Chlorfenapyr
(Synonyms: 虫螨腈) 目录号 : GC60106
Chlorfenapyr是一种吡咯类杀虫剂，可通过破坏线粒体功能发挥作用。
Cas No.:122453-73-0
Sample solution is provided at 25 µL, 10mM.
Chlorfenapyr, a pyrrole insecticide that impairs mitochondrial activity[1]. Oxidative removal of the N-ethoxymethyl group of Chlorfenapyr by mixed function oxidases results in a toxic form known as CL 303268 that acts to uncouple oxidative phosphorylation in the mitochondria, leading to a disruption of ATP production and loss of energy leading to cell dysfunction and ultimately death of the organism[2]. Commercial applications of Chlorfenapyr include termite control and protection of crops from multiple insect and mite pests[3]. Chlorfenapyr has moderate oral toxicity (LD50 = 662mg/kg bw for mouse by mouth) and low transdermal toxicity in mammals (LD50 > 2000mg/kg bw for rabbit by skin)[4].
In vitro, Chlorfenapyr treatment for 24h can inhibit the viability of human A549 and L02 cells, with IC50 values of 83.14μg/mL for A549 cells and 84.42μg/mL for L02 cells[5]. Treatment with 10ng/ml Chlorfenapyr for 24 hours induced cell death in HepG2 cells, decreased the levels of SOD1 and GSH, and enhanced oxidative stress[6]. At a concentration of 4.08μM, Chlorfenapyr treatment for 24 hours led to chromosomal aberrations in CHOK1 cells, and significantly increased the frequency of micronuclei[7].
In vivo, exposure to 10μg/L Chlorfenapyr for 21 days caused zebrafish liver and brain oxidative damage, disturbing the metabolism profiles [8].
References:
[1] Yunta C, Ooi J M F, Oladepo F, et al. Chlorfenapyr metabolism by mosquito P450s associated with pyrethroid resistance identifies potential activation markers[J]. Scientific Reports, 2023, 13(1): 14124.
[2] Raghavendra K, Barik T K, Sharma P, et al. Chlorfenapyr: a new insecticide with novel mode of action can control pyrethroid resistant malaria vectors[J]. Malaria journal, 2011, 10(1): 16.
[3] Baek B H, Kim S K, Yoon W, et al. Chlorfenapyr-induced toxic leukoencephalopathy with radiologic reversibility: a case report and literature review[J]. Korean journal of radiology, 2016, 17(2): 277-280.
[4] Huang P, Yan X, Yu B, et al. A comprehensive review of the current knowledge of chlorfenapyr: synthesis, mode of action, resistance, and environmental toxicology[J]. Molecules, 2023, 28(22): 7673.
[5] Wang L, Qu Z, Xu Y, et al. Insecticide chlorfenapyr confers induced toxicity in human cells through mitochondria-dependent pathways of apoptosis[J]. Ecotoxicology and Environmental Safety, 2025, 289: 117502.
[6] Elalfy M, Abomosallam M S, Sleem F R, et al. The Cytotoxic Combined Effects of Mixtures of Copper Oxychloride and Chlorfenapyr in HepG2 Cells and Postnatal Model of Toxicity in Female Sprague Dawleyrats and its Pups[J]. International Journal of Zoology and Animal Biology, 2020, 3(3): 1-10.
[7] Al-Sarar A S, Abobakr Y, Bayoumi A E, et al. Cytotoxic and genotoxic effects of abamectin, chlorfenapyr, and imidacloprid on CHOK1 cells[J]. Environmental Science and Pollution Research, 2015, 22(21): 17041-17052.
[8] Chen X, Zheng J, Teng M, et al. Bioaccumulation, metabolism and the toxic effects of chlorfenapyr in zebrafish (Danio rerio)[J]. Journal of Agricultural and Food Chemistry, 2021, 69(29): 8110-8119.
