Tolcapone (BioDeep_00000006636)

 

Secondary id: BioDeep_00000399159

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


5-(4-methylbenzoyl)-3-nitrobenzene-1,2-diol

化学式: C14H11NO5 (273.0637196)
中文名称: 托卡朋
谱图信息: 最多检出来源 Homo sapiens(blood) 14.96%

分子结构信息

SMILES: CC1=CC=C(C=C1)C(=O)C1=CC(=C(O)C(O)=C1)[N+]([O-])=O
InChI: InChI=1S/C14H11NO5/c1-8-2-4-9(5-3-8)13(17)10-6-11(15(19)20)14(18)12(16)7-10/h2-7,16,18H,1H3

描述信息

Tolcapone is a drug that inhibits the enzyme catechol-O-methyl transferase (COMT). It is used in the treatment of Parkinsons disease as an adjunct to levodopa/carbidopa medication. It is a yellow, odorless, non-hygroscopic, crystalline compound. Tolcapone is associated with a risk of hepatotoxicity. [Wikipedia]
D002491 - Central Nervous System Agents > D018726 - Anti-Dyskinesia Agents > D000978 - Antiparkinson Agents
D004791 - Enzyme Inhibitors > D065098 - Catechol O-Methyltransferase Inhibitors
N - Nervous system > N04 - Anti-parkinson drugs > N04B - Dopaminergic agents
C78272 - Agent Affecting Nervous System > C38149 - Antiparkinsonian Agent

同义名列表

9 个代谢物同义名

5-(4-methylbenzoyl)-3-nitrobenzene-1,2-diol; 4-Methyl-3,4-dihydroxy-5-nitrobenzophenone; 3,4-Dihydroxy-5-nitro-4-methylbenzophenone; 3,4-Dihydroxy-4-methyl-5-nitrobenzophenone; 3,4 Dihydroxy 5 methyl 5 nitrobenzophenone; 3,4-Dihydroxy-5-methyl-5-nitrobenzophenone; Roche brand OF tolcapone; Tolcapone; Tasmar



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

1 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(1)

PathBank(0)

PharmGKB(0)

