Pralidoxime (BioDeep_00000003476)

 

Secondary id: BioDeep_00000400260, BioDeep_00001867978

natural product human metabolite PANOMIX_OTCML-2023 blood metabolite Volatile Flavor Compounds


代谢物信息卡片


2-[(1E)-(hydroxyimino)methyl]-1-methylpyridin-1-ium

化学式: [C7H9N2O]+ (137.0714844)
中文名称:
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 14.49%

分子结构信息

SMILES: CN1C=CC=CC1=C[NH+]=O
InChI: InChI=1S/C7H8N2O/c1-9-5-3-2-4-7(9)6-8-10/h2-6H,1H3/p+1

描述信息

Pralidoxime is an antidote to organophosphate pesticides and chemicals. Organophosphates bind to the esteratic site of acetylcholinesterase, which results initially in reversible inactivation of the enzyme. If given within 24 hours,after organophosphate exposure, pralidoxime reactivates the enzyme cholinesterase by cleaving the phosphate-ester bond formed between the organophosphate and acetylcholinesterase.
V - Various > V03 - All other therapeutic products > V03A - All other therapeutic products > V03AB - Antidotes
D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D002801 - Cholinesterase Reactivators
Acquisition and generation of the data is financially supported in part by CREST/JST.
C78272 - Agent Affecting Nervous System > C47796 - Cholinergic Agonist
D020011 - Protective Agents > D000931 - Antidotes
D004793 - Enzyme Reactivators

同义名列表

7 个代谢物同义名

2-[(1E)-(hydroxyimino)methyl]-1-methylpyridin-1-ium; Pyridine-2-aldoxime methochloride; 1-Methyl-2-pyridinium aldoxime; Pralidoxime chloride; Pralidoximum; Pralidoxime; Pralidoxime



