent Clozapine. N-Desmethylclozapine is a potent, allosteric and partial M1 receptors agonist (EC50=115 nM) and is able to potentiate hippocampal N-methyl-d-aspartate (NMDA) receptor currents through M1 receptor activation. N-Desmethylclozapine is also a δ-opioid agonist[1][2].
同义名列表
数据库引用编号
25 个数据库交叉引用编号
- ChEBI: CHEBI:64050
- ChEBI: CHEBI:92174
- PubChem: 135409468
- PubChem: 2820
- ChEMBL: CHEMBL845
- CAS: 6104-71-8
- MoNA: AU156311
- MoNA: AU156310
- MoNA: AU156309
- MoNA: AU156308
- MoNA: AU156307
- MoNA: EQ360709
- MoNA: EQ360708
- MoNA: EQ360707
- MoNA: EQ360706
- MoNA: EQ360705
- MoNA: EQ360704
- MoNA: EQ360703
- MoNA: EQ360702
- MoNA: EQ360701
- MoNA: AU156305
- MoNA: AU156304
- MoNA: AU156303
- MoNA: AU156302
- medchemexpress: HY-G0021
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
0 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Robert James Flanagan, Samora Hunter, Stephen John Obee, Suzanne Reeves. Plasma Clozapine and Norclozapine After Use of Either Crushed Tablets or Suspension Compared With Tablets.
Journal of clinical psychopharmacology.
2022 Jul; 42(4):400-404. doi:
10.1097/jcp.0000000000001560. [PMID: 35652731] - K N Roy Chengappa, Jane Thomas, Charles E Kahn, Kimberly Clinebell, Kelly K Mullen, Lori Arbutiski, Emil Ivanov. COVID-19 infection, fluctuations in the clozapine/norclozapine levels and metabolic ratio and clozapine toxicity: An illustrative case-report.
Schizophrenia research.
2022 Jun; 244(?):66-68. doi:
10.1016/j.schres.2022.05.009. [PMID: 35605549] - Deepak K Sarpal, Annie Blazer, James D Wilson, Finnegan J Calabro, William Foran, Charles E Kahn, Beatriz Luna, K N Roy Chengappa. Relationship between plasma clozapine/N-desmethylclozapine and changes in basal forebrain-dorsolateral prefrontal cortex coupling in treatment-resistant schizophrenia.
Schizophrenia research.
2022 05; 243(?):170-177. doi:
10.1016/j.schres.2022.03.014. [PMID: 35381515] - Eliana Carniel, Karen Adams Dos Santos, Lucas de Andrade de Lima, Ramona Kohlrausch, Rafael Linden, Marina Venzon Antunes. Determination of clozapine and norclozapine in dried plasma spot and dried blood spot by liquid chromatography-tandem mass spectrometry.
Journal of pharmaceutical and biomedical analysis.
2022 Feb; 210(?):114591. doi:
10.1016/j.jpba.2022.114591. [PMID: 35033943] - Naomi T Jessurun, Hieronymus J Derijks, Rob J van Marum, Amy Jongkind, Eline L Giraud, Eugène P van Puijenbroek, Koen P Grootens. Body weight gain in clozapine-treated patients: Is norclozapine the culprit?.
British journal of clinical pharmacology.
2022 02; 88(2):853-857. doi:
10.1111/bcp.14992. [PMID: 34355423] - Madeleine S A Tan, Faraz Honarparvar, James R Falconer, Harendra S Parekh, Preeti Pandey, Dan J Siskind. A systematic review and meta-analysis of the association between clozapine and norclozapine serum levels and peripheral adverse drug reactions.
Psychopharmacology.
2021 Mar; 238(3):615-637. doi:
10.1007/s00213-020-05746-y. [PMID: 33410989] - Kenya A Costa-Dookhan, Tarek K Rajji, Veronica N Tran, Sylvie Bowden, Daniel J Mueller, Gary J Remington, Sri Mahavir Agarwal, Margaret K Hahn. Associations between plasma clozapine/N-desmethylclozapine ratio, insulin resistance and cognitive performance in patients with co-morbid obesity and ultra-treatment resistant schizophrenia.
Scientific reports.
2021 01; 11(1):2004. doi:
10.1038/s41598-021-81493-0. [PMID: 33479273] - Farhana Islam, Malgorzata Maciukiewicz, Natalie Freeman, Eric Huang, Arun Tiwari, Benoit H Mulsant, Bruce G Pollock, Gary Remington, James L Kennedy, Daniel J Müller, Tarek K Rajji. Contributions of cholinergic receptor muscarinic 1 and CYP1A2 gene variants on the effects of plasma ratio of clozapine/N-desmethylclozapine on working memory in schizophrenia.