1 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

  • Joana Rebouta, Luísa Dória, Ana Coelho, Miguel M Fonseca, Guillermo Castilla-Fernández, Nuno M Pires, M A Vieira-Coelho, Ana I Loureiro. HR/MS-based lipidome analysis of rat brain modulated by tolcapone. Journal of pharmaceutical and biomedical analysis. 2024 Jan; 241(?):115971. doi: 10.1016/j.jpba.2024.115971. [PMID: 38266454]
  • Luke T Nelson, Ryan J Paxman, Jin Xu, Bill Webb, Evan T Powers, Jeffery W Kelly. Blinded potency comparison of transthyretin kinetic stabilisers by subunit exchange in human plasma. Amyloid : the international journal of experimental and clinical investigation : the official journal of the International Society of Amyloidosis. 2021 Mar; 28(1):24-29. doi: 10.1080/13506129.2020.1808783. [PMID: 32811187]
  • Aaro Jalkanen, Veera Lassheikki, Tommi Torsti, Elham Gharib, Marko Lehtonen, Risto O Juvonen. Tissue and interspecies comparison of catechol-O-methyltransferase mediated catalysis of 6-O-methylation of esculetin to scopoletin and its inhibition by entacapone and tolcapone. Xenobiotica; the fate of foreign compounds in biological systems. 2021 Mar; 51(3):268-278. doi: 10.1080/00498254.2020.1853850. [PMID: 33289420]
  • Carlos G Moreira, Marta M Morawska, Aron Baumann, Sophie Masneuf, Michael Linnebank, Michael Sommerauer, Hans-Peter Landolt, Daniela Noain, Christian R Baumann. Improved functional and histochemical outcomes in l-DOPA plus tolcapone treated VMAT2-deficient mice. Neuropharmacology. 2020 12; 181(?):108353. doi: 10.1016/j.neuropharm.2020.108353. [PMID: 33038358]
  • Valentina Loconte, Michele Cianci, Ilaria Menozzi, Davide Sbravati, Francesco Sansone, Alessandro Casnati, Rodolfo Berni. Interactions of tolcapone analogues as stabilizers of the amyloidogenic protein transthyretin. Bioorganic chemistry. 2020 10; 103(?):104144. doi: 10.1016/j.bioorg.2020.104144. [PMID: 32791384]
  • Xin Wang, Murat Cirit, John S Wishnok, Linda G Griffith, Steven R Tannenbaum. Analysis of an Integrated Human Multiorgan Microphysiological System for Combined Tolcapone Metabolism and Brain Metabolomics. Analytical chemistry. 2019 07; 91(13):8667-8675. doi: 10.1021/acs.analchem.9b02224. [PMID: 31181164]
  • Shawn Stanley, Koos Van den Berg, Hsiao Ching Foo, Derek Deng. Metabolism and elimination of the catechol-o-methyltransferase inhibitor tolcapone in the horse. Drug testing and analysis. 2019 Apr; 11(4):578-585. doi: 10.1002/dta.2531. [PMID: 30367738]
  • Mark Miller, Arindom Pal, Wabel Albusairi, Hyun Joo, Beverly Pappas, Md Tariqul Haque Tuhin, Dengpan Liang, Raghavendra Jampala, Fang Liu, Jared Khan, Marjon Faaij, Miki Park, William Chan, Isabella Graef, Robert Zamboni, Neil Kumar, Jonathan Fox, Uma Sinha, Mamoun Alhamadsheh. Enthalpy-Driven Stabilization of Transthyretin by AG10 Mimics a Naturally Occurring Genetic Variant That Protects from Transthyretin Amyloidosis. Journal of medicinal chemistry. 2018 09; 61(17):7862-7876. doi: 10.1021/acs.jmedchem.8b00817. [PMID: 30133284]
  • David Grünig, Andrea Felser, Urs Duthaler, Jamal Bouitbir, Stephan Krähenbühl. Effect of the Catechol-O-Methyltransferase Inhibitors Tolcapone and Entacapone on Fatty Acid Metabolism in HepaRG Cells. Toxicological sciences : an official journal of the Society of Toxicology. 2018 08; 164(2):477-488. doi: 10.1093/toxsci/kfy101. [PMID: 29688484]
  • Ghobad Mohammadi, Elahe Faramarzi, Majid Mahmoudi, Sirous Ghobadi, Ali Reza Ghiasvand, Hector C Goicoechea, Ali R Jalalvand. Chemometrics-assisted investigation of interactions of Tasmar with human serum albumin at a glassy carbon disk: Application to electrochemical biosensing of electro-inactive serum albumin. Journal of pharmaceutical and biomedical analysis. 2018 Jul; 156(?):23-35. doi: 10.1016/j.jpba.2018.04.021. [PMID: 29684908]