数据库引用编号

21 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。

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

  • Brian S Backer, Edward C Meek, Matthew K Ross, Janice E Chambers. Pharmacokinetics of three novel pyridinium aldoxime acetylcholinesterase reactivators in female rats. Toxicology and applied pharmacology. 2022 07; 446(?):116046. doi: 10.1016/j.taap.2022.116046. [PMID: 35550885]
  • Yan-Jye Shyong, Yadira Sepulveda, Arnold Garcia, Nathan M Samskey, Zoran Radic, Rakesh K Sit, K Barry Sharpless, Jeremiah D Momper, Palmer Taylor. Enhancing Target Tissue Levels and Diminishing Plasma Clearance of Ionizing Zwitterionic Antidotes in Organophosphate Exposures. The Journal of pharmacology and experimental therapeutics. 2021 09; 378(3):315-321. doi: 10.1124/jpet.121.000715. [PMID: 34145064]
  • Jia-Ruei Yu, Yi-Chou Hou, Jen-Fen Fu, I-Kuan Wang, Ming-Jen Chan, Chao-Yu Chen, Cheng-Hao Weng, Wen-Hung Huang, Huang-Yu Yang, Ching-Wei Hsu, Tzung-Hai Yen. Outcomes of elderly patients with organophosphate intoxication. Scientific reports. 2021 06; 11(1):11615. doi: 10.1038/s41598-021-91230-2. [PMID: 34079035]
  • Yang Lv, Hongyu Liang, Jun Li, Xiuxiu Li, Xiaohui Tang, Songyu Gao, Hao Zou, Jing Zhang, Mei Wang, Liang Xiao. Central inhibition prevents the in vivo acute toxicity of harmine in mice. The Journal of toxicological sciences. 2021; 46(6):289-301. doi: 10.2131/jts.46.289. [PMID: 34078836]
  • Daina N Buzyurova, Tatiana N Pashirova, Irina V Zueva, Evgenia A Burilova, Zukhra M Shaihutdinova, Ildar Kh Rizvanov, Vasily M Babaev, Konstantin A Petrov, Eliana B Souto. Surface modification of pralidoxime chloride-loaded solid lipid nanoparticles for enhanced brain reactivation of organophosphorus-inhibited AChE: Pharmacokinetics in rat. Toxicology. 2020 11; 444(?):152578. doi: 10.1016/j.tox.2020.152578. [PMID: 32898602]
  • H-F Liu, C-H Ku, S-S Chang, C-M Chang, I-K Wang, H-Y Yang, C-H Weng, W-H Huang, C-W Hsu, T-H Yen. Outcome of patients with chlorpyrifos intoxication. Human & experimental toxicology. 2020 Oct; 39(10):1291-1300. doi: 10.1177/0960327120920911. [PMID: 32336155]
  • Tamara Kranawetvogl, Dirk Steinritz, Horst Thiermann, Harald John. A novel high-performance liquid chromatography with diode array detector method for the simultaneous quantification of the enzyme-reactivating oximes obidoxime, pralidoxime, and HI-6 in human plasma. Drug testing and analysis. 2020 Jul; 12(7):938-947. doi: 10.1002/dta.2800. [PMID: 32267631]
  • Vendula Hepnarova, Lubica Muckova, Avi Ring, Jaroslav Pejchal, David Herman, Jan Misik, Martina Hrabinova, Daniel Jun, Ondrej Soukup. Pharmacological and toxicological in vitro and in vivo effect of higher doses of oxime reactivators. Toxicology and applied pharmacology. 2019 11; 383(?):114776. doi: 10.1016/j.taap.2019.114776. [PMID: 31629733]
  • Amna Iqbal, Shahrukh Malik, Syed M Nurulain, Kamil Musilek, Kamil Kuca, Huba Kalasz, M Qaiser Fatmi. Reactivation potency of two novel oximes (K456 and K733) against paraoxon-inhibited acetyl and butyrylcholinesterase: In silico and in vitro models. Chemico-biological interactions. 2019 Sep; 310(?):108735. doi: 10.1016/j.cbi.2019.108735. [PMID: 31276662]
  • Alciene Almeida Siqueira, Alexandre Frinhani Cunha, Graziany Leite Moreira Marques, Igor Simões Assunção Felippe, Vitor Sampaio Minassa, Thallis Coelho da Silva Gramelich, Maria Aparecida Cicilini, Tamara Andrea Alarcon, Rita Gomes Wanderley Pires, Karla Nivea Sampaio, Vanessa Beijamini. Atropine counteracts the depressive-like behaviour elicited by acute exposure to commercial chlorpyrifos in rats. Neurotoxicology and teratology. 2019 Jan; 71(?):6-15. doi: 10.1016/j.ntt.2018.11.002. [PMID: 30458229]
  • Kiel D Neumann, Joseph E Blecha, Thomas R Hayes, Tony Huynh, Chih-Kai Chao, Nicolas Guilloteau, Kurt R Zinn, Henry F VanBrocklin, Charles M Thompson, John M Gerdes. Radiosynthesis, ex Vivo Biodistribution, and in Vivo Positron Emission Tomography Imaging Evaluations of [11C]2-Pyridinealdoxime Methiodide ([11C]2-PAM): A First-In-Class Antidote Tracer for Organophosphate Intoxication. ACS chemical neuroscience. 2018 12; 9(12):3007-3014. doi: 10.1021/acschemneuro.8b00212. [PMID: 30071719]
