| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| 250mg | |||
| Other Sizes |
| Targets |
Ethiprole's primary molecular target is the GABA-gated chloride channel, a ligand-gated ion channel that plays a crucial role in inhibitory neurotransmission in the insect nervous system. GABA is the major inhibitory neurotransmitter in insects, and it binds to the GABA receptor to open the chloride channel, allowing chloride ions to flow into the neuron. This influx of chloride hyperpolarizes the neuron, making it less likely to fire an action potential and thus inhibiting neural activity. Ethiprole acts as a noncompetitive antagonist of this receptor. This means it binds to a site on the receptor that is distinct from the GABA binding site, and its binding prevents the chloride channel from opening, even when GABA is present. By blocking the chloride channel, Ethiprole prevents the inhibitory effects of GABA, leading to neuronal hyperexcitation, uncontrolled firing of neurons, and ultimately, paralysis and death of the insect. This mechanism of action is similar to that of fipronil, and both compounds are noncompetitive antagonists of the GABA receptor. Ethiprole's selectivity for insect GABA receptors over mammalian GABA receptors is the basis for its safety in mammals, although it still has some toxicity to non-target organisms like bees.
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| ln Vitro |
In vitro studies have focused on characterizing Ethiprole's interaction with the GABA-gated chloride channel and its effects on insect cells. Its primary activity is its ability to inhibit the GABA-induced chloride current. This is typically studied using electrophysiological techniques, such as two-electrode voltage-clamp or patch-clamp, on oocytes or cells that express insect GABA receptors. In these experiments, the cells are bathed in a solution containing GABA, which activates the receptor and produces an inward chloride current. Ethiprole is then applied, and the reduction in the GABA-induced current is measured. As a noncompetitive antagonist, Ethiprole reduces the maximal response to GABA. In addition to its effects on the GABA receptor, Ethiprole has been shown to induce oxidative stress in honeybees in vitro. When honeybee cells are exposed to Ethiprole, there is an increase in the production of reactive oxygen species (ROS) and a decrease in antioxidant enzyme activity. This oxidative stress can activate immune responses, as indicated by the upregulation of specific genes. These in vitro studies are crucial for understanding the compound's mechanism of action and its sublethal effects on non-target organisms.
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| ln Vivo |
In vivo studies have demonstrated Ethiprole's efficacy as an insecticide against a wide range of pests, as well as its sublethal effects on non-target organisms like honeybees. In agricultural settings, Ethiprole is applied to crops, and its effectiveness is measured by the reduction in pest populations. It is particularly effective against rice planthoppers, a major pest of rice crops. In China, it is registered for this specific use. In laboratory and field studies, Ethiprole has been shown to cause mortality in target pests at low concentrations. However, in vivo studies have also revealed the compound's toxicity to non-target organisms. In honeybees, sublethal doses of Ethiprole have been shown to inhibit pupation and eclosion (the emergence of adult bees from their pupal cases) in a dose-dependent manner. This indicates that even at concentrations that do not cause immediate death, Ethiprole can have significant developmental effects. Furthermore, in vivo exposure to Ethiprole has been shown to induce oxidative stress in honeybees, as measured by increased levels of malondialdehyde (MDA) and altered activities of antioxidant enzymes like superoxide dismutase (SOD) and catalase (CAT). It also affects the expression of genes involved in detoxification and immunity. These in vivo findings are critical for assessing the environmental impact of Ethiprole.
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| Enzyme Assay |
In vitro receptor binding assays for Ethiprole are designed to measure its interaction with the GABA-gated chloride channel. A common approach is a radioligand binding assay. In this assay, membrane preparations from insect brains (e.g., housefly heads) are incubated with a radiolabeled ligand that binds to the GABA receptor, such as [³H]EBOB (an analog of the insecticide endosulfan that binds to the same site as fipronil and Ethiprole). Increasing concentrations of unlabeled Ethiprole are added to compete with the radiolabeled ligand for binding. After incubation, the bound and free ligand are separated (e.g., by filtration), and the radioactivity is measured. The data is used to calculate the binding affinity (Ki) of Ethiprole for the receptor. Ethiprole is a noncompetitive antagonist, and its binding is allosteric, meaning it binds to a site distinct from the GABA binding site. In functional assays, the effect of Ethiprole on GABA-induced chloride currents is measured using electrophysiological techniques on oocytes expressing insect GABA receptors. These assays provide a quantitative measure of Ethiprole's potency and its mechanism of action at the molecular level.
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| Cell Assay |
In vitro cell-based assays for Ethiprole are used to study its effects on insect cells and its toxicity to non-target organisms. A common assay for studying its insecticidal activity is to use insect neuronal cell cultures or cell lines that express GABA receptors. The cells are treated with Ethiprole, and cell viability is assessed using a dye such as MTT or resazurin. However, the primary cell-based assays used for Ethiprole are those that study its sublethal effects, particularly in honeybees. In these assays, honeybee cells (e.g., hemocytes or cell lines like AmE-711) are exposed to Ethiprole at sublethal concentrations. The production of reactive oxygen species (ROS) is measured using a fluorescent probe such as H2DCFDA. Oxidative stress is also assessed by measuring the activity of antioxidant enzymes (SOD, CAT) and the levels of malondialdehyde (MDA), a marker of lipid peroxidation. The expression of genes involved in detoxification (e.g., cytochrome P450s) and immunity is measured by quantitative real-time PCR. These assays are crucial for understanding the mechanisms of sublethal toxicity in non-target organisms.
