Propafenone (BioDeep_00000002059)

 

Secondary id: BioDeep_00000408817

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


1-(2-(2-Hydroxy-3-(propylamino)propoxy)phenyl)-3-phenyl-1-propanone

化学式: C21H27NO3 (341.1990832)
中文名称: 普罗帕酮
谱图信息: 最多检出来源 Homo sapiens(urine) 1.67%

分子结构信息

SMILES: CCCNCC(COC1=CC=CC=C1C(=O)CCC2=CC=CC=C2)O
InChI: InChI=1S/C21H27NO3/c1-2-14-22-15-18(23)16-25-21-11-7-6-10-19(21)20(24)13-12-17-8-4-3-5-9-17/h3-11,18,22-23H,2,12-16H2,1H3

描述信息

Propafenone is only found in individuals that have used or taken this drug. It is an antiarrhythmia agent that is particularly effective in ventricular arrhythmias. It also has weak beta-blocking activity. The drug is generally well tolerated. [PubChem]The electrophysiological effect of propafenone manifests itself in a reduction of upstroke velocity (Phase 0) of the monophasic action potential. In Purkinje fibers, and to a lesser extent myocardial fibers, propafenone reduces the fast inward current carried by sodium ions, which is responsible for the drugs antiarrhythmic actions. Diastolic excitability threshold is increased and effective refractory period prolonged. Propafenone reduces spontaneous automaticity and depresses triggered activity. At very high concentrations in vitro, propafenone can inhibit the slow inward current carried by calcium but this calcium antagonist effect probably does not contribute to antiarrhythmic efficacy.
C - Cardiovascular system > C01 - Cardiac therapy > C01B - Antiarrhythmics, class i and iii > C01BC - Antiarrhythmics, class ic
D002317 - Cardiovascular Agents > D026941 - Sodium Channel Blockers > D061567 - Voltage-Gated Sodium Channel Blockers
C78274 - Agent Affecting Cardiovascular System > C47793 - Antiarrhythmic Agent
D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents
CONFIDENCE standard compound; INTERNAL_ID 2285
D049990 - Membrane Transport Modulators
C93038 - Cation Channel Blocker
Propafenone (SA-79), a sodium-channel blocker, acts an antiarrhythmic agent. Propafenone also has high affinity for the β receptor (IC50=32 nM)[1]. Propafenone blocks the transient outward current (Ito) and the sustained delayed rectifier K current (Isus) with IC50 values of 4.9?μm and 8.6?μm, respectively[2]. Propafenone suppresses esophageal cancer proliferation through inducing mitochondrial dysfunction and induce apoptosis[3].

同义名列表

45 个代谢物同义名

1-(2-(2-Hydroxy-3-(propylamino)propoxy)phenyl)-3-phenyl-1-propanone; 1-{2-[2-hydroxy-3-(propylamino)propoxy]phenyl}-3-phenylpropan-1-one; 2-(2-Hydroxy-3-propylaminopropoxy)-omega-phenylpropiophenone; Merck dura brand OF propafenone hydrochloride; Azupharma brand OF propafenone hydrochloride; Kendrick brand OF propafenone hydrochloride; Alpharma brand OF propafenone hydrochloride; Q-Pharm brand OF propafenone hydrochloride; Abbott brand OF propafenone hydrochloride; Apotex brand OF propafenone hydrochloride; Aliud brand OF propafenone hydrochloride; Knoll brand OF propafenone hydrochloride; Juta brand OF propafenone hydrochloride; TAD brand OF propafenone hydrochloride; Propafenone hydrochloride, (S)-isomer; Propafenone hydrochloride, (R)-isomer; Hydrochloride, propafenone; Hexal brand OF propafenone; Propafenone hydrochloride; Propafenone, (+-)-isomer; Propafenone, (S)-isomer; Propafenone, (R)-isomer; Propafenon minden; Propafenon hexal; Apo-propafenone; Propafenon al; Propafenonum; propafenone; Propafenona; Rytmo-puren; Propamerck; Rytmogenat; Baxarytmon; Prolecofen; Rytmonorm; Cuxafenon; Pintoform; Fenoprain; Jutanorm; Arythmol; Nistaken; Norfenon; Rythmol; SA 79; SA-79