  • Eylem Ulaş Saz, Ali Yurtseven, Mehmet Arda Kilinç, Ferhat Sari, Hasan Ağin. The First Use of Pralidoxime in a Child With Rivastigmine Poisoning. Pediatric emergency care. 2018 Oct; 34(10):e184-e186. doi: 10.1097/pec.0000000000001086. [PMID: 28328690]
  • Evica Antonijevic, Jelena Kotur-Stevuljevic, Kamil Musilek, Andrea Kosvancova, Kamil Kuca, Danijela Djukic-Cosic, Vesna Spasojevic-Kalimanovska, Biljana Antonijevic. Effect of six oximes on acutely anticholinesterase inhibitor-induced oxidative stress in rat plasma and brain. Archives of toxicology. 2018 Feb; 92(2):745-757. doi: 10.1007/s00204-017-2101-z. [PMID: 29098328]
  • P Kumar, D Swami, D P Nagar, K P Singh, J Acharya, H N Karade, R Yadav. In vivo protection studies of bis-quaternary 2-(hydroxyimino)- N-(pyridin-3-yl) acetamide derivatives (HNK oximes) against tabun and soman poisoning in Swiss albino mice. Human & experimental toxicology. 2017 Dec; 36(12):1270-1285. doi: 10.1177/0960327116685888. [PMID: 28078916]
  • Tatiana N Pashirova, Irina V Zueva, Konstantin A Petrov, Vasily M Babaev, Svetlana S Lukashenko, Ildar Kh Rizvanov, Eliana B Souto, Evgeny E Nikolsky, Lucia Ya Zakharova, Patrick Masson, Oleg G Sinyashin. Nanoparticle-Delivered 2-PAM for Rat Brain Protection against Paraoxon Central Toxicity. ACS applied materials & interfaces. 2017 May; 9(20):16922-16932. doi: 10.1021/acsami.7b04163. [PMID: 28504886]
  • André-Guilhem Calas, José Dias, Catherine Rousseau, Mélanie Arboléas, Mélanie Touvrey-Loiodice, Guillaume Mercey, Ludovic Jean, Pierre-Yves Renard, Florian Nachon. An easy method for the determination of active concentrations of cholinesterase reactivators in blood samples: Application to the efficacy assessment of non quaternary reactivators compared to HI-6 and pralidoxime in VX-poisoned mice. Chemico-biological interactions. 2017 Apr; 267(?):11-16. doi: 10.1016/j.cbi.2016.03.009. [PMID: 26972668]
  • Ufuk Yükselmiş, Mustafa Özçetin, Yakup Çağ, Dinçer Yıldızdaş, Hayri Levent Yılmaz. The role of plasmapheresis in organophosphate poisoning: Case reports of three pediatric patients. The Turkish journal of pediatrics. 2017; 59(4):491-496. doi: 10.24953/turkjped.2017.04.020. [PMID: 29624234]
  • Chih-Chuan Lin, Dong-Zong Hung, Hsien-Yi Chen, Kuang-Hung Hsu. The effectiveness of patient-tailored treatment for acute organophosphate poisoning. Biomedical journal. 2016 Dec; 39(6):391-399. doi: 10.1016/j.bj.2016.11.001. [PMID: 28043418]
  • Chih-Kai Chao, S Kaleem Ahmed, John M Gerdes, Charles M Thompson. Novel Organophosphate Ligand O-(2-Fluoroethyl)-O-(p-Nitrophenyl)Methylphosphonate: Synthesis, Hydrolytic Stability and Analysis of the Inhibition and Reactivation of Cholinesterases. Chemical research in toxicology. 2016 11; 29(11):1810-1817. doi: 10.1021/acs.chemrestox.6b00160. [PMID: 27551891]
  • Osman Yesilbas, Hasan S Kihtir, Mohammad Altiti, Mey Talip Petmezci, Seda Balkaya, Burcu Bursal Duramaz, Melike Ersoy, Esra Sevketoglu. Acute severe organophosphate poisoning in a child who was successfully treated with therapeutic plasma exchange, high-volume hemodiafiltration, and lipid infusion. Journal of clinical apheresis. 2016 Oct; 31(5):467-9. doi: 10.1002/jca.21417. [PMID: 26273819]
  • Erin Gallagher, Il Minn, Janice E Chambers, Peter C Searson. In vitro characterization of pralidoxime transport and acetylcholinesterase reactivation across MDCK cells and stem cell-derived human brain microvascular endothelial cells (BC1-hBMECs). Fluids and barriers of the CNS. 2016 Jul; 13(1):10. doi: 10.1186/s12987-016-0035-0. [PMID: 27396356]
  • Nabeel I Uwaydah, Stephen L Hoskins, Stephen P Bruttig, Henry Farrar, Nick C Copper, Donald J Deyo, Michael A Dubick, George C Kramer. Intramuscular versus Intraosseous Delivery of Nerve Agent Antidote Pralidoxime Chloride in Swine. Prehospital emergency care : official journal of the National Association of EMS Physicians and the National Association of State EMS Directors. 2016 Jul; 20(4):485-92. doi: 10.3109/10903127.2014.942479. [PMID: 27158860]
  • Subham Banerjee, Pronobesh Chattopadhyay, Animesh Ghosh, Aseem Bhatnagar, Vijay Veer. Pharmacokinetic and biodistribution study of eserine and pralidoxime chloride in rabbits following a single application of a transdermal patch. European journal of drug metabolism and pharmacokinetics. 2016 Jun; 41(3):219-30. doi: 10.1007/s13318-014-0250-5. [PMID: 25547639]
