Fipronil (BioDeep_00000002249)

   

human metabolite blood metabolite


代谢物信息卡片


5-Amino-1-(2,6-dichloro-alpha,alpha,alpha-trifluoro-p-tolyl)-4-trifluoromethylsulfinylpyrazole-3-carbonitile

化学式: C12H4Cl2F6N4OS (435.93870660000005)
中文名称: 锐劲特
谱图信息: 最多检出来源 Homo sapiens(blood) 35.29%

分子结构信息

SMILES: C1=C(C=C(C(=C1Cl)N2C(=C(C(=N2)C#N)S(=O)C(F)(F)F)N)Cl)C(F)(F)F
InChI: InChI=1S/C12H4Cl2F6N4OS/c13-5-1-4(11(15,16)17)2-6(14)8(5)24-10(22)9(7(3-21)23-24)26(25)12(18,19)20/h1-2H,22H2

描述信息

CONFIDENCE standard compound; INTERNAL_ID 591; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5015; ORIGINAL_PRECURSOR_SCAN_NO 5012
CONFIDENCE standard compound; INTERNAL_ID 591; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5011; ORIGINAL_PRECURSOR_SCAN_NO 5006
CONFIDENCE standard compound; INTERNAL_ID 591; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4981; ORIGINAL_PRECURSOR_SCAN_NO 4979
CONFIDENCE standard compound; INTERNAL_ID 591; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5023; ORIGINAL_PRECURSOR_SCAN_NO 5019
CONFIDENCE standard compound; INTERNAL_ID 591; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5006; ORIGINAL_PRECURSOR_SCAN_NO 5004
D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 1041
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 8783
CONFIDENCE standard compound; INTERNAL_ID 3464
CONFIDENCE standard compound; INTERNAL_ID 2413
D010575 - Pesticides > D007306 - Insecticides
D016573 - Agrochemicals
Fipronil is a broad-spectrum insecticide effective against Lepidoptera species as well as thrips, locusts, ants, cockroaches, fleas and ticks. Fipronil selectively inhibits GABA receptor with IC50s of 30 nM and 1600 nM for cockroach and rat GABA receptors, respectively. Glutamate-gated chloride channels (GluCls), which are present in cockroaches but not in mammals, are sensitive to the blocking effect of Fipronil. Fipronil also induces apoptosis in HepG2 cells and promotes the expression of CYP1A1 and CYP3A4 mRNA in human hepatocytes[1][2].

同义名列表

3 个代谢物同义名

5-Amino-1-(2,6-dichloro-alpha,alpha,alpha-trifluoro-p-tolyl)-4-trifluoromethylsulfinylpyrazole-3-carbonitile; 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethanesulfinyl-1H-pyrazole-3-carbonitrile; Fipronil



数据库引用编号

36 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)

