Fipronil sulfone (BioDeep_00000179059)

   

human metabolite blood metabolite natural product


代谢物信息卡片


5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethanesulfonyl-1H-pyrazole-3-carbonitrile

化学式: C12H4Cl2F6N4O2S (451.93362160000004)
中文名称: 氟虫腈砜
谱图信息: 最多检出来源 Homo sapiens(blood) 62.07%

分子结构信息

SMILES: C1=C(C=C(C(=C1Cl)N2C(=C(C(=N2)C#N)S(=O)(=O)C(F)(F)F)N)Cl)C(F)(F)F
InChI: InChI=1S/C12H4Cl2F6N4O2S/c13-5-1-4(11(15,16)17)2-6(14)8(5)24-10(22)9(7(3-21)23-24)27(25,26)12(18,19)20/h1-2H,22H2

描述信息

D018377 - Neurotransmitter Agents > D018682 - GABA Agents > D018756 - GABA Antagonists
D010575 - Pesticides > D007306 - Insecticides
D016573 - Agrochemicals
Fipronil sulfone is the major metabolite of Fipronil.Fipronil sulfone selectively inhibits GABA receptor with IC50 of 175 nM (assayed by displacement of 4′-ethynyl-4-n-[2,3-3H2]- propylbicycloorthobenzoate ([3H]EBOB) from the noncompetitive blocker site).

同义名列表

6 个代谢物同义名

5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethanesulfonyl-1H-pyrazole-3-carbonitrile; 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethanesulfonylpyrazole-3-carbonitrile; Fipronil-sulphone; Fipronil sulphone; FIPRONIL-SULFONE; Fipronil sulfone



数据库引用编号

7 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)

