2. Others Neuronal Signaling Anti-infection
  3. Insecticide Cholinesterase (ChE) Dengue Virus Flavivirus
  4. Temephos

Temephos (Temefos) is an orally active, blood-brain barrier-permeable organophosphate insecticide and AChE inhibitor. By irreversibly inhibiting AChE to induce cholinergic overactivation, Temephos effectively blocks larval development of Aedes aegypti (yellow fever mosquito) and Aedes albopictus (Asian tiger mosquito), and is commonly used in studies related to Dengue Virus, Zika Virus and other relevant pathogens. Temephos exhibits genotoxicity and neurodevelopmental toxicity, and may also cause liver injury, reproductive system abnormalities and cholinergic poisoning symptoms in mammals. Temephos tends to accumulate in adipose tissues and aquatic organisms, and is excreted via feces after metabolism through oxidation and hydrolysis. Note that CYP-mediated metabolic detoxification may reduce the actual larvicidal efficacy of Temephos against some mosquito species. Temephos can be used in research related to dengue fever, Zika virus disease, chikungunya and dracunculiasis.

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Temephos

Temephos Chemical Structure

CAS No. : 3383-96-8

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Based on 2 publication(s) in Google Scholar

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Description

Temephos (Temefos) is an orally active, blood-brain barrier-permeable organophosphate insecticide and AChE inhibitor. By irreversibly inhibiting AChE to induce cholinergic overactivation, Temephos effectively blocks larval development of Aedes aegypti (yellow fever mosquito) and Aedes albopictus (Asian tiger mosquito), and is commonly used in studies related to Dengue Virus, Zika Virus and other relevant pathogens. Temephos exhibits genotoxicity and neurodevelopmental toxicity, and may also cause liver injury, reproductive system abnormalities and cholinergic poisoning symptoms in mammals. Temephos tends to accumulate in adipose tissues and aquatic organisms, and is excreted via feces after metabolism through oxidation and hydrolysis. Note that CYP-mediated metabolic detoxification may reduce the actual larvicidal efficacy of Temephos against some mosquito species. Temephos can be used in research related to dengue fever, Zika virus disease, chikungunya and dracunculiasis[1][2][3][4].
IC50 & Target

AChE

 

In Vitro

Temephos (10 μM) exerts extremely weak genotoxic effects on human lymphocytes and HepG2 cells, and induces DNA fragmentation in blood cells; however, such toxicity is weaker than that of 0.05% DMSO (HY-Y0320C)[1].
Temephos (0.01-0.15 ppm; 24 h) exhibits an LC50 value 15-fold higher and an LC95 value 14-fold higher in temephos-resistant Aedes aegypti (Cucuta strain) than in the susceptible New Orleans strain, with an LC50 of 0.066 ppm and an LC95 of 0.18 ppm[3].
Co-incubation with temephos (0.05-0.15 ppm; 24 h) and 0.5 ppm DEF increases the sensitivity of temephos-resistant Aedes aegypti (Cucuta strain) to temephos by 36-fold, reducing the LC50 of temephos to 0.0019 ppm[3].
When applied in the field, Temephos (1 ppm; 24 h) maintains 100% mortality of temephos-resistant Aedes aegypti (Cucuta strain) for 8 weeks without water change, but the mortality decreases with two water changes per week[3].
Temephos (LC60; 24 h) induces overexpression of CYP6N12, CYP6M11 and CYP6F3 in temephos-resistant Aedes aegypti (Cucuta strain) larvae[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Temephos Related Antibodies

Real Time qPCR[3]

Cell Line: Aedes aegypti larvae
Concentration: LC60
Incubation Time: 24 h
Result: Induced the overexpression of CYP6N12 (2.34-fold), CYP6M11 (2.32-fold) and CYP6F3 (1.71-fold) in temephos-resistant Aedes aegypti (Cucuta strain) larvae, compared with unexposed larvae.
Parmacokinetics
Species Dose Route T1/2 (Absorption) Tmax T1/2 (Elimination)
Rat[4] 300 mg/kg p.o. 0.38 h 2 h 8.6 h
In Vivo

