Fipronil-Sulfone

• CAS: 120068-36-2
• Catalog Number: ACM120068362
• Category: Main Products
• Molecular Weight: 453.15
• Molecular Formula: C₁₂H₄Cl₂F₆N₄O₂S
• Synonyms: 4-((trifluoromethyl)sulfonyl)-;5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1h-pyrazole-3-carbonitril;6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethanesulfonyl-1-(;m&b46136;FIPRONIL SULFONE STANDARD;5-AMino-1-(2,6-dichloro-4-trifluoroMethylphenyl)-3-cyano-4-trifluoroMethylsulfonylpyrazole;5-AMino-1-[2,6-Dichloro-4-(trifluoroMethyl)phenyl]-4-(trifluoroMethylsulfonyl)pyrazole-3-carbonitrile;1H-Pyrazole-3-carbonitrile, 5-aMino-1-[2,6-dichloro-4-(trifluoroMethyl)phenyl]-4-[(trifluoroMethyl)sulf onyl]-
• IUPAC Name: 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfonyl)pyrazole-3-carbonitrile
• Canonical 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 Key: LGHZJDKSVUTELU-UHFFFAOYSA-N
• Boiling Point: 531.6ºC at 760mmHg
• Flash Point: 275.3ºC
• Density: 1.85g/cm³
• Exact Mass: 451.93400
• Hazard Statements: T,N
• Safety Description: 45-61
• Supplemental Hazard Statements: H301-H400
• Symbol: GHS06,GHS09

Case Study

In-vitro Neurotoxicity Evaluation of Fipronil and Fipronil Sulfone

Romero A, et al. Toxicology letters, 2016, 252, 42-49.

Fipronil sulfone is a metabolite of the broad-spectrum insecticide fipronil. This work investigated the in vitro neurotoxicity of fipronil and fipronil sulfone, and evaluated the protective effects of several antioxidant compounds on SH-SY5Y cells. The results showed that fipronil sulfone was more potent in cytotoxicity than fipronil in SH-SY5Y cells. In addition, antioxidant compounds mitigated the cytotoxicity of fipronil and fipronil sulfone.
Experimental Methods and Results
· MTT and LDH assays were performed to evaluate the cytotoxicity of fipronil and fipronil sulfone at concentrations of 3-100 μM. This research revealed that the metabolite fipronil sulfone exhibits a greater cytotoxic effect compared to its parent compound, fipronil, in SH-SY5Y cells. The cytotoxicity of fipronil sulfone is believed to be triggered by the release of free radicals and lipid peroxidation. Both fipronil and fipronil sulfone contribute to neuronal cell toxicity through oxidative stress.
· The protective effects of Trolox, NAC, MEL, and Tempol were demonstrated in mitigating the negative impacts of both fipronil and fipronil sulfone in these cytotoxicity mechanisms. The study found that under the tested conditions, the four antioxidants were effective in significantly reducing the cytotoxicity caused by fipronil and its metabolite fipronil sulfone. The generation of reactive oxygen species (ROS) may be an initial or key step in the process leading to cell death.

Risk Assessment of Fipronil and Its Metabolite Fipronil Sulfone to Humans

Carrão D B, et al. Toxicology letters, 2019, 313, 196-204.

Fipronil is one of the most widely used pesticides, but it may also pose a potential for environmental contamination and increased risk of exposure to non-target organisms, including humans. This work investigated the inhibitory effects of fipronil and its derivative fipronil sulfone on human cytochrome P450 (CYP450) isoforms in order to assess the risk of contamination to humans. The results showed that CYP2D6 was the only CYP450 isoform inhibited by these xenobiotics.
Experimental conditions and results
· The standard stock solutions of rac-fipronil, S-fipronil, R-fipronil, and fipronil sulfone were prepared in ethanol at a concentration of 8000 μmol L-1. The microsomal medium (200 μL) included 2.5 μL of probe substrate for each CYP450 isoform, 2.5 μL of rac-fipronil, S-fipronil, R-fipronil, or fipronil sulfone, 40 μL of HLMs, 50 μL of the NADPH cofactor system, and 105 μL of phosphate buffer (0.1 mmol L-1, pH 7.4) with 0.19% (m/v) of poloxamer 407.
· Both the racemic mixture of fipronil and its isolated enantiomers are considered moderate inhibitors of the CYP2D6 isoform. However, fipronil sulfone, the metabolite of fipronil, is a potent inhibitor of the CYP2D6 isoform. This suggests that the conversion of fipronil into fipronil sulfone significantly increases the risk of pesticide-drug interactions involving this isoform. These interactions, specific to CYP2D6, have the potential to greatly reduce its enzymatic activity, resulting in elevated concentrations of drugs metabolized by CYP2D6 and potentially leading to toxic effects.