数据库引用编号

23 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

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)

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。

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文献列表

  • Jinlian Wei, Yongyun Li, Ruoxi Li, Xin Chen, Tiannuo Yang, Liang Liao, Yuqing Xie, Jin Zhu, Fei Mao, Renbing Jia, Xiaofang Xu, Jian Li. Drug repurposing of propafenone to discover novel anti-tumor agents by impairing homologous recombination to delay DNA damage recovery of rare disease conjunctival melanoma. European journal of medicinal chemistry. 2023 Feb; 250(?):115238. doi: 10.1016/j.ejmech.2023.115238. [PMID: 36868105]
  • Jiaru Li, Junzu Shi, Chenyang Jia, Wei Li, Ying Peng, Jiang Zheng. Metabolic Activation and Cytotoxicity of Propafenone Mediated by CYP2D6. Chemical research in toxicology. 2022 05; 35(5):829-839. doi: 10.1021/acs.chemrestox.2c00013. [PMID: 35442037]
  • Beata Ceynowa-Sielawko, Maciej T Wybraniec, Aleksandra Topp-Zielińska, Aleksander Maciąg, Dawid Miśkowiec, Paweł Balsam, Maciej Wójcik, Wojciech Wróbel, Michał M Farkowski, Edyta Ćwiek-Rębowska, Krzysztof Ozierański, Robert Błaszczyk, Karolina Bula, Tomasz Dembowski, Michał Peller, Bartosz Krzowski, Wojciech Wańha, Marek Koziński, Jarosław D Kasprzak, Hanna Szwed, Katarzyna Mizia-Stec, Marek Szołkiewicz. Pharmacological Cardioversion in Patients with Recent-Onset Atrial Fibrillation and Chronic Kidney Disease Subanalysis of the CANT II Study. International journal of environmental research and public health. 2022 04; 19(8):. doi: 10.3390/ijerph19084880. [PMID: 35457747]
  • Xiaokang Li, Jinwen Li, Yunyuan Huang, Qi Gong, Yan Fu, Yixiang Xu, Junyang Huang, Haolan You, Dong Zhang, Dan Zhang, Fei Mao, Jin Zhu, Huan Wang, Haiyan Zhang, Jian Li. The novel therapeutic strategy of vilazodone-donepezil chimeras as potent triple-target ligands for the potential treatment of Alzheimer's disease with comorbid depression. European journal of medicinal chemistry. 2022 Feb; 229(?):114045. doi: 10.1016/j.ejmech.2021.114045. [PMID: 34922191]
  • Han Ju, N Arul Murugan, Lingxin Hou, Ping Li, Laura Guizzo, Ying Zhang, Chiara Bertagnin, Xiujie Kong, Dongwei Kang, Ruifang Jia, Xiuli Ma, Ruikun Du, Vasanthanathan Poongavanam, Arianna Loregian, Bing Huang, Xinyong Liu, Peng Zhan. Identification of C5-NH2 Modified Oseltamivir Derivatives as Novel Influenza Neuraminidase Inhibitors with Highly Improved Antiviral Activities and Favorable Druggability. Journal of medicinal chemistry. 2021 12; 64(24):17992-18009. doi: 10.1021/acs.jmedchem.1c01366. [PMID: 34735766]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Bei-Er Jiang, Xingwu Jiang, Qiansen Zhang, Qiuwen Liang, Zi-Liang Qiu, Xiang-Bai Sun, Jun-Jie Yang, Si Chen, Chunyang Yi, Xiaolei Chai, Mingyao Liu, Li-Fang Yu, Weiqiang Lu, Han-Kun Zhang. From a Designer Drug to the Discovery of Selective Cannabinoid Type 2 Receptor Agonists with Favorable Pharmacokinetic Profiles for the Treatment of Systemic Sclerosis. Journal of medicinal chemistry. 2021 01; 64(1):385-403. doi: 10.1021/acs.jmedchem.0c01023. [PMID: 33382613]
  • Kosuke Doki, Yuki Shirayama, Yukio Sekiguchi, Kazutaka Aonuma, Yukinao Kohda, Masaki Ieda, Masato Homma. Effect of CYP2D6 genetic polymorphism on peak propafenone concentration: no significant effect of CYP2D6*10. Pharmacogenomics. 2020 12; 21(18):1279-1288. doi: 10.2217/pgs-2020-0105. [PMID: 33203295]