3 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

  • Ehssan Torabi, Khalil Talebi, Ahmad Ali Pourbabaee, Mohammad Homayoonzadeh, Mohamad Javad Ghamari, Seyedali Ebrahimi, Nastaran Faridy. Optimizing the QuEChERS method for efficient monitoring of fipronil, thiobencarb, and cartap residues in paddy soils with varying properties. Environmental monitoring and assessment. 2024 Jan; 196(2):125. doi: 10.1007/s10661-023-12279-2. [PMID: 38195960]
  • Camila C Pansa, Letícia R Molica, Fabiano C de Oliveira Júnior, Lara C Santello, Karen C M Moraes. Cellular and molecular effects of fipronil in lipid metabolism of HepG2 and its possible connection to non-alcoholic fatty liver disease. Journal of biochemical and molecular toxicology. 2024 Jan; 38(1):e23595. doi: 10.1002/jbt.23595. [PMID: 38050659]
  • Isaac Konig, Nazish Iftikhar, Evelyn Henry, Cole English, Emma Ivantsova, Christopher L Souders, Silvana Marcussi, Christopher J Martyniuk. Toxicity assessment of carvacrol and its acetylated derivative in early staged zebrafish (Danio rerio): Safer alternatives to fipronil-based pesticides?. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2023 Dec; 274(?):109762. doi: 10.1016/j.cbpc.2023.109762. [PMID: 37813296]
  • Leihong Zhang, Yirong Zhang, Jindong Li, Yanli Qi, Li Li, Kaikai Qin, Yongyue Lu, Chenglan Liu. Effect of fertilization on the degradation and enantioselectivity of fipronil in soil. Pest management science. 2023 Aug; ?(?):. doi: 10.1002/ps.7737. [PMID: 37615248]
  • Min Meng, Zhaochi Zhai, Zhenxing Zhang, Jeonghan Kim, Yongzhe Zhu. Metabolism of an insecticide fipronil by soil fungus Cunninghamella elegans ATCC36112. Archives of microbiology. 2023 Jun; 205(7):264. doi: 10.1007/s00203-023-03594-w. [PMID: 37316622]
  • Jowenna X F Sim, Barbara Drigo, Casey L Doolette, Sotirios Vasileiadis, Erica Donner, Dimitrios G Karpouzas, Enzo Lombi. Repeated applications of fipronil, propyzamide and flutriafol affect soil microbial functions and community composition: A laboratory-to-field assessment. Chemosphere. 2023 May; 331(?):138850. doi: 10.1016/j.chemosphere.2023.138850. [PMID: 37146771]
  • Lihua Qu, Xiaoyu Qi, Li Zhao, Yu Zhang, Ronghua Zhuge, Zhihui Hao, Congmin Liu. Development, validation, and use of a monitoring method for fipronil and its metabolites in chicken eggs by QuEChERS with online-SPE-LC-Q/Orbitrap analysis. Rapid communications in mass spectrometry : RCM. 2023 Apr; ?(?):e9518. doi: 10.1002/rcm.9518. [PMID: 37038653]
  • Shunhui Wang, Wenjian Lao, Huizhen Li, Liang Guo, Jing You. Assessing bioaccumulation potential of sediment associated fipronil degradates in oligochaete Lumbriculus variegatus based on passive sampler measured bioavailable concentration. The Science of the total environment. 2023 Mar; 863(?):160514. doi: 10.1016/j.scitotenv.2022.160514. [PMID: 36442630]
  • Qing-Qing Hou, Qiu-Tang Huang, Qi Xu, Cong Zhou, Yao-Yao Du, Yun-Fan Ji, Zhi-Ping Xu, Jia-Gao Cheng, Chun-Qing Zhao, Zhong Li, Xu-Sheng Shao. Synthesis and activity-detection of photoswitchable ligands with fipronil to insect. Pest management science. 2023 Mar; 79(3):1086-1093. doi: 10.1002/ps.7279. [PMID: 36334017]
  • Freylan Mena, Silvia Berrocal, Karla Solano, Eduardo Herrera, Mario Gallardo, Katherine Jiménez, Ingrid Aguilar, Margaret Pinnock-Branford. Comparison of the sensitivity of Tetragonisca angustula (Apidae-Meliponini) and Apis mellifera (Apidae-Apini) to three insecticides (malathion, imidacloprid and fipronil) used in Costa Rica. Environmental toxicology and chemistry. 2023 Feb; ?(?):. doi: 10.1002/etc.5587. [PMID: 36807197]
  • Yasmin E Abdel-Mobdy, Ahmed E Abdel-Mobdy, Ammar Al-Farga. Evaluation of therapeutic effects of camel milk against the hepatotoxicity and nephrotoxicity induced by fipronil and lead acetate and their mixture. Environmental science and pollution research international. 2023 Jan; ?(?):. doi: 10.1007/s11356-022-25092-0. [PMID: 36697983]
  • Pankaj Bhatt, Saurabh Gangola, Sudipta Ramola, Muhammad Bilal, Kalpana Bhatt, Yaohua Huang, Zhe Zhou, Shaohua Chen. Insights into the toxicity and biodegradation of fipronil in contaminated environment. Microbiological research. 2023 Jan; 266(?):127247. doi: 10.1016/j.micres.2022.127247. [PMID: 36403315]
  • Allan Pretti Ogura, Jacqueline Zanin Lima, Laís Conceição Menezes da Silva, Mariana Amaral Dias, Valéria Guimarães Silvestre Rodrigues, Cassiana Carolina Montagner, Evaldo Luiz Gaeta Espíndola. Phytotoxicity of 2,4-D and fipronil mixtures to three green manure species. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2023; 58(3):262-272. doi: 10.1080/03601234.2023.2178789. [PMID: 36799483]