6 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

  • Ya-Ning Chang, Tung-Hu Tsai. Preclinical Transplacental Transfer and Pharmacokinetics of Fipronil in Rats. Drug metabolism and disposition: the biological fate of chemicals. 2020 10; 48(10):886-893. doi: 10.1124/dmd.120.000088. [PMID: 32723848]
  • Gabriela Carmelinda Martins Dos Santos, Luiz Henrique Guerreiro Rosado, Melina Cardilo Campos Alves, Isabela de Paula Lima, Thais Paes Ferreira, Debora Azevedo Borges, Priscila Cardim de Oliveira, Viviane de Sousa Magalhães, Fabio Barbour Scott, Yara Peluso Cid. Fipronil Tablets: Development and Pharmacokinetic Profile in Beagle Dogs. AAPS PharmSciTech. 2019 Dec; 21(1):9. doi: 10.1208/s12249-019-1571-0. [PMID: 31797083]
  • Angeliki C Charalampous, Konstantinos S Liapis, Eleftheria D Bempelou. Fipronil in eggs. Is LC-MS/MS the only option? A comparison study of LC-MS/MS and GC-ECD for the analysis of fipronil. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2019 Oct; 1129(?):121785. doi: 10.1016/j.jchromb.2019.121785. [PMID: 31677523]
  • Saurabh Bhatti, G N V Satyanarayana, Devendra Kumar Patel, Aruna Satish. Bioaccumulation, biotransformation and toxic effect of fipronil in Escherichia coli. Chemosphere. 2019 Sep; 231(?):207-215. doi: 10.1016/j.chemosphere.2019.05.124. [PMID: 31129401]
  • Young Ah Kim, Yeong Sook Yoon, Hee Sun Kim, Se Jeong Jeon, Elizabeth Cole, Jeongsun Lee, Younglim Kho, Yoon Hee Cho. Distribution of fipronil in humans, and adverse health outcomes of in utero fipronil sulfone exposure in newborns. International journal of hygiene and environmental health. 2019 04; 222(3):524-532. doi: 10.1016/j.ijheh.2019.01.009. [PMID: 30718154]
  • Natalia Vasylieva, Bogdan Barnych, Debin Wan, El-Sayed A El-Sheikh, Hai M Nguyen, Heike Wulff, Rebecca McMahen, Mark Strynar, Shirley J Gee, Bruce D Hammock. Hydroxy-fipronil is a new urinary biomarker of exposure to fipronil. Environment international. 2017 06; 103(?):91-98. doi: 10.1016/j.envint.2017.03.012. [PMID: 28343720]
  • Hortênsia S Gripp, Juliane S Freitas, Eduardo A Almeida, Márcia C Bisinoti, Altair B Moreira. Biochemical effects of fipronil and its metabolites on lipid peroxidation and enzymatic antioxidant defense in tadpoles (Eupemphix nattereri: Leiuperidae). Ecotoxicology and environmental safety. 2017 Feb; 136(?):173-179. doi: 10.1016/j.ecoenv.2016.10.027. [PMID: 27870966]
  • A Romero, E Ramos, I Ares, V Castellano, M Martínez, M R Martínez-Larrañaga, A Anadón, M A Martínez. Fipronil sulfone induced higher cytotoxicity than fipronil in SH-SY5Y cells: Protection by antioxidants. Toxicology letters. 2016 Jun; 252(?):42-9. doi: 10.1016/j.toxlet.2016.04.005. [PMID: 27067106]
  • Shivani Uniyal, Rashmi Paliwal, Megha Verma, R K Sharma, J P N Rai. Isolation and Characterization of Fipronil Degrading Acinetobacter calcoaceticus and Acinetobacter oleivorans from Rhizospheric Zone of Zea mays. Bulletin of environmental contamination and toxicology. 2016 Jun; 96(6):833-8. doi: 10.1007/s00128-016-1795-6. [PMID: 27084098]
  • Rebecca L McMahen, Mark J Strynar, Sonia Dagnino, David W Herr, Virginia C Moser, Stavros Garantziotis, Erik M Andersen, Danielle L Freeborn, Larry McMillan, Andrew B Lindstrom. Identification of fipronil metabolites by time-of-flight mass spectrometry for application in a human exposure study. Environment international. 2015 May; 78(?):16-23. doi: 10.1016/j.envint.2015.01.016. [PMID: 25687022]
  • J P Cravedi, G Delous, D Zalko, C Viguié, L Debrauwer. Disposition of fipronil in rats. Chemosphere. 2013 Nov; 93(10):2276-83. doi: 10.1016/j.chemosphere.2013.07.083. [PMID: 24016625]
  • Béatrice B Roques, Marlène Z Lacroix, Sylvie Puel, Véronique Gayrard, Nicole Picard-Hagen, Isabelle Jouanin, Elisabeth Perdu, Pascal G Martin, Catherine Viguié. CYP450-dependent biotransformation of the insecticide fipronil into fipronil sulfone can mediate fipronil-induced thyroid disruption in rats. Toxicological sciences : an official journal of the Society of Toxicology. 2012 May; 127(1):29-41. doi: 10.1093/toxsci/kfs094. [PMID: 22447239]
  • Fabrice Herin, Elisa Boutet-Robinet, Aude Levant, Sylvain Dulaurent, Mimoza Manika, Florence Galatry-Bouju, Philippe Caron, Jean-Marc Soulat. Thyroid function tests in persons with occupational exposure to fipronil. Thyroid : official journal of the American Thyroid Association. 2011 Jul; 21(7):701-6. doi: 10.1089/thy.2010.0449. [PMID: 21615307]
  • M Z Lacroix, S Puel, P L Toutain, C Viguié. Quantification of fipronil and its metabolite fipronil sulfone in rat plasma over a wide range of concentrations by LC/UV/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Jul; 878(22):1934-8. doi: 10.1016/j.jchromb.2010.05.018. [PMID: 20599175]
  • Julien Leghait, Véronique Gayrard, Pierre-Louis Toutain, Nicole Picard-Hagen, Catherine Viguié. Is the mechanisms of fipronil-induced thyroid disruption specific of the rat: Re-evaluation of fipronil thyroid toxicity in sheep?. Toxicology letters. 2010 May; 194(3):51-7. doi: 10.1016/j.toxlet.2010.01.018. [PMID: 20117195]