  • Yuzhou Gui, Youli Lu, Shuijun Li, Mengqi Zhang, Xiaokun Duan, Charles C Liu, Jingying Jia, Gangyi Liu. Direct analysis in real time-mass spectrometry for rapid quantification of five anti-arrhythmic drugs in human serum: application to therapeutic drug monitoring. Scientific reports. 2020 09; 10(1):15550. doi: 10.1038/s41598-020-72490-w. [PMID: 32968164]
  • Xiaodan Wang, Zhengqing Liu, Pengfei Gao, Yanjie Li, Xiaoyan Qu. Surface functionalized quantum dots as biosensor for highly selective and sensitive detection of ppb level of propafenone. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2020 Feb; 227(?):117709. doi: 10.1016/j.saa.2019.117709. [PMID: 31699588]
  • Xusheng An, Yong Mei, Hao Sun, Jinsong Zhang. Detoxification effects of long-chain versus a mixture of medium- and long-chain triglyceride-based fat emulsion on propafenone poisoning. Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas. 2020; 53(7):e9491. doi: 10.1590/1414-431x20209491. [PMID: 32520203]
  • Kuanglei Wang, Zaiqiang Lei, Lei Zhao, Binfeng Chen, Fei Yang, Kemin Liu, Hongxi Zhu, Hongqian Zhao, Ruiyuan Cao, Kun Zhang, Yongshou Tian. Design, synthesis and biological evaluation of oseltamivir derivatives containing pyridyl group as potent inhibitors of neuraminidase for influenza A. European journal of medicinal chemistry. 2020 Jan; 185(?):111841. doi: 10.1016/j.ejmech.2019.111841. [PMID: 31708183]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Wei Zhang, Shichun Lun, Ling-Ling Liu, Shiqi Xiao, Guanfu Duan, Hendra Gunosewoyo, Fan Yang, Jie Tang, William R Bishai, Li-Fang Yu. Identification of Novel Coumestan Derivatives as Polyketide Synthase 13 Inhibitors against Mycobacterium tuberculosis. Part II. Journal of medicinal chemistry. 2019 04; 62(7):3575-3589. doi: 10.1021/acs.jmedchem.9b00010. [PMID: 30875203]
  • Jian Zhang, Natarajan Arul Murugan, Ye Tian, Chiara Bertagnin, Zengjun Fang, Dongwei Kang, Xiujie Kong, Haiyong Jia, Zhuosen Sun, Ruifang Jia, Ping Gao, Vasanthanathan Poongavanam, Arianna Loregian, Wenfang Xu, Xiuli Ma, Xiao Ding, Bing Huang, Peng Zhan, Xinyong Liu. Structure-Based Optimization of N-Substituted Oseltamivir Derivatives as Potent Anti-Influenza A Virus Agents with Significantly Improved Potency against Oseltamivir-Resistant N1-H274Y Variant. Journal of medicinal chemistry. 2018 11; 61(22):9976-9999. doi: 10.1021/acs.jmedchem.8b01065. [PMID: 30365885]
  • Beatrice Severino, Giancarlo Luisi, Renan Donomae Iwamoto, Ronilson Agnaldo Moreno, Victor Perez Teixeira, Paola Di Vaio, Irene Saccone, Elisa Magli, Vincenzo Santagada, Giuseppe Caliendo, Gustavo D Mendes, Gilberto De Nucci. Propafenone quantification in human plasma by high-performance liquid chromatography coupled with electrospray tandem mass spectrometry in a bioequivalence study
. International journal of clinical pharmacology and therapeutics. 2018 Jun; 56(6):280-291. doi: 10.5414/cp203181. [PMID: 29648531]
  • Yuki Shirayama, Kosuke Doki, Yukio Sekiguchi, Kazutaka Aonuma, Yukinao Kohda, Masato Homma. Simultaneous determination of serum propafenone and its metabolites using high-performance liquid chromatography. Biomedical chromatography : BMC. 2018 Feb; 32(2):. doi: 10.1002/bmc.4099. [PMID: 28929504]