  • Sukun Lin, Li Zhang, Peiwen Zhang, Rilin Huang, Muhammad Musa Khan, Shah Fahad, Dongmei Cheng, Zhixiang Zhang. Effects of glycosylation on the accumulation and transport of fipronil in earthworm (Eisenia fetida). Environmental science and pollution research international. 2023 Jan; 30(2):3688-3696. doi: 10.1007/s11356-022-22417-x. [PMID: 35953750]
  • Juliana Galan Viana, Willian Garcia Birolli, André Luiz Meleiro Porto. Biodegradation of the Pesticides Bifenthrin and Fipronil by Bacillus Isolated from Orange Leaves. Applied biochemistry and biotechnology. 2022 Dec; ?(?):. doi: 10.1007/s12010-022-04294-9. [PMID: 36585549]
  • Isaac Filipe Moreira Konig, Aline Chaves Reis, Mariana Aparecida Braga, Dirceu De Sousa Melo, Erika Aparecida Oliveira, Elaine Maria Seles Dorneles, Sérgio Scherrer Thomasi, Rafael Neodini Remedio, Silvana Marcussi. Comparative toxicological evaluation of carvacrol, acetylcarvacrol anda fipronil-based pesticide in human blood cells. Drug and chemical toxicology. 2022 Dec; ?(?):1-10. doi: 10.1080/01480545.2022.2159428. [PMID: 36541066]
  • Hemat K Mahmoud, Mayada R Farag, Fayiz M Reda, Mahmoud Alagawany, Hany M R Abdel-Latif. Dietary supplementation with Moringa oleifera leaves extract reduces the impacts of sub-lethal fipronil in Nile tilapia, Oreochromis niloticus. Scientific reports. 2022 12; 12(1):21748. doi: 10.1038/s41598-022-25611-6. [PMID: 36526884]
  • Amira Abo Bakr, Mohamed Ali, Khairy Ibrahim. Garlic and allopurinol alleviate the apoptotic pathway in rats' brain following exposure to fipronil insecticide. Environmental analysis, health and toxicology. 2022 Dec; 37(4):e2022037-0. doi: 10.5620/eaht.2022037. [PMID: 36916050]
  • Hossam El Din H Abdelhafez, Amr A Abdallah, Asmaa A El-Dahshan, Yasser A Abd El-Baset, Osama M Morsy, Mohamed Bedair M Ahmed. Ameliorative effects of the phytochemicals in dates (Phoenix dactylifera) against the toxicological changes induced by fipronil in male albino rats. Toxicology. 2022 10; 480(?):153313. doi: 10.1016/j.tox.2022.153313. [PMID: 36113622]
  • María A González-Morales, Zachary C DeVries, Richard G Santangelo, Madhavi L Kakumanu, Coby Schal. Multiple Mechanisms Confer Fipronil Resistance in the German Cockroach: Enhanced Detoxification and Rdl Mutation. Journal of medical entomology. 2022 09; 59(5):1721-1731. doi: 10.1093/jme/tjac100. [PMID: 35943144]
  • Andre J Riveros, Wulfila Gronenberg. The flavonoid rutin protects the bumble bee Bombus impatiens against cognitive impairment by imidacloprid and fipronil. The Journal of experimental biology. 2022 09; 225(17):. doi: 10.1242/jeb.244526. [PMID: 36000283]
  • Waqas Wakil, Nickolas G Kavallieratos, Muhammad Usman Ghazanfar, Muhammad Usman. Laboratory and field studies on the combined application of Beauveria bassiana and fipronil against four major stored-product coleopteran insect pests. Environmental science and pollution research international. 2022 May; 29(23):34912-34929. doi: 10.1007/s11356-021-17527-x. [PMID: 35040065]
  • Juliane Silberschmidt Freitas, Thandy Junio da Silva Pinto, Maria Paula Cardoso Yoshii, Laís Conceição Menezes da Silva, Laís Fernanda de Palma Lopes, Allan Pretti Ogura, Laís Girotto, Cassiana Carolina Montagner, Lays de Oliveira Gonçalves Alho, Renan Castelhano Gebara, Luís Schiesari, Evaldo Luiz Gaeta Espíndola. Realistic exposure to fipronil, 2,4-D, vinasse and their mixtures impair larval amphibian physiology. Environmental pollution (Barking, Essex : 1987). 2022 Apr; 299(?):118894. doi: 10.1016/j.envpol.2022.118894. [PMID: 35085654]
  • Kien Hong Trinh, Ulhas Sopanrao Kadam, Shailima Rampogu, Yuhan Cho, Kyung-Ae Yang, Chang Ho Kang, Keun-Woo Lee, Kyun Oh Lee, Woo Sik Chung, Jong Chan Hong. Development of novel fluorescence-based and label-free noncanonical G4-quadruplex-like DNA biosensor for facile, specific, and ultrasensitive detection of fipronil. Journal of hazardous materials. 2022 04; 427(?):127939. doi: 10.1016/j.jhazmat.2021.127939. [PMID: 34893377]
  • Hannes Reinwald, Julia Alvincz, Gabriela Salinas, Christoph Schäfers, Henner Hollert, Sebastian Eilebrecht. Toxicogenomic profiling after sublethal exposure to nerve- and muscle-targeting insecticides reveals cardiac and neuronal developmental effects in zebrafish embryos. Chemosphere. 2022 Mar; 291(Pt 1):132746. doi: 10.1016/j.chemosphere.2021.132746. [PMID: 34748799]
  • Jing-Xin Wang, Yan-Fang Cheng, Xin-Hong Pan, Pei Luo. Tissue-specific accumulation, transformation, and depuration of fipronil in adult crucian carp (Carassius auratus). Ecotoxicology and environmental safety. 2022 Mar; 232(?):113234. doi: 10.1016/j.ecoenv.2022.113234. [PMID: 35085889]
  • Ziyuan Xu, Yanjian Wan, Wei Xia, Lixiao Zhou, Aizhen Wang, Lisha Shi, Yinsheng Guo, Zhenyu He, Shunqing Xu, Rong Zhang. Fipronil and its metabolites in human seminal plasma from Shijiazhuang, north China. Chemosphere. 2022 Feb; 289(?):133238. doi: 10.1016/j.chemosphere.2021.133238. [PMID: 34896427]