Temephos (0.0043 mg/kg; daily; 18 consecutive days during gestation) exhibits a low-level, concentration-dependent genotoxic effect in pregnant Swiss mice during mid-gestation without causing fetal physiological malformations[1].
Temephos (50 mg/kg; days 6-13 of gestation) causes hyperactivity and impaired social interaction in offspring of pregnant Swiss mice, indicating neurodevelopmental toxicity[1].
Temephos (100 ppm; dietary; continuous exposure via feed) reduces offspring duckling weight and increases liver damage indicators in mallard hens without causing miscarriage or fetal deformities[1].
Temephos (10-100 ppm; via drinking water) at 100 ppm is toxic to mallard ducklings, increasing mortality and inhibiting AChE activity, while 10 ppm does not increase mortality[1].
Temephos (LC50 concentration; egg exposure) causes general growth reduction in mallard embryos without inducing organ-specific defects or deformities[1].
Temephos (2.3-100 mg/kg/day; up to 44-90 days) exhibits a no-observed adverse effect level of 2.3 mg/kg/day over 90 days and a lowest observable adverse effect level of 100 mg/kg/day over 44 days in rats, with additional low-dose toxic effects including genotoxicity, reproductive harm, and liver damage[2].
Temephos (300 mg/kg; p.o.; single dose) is well absorbed, extensively metabolized into reactive metabolites including Tem-oxons and Tem-dioxons, widely distributed across rat tissues with preferential accumulation in fat, eliminated with an 8.6-hour elimination half-life, and produces temephos-sulfone-monohydrolyzed, which remains stable in blood until 36 hours, accumulates in the kidney, and may serve as an exposure biomarker[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model: Swiss mice (female, pregnant, embryofetal developmental toxicity model)[1]
Dosage: 0.0043 mg/kg
Administration: daily; 18 consecutive days during gestation
Result: Was detected in the placenta.
Did not cause physiological malformations in mouse fetuses.
Showed a concentration-dependent genotoxic effect in female mice on the 16th and 17th days of gestation, as measured by micronucleus assay.
Animal Model: Swiss mice (female, pregnant, prenatal exposure model)[1]
Dosage: 50 mg/kg
Administration: days 6-13 of gestation
Result: Induced hyperactivity in offspring in the open field test.
Caused reduced social interaction in offspring in the reciprocal social interaction test.
Animal Model: Mallard ducklings[1]
Dosage: 100 ppm (mortality, AChE inhibition); 10 ppm (mortality)
Administration: via drinking water
Result: As for add to drinking water:
Caused higher mortality and depression of AChE activity at 100 ppm.
Did not increase mortality at 10 ppm.
As for add to via dietary feed:
Reduced body weight in offspring ducklings.
Increased indicators of liver damage in offspring ducklings.
Did not cause miscarriage or fetal abnormalities.
Animal Model: Rats (specific strain not specified)[2]
Dosage: 2.3 mg/kg/day; 100 mg/kg/day
Administration: up to 90 days (for 2.3 mg/kg/day); up to 44 days (for 100 mg/kg/day)
Result: Identified a no-observed adverse effect level (NOAEL) of 2.3 mg/kg/day based on brain acetylcholinesterase (AChE) inhibition.
Identified a lowest observable adverse effect level (LOAEL) of 100 mg/kg/day based on cholinergic symptoms.
Caused genotoxic effects, adverse effects on male reproduction and fertility, and liver damage even at low doses.
Animal Model: Wistar rats (adult, male)[4]
Dosage: 300 mg/kg
Administration: p.o.; single dose
Result: Reached peak blood concentrations at 2 hours (absorption half-life = 0.38 h), with only trace levels detected at 36 hours (elimination half-life = 8.6 h).
Was detected in all analyzed tissues and preferentially accumulated in fat tissue.
Detected at least eleven metabolites, including temephos-sulfoxide, temephos-oxon, temephos-oxon-sulfoxide, temephos-oxon-sulfoxide-monohydrolyzed, 4,4'-thiodiphenol, 4,4'-sulfinyldiphenol, and 4,4'-sulfonyldiphenol (bisphenol S).
Maintained constant temephos-sulfone-monohydrolyzed (Tem-SO2-OH) blood levels until 36 h, which gradually accumulated in the kidney.
Detected Tem-oxon in the brain, liver, kidney, and fat.
Exhibited liver and kidney clearance values of 7.59 and 5.52 mL/min, respectively.
Molecular Weight