Journal of psychopharmacology (Oxford, England).
2021 01; 35(1):31-39. doi:
10.1177/0269881120946288. [PMID: 33143542] - Lisbeth Patteet, Kristof Maudens, Sarah Wille, Peter Blanckaert, Hugo Neels, Paul Calle. When clozapine appears at a dance event….
Acta clinica Belgica.
2020 Dec; 75(6):416-420. doi:
10.1080/17843286.2019.1630068. [PMID: 31199195] - Shuhei Ishikawa, Masaki Kobayashi, Naoki Hashimoto, Hideaki Mikami, Akihiko Tanimura, Katsuya Narumi, Ayako Furugen, Ichiro Kusumi, Ken Iseki. Association Between N-Desmethylclozapine and Clozapine-Induced Sialorrhea: Involvement of Increased Nocturnal Salivary Secretion via Muscarinic Receptors by N-Desmethylclozapine.
The Journal of pharmacology and experimental therapeutics.
2020 11; 375(2):376-384. doi:
10.1124/jpet.120.000164. [PMID: 32862145] - Yağmur Kır, Bora Baskak, Adnan Kuşman, Damla Sayar-Akaslan, Fezile Özdemir, Nilay Sedes-Baskak, Halit Sinan Süzen, Zeynel Baran. The relationship between plasma levels of clozapine and N-desmethyclozapine as well as M1 receptor polymorphism with cognitive functioning and associated cortical activity in schizophrenia.
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10.1016/j.pscychresns.2020.111128. [PMID: 32593951] - Ebenezer Oloyede, Olubanke Dzahini, Eromona Whiskey, David Taylor. Clozapine and Norclozapine Plasma Levels in Patients Switched Between Different Liquid Formulations.
Therapeutic drug monitoring.
2020 06; 42(3):491-496. doi:
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Journal of pharmaceutical and biomedical analysis.
2020 Feb; 180(?):113056. doi:
10.1016/j.jpba.2019.113056. [PMID: 31887669] - Maria Concepcion Turrion, Jesus Perez, Miguel Bernardo, Emilio Fernandez-Egea. Intra-individual variation of clozapine and norclozapine plasma levels in clinical practice.
Revista de psiquiatria y salud mental.
2020 Jan; 13(1):31-35. doi:
10.1016/j.rpsm.2019.03.002. [PMID: 31122757] - Mayela Vaquero-Baez, Araceli Díaz-Ruíz, Luis Tristán-López, Carlos Aviña-Cervantes, Carlos Torner, Jesús Ramírez-Bermúdez, Sergio Montes, Camilo Ríos. Clozapine and desmethylclozapine: correlation with neutrophils and leucocytes counting in Mexican patients with schizophrenia.
BMC psychiatry.
2019 10; 19(1):295. doi:
10.1186/s12888-019-2286-1. [PMID: 31597566] - Robert L Smith, Lennart Kyllesø, Tore Haslemo, Ole Andreas Andreassen, Espen Molden. Reduction in N-Desmethylclozapine Level Is Determined by Daily Dose But Not Serum Concentration of Valproic Acid-Indications of a Presystemic Interaction Mechanism.
Therapeutic drug monitoring.
2019 08; 41(4):503-508. doi:
10.1097/ftd.0000000000000619. [PMID: 31259880] - Georgios Schoretsanitis, John M Kane, Can-Jun Ruan, Edoardo Spina, Christoph Hiemke, Jose de Leon. A comprehensive review of the clinical utility of and a combined analysis of the clozapine/norclozapine ratio in therapeutic drug monitoring for adult patients.
Expert review of clinical pharmacology.
2019 Jul; 12(7):603-621. doi:
10.1080/17512433.2019.1617695. [PMID: 31075044] - Antonio F Pardiñas, Mariana Nalmpanti, Andrew J Pocklington, Sophie E Legge, Christopher Medway, Adrian King, John Jansen, Marinka Helthuis, Stanley Zammit, James MacCabe, Michael J Owen, Michael C O'Donovan, James T R Walters. Pharmacogenomic Variants and Drug Interactions Identified Through the Genetic Analysis of Clozapine Metabolism.
The American journal of psychiatry.