  • Gabriela Carmelinda Martins Dos Santos, Fabio Barbour Scott, Diefrey Ribeiro Campos, Viviane de Sousa Magalhães, Debora Azevedo Borges, Fernando Rocha Miranda, Melina Cardilo Campos Alves, Geraldo Augusto Pereira, Leandra Oliveira Moreira, Emily Andressa Santos Lima, Marisa Beatriz da Silva Rocha, Yara Peluso Cid. Oral pharmacokinetic profile of fipronil and efficacy against flea and tick in dogs. Journal of veterinary pharmacology and therapeutics. 2022 Jan; 45(1):23-33. doi: 10.1111/jvp.13004. [PMID: 34331772]
  • Sonam Sarita Bal, Geeta Devi Leishangthem, Ram Saran Sethi, Amarjit Singh. P-coumaric acid ameliorates fipronil induced liver injury in mice through attenuation of structural changes, oxidative stress and inflammation. Pesticide biochemistry and physiology. 2022 Jan; 180(?):104997. doi: 10.1016/j.pestbp.2021.104997. [PMID: 34955181]
  • Xiuping He, Junhui Chen, Xiaotong Li, Jiuming Wang, Ming Xin, Xia Sun, Wei Cao, Baodong Wang. Pollution status, influencing factors and environmental risks of neonicotinoids, fipronil and its metabolites in a typical semi-closed bay in China. Environmental pollution (Barking, Essex : 1987). 2021 Dec; 291(?):118210. doi: 10.1016/j.envpol.2021.118210. [PMID: 34582920]
  • Natália Portruneli, Rocío Inés Bonansea, Maria Eugenia Valdés, Laís Conceição Menezes da Silva, Natália Prudêncio Viana, Bianca V Goulart, Iara da Costa Souza, Evaldo Luiz Gaeta Espíndola, Cassiana Carolina Montagner, Daniel Alberto Wunderlin, Marisa Narciso Fernandes. Whole-body bioconcentration and biochemical and morphological responses of gills of the neotropical fish Prochilodus lineatus exposed to 2,4-dichlorophenoxyacetic acid or fipronil individually or in a mixture. Aquatic toxicology (Amsterdam, Netherlands). 2021 Nov; 240(?):105987. doi: 10.1016/j.aquatox.2021.105987. [PMID: 34644674]
  • Mohamed Seif, Mohamed Deabes, Ahmad El-Askary, Attalla F El-Kott, Ghadeer M Albadrani, Amr Seif, Zaizhao Wang. Ephedra sinica mitigates hepatic oxidative stress and inflammation via suppressing the TLR4/MyD88/NF-κB pathway in fipronil-treated rats. Environmental science and pollution research international. 2021 Nov; 28(44):62943-62958. doi: 10.1007/s11356-021-15142-4. [PMID: 34218381]
  • Ali Abdulameer Al-Badran, Masami Fujiwara, Miguel A Mora, Delbert M Gatlin. The adverse effects of the phenylpyrazole, fipronil, on juvenile white shrimp Litopenaeus setiferus. Environmental science and pollution research international. 2021 Nov; 28(41):58688-58700. doi: 10.1007/s11356-021-14651-6. [PMID: 34120279]
  • Tarcísio M M Mota Filho, Roberto S Camargo, José C Zanuncio, Luis E P Stefanelli, Carlos A O de Matos, Luiz C Forti. Contamination routes and mortality of the leaf-cutting ant Atta sexdens (Hymenoptera: Formicidae) by the insecticides fipronil and sulfluramid through social interactions. Pest management science. 2021 Oct; 77(10):4411-4417. doi: 10.1002/ps.6475. [PMID: 33982404]
  • Zhe Zhou, Xiaozhen Wu, Ziqiu Lin, Shimei Pang, Sandhya Mishra, Shaohua Chen. Biodegradation of fipronil: current state of mechanisms of biodegradation and future perspectives. Applied microbiology and biotechnology. 2021 Oct; 105(20):7695-7708. doi: 10.1007/s00253-021-11605-3. [PMID: 34586458]
  • Lisha Shi, Yanjian Wan, Juan Liu, Zhenyu He, Shunqing Xu, Wei Xia. Insecticide fipronil and its transformation products in human blood and urine: Assessment of human exposure in general population of China. The Science of the total environment. 2021 Sep; 786(?):147342. doi: 10.1016/j.scitotenv.2021.147342. [PMID: 33964773]
  • David M Poché, Kelsey Dawson, Batchimeg Tseveenjav, Richard M Poché. Efficacy of low-dose fipronil bait against blacklegged tick (Ixodes scapularis) larvae feeding on white-footed mice (Peromyscus leucopus) under simulated field conditions. Parasites & vectors. 2021 Sep; 14(1):459. doi: 10.1186/s13071-021-04930-z. [PMID: 34493330]
  • Asmaa F Khafaga, Sara E El-Kazaz, Ahmed E Noreldin. Boswellia serrata suppress fipronil-induced neuronal necrosis and neurobehavioral alterations via promoted inhibition of oxidative/inflammatory/apoptotic pathways. The Science of the total environment. 2021 Sep; 785(?):147384. doi: 10.1016/j.scitotenv.2021.147384. [PMID: 33933775]
  • Thandy Junio da Silva Pinto, Giseli Swerts Rocha, Raquel Aparecida Moreira, Laís Conceição Menezes da Silva, Maria Paula Cardoso Yoshii, Bianca Veloso Goulart, Cassiana Carolina Montagner, Michiel Adriaan Daam, Evaldo Luiz Gaeta Espindola. Multi-generational exposure to fipronil, 2,4-D, and their mixtures in Chironomus sancticaroli: Biochemical, individual, and population endpoints. Environmental pollution (Barking, Essex : 1987). 2021 Aug; 283(?):117384. doi: 10.1016/j.envpol.2021.117384. [PMID: 34030066]
