Fipronil
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| Category | Animal Health |
| Catalog number | BBF-05824 |
| CAS | 120068-37-3 |
| Molecular Weight | 437.15 |
| Molecular Formula | C12H4Cl2F6N4OS |
| Purity | > 95% |
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Description
Fipronil is a broad-spectrum insecticide that disrupts the insect central nervous system by blocking GABA-gated chloride channels and glutamate-gated chloride channels, resulting in central nervous system toxicity. Fipronil can be used to kill parasites such as fleas and lice on cats and dogs.
Specification
| Synonyms | Fluocyanobenpyrazole; (RS)-5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrazole-3-carbonitrile; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile; (+/-)-Fipronil; 1-(2,6-Dichloro-4-trifluoromethylphenyl)-3-cyano-5-amino-4-(trifluoromethylsulfinyl)pyrazole; Frontline Spot-on; Frontline Spray; Frontline Top Spot; Goliath gel; Granedo MC; Grenade MC; Maxforce FC; Maxforce FC Select Roach Killer Bait Gel; Over'n Out; Regent; Regent TS; Termidor; Termidor 80WG; TopChoice; RM 1601; NSC-758960 |
| Shelf Life | Limited shelf life, expiry date on the label |
| Storage | Store at 2-8°C |
| IUPAC Name | 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrazole-3-carbonitrile |
| Canonical 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 |
| InChI Key | ZOCSXAVNDGMNBV-UHFFFAOYSA-N |
Properties
| Appearance | Off-White to Light Beige Solid |
| Antibiotic Activity Spectrum | Parasites |
| Boiling Point | 510.1±50.0°C(Predicted) |
| Melting Point | 200-201°C |
| Density | 1.55 g/cm3 |
| Solubility | Soluble in DMSO (Slightly), Methanol (Very Slightly) |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Fipronil blocks the passage of chloride ions through the GABA-regulated chloride channel, disrupting CNS activity. Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. |
| Toxicity | Fipronil exposure in red-legged partridge (Alectoris rufa) altered blood biochemistry and sexual hormone levels and reduced cellular immune response, antioxidant levels, and carotenoid-based coloration. No skin irritation was observed in rabbits. Some signs of toxicity and body-weight loss were still evident when the observation period ended at day 7 after treatment. |
Reference Reading
1. Human Exposure of Fipronil Insecticide and the Associated Health Risk
Dawei Chen, Jingguang Li, Yunfeng Zhao, Yongning Wu J Agric Food Chem. 2022 Jan 12;70(1):63-71. doi: 10.1021/acs.jafc.1c05694. Epub 2021 Dec 31.
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.
2. Fipronil use and associated effects on hematological and biochemical parameters of blue land crab (Cardisoma guanhumi Latreille): Ecological implication
Grace N Onwubiko, Eleazar C Anorue, Henry A Onwubiko, Parker E Joshua, Fabian I Eze, Christian C Amah, Blessing E Onah J Exp Zool A Ecol Integr Physiol. 2022 Mar;337(3):258-267. doi: 10.1002/jez.2563. Epub 2021 Nov 29.
Fipronil is used to control pests to improve farm yield, however, indiscriminate use of fipronil has been reported to endanger crabs leading to their extinction. Therefore, this study investigated the impact of fipronil on several hematological and biochemical parameters of blue land crabs. We exposed blue land crabs to either fipronil or to a control treatment; fipronil reduced the protein content of the crab and also led to hematological and oxidative damages to the crabs' oxy-hemocyanin. Based on our results, there is need for guided use of agrochemicals such as fipronil to avoid/reduce their adverse effects on economically important species such as crabs.
3. Fipronil and fipronil sulfone in chicken: From in vitro experiments to in vivo PBK model predictions
L S Lautz, G Stoopen, A J Ginting, R L A P Hoogenboom, A Punt Food Chem Toxicol. 2022 Jul;165:113086. doi: 10.1016/j.fct.2022.113086. Epub 2022 Apr 29.
In 2017 a large-scale fipronil contamination in eggs occurred in several European countries. Fipronil and its metabolites have the potential to be transferred into the eggs of laying hens, thereby entering the human food chain. Here, first the metabolism of fipronil was measured in vitro using chicken liver S9. The results show that fipronil is mainly metabolised into fipronil sulfone and the clearance obtained in vitro was extrapolated to in vivo liver clearance. In a second step a physiologically based kinetic model was developed with a focus on fipronil and its major sulfone metabolite and the model outcome was compared to available in vivo data in eggs from the literature. The experimentally obtained clearance was used as model input to evaluate whether such an in vitro-based model can be used in an early phase of a contamination incident to predict the time-concentration curves. Overall, all model predictions were within a 10-fold difference and the estimated elimination half-life for fipronil equivalents was 14 days. In vitro experiments are definitely recommended compared to in vivo studies, since they provide a fast first insight into the behaviour of a chemical in an organism.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C12H4Cl2F6N4OS
Molecular Weight (Monoisotopic Mass): 435.9387 Da
Molecular Weight (Avergae Mass): 437.148 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C12H4Cl2F6N4OS
Molecular Weight (Monoisotopic Mass): 435.9387 Da
Molecular Weight (Avergae Mass): 437.148 Da
LC-MS/MS Spectrum - LC-ESI-ITFT 30V, positive
Experimental Conditions
Instrument Type: LC-ESI-ITFT
Collision Energy Level: low
Collision Energy Voltage: 30
Ionization Mode: positive
Collision Energy Level: low
Collision Energy Voltage: 30
Ionization Mode: positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C12H4Cl2F6N4OS
Molecular Weight (Monoisotopic Mass): 435.9387 Da
Molecular Weight (Avergae Mass): 437.148 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C12H4Cl2F6N4OS
Molecular Weight (Monoisotopic Mass): 435.9387 Da
Molecular Weight (Avergae Mass): 437.148 Da
1H NMR Spectrum
Experimental Conditions
Solvent: DMSO-d6
Instrument Type: JEOL
Nucleus: 1H
Frequency: 400 MHz
Chemical Shift Reference: TMS
Instrument Type: JEOL
Nucleus: 1H
Frequency: 400 MHz
Chemical Shift Reference: TMS
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