  • Joana Bicker, Ana Fortuna, Gilberto Alves, Patrício Soares-da-Silva, Amílcar Falcão. Elucidation of the Impact of P-glycoprotein and Breast Cancer Resistance Protein on the Brain Distribution of Catechol-O-Methyltransferase Inhibitors. Drug metabolism and disposition: the biological fate of chemicals. 2017 12; 45(12):1282-1291. doi: 10.1124/dmd.117.077883. [PMID: 28916530]
  • Xia Lv, Xin-Xin Wang, Jie Hou, Zhong-Ze Fang, Jing-Jing Wu, Yun-Feng Cao, Shu-Wen Liu, Guang-Bo Ge, Ling Yang. Comparison of the inhibitory effects of tolcapone and entacapone against human UDP-glucuronosyltransferases. Toxicology and applied pharmacology. 2016 06; 301(?):42-9. doi: 10.1016/j.taap.2016.04.009. [PMID: 27089846]
  • Ricardo Sant'Anna, Pablo Gallego, Lei Z Robinson, Alda Pereira-Henriques, Nelson Ferreira, Francisca Pinheiro, Sebastian Esperante, Irantzu Pallares, Oscar Huertas, Maria Rosário Almeida, Natàlia Reixach, Raul Insa, Adrian Velazquez-Campoy, David Reverter, Núria Reig, Salvador Ventura. Repositioning tolcapone as a potent inhibitor of transthyretin amyloidogenesis and associated cellular toxicity. Nature communications. 2016 Feb; 7(?):10787. doi: 10.1038/ncomms10787. [PMID: 26902880]
  • D M Longo, Y Yang, P B Watkins, B A Howell, S Q Siler. Elucidating Differences in the Hepatotoxic Potential of Tolcapone and Entacapone With DILIsym(®), a Mechanistic Model of Drug-Induced Liver Injury. CPT: pharmacometrics & systems pharmacology. 2016 01; 5(1):31-9. doi: 10.1002/psp4.12053. [PMID: 26844013]
  • M J Bonifácio, L Torrão, A I Loureiro, P N Palma, L C Wright, P Soares-da-Silva. Pharmacological profile of opicapone, a third-generation nitrocatechol catechol-O-methyl transferase inhibitor, in the rat. British journal of pharmacology. 2015 Apr; 172(7):1739-52. doi: 10.1111/bph.13020. [PMID: 25409768]
  • Rômulo Pereira Ribeiro, João Cleverson Gasparetto, Raquel de Oliveira Vilhena, Thais Martins Guimarães de Francisco, Thais Martins Guimarães de Francisco, Cleverson Antônio Ferreira Martins, Marco André Cardoso, Roberto Pontarolo, Katherine Athayde Teixeira de Carvalho. Simultaneous determination of levodopa, carbidopa, entacapone, tolcapone, 3-O-methyldopa and dopamine in human plasma by an HPLC-MS/MS method. Bioanalysis. 2015; 7(2):207-20. doi: 10.4155/bio.14.230. [PMID: 25587837]
  • Qu Qi, Lijuan Cao, Feiyan Li, Hong Wang, Huiying Liu, Haiping Hao, Kun Hao. Salvianolic acid B as a substrate and weak catechol-O-methyltransferase inhibitor in rats. Xenobiotica; the fate of foreign compounds in biological systems. 2015; 45(9):820-7. doi: 10.3109/00498254.2015.1017753. [PMID: 25869243]
  • Siegfried Muhlack, Lennard Herrmann, Stephan Salmen, Thomas Müller. Fewer fluctuations, higher maximum concentration and better motor response of levodopa with catechol-O-methyltransferase inhibition. Journal of neural transmission (Vienna, Austria : 1996). 2014 Nov; 121(11):1357-66. doi: 10.1007/s00702-014-1213-3. [PMID: 24770794]
  • Sarah C Forester, Joshua D Lambert. Synergistic inhibition of lung cancer cell lines by (-)-epigallocatechin-3-gallate in combination with clinically used nitrocatechol inhibitors of catechol-O-methyltransferase. Carcinogenesis. 2014 Feb; 35(2):365-72. doi: 10.1093/carcin/bgt347. [PMID: 24148818]
  • Dominika Zajac, Grzegorz Spolnik, Piotr Roszkowski, Witold Danikiewicz, Zbigniew Czarnocki, Mieczyslaw Pokorski. Metabolism of N-acylated-dopamine. PloS one. 2014; 9(1):e85259. doi: 10.1371/journal.pone.0085259. [PMID: 24465516]
  • Frida Gustafsson, Alison J Foster, Sunil Sarda, Matthew H Bridgland-Taylor, J Gerry Kenna. A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans. Toxicological sciences : an official journal of the Society of Toxicology. 2014 Jan; 137(1):189-211. doi: 10.1093/toxsci/kft223. [PMID: 24085192]
  • Daphna Laifenfeld, Luping Qiu, Rachel Swiss, Jennifer Park, Michael Macoritto, Yvonne Will, Husam S Younis, Michael Lawton. Utilization of causal reasoning of hepatic gene expression in rats to identify molecular pathways of idiosyncratic drug-induced liver injury. Toxicological sciences : an official journal of the Society of Toxicology. 2014 Jan; 137(1):234-48. doi: 10.1093/toxsci/kft232. [PMID: 24136188]