  • Antonela Santillán Deiú, Paola M Ondarza, Karina S B Miglioranza, Fernando R de la Torre. Multibiomarker responses and bioaccumulation of fipronil in Prochilodus lineatus exposed to spiked sediments: Oxidative stress and antioxidant defenses. Pesticide biochemistry and physiology. 2021 Aug; 177(?):104876. doi: 10.1016/j.pestbp.2021.104876. [PMID: 34301349]
  • Antonela Santillán Deiú, Karina S B Miglioranza, Paola M Ondarza, Fernando R de la Torre. Exposure to environmental concentrations of fipronil induces biochemical changes on a neotropical freshwater fish. Environmental science and pollution research international. 2021 Aug; 28(32):43872-43884. doi: 10.1007/s11356-021-13786-w. [PMID: 33840019]
  • Haoli Gao, Xumin Lin, Baojun Yang, Zewen Liu. The roles of GSTs in fipronil resistance in Nilaparvata lugens: Over-expression and expression induction. Pesticide biochemistry and physiology. 2021 Aug; 177(?):104880. doi: 10.1016/j.pestbp.2021.104880. [PMID: 34301351]
  • María A González-Morales, Zachary DeVries, Angela Sierras, Richard G Santangelo, Madhavi L Kakumanu, Coby Schal. Resistance to Fipronil in the Common Bed Bug (Hemiptera: Cimicidae). Journal of medical entomology. 2021 07; 58(4):1798-1807. doi: 10.1093/jme/tjab040. [PMID: 33822102]
  • Shimaa M Abou-Zeid, Enas A Tahoun, Huda O AbuBakr. Ameliorative effects of jojoba oil on fipronil-induced hepatorenal- and neuro-toxicity: the antioxidant status and apoptotic markers expression in rats. Environmental science and pollution research international. 2021 May; 28(20):25959-25971. doi: 10.1007/s11356-020-12083-2. [PMID: 33481197]
  • 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]
  • Ido Tsurim, Gideon Wasserberg, Gil Ben Natan, Zvika Abramsky. The Potential of Systemic Control of Sand Flies Using Fipronil in the Novel Leishmania major (Kinetoplastida: Trypanosomatidae) Reservoirs Meriones tristrami (Rodentia: Muridea) and Meriones crassus (Rodentia: Muridea). Journal of medical entomology. 2021 03; 58(2):969-973. doi: 10.1093/jme/tjaa200. [PMID: 33155653]
  • Enayatollah Seydi, Leila Mehrpouya, Hadiseh Sadeghi, Shabnam Rahimi, Jalal Pourahmad. Luteolin attenuates Fipronil-induced neurotoxicity through reduction of the ROS-mediated oxidative stress in rat brain mitochondria. Pesticide biochemistry and physiology. 2021 Mar; 173(?):104785. doi: 10.1016/j.pestbp.2021.104785. [PMID: 33771263]
  • Maria Carolina Triques, Dayane Oliveira, Bianca Veloso Goulart, Cassiana Carolina Montagner, Evaldo Luiz Gaeta Espíndola, Vanessa Bezerra de Menezes-Oliveira. Assessing single effects of sugarcane pesticides fipronil and 2,4-D on plants and soil organisms. Ecotoxicology and environmental safety. 2021 Jan; 208(?):111622. doi: 10.1016/j.ecoenv.2020.111622. [PMID: 33396142]
  • Lamiaa Wasef, Atef M K Nassar, Yasser S El-Sayed, Dalia Samak, Ahmed Noreldin, Norhan Elshony, Hamida Saleh, Yaser H A Elewa, Shaimaa M A Hassan, Abdullah A Saati, Helal F Hetta, Gaber El-Saber Batiha, Masakazu Umezawa, Hazem M Shaheen. The potential ameliorative impacts of cerium oxide nanoparticles against fipronil-induced hepatic steatosis. Scientific reports. 2021 01; 11(1):1310. doi: 10.1038/s41598-020-79479-5. [PMID: 33446707]
  • Raquel Aparecida Moreira, Giseli Swerts Rocha, Laís Conceição Menezes da Silva, Bianca Veloso Goulart, Cassiana Carolina Montagner, Maria da Graça Gama Melão, Evaldo Luiz Gaeta Espindola. Exposure to environmental concentrations of fipronil and 2,4-D mixtures causes physiological, morphological and biochemical changes in Raphidocelis subcapitata. Ecotoxicology and environmental safety. 2020 Dec; 206(?):111180. doi: 10.1016/j.ecoenv.2020.111180. [PMID: 32861006]
  • Mabrouk Attia Abd Abd Eldaim, Amira Shehata Abd El Latif, Azza Hassan, Nermeen Borai El-Borai. Ginseng attenuates fipronil-induced hepatorenal toxicity via its antioxidant, anti-apoptotic, and anti-inflammatory activities in rats. Environmental science and pollution research international. 2020 Dec; 27(36):45008-45017. doi: 10.1007/s11356-020-10306-0. [PMID: 32772290]
  • A A Khalaf, Marwa A Ibrahim, Mona K Galal, Amr A Abdallah, Ragaa Mansour, Mostafa M Afify. The protective effects of Terminalia laxiflora extract on hepato-nephrotoxicity induced by fipronil in male rats. Environmental science and pollution research international. 2020 Nov; 27(31):39507-39515. doi: 10.1007/s11356-020-10018-5. [PMID: 32651782]
  • Yiping Zhang, Qiuping Zhang, Shaohua Li, Yunfeng Zhao, Dawei Chen, Yongning Wu. Simultaneous determination of neonicotinoids and fipronils in tea using a modified QuEChERS method and liquid chromatography-high resolution mass spectrometry. Food chemistry. 2020 Nov; 329(?):127159. doi: 10.1016/j.foodchem.2020.127159. [PMID: 32497845]