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| Animal Protocol |
In vivo animal experiments for Ethiprole are conducted to evaluate its efficacy as an insecticide and its toxicity to non-target organisms. For efficacy testing, the most common model is the use of agricultural pests, such as rice planthoppers. In a typical protocol, the pests are exposed to Ethiprole (e.g., by contact or by feeding on treated plants) at various concentrations. Mortality is recorded at different time points (e.g., 24, 48, 72 hours) to determine the LC50 (lethal concentration for 50% of the population). For studying toxicity to non-target organisms, the most extensively studied model is the honeybee (Apis mellifera). In a typical protocol, honeybees are exposed to Ethiprole orally (through contaminated sugar water) or topically. Sublethal effects are assessed by monitoring behavior, such as foraging activity and learning. Development is assessed by measuring the rate of pupation and eclosion. Biochemical markers of oxidative stress are measured in the bee's tissues. Gene expression analysis is performed on the bee's brain or other tissues to study the effects on detoxification and immune pathways. These in vivo studies are essential for the risk assessment of Ethiprole in the environment.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Ethiprole's known metabolites in the human body include Ethiprole sulfone. The pharmacokinetic properties of Ethiprole are relevant to its use as a pesticide. It is metabolized in insects and mammals primarily by cytochrome P450 enzymes. Ethiprole is known to be metabolized to its sulfone derivative, and this metabolism occurs faster in CYP3A4-expressing cells and in vivo in mouse brain and liver compared to fipronil. This difference in metabolism can affect its toxicity and persistence. Ethiprole has a molecular weight of 397.2 g/mol and a molecular formula of C13H9Cl2F3N4OS. As a phenylpyrazole, it is a lipophilic compound, which facilitates its penetration into the insect cuticle. Its environmental fate is also influenced by its metabolism and degradation in soil and water. For research use, Ethiprole is typically supplied as a solid and is soluble in organic solvents. Its stability is ensured by storing it under recommended conditions. Understanding its metabolism and elimination is important for assessing its environmental persistence and its potential for bioaccumulation. |
| Toxicity/Toxicokinetics |
Ethiprole is toxic to non-target organisms, particularly bees. Sublethal doses of Ethiprole have been shown to affect honeybee development, including inhibiting pupation and eclosion. It also induces oxidative stress in honeybees, as evidenced by increased levels of reactive oxygen species (ROS), lipid peroxidation (MDA), and altered activities of antioxidant enzymes like SOD and CAT. Furthermore, it affects the expression of genes involved in detoxification (e.g., cytochrome P450s) and immune responses. These effects can compromise the health and survival of honeybee colonies. In mammals, Ethiprole is considered to be of low to moderate toxicity. However, it is an insecticide, and concentrated solutions can be harmful if ingested, inhaled, or absorbed through the skin. As with other pesticides, it is important to handle Ethiprole with caution, using appropriate personal protective equipment (PPE) and following safety guidelines. Its toxicity to aquatic organisms is also a concern, and it is classified as hazardous to the environment.
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| Additional Infomation |
Ethiprole belongs to the pyrazole class of compounds, which is a cyclic compound.
Ethiprole is a commercial insecticide developed by Bayer, and it is registered for agricultural use in several countries. In China, it is specifically registered for the control of rice planthoppers (Nilaparvata lugens). It is effective against a wide range of chewing and sucking pests at low dosages, making it a valuable tool for crop protection. Its mechanism of action as a noncompetitive antagonist of the GABA-gated chloride channel is well-characterized. This mechanism is shared with fipronil, another phenylpyrazole insecticide. Ethiprole is considered a second-generation GABAergic insecticide. Its use is governed by regulations to minimize its impact on the environment and non-target organisms. Due to its toxicity to bees, its use is often restricted during flowering periods. While it is an important agricultural chemical, it is not a therapeutic drug and is not approved for any medical use. It is used as a research tool to study insect GABA receptors and the mechanisms of insecticide action and resistance. |
| Molecular Formula |
C13H9CL2F3N4OS
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| Molecular Weight |
397.2
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| Exact Mass |
395.983
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| CAS # |
181587-01-9
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| Related CAS # |
181587-01-9 Kirappu
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| PubChem CID |
9930667
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.69g/cm3
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| Boiling Point |
563.5ºC at 760mmHg
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| Melting Point |
~174°
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| Flash Point |
294.6ºC
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| Vapour Pressure |
0mmHg at 25°C
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| Index of Refraction |
1.655
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| LogP |
5.226
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
24
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| Complexity |
531
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCS(=O)C1=C(N)N(C2=C(C=C(C=C2Cl)C(F)(F)F)Cl)N=C1C#N
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| InChi Key |
FNELVJVBIYMIMC-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C13H9Cl2F3N4OS/c1-2-24(23)11-9(5-19)21-22(12(11)20)10-7(14)3-6(4-8(10)15)13(16,17)18/h3-4H,2,20H2,1H3
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| Chemical Name |
5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfinylpyrazole-3-carbonitrile
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| Synonyms |
Ethiprole
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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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5176 mL | 12.5881 mL | 25.1762 mL | |
| 5 mM | 0.5035 mL | 2.5176 mL | 5.0352 mL | |
| 10 mM | 0.2518 mL | 1.2588 mL | 2.5176 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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