  • Liang Guo, Luke Coyle, Rory M C Abrams, Raymond Kemper, Eric T Chiao, Kyle L Kolaja. Refining the human iPSC-cardiomyocyte arrhythmic risk assessment model. Toxicological sciences : an official journal of the Society of Toxicology. 2013 Dec; 136(2):581-94. doi: 10.1093/toxsci/kft205. [PMID: 24052561]
  • Susanne N E Boehn, Sonja Spahn, Sabine Neudecker, Andrea Keppler, Marie-Thérèse Bihoreau, Bettina Kränzlin, Priyanka Pandey, Sigrid C Hoffmann, Li Li, Vicente E Torres, Hermann-Josef Gröne, Norbert Gretz. Inhibition of Comt with tolcapone slows progression of polycystic kidney disease in the more severely affected PKD/Mhm (cy/+) substrain of the Hannover Sprague-Dawley rat. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2013 Aug; 28(8):2045-58. doi: 10.1093/ndt/gft014. [PMID: 23543593]
  • Daniel J Warner, Hongming Chen, Louis-David Cantin, J Gerry Kenna, Simone Stahl, Clare L Walker, Tobias Noeske. Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification. Drug metabolism and disposition: the biological fate of chemicals. 2012 Dec; 40(12):2332-41. doi: 10.1124/dmd.112.047068. [PMID: 22961681]
  • Robert N McBurney, Wade M Hines, Linda S VonTungeln, Laura K Schnackenberg, Richard D Beger, Carrie L Moland, Tao Han, James C Fuscoe, Ching-Wei Chang, James J Chen, Zhenqiang Su, Xiao-hui Fan, Weida Tong, Shelagh A Booth, Raji Balasubramanian, Paul L Courchesne, Jennifer M Campbell, Armin Graber, Yu Guo, Peter Juhasz, Tricia Y Li, Moira D Lynch, Nicole M Morel, Thomas N Plasterer, Edward J Takach, Chenhui Zeng, Frederick A Beland. The liver toxicity biomarker study phase I: markers for the effects of tolcapone or entacapone. Toxicologic pathology. 2012 Aug; 40(6):951-64. doi: 10.1177/0192623312444026. [PMID: 22573522]
  • D Nyholm, A Johansson, H Lennernäs, H Askmark. Levodopa infusion combined with entacapone or tolcapone in Parkinson disease: a pilot trial. European journal of neurology. 2012 Jun; 19(6):820-6. doi: 10.1111/j.1468-1331.2011.03614.x. [PMID: 22136163]
  • Lieve Desbonnet, Orna Tighe, Maria Karayiorgou, Joseph A Gogos, John L Waddington, Colm M P O'Tuathaigh. Physiological and behavioural responsivity to stress and anxiogenic stimuli in COMT-deficient mice. Behavioural brain research. 2012 Mar; 228(2):351-8. doi: 10.1016/j.bbr.2011.12.014. [PMID: 22192380]
  • Ronald G Robinson, Sean M Smith, Scott E Wolkenberg, Monika Kandebo, Lihang Yao, Christopher R Gibson, Scott T Harrison, Stacey Polsky-Fisher, James C Barrow, Peter J Manley, James J Mulhearn, Kausik K Nanda, Jeffrey W Schubert, B Wesley Trotter, Zhijian Zhao, John M Sanders, Robert F Smith, Debra McLoughlin, Sujata Sharma, Dawn L Hall, Tiffany L Walker, Jennifer L Kershner, Neetesh Bhandari, Pete H Hutson, Nancy A Sachs. Characterization of non-nitrocatechol pan and isoform specific catechol-O-methyltransferase inhibitors and substrates. ACS chemical neuroscience. 2012 Feb; 3(2):129-40. doi: 10.1021/cn200109w. [PMID: 22860182]
  • Daniela Gonçalves, Gilberto Alves, Patrício Soares-da-Silva, Amílcar Falcão. Bioanalytical chromatographic methods for the determination of catechol-O-methyltransferase inhibitors in rodents and human samples: a review. Analytica chimica acta. 2012 Jan; 710(?):17-32. doi: 10.1016/j.aca.2011.10.026. [PMID: 22123108]
  • Takako Furukawa, Fumihiro Nakamori, Kazuhiro Tetsuka, Yoichi Naritomi, Hiroyuki Moriguchi, Katsuhiro Yamano, Shigeyuki Terashita, Toshio Teramura. Quantitative prediction of intestinal glucuronidation of drugs in rats using in vitro metabolic clearance data. Drug metabolism and pharmacokinetics. 2012; 27(2):171-80. doi: 10.2133/dmpk.dmpk-11-rg-088. [PMID: 21970858]
