| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
(-)-cis-Permethrin targets insect voltage-gated sodium channels, which are critical for the generation and propagation of action potentials in the nervous system. As a pyrethroid insecticide, it binds to these channels and prolongs their opening, leading to neuronal hyperexcitation and paralysis in insects. The compound also affects mitochondrial complex I. The cis enantiomer exhibits different biological activity compared to the trans enantiomer.
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| ln Vitro |
As a pyrethroid insecticide, (-)-cis-Permethrin shows potent insecticidal activity in vitro against a wide range of insect pests. The compound acts on insect sodium channels, prolonging their activation and causing hyperexcitation. The cis enantiomer is one of the active isomers of permethrin, with specific activity against target insects. The compound is not evaluated for traditional pharmacological activity against mammalian cells.
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| ln Vivo |
(-)-cis-Permethrin is used in vivo as an insecticide for the control of insect pests. It is also commonly used in the treatment of lice infestations and scabies in humans. The compound is applied topically for these indications. As a pyrethroid, it exhibits rapid insecticidal activity with low mammalian toxicity.
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| Enzyme Assay |
Non-cell-based binding assays for (-)-cis-Permethrin typically involve measuring the affinity of the compound for insect sodium channels using radioligand binding or electrophysiological techniques. A standard protocol includes preparing membrane preparations from insect nervous tissue, incubating with radiolabeled permethrin or a related pyrethroid, and measuring displacement by (-)-cis-Permethrin at various concentrations to determine binding affinity (Ki).
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| Cell Assay |
Cell-based assays for (-)-cis-Permethrin typically involve insect cell lines or primary neuronal cultures to assess sodium channel modulation. A representative protocol includes culturing insect cells (e.g., Drosophila S2 cells) in appropriate medium, treating with (-)-cis-Permethrin at various concentrations (0.001–100 μM), and measuring sodium channel activity using patch-clamp electrophysiology or fluorescence-based membrane potential assays.
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| Animal Protocol |
In vivo animal studies with (-)-cis-Permethrin are conducted in insect models to assess insecticidal efficacy. A typical protocol involves applying the compound to insects (e.g., mosquitoes, cockroaches, or agricultural pests) at various concentrations, monitoring mortality and behavioral changes over time, and calculating LD50 values. The compound is also used in mammalian models for toxicological studies to assess safety.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of (-)-cis-Permethrin are characteristic of pyrethroid insecticides. The compound has low water solubility, high lipophilicity, and is rapidly metabolized in mammals by ester hydrolysis and oxidation. It has a short half-life in mammals and is primarily excreted in urine and feces. The compound is typically stored as a solid at -20°C for long-term stability.
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| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation
◉ Overview of Use During Lactation Because the absorption rate after topical application is less than 2%, and it is rapidly metabolized into inactive metabolites, it can be safely applied directly to the infant's skin. Therefore, breastfeeding women can safely use topical permethrin products. However, if there is extensive exposure due to agricultural use or malaria prevention, there may be long-term health risks, as residues may be present in breast milk. Only water-soluble creams, gels, or liquids should be applied to the breasts, as ointments may expose the infant to high concentrations of mineral oil through licking. ◉ Effects on Breastfed Infants In a telephone follow-up study, five mothers who used permethrin while breastfeeding reported no adverse reactions in their breastfed infants. ◉ Effects on Lactation and Breast Milk As of the revision date, no relevant published information was found. (-)-cis-Permethrin is a pyrethroid insecticide with well-established toxicological properties. It has low acute toxicity in mammals but can cause skin and eye irritation. The compound is classified as a pesticide and is subject to regulatory safety assessments for agricultural and public health applications. Appropriate safety precautions should be followed when handling the compound. |
| References | |
| Additional Infomation |
A pyrethroid insecticide commonly used to treat lice infestations and scabies.
See also: Permethrin (note moved to). (-)-cis-Permethrin (CAS 54774-46-8) is the cis enantiomer of permethrin, a synthetic pyrethroid insecticide. The compound is provided as a research-grade reagent for laboratory studies of insect sodium channels and mitochondrial complex I. It is used in biological, pharmacological, and toxicological research applications. The compound has high enantiomeric purity (98.1%) and is supplied as a powder suitable for dissolution in organic solvents. |
| Molecular Formula |
C21H20O3CL2
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|---|---|
| Molecular Weight |
391.2877
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| Exact Mass |
390.078
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| CAS # |
54774-46-8
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| PubChem CID |
62086
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| Appearance |
White to off-white solid powder
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| LogP |
6.5
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
26
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| Complexity |
521
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| Defined Atom Stereocenter Count |
2
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| SMILES |
Cl/C(/Cl)=C\C1C(C(OCC2C=CC=C(OC3C=CC=CC=3)C=2)=O)C1(C)C
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| InChi Key |
RLLPVAHGXHCWKJ-IEBWSBKVSA-N
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| InChi Code |
InChI=1S/C21H20Cl2O3/c1-21(2)17(12-18(22)23)19(21)20(24)25-13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17,19H,13H2,1-2H3/t17-,19-/m1/s1
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| Chemical Name |
(3-phenoxyphenyl)methyl (1S,3S)-3-(2,2-dichloroethenyl)-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) |
Typically soluble in DMSO (e.g. 10 mM)
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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 | 2.5556 mL | 12.7782 mL | 25.5565 mL | |
| 5 mM | 0.5111 mL | 2.5556 mL | 5.1113 mL | |
| 10 mM | 0.2556 mL | 1.2778 mL | 2.5556 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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