  • Zhiyan Chi, Ruijuan Liu, Y Li, Keli Wang, Chang Shu, L Ding. A Sensitive and Rapid LC-MS-MS Method for Simultaneous Determination of Propafenone and Its Active Metabolite 5-Hydroxypropafenone in Human Plasma and Its Application in a Pharmacokinetic Study. Journal of chromatographic science. 2017 Oct; 55(9):911-917. doi: 10.1093/chromsci/bmx049. [PMID: 28985274]
  • Harilal Patel, Ashok Ghoghari, Chandrakant Bhatt, Shaival Shah, Anilkumar Jha, Nirmal Desai, Nuggehally R Srinivas. A sensitive quantitative assay for the determination of propafenone and two metabolites, 5-hydroxypropafenone and N-depropylpropafenone, in human K2EDTA plasma using LC-MS/MS with ESI operated in positive mode. Biomedical chromatography : BMC. 2017 Oct; 31(10):. doi: 10.1002/bmc.3967. [PMID: 28261841]
  • Ivana Kacirova, Milan Grundmann, Martin Kolek, Erika Vyskocilova-Hrudikova, Romana Urinovska, Petr Handlos. Lethal suicide attempt with a mixed-drug intoxication of metoprolol and propafenone - A first pediatric case report. Forensic science international. 2017 Sep; 278(?):e34-e40. doi: 10.1016/j.forsciint.2017.06.025. [PMID: 28716517]
  • Mohammad-Reza Rouini, Minoo Afshar. Effect of CYP2D6 polymorphisms on the pharmacokinetics of propafenone and its two main metabolites. Therapie. 2017 Jun; 72(3):373-382. doi: 10.1016/j.therap.2016.10.005. [PMID: 28087064]
  • Talha Shafi, Ishrat Jabeen. Grid-independent Descriptors (GRIND) Analysis and SAR Guided Molecular Docking Studies to Probe Selectivity Profiles of Inhibitors of Multidrug Resistance Transporters ABCB1 and ABCG2. Current cancer drug targets. 2017; 17(2):177-190. doi: 10.2174/1568009616666160901094140. [PMID: 27585695]
  • Kurt Stoschitzky, Gergana Stoschitzky, Peter Lercher, Helmut Brussee, Günter Lamprecht, Wolfgang Lindner. Propafenone shows class Ic and class II antiarrhythmic effects. Europace : European pacing, arrhythmias, and cardiac electrophysiology : journal of the working groups on cardiac pacing, arrhythmias, and cardiac cellular electrophysiology of the European Society of Cardiology. 2016 Apr; 18(4):568-71. doi: 10.1093/europace/euv195. [PMID: 26056191]
  • Yinsong Zhu, Jiong Hu, Wenjuan He, Xiujuan Gao, Ping Ren, Hui Chen. DDPH, a novel antihypertensive agent, is a potential dual inhibitor of hepatic CYP2D and CYP3A. Chemico-biological interactions. 2016 Mar; 247(?):55-63. doi: 10.1016/j.cbi.2016.01.019. [PMID: 26827781]
  • Matthew H Slawson, Kamisha L Johnson-Davis. Quantitation of Flecainide, Mexiletine, Propafenone, and Amiodarone in Serum or Plasma Using Liquid Chromatography-Tandem Mass Spectrometry (LC-MS/MS). Methods in molecular biology (Clifton, N.J.). 2016; 1383(?):11-9. doi: 10.1007/978-1-4939-3252-8_2. [PMID: 26660169]
  • Başak Bayram, Işıl Köse, Sinem Avcı, Abdulla Arslan, Çağdaş Acara. Successful Treatment of Propafenone Intoxication With Intravenous Lipid Emulsion. Pharmacotherapy. 2015 Oct; 35(10):e149-52. doi: 10.1002/phar.1637. [PMID: 26497484]
  • Guirong Borijihan, Youxin Li, Jianguo Gao, James J Bao. Development of a novel 96-well format for liquid-liquid microextraction and its application in the HPLC analysis of biological samples. Journal of separation science. 2014 May; 37(9-10):1155-61. doi: 10.1002/jssc.201300954. [PMID: 24574156]