2019 06; 176(6):477-486. doi:
10.1176/appi.ajp.2019.18050589. [PMID: 30922102] - Yin Cheong Wong, Maddalena Centanni, Elizabeth C M de Lange. Physiologically Based Modeling Approach to Predict Dopamine D2 Receptor Occupancy of Antipsychotics in Brain: Translation From Rat to Human.
Journal of clinical pharmacology.
2019 05; 59(5):731-747. doi:
10.1002/jcph.1365. [PMID: 30676661] - Maike Scherf-Clavel, Lydia Samanski, Leif G Hommers, Jürgen Deckert, Andreas Menke, Stefan Unterecker. Analysis of smoking behavior on the pharmacokinetics of antidepressants and antipsychotics: evidence for the role of alternative pathways apart from CYP1A2.
International clinical psychopharmacology.
2019 03; 34(2):93-100. doi:
10.1097/yic.0000000000000250. [PMID: 30557209] - Donatella Marazziti, Lionella Palego, Laura Betti, Gino Giannaccini, Enrico Massimetti, Stefano Baroni, Antonio Ciapparelli, Antonio Lucacchini, Federico Mucci, Liliana DellʼOsso. Effect of Valproate and Antidepressant Drugs on Clozapine Metabolism in Patients With Psychotic Mood Disorders.
Therapeutic drug monitoring.
2018 08; 40(4):443-451. doi:
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Journal of clinical psychopharmacology.
2018 Jun; 38(3):188-192. doi:
10.1097/jcp.0000000000000877. [PMID: 29620699] - Heidi J Wehring, Teresa Elsobky, Joseph P McEvoy, Gopal Vyas, Charles M Richardson, Robert P McMahon, Bethany A DiPaula, Fang Liu, Kelli Sullivan, Robert W Buchanan, Stephanie Feldman, Elizabeth M McMahon, Deanna L Kelly. Adjunctive Minocycline in Clozapine-Treated Patients with Schizophrenia: Analyzing the Effects of Minocycline on Clozapine Plasma Levels.
The Psychiatric quarterly.
2018 03; 89(1):73-80. doi:
10.1007/s11126-017-9515-x. [PMID: 28466366] - Handley Sa, Silk Sw Fisher, Subramaniam K, Flanagan Rj. Clozapine and Norclozapine Concentrations in Paired Human Plasma and Serum Samples.
Therapeutic drug monitoring.
2018 02; 40(1):148-150. doi:
10.1097/ftd.0000000000000478. [PMID: 29240616] - Lewis Couchman, Danielle S Fisher, Krithika Subramaniam, Simon A Handley, Robert J Boughtflower, Christopher M Benton, Robert J Flanagan. Ultra-fast LC-MS/MS in therapeutic drug monitoring: Quantification of clozapine and norclozapine in human plasma.
Drug testing and analysis.
2018 Feb; 10(2):323-329. doi:
10.1002/dta.2223. [PMID: 28585411] - David B Menkes, Paul Glue, Christopher Gale, Frederic Lam, Cheung-Tak Hung, Noelyn Hung. Steady-State Clozapine and Norclozapine Pharmacokinetics in Maori and European Patients.
EBioMedicine.
2018 Jan; 27(?):134-137. doi:
10.1016/j.ebiom.2017.11.030. [PMID: 29254680] - Conrad Molins, Mar Carceller-Sindreu, Helena Navarro, Cristina Carmona, Marina Piñeiro, Estrella Martínez, Enric Álvarez, Maria J Portella. Plasma ratio of clozapine to N-desmethylclozapine can predict cognitive performance in treatment-resistant psychotic patients.
Psychiatry research.
2017 12; 258(?):153-157. doi:
10.1016/j.psychres.2017.10.010. [PMID: 29024893] - Yumiko Akamine, Yuka Sugawara-Kikuchi, Tsukasa Uno, Tetsuo Shimizu, Masatomo Miura. Quantification of the steady-state plasma concentrations of clozapine and N-desmethylclozapine in Japanese patients with schizophrenia using a novel HPLC method and the effects of CYPs and ABC transporters polymorphisms.
Annals of clinical biochemistry.
2017 Nov; 54(6):677-685. doi:
10.1177/0004563216686377. [PMID: 27932669] - Lisanne M Geers, Dan Cohen, Laura M Wehkamp, Kai van Hateren, Remco A Koster, Olga Yu Fedorenko, Arkadyi V Semke, Nikolay Bokhan, Svetlana A Ivanova, Jos G W Kosterink, Anton J M Loonen, Daan J Touw. Dried Blood Spot Analysis for Therapeutic Drug Monitoring of Clozapine.