  • Iván Felsztyna, Mariela E Sánchez-Borzone, Virginia Miguel, Daniel A García. The insecticide fipronil affects the physical properties of model membranes: A combined experimental and molecular dynamics simulations study in Langmuir monolayers. Biochimica et biophysica acta. Biomembranes. 2020 10; 1862(10):183378. doi: 10.1016/j.bbamem.2020.183378. [PMID: 32464131]
  • 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]
  • Oswaldo Gomes Júnior, Letícia L Batista, Carlos Ueira-Vieira, Raquel M F Sousa, Maria Clara V M Starling, Alam G Trovó. Degradation mechanism of fipronil and its transformation products, matrix effects and toxicity during the solar/photo-Fenton process using ferric citrate complex. Journal of environmental management. 2020 Sep; 269(?):110756. doi: 10.1016/j.jenvman.2020.110756. [PMID: 32560986]
  • Kunming Hu, Liangliang Zhou, Yingying Gao, Qi Lai, Haiyan Shi, Minghua Wang. Enantioselective endocrine-disrupting effects of the phenylpyrazole chiral insecticides in vitro and in silico. Chemosphere. 2020 Aug; 252(?):126572. doi: 10.1016/j.chemosphere.2020.126572. [PMID: 32224362]
  • David M Poché, Gregory Franckowiak, Tyler Clarke, Batchimeg Tseveenjav, Larisa Polyakova, Richard M Poché. Efficacy of a low dose fipronil bait against blacklegged tick (Ixodes scapularis) larvae feeding on white-footed mice (Peromyscus leucopus) under laboratory conditions. Parasites & vectors. 2020 Jul; 13(1):391. doi: 10.1186/s13071-020-04258-0. [PMID: 32736585]
  • Hamida Saleh, Atef M K Nassar, Ahmed E Noreldin, Dalia Samak, Norhan Elshony, Lamiaa Wasef, Yaser H A Elewa, Shaimaa M A Hassan, Abdullah A Saati, Helal F Hetta, Gaber El-Saber Batiha, Masakazu Umezawa, Hazem M Shaheen, Yasser S El-Sayed. Chemo-Protective Potential of Cerium Oxide Nanoparticles against Fipronil-Induced Oxidative Stress, Apoptosis, Inflammation and Reproductive Dysfunction in Male White Albino Rats. Molecules (Basel, Switzerland). 2020 Jul; 25(15):. doi: 10.3390/molecules25153479. [PMID: 32751827]
  • Shunhui Wang, Wenjian Lao, Huizhen Li, Jing You. Measuring bioconcentration factors of sediment-associated fipronil in Lumbriculus variegatus using passive sampling techniques. Journal of hazardous materials. 2020 07; 393(?):122420. doi: 10.1016/j.jhazmat.2020.122420. [PMID: 32143163]
  • Roger D Lawrie, Robert D Mitchell, Anirudh Dhammi, Andrew Wallace, Ernest Hodgson, R Michael Roe. Role of long non-coding RNA in DEET- and fipronil-mediated alteration of transcripts associated with Phase I and Phase II xenobiotic metabolism in human primary hepatocytes. Pesticide biochemistry and physiology. 2020 Jul; 167(?):104607. doi: 10.1016/j.pestbp.2020.104607. [PMID: 32527422]
  • Rachel-Ann Suraj, Rhea Rambarran, Krista Ali, Danyelle Harbajan, Roxanne Charles, Candice Sant, Karla Georges, Sharianne Suepaul. A comparison of the efficacy of two commercial acaricides (fipronil and amitraz) with Azadirachta indica (neem) on the brown dog tick (Rhipicephalus sanguineus) from canines in Trinidad. Transboundary and emerging diseases. 2020 Jul; 67 Suppl 2(?):142-148. doi: 10.1111/tbed.13388. [PMID: 31746117]
  • Huixian Li, Ruiqing Zhang, Fuhong Sun, Yahui Zhang. Evaluation of toxicological responses and promising biomarkers of topmouth gudgeon (Pseudorasbora parva) exposed to fipronil at environmentally relevant levels. Environmental science and pollution research international. 2020 Jul; 27(19):24081-24089. doi: 10.1007/s11356-020-08555-0. [PMID: 32304060]
  • Rieta Gols, Michiel F WallisDeVries, Joop J A van Loon. Reprotoxic effects of the systemic insecticide fipronil on the butterfly Pieris brassicae. Proceedings. Biological sciences. 2020 03; 287(1922):20192665. doi: 10.1098/rspb.2019.2665. [PMID: 32156210]
  • Gamal E Abouelghar, Zeinab A El-Bermawy, Hagar M S Salman. Oxidative stress, hematological and biochemical alterations induced by sub-acute exposure to fipronil (COACH®) in albino mice and ameliorative effect of selenium plus vitamin E. Environmental science and pollution research international. 2020 Mar; 27(8):7886-7900. doi: 10.1007/s11356-019-06579-9. [PMID: 31889272]
  • Douxin Xiao, Wenlong Liang, Zhongshan Li, Jingli Cheng, Yongjun Du, Jinhao Zhao. High foliar affinity cellulose for the preparation of efficient and safe fipronil formulation. Journal of hazardous materials. 2020 02; 384(?):121408. doi: 10.1016/j.jhazmat.2019.121408. [PMID: 31677913]
  • Gadah AlBasher, Mohamed M Abdel-Daim, Rafa Almeer, Khairy A Ibrahim, Reham Z Hamza, Simona Bungau, Lotfi Aleya. Synergistic antioxidant effects of resveratrol and curcumin against fipronil-triggered oxidative damage in male albino rats. Environmental science and pollution research international. 2020 Feb; 27(6):6505-6514. doi: 10.1007/s11356-019-07344-8. [PMID: 31873888]