  • Janice E Chambers, Edward C Meek, Joshua P Bennett, W Shane Bennett, Howard W Chambers, C Andrew Leach, Ronald B Pringle, Robert W Wills. Novel substituted phenoxyalkyl pyridinium oximes enhance survival and attenuate seizure-like behavior of rats receiving lethal levels of nerve agent surrogates. Toxicology. 2016 Jan; 339(?):51-57. doi: 10.1016/j.tox.2015.12.001. [PMID: 26705700]
  • Bo Zhao, Lanju Yang, Lei Xiao, Baoquan Sun, Xianbao Zou, Dongmei Gao, Xiandong Jian. [The influence of sodium bicarbonate combined with ulinastatin on cholinesterase activity for patients with acute phoxim pesticide poisoning]. Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases. 2016 Jan; 34(1):53-5. doi: 10.3760/cma.j.issn.1001-9391.2016.01.015. [PMID: 27014821]
  • Sahajal Dhooria, Digambar Behera, Ritesh Agarwal. Amitraz: a mimicker of organophosphate poisoning. BMJ case reports. 2015 Oct; 2015(?):. doi: 10.1136/bcr-2015-210296. [PMID: 26430228]
  • P Kumar, D Swami, H N Karade, J Acharya, P C Jatav, A Kumar, M K Meena. In vivo protection of diisopropylphosphorofluoridate (DFP) poisoning by three bis-quaternary 2 -(hydroxyimino) -N -(pyridin-3-yl) acetamide derivatives in Swiss mice. Cellular and molecular biology (Noisy-le-Grand, France). 2014 Oct; 60(3):53-9. doi: . [PMID: 25346249]
  • Duk Hee Lee, Koo Young Jung, Yoon Hee Choi, Young Jin Cheon. Body mass index as a prognostic factor in organophosphate-poisoned patients. The American journal of emergency medicine. 2014 Jul; 32(7):693-6. doi: 10.1016/j.ajem.2014.04.030. [PMID: 24856742]
  • Lisa A Konickx, Franz Worek, Shaluka Jayamanne, Horst Thiermann, Nicholas A Buckley, Michael Eddleston. Reactivation of plasma butyrylcholinesterase by pralidoxime chloride in patients poisoned by WHO class II toxicity organophosphorus insecticides. Toxicological sciences : an official journal of the Society of Toxicology. 2013 Dec; 136(2):274-83. doi: 10.1093/toxsci/kft217. [PMID: 24052565]
  • Slavica Vučinić, Milica Zlatković, Biljana Antonijević, Marijana Ćurčić, Bogdan Bošković. Fresh frozen plasma as a successful antidotal supplement in acute organophosphate poisoning. Arhiv za higijenu rada i toksikologiju. 2013 Jun; 64(2):87-91. doi: 10.2478/10004-1254-64-2013-2378. [PMID: 23819936]
  • C H Chaou, C C Lin, H Y Chen, C H Lee, T H H Chen. Chlorpyrifos is associated with slower serum cholinesterase recovery in acute organophosphate-poisoned patients. Clinical toxicology (Philadelphia, Pa.). 2013 Jun; 51(5):402-8. doi: 10.3109/15563650.2013.782035. [PMID: 23590812]
  • Michael Eddleston. Applied clinical pharmacology and public health in rural Asia--preventing deaths from organophosphorus pesticide and yellow oleander poisoning. British journal of clinical pharmacology. 2013 May; 75(5):1175-88. doi: 10.1111/j.1365-2125.2012.04449.x. [PMID: 22943579]
  • Jayendra B Bhonsle, Robert Causey, Benjamin L Oyler, Cecilia Bartolucci, Doriano Lamba, Alessandro Pesaresi, Nanaji K Bhamare, Iswarduth Soojhawon, Gregory E Garcia. Evaluation and computational characterization of the facilitated transport of Glc carbon C-1 oxime reactivators across a blood brain barrier model. Chemico-biological interactions. 2013 Mar; 203(1):129-34. doi: 10.1016/j.cbi.2012.09.012. [PMID: 23073172]
  • A Bayir, H Kara, O Köylü, R Kocabas, A Ak. The effects of ubiquinone (CoQ10) on heart tissue in cardiac toxicity related to organophosphate poisoning. Human & experimental toxicology. 2013 Jan; 32(1):45-52. doi: 10.1177/0960327112455070. [PMID: 23060413]
  • A Basher, S H Rahman, A Ghose, S M Arif, M A Faiz, A H Dawson. Phase II study of magnesium sulfate in acute organophosphate pesticide poisoning. Clinical toxicology (Philadelphia, Pa.). 2013 Jan; 51(1):35-40. doi: 10.3109/15563650.2012.757318. [PMID: 23311540]