466.47

Formula

C16H20O6P2S3
CAS No.
Appearance

Liquid (Density: 1.3200 g/cm3)

Color

Colorless to light yellow

SMILES

COP(OC(C=C1)=CC=C1SC2=CC=C(OP(OC)(OC)=S)C=C2)(OC)=S
Shipping

Room temperature in continental US; may vary elsewhere.
Storage
Pure form -20°C 3 years
4°C 2 years
In solvent -80°C 6 months
-20°C 1 month
Solvent & Solubility
In Vitro: 

DMSO : 100 mg/mL (214.38 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 2.1438 mL 10.7188 mL 21.4376 mL
5 mM 0.4288 mL 2.1438 mL 4.2875 mL
View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

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In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

  • Protocol 1

    Add each solvent one by one:  10% DMSO    40% PEG300    5% Tween-80    45% Saline

    Solubility: 2.5 mg/mL (5.36 mM); Suspended solution; Need ultrasonic

    This protocol yields a suspended solution of 2.5 mg/mL. Suspended solution can be used for oral and intraperitoneal injection.

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

    Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
  • Protocol 2

    Add each solvent one by one:  10% DMSO    90% Corn Oil

    Solubility: ≥ 2.5 mg/mL (5.36 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:

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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Calculation results:
Working solution concentration: mg/mL
Method for preparing stock solution: mg drug dissolved in μL  DMSO (Stock solution concentration: mg/mL).
The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).
Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.
 If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Purity & Documentation

Purity: 99.35%

SDS (563 KB)

COA (249 KB) HNMR (237 KB) LCMS (93 KB)

Handling Instructions (2659 KB)
References

Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
DMSO 1 mM 2.1438 mL 10.7188 mL 21.4376 mL 53.5940 mL
5 mM 0.4288 mL 2.1438 mL 4.2875 mL 10.7188 mL
10 mM 0.2144 mL 1.0719 mL 2.1438 mL 5.3594 mL
15 mM 0.1429 mL 0.7146 mL 1.4292 mL 3.5729 mL
20 mM 0.1072 mL 0.5359 mL 1.0719 mL 2.6797 mL
25 mM 0.0858 mL 0.4288 mL 0.8575 mL 2.1438 mL
30 mM 0.0715 mL 0.3573 mL 0.7146 mL 1.7865 mL
40 mM 0.0536 mL 0.2680 mL 0.5359 mL 1.3399 mL
50 mM 0.0429 mL 0.2144 mL 0.4288 mL 1.0719 mL
60 mM 0.0357 mL 0.1786 mL 0.3573 mL 0.8932 mL
80 mM 0.0268 mL 0.1340 mL 0.2680 mL 0.6699 mL
100 mM 0.0214 mL 0.1072 mL 0.2144 mL 0.5359 mL
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Help & FAQs
  • Do most proteins show cross-species activity?

    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

Temephos3383-96-8TemefosInsecticideCholinesterase (ChE)Dengue VirusFlavivirusDENVSwiss miceAedes albopictusmallard ducklingsHepG2 cellsAedes aegyptiacetylcholineacetylcholinesteraseCucuta straincytochrome P450human lymphocytesInhibitorinhibitorinhibit

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