Fipronil
(Synonyms: 氟虫腈) 目录号 : GC60167
An insecticide
Cas No.:120068-37-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Fipronil is an insecticide that acts as a selective antagonist of insect GABA receptors (IC50s = 30 and 1,600 nM for cockroach and rat receptors, respectively).1 It also inhibits desensitizing and non-desensitizing glutamate-induced chloride currents in cockroach neurons (IC50s = 800 and 10 nM, respectively). Fipronil induces activity of the cytochrome P450 (CYP) isoforms CYP1A1/2, CYP2B1/2, and CYP3A1/2 in isolated rat liver microsomes.2 Formulations containing fipronil have been used as insecticides in veterinary care.
1.Narahashi, T., Zhao, X., Ikeda, T., et al.Glutamate-activated chloride channels: Unique fipronil targets present in insects but not in mammalsPestic. Biochem. Physiol.97(2)149-152(2010) 2.Caballero, M.V., Ares, I., Martínez, M., et al.Fipronil induces CYP isoforms in ratsFood Chem. Toxicol.83215-221(2015)
| Cas No. | 120068-37-3 | SDF | |
| 别名 | 氟虫腈 | ||
| Canonical SMILES | N#CC1=NN(C2=C(Cl)C=C(C(F)(F)F)C=C2Cl)C(N)=C1S(C(F)(F)F)=O | ||
| 分子式 | C12H4Cl2F6N4OS | 分子量 | 437.15 |
| 溶解度 | DMSO: 250 mg/mL (571.89 mM) | 储存条件 | 4°C, protect from light, stored under nitrogen |
| 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。 |
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| 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 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.2875 mL | 11.4377 mL | 22.8754 mL |
| 5 mM | 0.4575 mL | 2.2875 mL | 4.5751 mL |
| 10 mM | 0.2288 mL | 1.1438 mL | 2.2875 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。
Preclinical Transplacental Transfer and Pharmacokinetics of Fipronil in Rats
Drug Metab Dispos 2020 Oct;48(10):886-893.PMID:32723848DOI:10.1124/dmd.120.000088.
Fipronil, a widely used insecticide and pesticide, with its toxic metabolite Fipronil sulfone was detected in fipronil-contaminated eggs as a result of inappropriate use. However, little is known about whether Fipronil and Fipronil sulfone transfer into fetus through the blood-placenta barrier. Our objectives were to investigate the transplacental transfer and the pharmacokinetics of Fipronil and Fipronil sulfone in rats. Male and female (with 13 days of gestation) Sprague-Dawley rats were used in pharmacokinetics and transplacental transfer experiments, respectively. Biologic samples were collected at each time point after Fipronil intravenous or oral administration. To monitor Fipronil and Fipronil sulfone in the plasma, placenta, amniotic fluid, and fetus, a validated liquid chromatography tandem mass spectrometry method was developed. After Fipronil administration in male rats, the oral bioavailability decreased, whereas the biotransformation increased as the dose increased, revealing an enhancement of first-pass effect and a fast metabolism in vivo. The results of Fipronil transplacental transfer in pregnant rats demonstrated that the concentration of Fipronil and Fipronil sulfone varied in the following order, respectively: placenta > plasma > fetus > amniotic fluid and plasma > placenta > fetus > amniotic fluid. This is the first direct evidence that Fipronil and Fipronil sulfone cross the blood placental barriers and enter the fetus. The amount of Fipronil distributed to the fetus was greater than that of Fipronil sulfone in the short term, but by contrast, pharmacokinetic data showed that the latter stayed longer in the body. These findings provide constructive information for public health alarm. SIGNIFICANCE STATEMENT: Fipronil and Fipronil sulfone interfere with the GABAergic system. Fipronil can cause thyroid dysfunction, which may affect brain growth and nerve development. Although we knew that Fipronil and Fipronil sulfone could enter eggs, there was no direct evidence that they would enter fetuses. This research provided evidence on the pharmacokinetics and transplacental transfer of Fipronil and Fipronil sulfone, confirming our hypothesis.
Biodegradation of Fipronil: current state of mechanisms of biodegradation and future perspectives
Appl Microbiol Biotechnol 2021 Oct;105(20):7695-7708.PMID:34586458DOI:10.1007/s00253-021-11605-3.