  • Thiago Henrique Lugokenski, Priscila Gubert, Diones Caeran Bueno, Pablo Andrei Nogara, Rogério de Aquino Saraiva, Rômulo Pillon Barcelos, Vanessa Santana Carratu, Leandro Bresolin, Nilda Berenice de Vargas Barbosa, Maria Ester Pereira, João Batista Teixeira da Rocha, Félix Alexandre Antunes Soares. Effect of different oximes on rat and human cholinesterases inhibited by methamidophos: a comparative in vitro and in silico study. Basic & clinical pharmacology & toxicology. 2012 Dec; 111(6):362-70. doi: 10.1111/j.1742-7843.2012.00912.x. [PMID: 22703537]
  • Douglas B Murray, Michael Eddleston, Simon Thomas, Robert D Jefferson, Adrian Thompson, Mick Dunn, Daniel S Vidler, R Eddie Clutton, Peter G Blain. Rapid and complete bioavailability of antidotes for organophosphorus nerve agent and cyanide poisoning in minipigs after intraosseous administration. Annals of emergency medicine. 2012 Oct; 60(4):424-30. doi: 10.1016/j.annemergmed.2012.05.013. [PMID: 22738685]
  • Yonghua Xu, Wenli Cai, Janne Nappi, Hiro Yoshida. Fecal-tagging CT colonography with structure-analysis electronic cleansing for detection of colorectal flat lesions. European journal of radiology. 2012 Aug; 81(8):1712-6. doi: 10.1016/j.ejrad.2011.04.051. [PMID: 21596500]
  • Harald John, Marc-Michael Blum. Review of UV spectroscopic, chromatographic, and electrophoretic methods for the cholinesterase reactivating antidote pralidoxime (2-PAM). Drug testing and analysis. 2012 Mar; 4(3-4):179-93. doi: 10.1002/dta.327. [PMID: 21953823]
  • Preeti Yadav, Sunil E Jadhav, Vinesh Kumar, Kirtee K Kaul, Satish C Pant, Swaran J S Flora. Protective efficacy of 2-PAMCl, atropine and curcumin against dichlorvos induced toxicity in rats. Interdisciplinary toxicology. 2012 Mar; 5(1):1-8. doi: 10.2478/v10102-012-0001-x. [PMID: 22783142]
  • Harald John, Michael Eddleston, R Eddie Clutton, Franz Worek, Horst Thiermann. Quantification of pralidoxime (2-PAM) in urine by ion pair chromatography-diode array detection: application to in vivo samples from minipig. Drug testing and analysis. 2012 Mar; 4(3-4):169-78. doi: 10.1002/dta.340. [PMID: 22102522]
  • Alessandra Antunes dos Santos, Danúbia Bonfanti dos Santos, Renata Pietsch Ribeiro, Dirleise Colle, Kaite Cristiane Peres, Júlia Hermes, Anderson Machado Barbosa, Alcir Luiz Dafré, Andreza Fabro de Bem, Kamil Kuca, Marcelo Farina. Effects of K074 and pralidoxime on antioxidant and acetylcholinesterase response in malathion-poisoned mice. Neurotoxicology. 2011 Dec; 32(6):888-95. doi: 10.1016/j.neuro.2011.05.008. [PMID: 21723318]
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  • Maya Kayouka, Pascal Houzé, Frederic J Baud, Salvatore Cisternino, Marcel Debray, Patricia Risède, Alfred H Schinkel, Jean-Michel Warnet. Does modulation of organic cation transporters improve pralidoxime activity in an animal model of organophosphate poisoning?. Critical care medicine. 2011 Apr; 39(4):803-11. doi: 10.1097/ccm.0b013e318206d52f. [PMID: 21242797]
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  • Sara Bohnert, Cory Vair, John Mikler. Development and validation of a sensitive HPLC method for the quantification of HI-6 in guinea pig plasma and evaluated in domestic swine. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 May; 878(17-18):1407-13. doi: 10.1016/j.jchromb.2010.03.018. [PMID: 20395179]
  • Hsien-Yi Chen, Warren Wei-Jen Wang, Chung-Hsien Chaou, Chih-Chuan Lin. Prognostic value of serial serum cholinesterase activities in organophosphate poisoned patients. The American journal of emergency medicine. 2009 Nov; 27(9):1034-9. doi: 10.1016/j.ajem.2008.07.006. [PMID: 19931747]
  • Maya Kayouka, Pascal Houzé, Marcel Debray, Frederic J Baud. Acute renal failure enhances the antidotal activity of pralidoxime towards paraoxon-induced respiratory toxicity. Toxicology letters. 2009 Aug; 189(1):48-56. doi: 10.1016/j.toxlet.2009.04.020. [PMID: 19406220]
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  • Michael Eddleston, Peter Eyer, Franz Worek, Edmund Juszczak, Nicola Alder, Fahim Mohamed, Lalith Senarathna, Ariyasena Hittarage, Shifa Azher, K Jeganathan, Shaluka Jayamanne, Ludwig von Meyer, Andrew H Dawson, Mohamed Hussain Rezvi Sheriff, Nick A Buckley. Pralidoxime in acute organophosphorus insecticide poisoning--a randomised controlled trial. PLoS medicine. 2009 Jun; 6(6):e1000104. doi: 10.1371/journal.pmed.1000104. [PMID: 19564902]
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