  • David M Poché, Hsiao-Hsuan Wang, William E Grant. Visceral leishmaniasis on the Indian Subcontinent: Efficacy of fipronil-based cattle treatment in controlling sand fly populations is dependent on specific aspects of sand fly ecology. PLoS neglected tropical diseases. 2020 02; 14(2):e0008011. doi: 10.1371/journal.pntd.0008011. [PMID: 32069283]
  • Sara Dallarés, Priscila Dourado, Ignasi Sanahuja, Mikhail Solovyev, Enric Gisbert, Nicola Montemurro, Amparo Torreblanca, Mercedes Blázquez, Montserrat Solé. Multibiomarker approach to fipronil exposure in the fish Dicentrarchus labrax under two temperature regimes. Aquatic toxicology (Amsterdam, Netherlands). 2020 Feb; 219(?):105378. doi: 10.1016/j.aquatox.2019.105378. [PMID: 31841729]
  • Pascal G P Martin, Véronique Dupouy, Julien Leghait, Thierry Pineau, Arnaud Polizzi, Frédéric Lasserre, Béatrice B Roques, Catherine Viguié. Transcriptomic modifications of the thyroid gland upon exposure to phytosanitary-grade fipronil: Evidence for the activation of compensatory pathways. Toxicology and applied pharmacology. 2020 01; 389(?):114873. doi: 10.1016/j.taap.2019.114873. [PMID: 31881178]
  • Farhad Bano, Banalata Mohanty. Thyroxine modulation of immune toxicity induced by mixture pesticides mancozeb and fipronil in mice. Life sciences. 2020 Jan; 240(?):117078. doi: 10.1016/j.lfs.2019.117078. [PMID: 31759041]
  • 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]
  • 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]
  • Amira A Sayed, Mohamed A El-Desouky, Khairy A Ibrahim. Garlic and allopurinol attenuate hepatic apoptosis induced by fipronil in male albino rats. Regulatory toxicology and pharmacology : RTP. 2019 Oct; 107(?):104400. doi: 10.1016/j.yrtph.2019.05.025. [PMID: 31152858]
  • Fabiele da Costa Chaulet, Heloísa Helena de Alcantara Barcellos, Débora Fior, Aline Pompermaier, Gessi Koakoski, João Gabriel Santos da Rosa, Michele Fagundes, Leonardo José Gil Barcellos. Glyphosate- and Fipronil-Based Agrochemicals and Their Mixtures Change Zebrafish Behavior. Archives of environmental contamination and toxicology. 2019 Oct; 77(3):443-451. doi: 10.1007/s00244-019-00644-7. [PMID: 31190101]
  • 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]
  • Samah R Khalil, Wafaa A Mohammed, Asmaa W Zaglool, Walaa M Elhady, Mayada R Farag, Shafika A M El Sayed. Inflammatory and oxidative injury is induced in cardiac and pulmonary tissue following fipronil exposure in Japanese quail: mRNA expression of the genes encoding interleukin 6, nuclear factor kappa B, and tumor necrosis factor-alpha. Environmental pollution (Barking, Essex : 1987). 2019 Aug; 251(?):564-572. doi: 10.1016/j.envpol.2019.05.012. [PMID: 31108289]
  • Qianqian Li, Yue Huang, Xiangzhong Song, Jixiong Zhang, Shungeng Min. Spectral interval optimization on rapid determination of prohibited addition in pesticide by ATR-FTIR. Pest management science. 2019 Jun; 75(6):1743-1749. doi: 10.1002/ps.5295. [PMID: 30537090]
  • Akash M Sadaria, Cameron W Labban, Joshua C Steele, Megan M Maurer, Rolf U Halden. Retrospective nationwide occurrence of fipronil and its degradates in U.S. wastewater and sewage sludge from 2001 - 2016. Water research. 2019 May; 155(?):465-473. doi: 10.1016/j.watres.2019.02.045. [PMID: 30870636]
  • 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]
  • A A Khalaf, Mona K Galal, Marwa A Ibrahim, A A Abd Allah, Mostafa M Afify, Rasha Refaat. The Terminalia laxiflora modulates the neurotoxicity induced by fipronil in male albino rats. Bioscience reports. 2019 03; 39(3):. doi: 10.1042/bsr20181363. [PMID: 30777931]
  • Yingjie Wen, Xunyuan Jiang, Chen Yang, Huayue Meng, Binfeng Wang, Hanxiang Wu, Zhixiang Zhang, Hanhong Xu. The linker length of glucose-fipronil conjugates has a major effect on the rate of bioactivation by β-glucosidase. Pest management science. 2019 Mar; 75(3):708-717. doi: 10.1002/ps.5170. [PMID: 30182531]
  • Po-Hung Chen, Wen-Jer Wu, Ju-Chun Hsu. Detection of Male Oriental Fruit Fly (Diptera: Tephritidae) Susceptibility to Naled- and Fipronil-Intoxicated Methyl Eugenol. Journal of economic entomology. 2019 02; 112(1):316-323. doi: 10.1093/jee/toy278. [PMID: 30260395]
  • Mohamed M Abdel-Daim, Amina A Dessouki, Haidy G Abdel-Rahman, Rasha Eltaysh, Saad Alkahtani. Hepatorenal protective effects of taurine and N-acetylcysteine against fipronil-induced injuries: The antioxidant status and apoptotic markers expression in rats. The Science of the total environment. 2019 Feb; 650(Pt 2):2063-2073. doi: 10.1016/j.scitotenv.2018.09.313. [PMID: 30290348]
  • Subrata Biswas, Rahul Mondal, Ayan Mukherjee, Mitali Sarkar, Ramen Kumar Kole. Simultaneous determination and risk assessment of fipronil and its metabolites in sugarcane, using GC-ECD and confirmation by GC-MS/MS. Food chemistry. 2019 Jan; 272(?):559-567. doi: 10.1016/j.foodchem.2018.08.087. [PMID: 30309581]