The Journal of clinical psychiatry.
2017 Nov; 78(9):e1211-e1218. doi:
10.4088/jcp.16m11164. [PMID: 29068609] - Robert L Smith, Tore Haslemo, Ole A Andreassen, Erik Eliasson, Marja-Liisa Dahl, Olav Spigset, Espen Molden. Correlation Between Serum Concentrations of N-Desmethylclozapine and Granulocyte Levels in Patients with Schizophrenia: A Retrospective Observational Study.
CNS drugs.
2017 Nov; 31(11):991-997. doi:
10.1007/s40263-017-0469-1. [PMID: 28948574] - Danielle S Fisher, Chad Beyer, Gerrit van Schalkwyk, Soraya Seedat, Robert J Flanagan. Measurement of Clozapine, Norclozapine, and Amisulpride in Plasma and in Oral Fluid Obtained Using 2 Different Sampling Systems.
Therapeutic drug monitoring.
2017 04; 39(2):109-117. doi:
10.1097/ftd.0000000000000377. [PMID: 28125503] - M I Jakobsen, J R Larsen, C K Svensson, S S Johansen, K Linnet, J Nielsen, A Fink-Jensen. The significance of sampling time in therapeutic drug monitoring of clozapine.
Acta psychiatrica Scandinavica.
2017 Feb; 135(2):159-169. doi:
10.1111/acps.12673. [PMID: 27922183] - Wei Wang, Dan-Dan Tian, Zhang-Jin Zhang. In Vitro Effects of Concomitant Use of Herbal Preparations on Cytochrome P450s Involved in Clozapine Metabolism.
Molecules (Basel, Switzerland).
2016 May; 21(5):. doi:
10.3390/molecules21050597. [PMID: 27164071] - Jimmy Lee, Robert Bies, Hiroyoshi Takeuchi, Gagan Fervaha, Amaal Bhaloo, Valerie Powell, Gary Remington. Quantifying intraindividual variations in plasma clozapine levels: a population pharmacokinetic approach.
The Journal of clinical psychiatry.
2016 05; 77(5):681-7. doi:
10.4088/jcp.14m09714. [PMID: 27136679] - Lewis Couchman, Krithika Subramaniam, Danielle S Fisher, Sarah L Belsey, Simon A Handley, Robert J Flanagan. Automated Analysis of Clozapine and Norclozapine in Human Plasma Using Novel Extraction Plate Technology and Flow-Injection Tandem Mass Spectrometry.
Therapeutic drug monitoring.
2016 Feb; 38(1):42-9. doi:
10.1097/ftd.0000000000000231. [PMID: 26349082] - Mei-Ling Hou, Chi-Hung Lin, Lie-Chwen Lin, Tung-Hu Tsai. The Drug-Drug Effects of Rhein on the Pharmacokinetics and Pharmacodynamics of Clozapine in Rat Brain Extracellular Fluid by In Vivo Microdialysis.
The Journal of pharmacology and experimental therapeutics.
2015 Oct; 355(1):125-34. doi:
10.1124/jpet.115.225763. [PMID: 26220937] - Martina Curto, Anna Comparelli, Giuseppino M Ciavarella, Carlotta Gasperoni, Luana Lionetto, Valentina Corigliano, Arianna Uccellini, Iginia Mancinelli, Stefano Ferracuti, Paolo Girardi, Ross J Baldessarini. Impairment of left ventricular function early in treatment with clozapine: a preliminary study.
International clinical psychopharmacology.
2015 Sep; 30(5):282-9. doi:
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The American journal of psychiatry.
2015 Jun; 172(6):579-85. doi:
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Journal of translational medicine.
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Analytical and bioanalytical chemistry.
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2012; 2012(?):592784. doi:
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Analytical and bioanalytical chemistry.
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Therapeutic drug monitoring.
2010 Oct; 32(5):624-7. doi:
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Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2010 Sep; 878(25):2327-32. doi:
10.1016/j.jchromb.2010.07.001. [PMID: 20674521] - Lewis Couchman, Phillip Edgar Morgan, Edgar Pathrose Spencer, Robert James Flanagan. Plasma clozapine, norclozapine, and the clozapine:norclozapine ratio in relation to prescribed dose and other factors: data from a therapeutic drug monitoring service, 1993-2007.
Therapeutic drug monitoring.
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