  • Lara B Younan, Kassem A Barada, Walid G Faraj, Ayman N Tawil, Mark N Jabbour, Maurice Y Khoury, Nadim Mw El-Majzoub, Mohamad A Eloubeidi. Propafenone hepatotoxicity: report of a new case and review of the literature. Saudi journal of gastroenterology : official journal of the Saudi Gastroenterology Association. 2013 Sep; 19(5):235-7. doi: 10.4103/1319-3767.118137. [PMID: 24045598]
  • Cho-Ming Loi, Dennis A Smith, Deepak Dalvie. Which metabolites circulate?. Drug metabolism and disposition: the biological fate of chemicals. 2013 May; 41(5):933-51. doi: 10.1124/dmd.112.050278. [PMID: 23454828]
  • J Flores Pérez, B Ramírez Mendiola, C Flores Pérez, R García Álvarez, H Juárez Olguín. Preparation and evaluation of unitary doses of propafenone used in children with supraventricular tachycardia: a pilot study. European review for medical and pharmacological sciences. 2013 Jan; 17(2):189-94. doi: . [PMID: 23377806]
  • 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]
  • Qin-You Tan, Rong-Hua Zhu, Huan-de Li, Ping-Fei Fang, Miao Yan, Qi-Zhi Zhang, Wen-Xing Peng. Development and validation of a sensitive U-HPLC-MS/MS method with electrospray ionization for quantitation of ranolazine in human plasma: application to a clinical pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Jul; 901(?):119-24. doi: 10.1016/j.jchromb.2012.06.011. [PMID: 22749688]
  • Ishrat Jabeen, Karin Pleban, Uwe Rinner, Peter Chiba, Gerhard F Ecker. Structure-activity relationships, ligand efficiency, and lipophilic efficiency profiles of benzophenone-type inhibitors of the multidrug transporter P-glycoprotein. Journal of medicinal chemistry. 2012 Apr; 55(7):3261-73. doi: 10.1021/jm201705f. [PMID: 22452412]
  • A Sestito, E Molina. Atrial fibrillation and the pharmacological treatment: the role of propafenone. European review for medical and pharmacological sciences. 2012 Feb; 16(2):242-53. doi: . [PMID: 22428477]
  • Gilles E O'Hara, François Philippon, Marcel Gilbert, Jean Champagne, Véronique Michaud, Lyne Charbonneau, Guylaine Pruneau, Bettina A Hamelin, Peter Geelen, Jacques Turgeon. Combined administration of quinidine and propafenone for atrial fibrillation: the CAQ-PAF study. Journal of clinical pharmacology. 2012 Feb; 52(2):171-9. doi: 10.1177/0091270011399574. [PMID: 21508180]
  • Thomas Meinertz, Wilhelm Kirch, Ludger Rosin, David Pittrow, Stefan N Willich, Paulus Kirchhof. Management of atrial fibrillation by primary care physicians in Germany: baseline results of the ATRIUM registry. Clinical research in cardiology : official journal of the German Cardiac Society. 2011 Oct; 100(10):897-905. doi: 10.1007/s00392-011-0320-5. [PMID: 21533828]
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  • Giuseppe Boriani, Mauro Biffi, Igor Diemberger, Giulia Domenichini, Alessandro Marziali, Cristian Martignani. Atrial fibrillation: adverse effects of 'pill-in-the-pocket' treatment and propafenone-carvedilol interaction. International journal of cardiology. 2010 Apr; 140(2):242-3; author reply 243. doi: 10.1016/j.ijcard.2008.11.028. [PMID: 19062111]
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  • G Lamprecht, K Stoschitzky. Enantioselective analysis of R- and S-propafenone in plasma by HPLC applying column switching and liquid-liquid extraction. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2009 Nov; 877(29):3489-94. doi: 10.1016/j.jchromb.2009.08.024. [PMID: 19736049]
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