Fipronil is a broad-spectrum phenyl-pyrazole insecticide that is widely used in agriculture. However, in the environment, its residues are toxic to aquatic animals, crustaceans, bees, termites, rabbits, lizards, and humans, and it has been classified as a C carcinogen. Due to its residual environmental hazards, various effective approaches, such as adsorption, ozone oxidation, catalyst coupling, inorganic plasma degradation, and microbial degradation, have been developed. Biodegradation is deemed to be the most effective and environmentally friendly method, and several pure cultures of bacteria and fungi capable of degrading Fipronil have been isolated and identified, including Streptomyces rochei, Paracoccus sp., Bacillus firmus, Bacillus thuringiensis, Bacillus spp., Stenotrophomonas acidaminiphila, and Aspergillus glaucus. The metabolic reactions of Fipronil degradation appear to be the same in different bacteria and are mainly oxidation, reduction, photolysis, and hydrolysis. However, the enzymes and genes responsible for the degradation are somewhat different. The ligninolytic enzyme MnP, the cytochrome P450 enzyme, and esterase play key roles in different strains of bacteria and fungal. Many unanswered questions exist regarding the environmental fate and degradation mechanisms of this pesticide. The genes and enzymes responsible for biodegradation remain largely unexplained, and biomolecular techniques need to be applied in order to gain a comprehensive understanding of these issues. In this review, we summarize the literature on the degradation of Fipronil, focusing on biodegradation pathways and identifying the main knowledge gaps that currently exist in order to inform future research. KEY POINTS: • Biodegradation is a powerful tool for the removal of Fipronil. • Oxidation, reduction, photolysis, and hydrolysis play key roles in the degradation of Fipronil. • Possible biochemical pathways of Fipronil in the environment are described.
A comprehensive review of environmental fate and degradation of Fipronil and its toxic metabolites
Environ Res 2021 Aug;199:111316.PMID:33989624DOI:10.1016/j.envres.2021.111316.
The use of pesticides to increase crop production has become one of the inevitable components of modern agriculture. Fipronil, a phenylpyrazoles insecticide, is one of the most widely used, systemic, broad-spectrum insecticides. Owing to its unique mode of action and selective toxicity, it was once regarded as safer alternatives to more toxic and persistent organochlorine insecticides. However, with the increased use, many studies have reported the toxicity of Fipronil and its metabolites in various non-target organisms during the last two decades. Currently, it is regarded as one of the most persistent and lipophilic insecticides in the market. In the environment, Fipronil can undergo oxidation, reduction, hydrolysis, or photolysis to form Fipronil sulfone, Fipronil sulfide, Fipronil amide, or Fipronil desulfinyl respectively. These metabolites except Fipronil amide are more or less toxic and persistent than Fipronil and have been reported from diverse environmental samples. Recently many studies have focused on the degradation and removal of Fipronil residues from the environment. However, a comprehensive review summarizing and combining these recent findings is lacking. In the present review, we evaluate, summarize, and combine important findings from recent degradation studies of Fipronil and its metabolites. An attempt has been made to elucidate the possible mechanism and pathways of degradation of Fipronil and its toxic metabolites.
Insights into the toxicity and biodegradation of Fipronil in contaminated environment
Microbiol Res 2023 Jan;266:127247.PMID:36403315DOI:10.1016/j.micres.2022.127247.
Fipronil is a phenylpyrazole insecticide used in various agricultural, horticulture, and veterinary practices. Besides its wide range of applications, it also causes severe health hazards to the non-targeted organisms especially in developing countries. Fipronil showed hepatotoxic, nephrotoxic, neurotoxic, and altered reproductive development and endocrine system in humans and animals. Several methods have been already introduced for the removal of toxic Fipronil including physicochemical and by the implementation of microorganisms. The microbial methods of Fipronil degradation are the most promising and environmentally sustainable. The remediation of Fipronil from the environment is an emerging task due to its enhanced residual concentration. Herein, we discuss the bioremediation potential of microbial strains in contaminated soil and water. It is shown that Fipronil can be remediated from the environment using combined ecotechnologies. This review discusses the toxicity, different physico-chemical and biological methods, and sustainable developments in fipronil-contaminated agriculture and aquatic environments.
Human Exposure of Fipronil Insecticide and the Associated Health Risk
J Agric Food Chem 2022 Jan 12;70(1):63-71.PMID:34971309DOI:10.1021/acs.jafc.1c05694.
Fipronil, as an emerging phenylpyrazole insecticide, is ubiquitous in the environment and food due to its broad spectrum and persistent characteristics, but the research on pathways of human exposure to Fipronil and the associated health risk is relatively unclear. In this regard, we summarize potential human exposures to Fipronil through ingestion and inhalation, as well as results of human biomonitoring studies. This scientific information will contribute to future assessment of Fipronil exposure and subsequent characterization of human health risks. Additionally, this Perspective highlights the lack of epidemiological studies and total diet studies for the general population on Fipronil.