Chlorfenapyr是一种吡咯类杀虫剂，可通过破坏线粒体功能发挥作用。Chlorfenapyr的N-乙氧甲基基团经混合功能氧化酶氧化脱除后，生成的代谢产物CL 303268能够解耦线粒体中的氧化磷酸化过程，导致ATP合成中断、能量耗竭，进而引发细胞功能障碍直至机体死亡[2]。Chlorfenapyr广泛应用于白蚁防治及作物害虫螨治理[3]。毒理学数据显示，Chlorfenapyr对哺乳动物具有中度经口毒性（小鼠经口LD50 = 662 mg/kg）和低经皮毒性（家兔经皮肤LD50 > 2000 mg/kg）[4]。
在体外，Chlorfenapyr处理24小时可抑制人A549和L02细胞活力，IC50值分别为83.14μg/mL和84.42μg/mL[5]。10ng/ml浓度的Chlorfenapyr处理24小时会诱导HepG2细胞死亡，降低SOD1和GSH水平并增强氧化应激[6]。4.08μM浓度的Chlorfenapyr处理24小时可导致CHOK1细胞发生染色体畸变及微核率升高[7]。
在体内，10μg/L浓度的Chlorfenapyr暴露21天可引起斑马鱼肝脏和脑部氧化损伤，并扰乱代谢谱[8]。
| Cell experiment [1]: | |
Cell lines | A549 cells |
Preparation Method | Dulbecco’s modified eagle medium (DMEM) supplemented with 1 % antibiotics (streptomycin and penicillin) and 10 % fetal bovine serum was used to prepare the medium. The freshly prepared medium was used to culture A549 cells, which were incubated in the incubator at 37 °C, 5 % CO2. The cytotoxic effect of Chlorfenapyr on the viability of A549 cells was measured by MTT assay. The treated concentrations of Chlorfenapyr for A549 cells were 0, 25, 37.5, 50, 75 and 100μg/mL for 24h. Chlorfenapyr was dissolved in dimethyl sulfoxide (DMSO, analytical reagent) and diluted 1000 times with the culture medium before use. The color developed was measured at 570nm using a multi-plates spectrophotomter reader. Percent cell viability inhibition was calculated by the following equation: Cell inhibition (%) = (ODcontrol-ODtreatment)/ODcontrol× 100%. |
Reaction Conditions | 0, 25, 37.5, 50, 75 and 100μg/mL; 24h |
Applications | Chlorfenapyr dose-dependently inhibited the viability of A549 cells. |
| Animal experiment [2]: | |
Animal models | Adult wild-type zebrafish |
Preparation Method | Zebrafish were exposed to 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10ug/L Chlorfenapyr for 21 days. Then the fish were transferred to a tank containing Chlorfenapyr-free standard water for 9 days. The selected exposure concentrations were half and five times of environmental concentrations (2.03ug/L), respectively. The solvent (acetone) control was included. The final content of acetone was <0.01% in control and Chlorfenapyr treatment groups, and the exposure media were renewed every 24h. The exposure external condition (temperature, photoperiod, dissolved oxygen) was the same as the culture environment. For enzyme activity, bioaccumulation and gene transcription analysis, each test concentration was run in triplicate in three glass tanks (30L), with 20L of working solution and 52 zebrafish in each tank. For the metabolomic analysis, there were six replicates per concentration in six 5 L beakers (each beaker contained 4L exposure solution and 10 zebrafish). During the test, the zebrafish were fed twice a day with live brine shrimp (equivalent to 2% of bodyweight), except for 24h before killing. During the experiment, two whole zebrafish were withdrawn from each tank for Chlorfenapyr content analysis on days 1, 2, 3, 5, 7, 10, 14, 21, 23, 27 and 30. The sampled zebrafish were rinsed five times with dechlorinated tap water, blotted dry on absorbent paper, weighed, and then stored at −20 °C until analysis. At day 21 and day 30, the zebrafish for each replicate were divided into four samples as follows: five zebrafish for histopathology analysis, four zebrafish for gene expression analysis, and five zebrafish for metabolomic analysis. |
Dosage form | 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10ug/L for 21 days; water environment |
Applications | High concentrations of Chlorfenapyr led to a significant decrease in the antioxidant enzyme activity in the liver and brain of zebrafish, resulting in oxidative damage to the liver and necrosis of neuronal cells, and significantly disrupting the metabolic profiles of the zebrafish liver and brain. |
References: | |
| Cas No. | 122453-73-0 | SDF | |
| 别名 | 虫螨腈 | ||
| Canonical SMILES | N#CC1=C(C2=CC=C(Cl)C=C2)N(COCC)C(C(F)(F)F)=C1Br | ||
| 分子式 | C15H11BrClF3N2O | 分子量 | 407.61 |
| 溶解度 | DMSO: 250 mg/mL (613.33 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
||
| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 2.4533 mL | 12.2666 mL | 24.5333 mL |
| 5 mM | 490.7 μL | 2.4533 mL | 4.9067 mL |
| 10 mM | 245.3 μL | 1.2267 mL | 2.4533 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Quality Control & SDS
- View current batch:
- Purity: >97.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet