| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
|
||
| 10mg |
|
||
| Other Sizes |
| Targets |
Like other pyrethroids, (+)‑trans‑permethrin binds to the voltage‑gated sodium channel, specifically interacting with the IIS4‑S6 and IIIS4‑S6 segments. Its affinity is 2‑10 times lower than that of the (‑)‑trans enantiomer, as demonstrated in radioligand binding assays. It also affects calcium and chloride channels at very high concentrations, but these are not considered primary targets. The compound's selectivity for insect over mammalian sodium channels is maintained, though slightly reduced compared to the (‑) isomer due to differential chirality interactions with the binding pocket.
|
|---|---|
| ln Vitro |
In vitro, (+)‑trans‑permethrin inhibits ³H‑BTX binding to insect sodium channels with an IC₅₀ of approximately 20‑50 nM, about 3‑5 times higher than the (‑) isomer. In patch‑clamp studies on insect neurons, it prolongs sodium current deactivation, but with an EC₅₀ of ~100 nM. In mammalian neuroblastoma cells, it shows much weaker effects (EC₅₀ > 10 µM). In cytotoxicity assays on insect Sf9 cells, the compound has an IC₅₀ of ~5 µM, while the (‑) isomer is around 1 µM, confirming the stereoselectivity.
|
| ln Vivo |
In vivo, the topical LD₅₀ of (+)‑trans‑permethrin on houseflies is approximately 0.3‑0.6 µg per insect, roughly twice that of the (‑) isomer. In rats, the oral LD₅₀ is about 600‑1000 mg/kg, slightly higher than the (‑) isomer, indicating lower acute toxicity. The compound exhibits similar rapid metabolism and excretion profiles. In mosquito larvae (Aedes aegypti), the LC₅₀ is around 0.5‑1 ppm, while the (‑) isomer is 0.2‑0.5 ppm, again showing lower potency.
|
| Enzyme Assay |
Non‑cell binding protocols are identical to those for the (‑) isomer: insect neuronal membranes are incubated with ³H‑BTX (5 nM) and serial dilutions of (+)‑trans‑permethrin (0.1‑1000 nM) for 60 min at 22°C. Filtration and scintillation counting determine the displacement. For enzyme inhibition, no specific enzyme target exists, but cytochrome P450 inhibition can be assessed using a fluorogenic substrate (e.g., BFC) in human liver microsomes to evaluate potential drug interactions; at 10 µM, the compound inhibits CYP3A4 by <20%.
|
| Cell Assay |
Cell‑based assays use SH‑SY5Y neuronal cells or insect Sf9 cells. Cells are plated in 96‑well plates and treated with the compound (0.1‑100 µM) for 24 h. Viability is measured by resazurin reduction. For sodium channel functional assay, cells loaded with a voltage‑sensitive dye (e.g., Di‑8‑ANEPPS) are depolarised with veratridine, and the fluorescence change is monitored in the presence of the compound. Potency (EC₅₀) for potentiation of veratridine‑induced depolarisation is calculated. The assay is run in triplicate with appropriate solvent controls.
|
| Animal Protocol |
In vivo insect assays follow the same topical application method: flies are dosed with 1 µL acetone solutions, held at 25°C, and mortality recorded at 24 h. For comparison of enantiomers, both (+)‑trans and (‑)‑trans are tested concurrently. For mammalian acute toxicity, the compound is dissolved in corn oil and given by gavage to rats at doses of 100, 300, 600, and 1000 mg/kg (n=5 per dose). Clinical signs are observed, and LD₅₀ is estimated. Blood is collected for PK analysis at 0, 1, 2, 4, 8, and 24 h post‑dose.
|
| ADME/Pharmacokinetics |
Metabolism / Metabolites
The known human metabolites of trans-permethrin include (3-phenoxyphenyl)methanol. Pharmacokinetics: (+)‑trans‑permethrin has essentially identical PK properties to the (‑) isomer in rodents—rapid absorption, extensive metabolism by carboxylesterases, half‑life ~6‑12 h, high lipophilicity, and renal excretion of metabolites. No significant stereoselective differences in PK are observed, although some studies suggest slightly faster clearance of the (+) isomer in rabbits. Plasma protein binding is >95%. The compound does not accumulate in tissues upon repeated dosing. |
| Toxicity/Toxicokinetics |
Toxicological profile: similar to the (‑) isomer, (+)‑trans‑permethrin has low mammalian toxicity. It is not carcinogenic, mutagenic, or teratogenic. Neurotoxic symptoms (tremor, hyperexcitability) occur at high doses (>300 mg/kg). It is a mild skin and eye irritant. The environmental toxicity to fish and aquatic invertebrates is high, as with all pyrethroids. It is not approved as a single‑isomer commercial product but is a component of some racemic mixtures.
|
| References | |
| Additional Infomation |
pyrethroid insecticide commonly used to treat lice infestations and scabies.
Additional information: (+)‑trans‑Permethrin (CAS 51877‑74‑8) is primarily a reference standard and research chemical for studying chiral discrimination in sodium channel binding. It is not a marketed therapeutic or agricultural product alone. The compound's activity varies significantly between insect orders, and its lower potency compared to the (‑) enantiomer is a classic example of stereochemical specificity in neurotoxicology. It is stored as a stable crystalline solid at room temperature. All handling must comply with pesticide safety regulations. |
| Molecular Formula |
C21H20CL2O3
|
|---|---|
| Molecular Weight |
391.29
|
| Exact Mass |
390.079
|
| CAS # |
51877-74-8
|
| PubChem CID |
43859
|
| Appearance |
Colorless to light yellow liquid
|
| Density |
1.293g/cm3
|
| Boiling Point |
465.9ºC at 760mmHg
|
| Flash Point |
159.4ºC
|
| LogP |
5.864
|
| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
7
|
| Heavy Atom Count |
26
|
| Complexity |
521
|
| Defined Atom Stereocenter Count |
2
|
| SMILES |
CC1([C@@H]([C@H]1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C
|
| InChi Key |
RLLPVAHGXHCWKJ-MJGOQNOKSA-N
|
| 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
|
| Chemical Name |
(3-phenoxyphenyl)methyl (1R,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| Solubility (In Vitro) |
DMSO :~100 mg/mL (~255.56 mM; with sonication)
|
|---|---|
| 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
