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| Targets |
Epsilon-momfluorothrin targets the nervous system of insects by acting as an axonic poison. As a pyrethroid, its primary mechanism of action is to disrupt the normal function of voltage-gated sodium channels in neuronal membranes, prolonging their opening and causing paralysis and death. In mammalian models, it also targets the constitutive androstane receptor (CAR), a nuclear receptor that regulates the expression of genes involved in xenobiotic metabolism.
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| ln Vitro |
In vitro studies use Epsilon-momfluorothrin to investigate pyrethroid toxicology and CAR signaling pathways. It has been shown to induce altered hepatic gene expression in rat models. The compound's activity is characterized by its potent knockdown effect, demonstrated to be 20-30-fold greater than that of tetramethrin, enabling effective pest control at lower use rates.
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| ln Vivo |
In vivo, Epsilon-momfluorothrin has been studied in rat models where it activates CAR, leading to hepatocellular tumor formation. These in vivo investigations are crucial for risk-assessment, linking pesticide exposure to adaptive and adverse liver outcomes. Its potent insecticidal activity has also been confirmed in vivo against various flying and crawling insects.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for Epsilon-momfluorothrin focus on its interaction with the constitutive androstane receptor (CAR). These assays typically involve treating primary hepatocytes or cell lines expressing CAR with the compound and measuring the activation of CAR-responsive reporter genes or the induction of downstream target genes like CYP2B. The selectivity of the (Z,1R,3R)-isomer for CAR can be validated using CAR-knockout (CAR-KO) models.
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| Cell Assay |
Cellular assays for Epsilon-momfluorothrin are typically conducted in hepatic cell lines to study its effects on nuclear receptor signaling. Cells are treated with the compound, and the expression of CAR target genes is measured via qPCR or reporter gene assays. These experiments help elucidate the molecular pathways linking pesticide exposure to liver outcomes and are used to study species differences in CAR signaling.
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| Animal Protocol |
In vivo animal experiments with Epsilon-momfluorothrin are performed in rodent models to study its toxicological and carcinogenic potential. Rats are administered the compound, and endpoints such as liver hypertrophy, altered hepatic gene expression, and tumor formation are assessed. These studies are critical for understanding the risk-assessment-relevant pathways and the non-genotoxic mechanisms of rodent hepatocarcinogenesis.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of Epsilon-momfluorothrin are characteristic of synthetic pyrethroids. The compound has a molecular weight of 385.35 g/mol and a molecular formula of C19H19F4NO3. It is a lipophilic molecule that can be absorbed and distributed to tissues, where it is metabolized and excreted. Its stability and persistence in biological systems are key factors in its toxicological profile.
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| Toxicity/Toxicokinetics |
The toxicological profile of Epsilon-momfluorothrin is a primary focus of research. In rat models, it activates CAR, leading to altered hepatic gene expression and hepatocellular tumor formation, making it a model for studying non-genotoxic carcinogenesis. It is also used in investigations of pyrethroid toxicology. Its 20-30-fold greater knockdown activity than tetramethrin indicates high insecticidal potency.
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| References | |
| Additional Infomation |
ε-Methylflufenicol is a carboxylic acid ester formed by the condensation of the carboxyl group of (1R,3R)-3-[(1Z)-2-cyanoprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylic acid with the benzyl hydroxyl group of [2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methanol. It is a pyrethroid insecticide and agrochemical. It is a carboxylic acid ester belonging to the cyclopropane class of compounds, and is also an ether compound, organofluorine insecticide, tetrafluorobenzene compound, and nitrile compound. Its function is similar to that of chrysanthemic acid.
Epsilon-momfluorothrin is a synthetic pyrethroid insecticide with the development code S-1563, discovered by Sumitomo Chemical Co., Ltd.. It is used in professional aerosol and crack-and-crevice formulations for pest control. Beyond its agricultural applications, it is a selective CAR agonist for mechanistic toxicology studies. It is available for research use only and is not for therapeutic use. |
| Molecular Formula |
C₁₉H₁₉F₄NO₃
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|---|---|
| Molecular Weight |
385.35
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| Exact Mass |
385.13
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| CAS # |
1065124-65-3
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| PubChem CID |
25015075
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| Appearance |
White to off-white solid powder
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| LogP |
4.174
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
27
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| Complexity |
628
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| Defined Atom Stereocenter Count |
2
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| SMILES |
C/C(=C/[C@@H]1[C@H](C1(C)C)C(=O)OCC2=C(C(=C(C(=C2F)F)COC)F)F)/C#N
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| InChi Key |
DPJITPZADZSLBP-DQXQJKBJSA-N
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| InChi Code |
InChI=1S/C19H19F4NO3/c1-9(6-24)5-12-13(19(12,2)3)18(25)27-8-11-16(22)14(20)10(7-26-4)15(21)17(11)23/h5,12-13H,7-8H2,1-4H3/b9-5-/t12-,13+/m1/s1
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| Chemical Name |
[2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl (1R,3R)-3-[(Z)-2-cyanoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~5 mg/mL (~12.98 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 0.5 mg/mL (1.30 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 5.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 0.5 mg/mL (1.30 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 5.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 0.5 mg/mL (1.30 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5950 mL | 12.9752 mL | 25.9504 mL | |
| 5 mM | 0.5190 mL | 2.5950 mL | 5.1901 mL | |
| 10 mM | 0.2595 mL | 1.2975 mL | 2.5950 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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