  • Xiongfeng Hu, Haifu Jiang, Yanjie Zhang, Fuchuan Huang, Mingsheng Jiang. Effect of fipronil on biogas production performance during anaerobic digestion of chicken manure and corn straw. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2019; 54(6):449-458. doi: 10.1080/03601234.2019.1592639. [PMID: 30939985]
  • Xingliang Wang, Andrias O O Reilly, Martin S Williamson, Alin M Puinean, Yihua Yang, Shuwen Wu, Yidong Wu. Function and pharmacology of glutamate-gated chloride channel exon 9 splice variants from the diamondback moth Plutella xylostella. Insect biochemistry and molecular biology. 2019 01; 104(?):58-64. doi: 10.1016/j.ibmb.2018.12.005. [PMID: 30550974]
  • Rania Abdelrahman Elgawish, Heba M A Abdelrazek, Shimaa A A Ismail, Naglaa M Loutfy, Mohamed T A Soliman. Hepatoprotective activity of Uncaria tomentosa extract against sub-chronic exposure to fipronil in male rats. Environmental science and pollution research international. 2019 Jan; 26(1):199-207. doi: 10.1007/s11356-018-3615-5. [PMID: 30387063]
  • Talyta Zortéa, Aleksandro Schafer da Silva, Tamires Rodrigues Dos Reis, Julia Corá Segat, Alexandre Tadeu Paulino, José Paulo Sousa, Dilmar Baretta. Ecotoxicological effects of fipronil, neem cake and neem extract in edaphic organisms from tropical soil. Ecotoxicology and environmental safety. 2018 Dec; 166(?):207-214. doi: 10.1016/j.ecoenv.2018.09.061. [PMID: 30269016]
  • Verena Christen, Petra Y Kunz, Karl Fent. Endocrine disruption and chronic effects of plant protection products in bees: Can we better protect our pollinators?. Environmental pollution (Barking, Essex : 1987). 2018 Dec; 243(Pt B):1588-1601. doi: 10.1016/j.envpol.2018.09.117. [PMID: 30296754]
  • Hanqing Xu, Xingang Liu, Yang Jia, Fengshou Dong, Jun Xu, Xiaohu Wu, Yang Yang, Yongquan Zheng. Fipronil-induced toxic effects in zebrafish (Danio rerio) larvae by using digital gene expression profiling. The Science of the total environment. 2018 Oct; 639(?):550-559. doi: 10.1016/j.scitotenv.2018.05.159. [PMID: 29800848]
  • Paolo Ascenzi, Loris Leboffe, Daniele Toti, Fabio Polticelli, Viviana Trezza. Fipronil recognition by the FA1 site of human serum albumin. Journal of molecular recognition : JMR. 2018 08; 31(8):e2713. doi: 10.1002/jmr.2713. [PMID: 29656610]
  • Mohamed M Abdel-Daim, Hazem M Shaheen, Abdelrahman Ibrahim Abushouk, Eman A Toraih, Manal S Fawzy, Wafa S Alansari, Lotfi Aleya, Simona Bungau. Thymoquinone and diallyl sulfide protect against fipronil-induced oxidative injury in rats. Environmental science and pollution research international. 2018 Aug; 25(24):23909-23916. doi: 10.1007/s11356-018-2386-3. [PMID: 29881965]
  • Xunyuan Jiang, Yun Xie, Zhanfu Ren, Ulrika Ganeteg, Fei Lin, Chen Zhao, Hanhong Xu. Design of a New Glutamine-Fipronil Conjugate with α-Amino Acid Function and Its Uptake by A. thaliana Lysine Histidine Transporter 1 ( AtLHT1). Journal of agricultural and food chemistry. 2018 Jul; 66(29):7597-7605. doi: 10.1021/acs.jafc.8b02287. [PMID: 29944366]
  • Jessica M Abbate, Ettore Napoli, Francesca Arfuso, Gabriella Gaglio, Salvatore Giannetto, Lenaig Halos, Frederic Beugnet, Emanuele Brianti. Six-month field efficacy and safety of the combined treatment of dogs with Frontline Tri-Act® and NexGard Spectra®. Parasites & vectors. 2018 Jul; 11(1):425. doi: 10.1186/s13071-018-2957-7. [PMID: 30012179]
  • Shasha Li, Pingping Wang, Xingang Liu, Xiaohu Wu, Fengshou Dong, Jun Xu, Yongquan Zheng. Polyoxymethylene passive samplers to assess the effectiveness of biochar by reducing the content of freely dissolved fipronil and ethiprole. The Science of the total environment. 2018 Jul; 630(?):960-966. doi: 10.1016/j.scitotenv.2018.02.221. [PMID: 29554781]
  • Bo Zhang, Lei Zhang, Lujue He, Xiaodong Yang, Yali Shi, Shaowei Liao, Shan Yang, Jiagao Cheng, Tianrui Ren. Interactions of Fipronil within Fish and Insects: Experimental and Molecular Modeling Studies. Journal of agricultural and food chemistry. 2018 Jun; 66(23):5756-5761. doi: 10.1021/acs.jafc.8b00573. [PMID: 29627978]
  • Mohamed M Abdel-Daim, Ahmed Abdeen. Protective effects of rosuvastatin and vitamin E against fipronil-mediated oxidative damage and apoptosis in rat liver and kidney. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2018 Apr; 114(?):69-77. doi: 10.1016/j.fct.2018.01.055. [PMID: 29432839]
  • Qingqing Sheng, Xinxin Liu, Yun Xie, Fei Lin, Zhixiang Zhang, Chen Zhao, Hanhong Xu. Synthesis of Novel Amino Acid-Fipronil Conjugates and Study on Their Phloem Loading Mechanism. Molecules (Basel, Switzerland). 2018 Mar; 23(4):. doi: 10.3390/molecules23040778. [PMID: 29597301]