  • Sarah Dawson, Simone Stahl, Nikki Paul, Jane Barber, J Gerald Kenna. In vitro inhibition of the bile salt export pump correlates with risk of cholestatic drug-induced liver injury in humans. Drug metabolism and disposition: the biological fate of chemicals. 2012 Jan; 40(1):130-8. doi: 10.1124/dmd.111.040758. [PMID: 21965623]
  • Ching-Wei Chang, Frederick A Beland, Wade M Hines, James C Fuscoe, Tao Han, James J Chen. Identification and categorization of liver toxicity markers induced by a related pair of drugs. International journal of molecular sciences. 2011; 12(7):4609-24. doi: 10.3390/ijms12074609. [PMID: 21845099]
  • Angelo Antonini, Daniela Calandrella. Once-daily pramipexole for the treatment of early and advanced idiopathic Parkinson's disease: implications for patients. Neuropsychiatric disease and treatment. 2011; 7(?):297-302. doi: 10.2147/ndt.s10097. [PMID: 21654875]
  • Mikael Palner, Patrick McCormick, Jun Parkes, Gitte M Knudsen, Alan A Wilson. Systemic catechol-O-methyl transferase inhibition enables the D1 agonist radiotracer R-[11C]SKF 82957. Nuclear medicine and biology. 2010 Oct; 37(7):837-43. doi: 10.1016/j.nucmedbio.2010.04.193. [PMID: 20870159]
  • Paolo Solla, Antonino Cannas, Francesco Marrosu, Maria Giovanna Marrosu. Therapeutic interventions and adjustments in the management of Parkinson disease: role of combined carbidopa/levodopa/entacapone (Stalevo). Neuropsychiatric disease and treatment. 2010 Sep; 6(?):483-90. doi: 10.2147/ndt.s5190. [PMID: 20856911]
  • Ki Sung Kang, Yujing Wen, Noriko Yamabe, Masayuki Fukui, Stephanie C Bishop, Bao Ting Zhu. Dual beneficial effects of (-)-epigallocatechin-3-gallate on levodopa methylation and hippocampal neurodegeneration: in vitro and in vivo studies. PloS one. 2010 Aug; 5(8):e11951. doi: 10.1371/journal.pone.0011951. [PMID: 20700524]
  • Yoshitatsu Sei, Zhen Li, Jian Song, Renee Ren-Patterson, Elizabeth M Tunbridge, Yukihiko Iizuka, Masahiro Inoue, Berenice T Alfonso, Senda Beltaifa, Yoko Nakai, Bhaskar S Kolachana, Jingshan Chen, Daniel R Weinberger. Epistatic and functional interactions of catechol-o-methyltransferase (COMT) and AKT1 on neuregulin1-ErbB signaling in cell models. PloS one. 2010 May; 5(5):e10789. doi: 10.1371/journal.pone.0010789. [PMID: 20520724]
  • Urszula Adamiak, Maria Kaldonska, Gabriela Klodowska-Duda, Elzbieta Wyska, Krzysztof Safranow, Monika Bialecka, Barbara Gawronska-Szklarz. Pharmacokinetic-pharmacodynamic modeling of levodopa in patients with advanced Parkinson disease. Clinical neuropharmacology. 2010 May; 33(3):135-41. doi: 10.1097/wnf.0b013e3181d47849. [PMID: 20216409]
  • Maria Luigia De Bonis, Alessandro Tessitore, Maria Teresa Pellecchia, Katia Longo, Anna Salvatore, Antonio Russo, Diego Ingrosso, Vincenzo Zappia, Paolo Barone, Patrizia Galletti, Gioacchino Tedeschi. Impaired transmethylation potential in Parkinson's disease patients treated with L-Dopa. Neuroscience letters. 2010 Jan; 468(3):287-91. doi: 10.1016/j.neulet.2009.11.014. [PMID: 19909787]
  • Jinchun Sun, Linda S Von Tungeln, Wade Hines, Richard D Beger. Identification of metabolite profiles of the catechol-O-methyl transferase inhibitor tolcapone in rat urine using LC/MS-based metabonomics analysis. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2009 Aug; 877(24):2557-65. doi: 10.1016/j.jchromb.2009.06.033. [PMID: 19615953]
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  • Robert N McBurney, Wade M Hines, Linda S Von Tungeln, Laura K Schnackenberg, Richard D Beger, Carrie L Moland, Tao Han, James C Fuscoe, Ching-Wei Chang, James J Chen, Zhenqiang Su, Xiao-Hui Fan, Weida Tong, Shelagh A Booth, Raji Balasubramanian, Paul L Courchesne, Jennifer M Campbell, Armin Graber, Yu Guo, Peter J Juhasz, Tricin Y Li, Moira D Lynch, Nicole M Morel, Thomas N Plasterer, Edward J Takach, Chenhui Zeng, Frederick A Beland. The liver toxicity biomarker study: phase I design and preliminary results. Toxicologic pathology. 2009 Jan; 37(1):52-64. doi: 10.1177/0192623308329287. [PMID: 19171931]
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