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Phenthoate

Alias: Dimephenthioate; Phenthoate; Phenthoate
Cat No.:V16382 Purity: ≥98%
Phenthoate is an organophosphorus pesticide with low toxicity to animals and an AChE inhibitor.
Phenthoate
Phenthoate Chemical Structure CAS No.: 2597-03-7
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
50mg
100mg
Other Sizes
Official Supplier of:
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Product Description
Phenthoate is an organophosphorus pesticide with low toxicity to animals and an AChE inhibitor.
Biological Activity I Assay Protocols (From Reference)
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
Most organophosphate compounds are ... absorbed from skin, conjunctiva, gastrointestinal tract, & lung. /Organophosphate compounds/
The rate of dermal absorption /of organophosphorus pesticides/ may be ... influenced by the solvent used. /Organophosphorus pesticides/
Many of the organophosphorus insecticides are excreted in the milk ... /Organophosphorus insecticides/
Following their absorption, most organophosphorus cmpd are excreted almost entirely as hydrolysis products in the urine. /Anticholinesterase agents/
For more Absorption, Distribution and Excretion (Complete) data for PHENTHOATE (6 total), please visit the HSDB record page.
Metabolism / Metabolites
ELSAN DEGRADED RAPIDLY IN /CABBAGE SEEDLING, STRAWBERRY & APPLE FRUIT/ ... & WAS HYDROLYZED TO NON-TOXIC DERIVATIVES. MAIN METABOLITES ... WERE ELSAN CARBOXY DERIVATIVES, MANDELIC ACID & BIS(CARBETHOXYBENZYL)DISULFIDE.
MAJOR URINARY METABOLITES /OF PHENTHOATE IN MICE/ @ DOSAGE OF 30 MG/KG WERE THE O-DEMETHYLATED ACID (25.8%), THE O-DEMETHYLATED OXON ACID (18.4%) & DIMETHYL PHOSPHORODITHIONATE (16.9%). INITIAL PRODUCT OF P-S CLEAVAGE ... WAS FURTHER METABOLIZED INTO CORRESPONDING SULFIDE, MANDELIC ACID, & S-METHYLATED DERIV.
In plants, there is oxidation to the thiophosphate, followed by hydrolysis. Identified metabolites are phosphoric acid, dimethyl and monomethyl phosphate.
Five metabolites were detected in the plasma and urine of a patient following ingestion of the organophosphate insecticide, phenthoate. Intact phenthoate was detected only in gastric lavage fluid. After methylation of acidic extracts of plasma and urine, phenthoate acid, demethyl phenthoate, demethyl phenthoate oxon acid, demethyl phenthoate S-isomer, and demethyl phenthoate acid S-isomer were identified with synthesized phenthoate analogues by gas chromatography and gas chromatograph-mass spectrometry. The main metabolites were phenthoate acid and demethyl phenthoate oxon acid. Although demethyl phenthoate oxon acid was a significant metabolite, no phenthoate oxon, phenthoate oxon acid or demethyl phenthoate oxon were detected. If the oxon was formed in the patient, it may have been rapidly degraded by carboxylesterase or glutathione transferase to demethyl phenthoate oxon acid.
For more Metabolism/Metabolites (Complete) data for PHENTHOATE (7 total), please visit the HSDB record page.
Toxicity/Toxicokinetics
Toxicity Data
LC50 (rat) = 59 mg/m3/4h
Interactions
Phenthoate ... was rapidly hydrolyzed by rat liver and plasma carboxylesterases to the corresponding non-toxic metabolite, phenthoate acid. A partially purified enzyme isolated from rat liver microsomes was 7-fold more effective in hydrolyzed phenthoate than the microsomal fraction. O,S,S-Trimethyl phosphorodithioate (TMPDT) and O,O,S-trimethyl phosphorothioate (TMPT), 2 impurities present in technical formulations of phenthoate, were examined for their inhibiting effects on the esterase degradation of (phenyl-14)C-phenthoate in vitro. Incubation of (14)C-phenthoate with rat liver and plasma carboxylesterases in the presence of these impurities greatly diminished the amount of phenthoate acid formed. TMPDT was superior in its inhibitory action against rat liver carboxylesterase to that of TMPT. TMPDT was equipotent in inhibiting crude rat liver and plasma carboxylesterases than rat liver carboxylesterases.
The in vitro metabolism of phenthoate (O,O-dimethyl S-(alpha-(carboethoxy)benzyl)phosphorodithioate) was followed in rats after oral administration of a nontoxic dose of 100 mg/kg. The same metabolic study was conducted following coadministration of 0.5% O,S,S-trimethyl phosphorodithioate (OSS-Me). When administered alone, phenthoate was metabolized principally by carboethoxy ester hydrolysis and cleavage of the P-O and C-S bonds, resulting in at least 6 metabolites. The primary urinary metabolite excreted was phenthoate acid. Coadministration of 0.5% OSS-Me did not alter the types of metabolites excreted. However, a reduction of the carboxylesterase-catalyzed product (phenthoate acid) was observed, indicating that the enzyme responsible for the major pathway of phenthoate detoxication was inhibited.
The levels of total lipids, free fatty acids, cholesterol, and lipase activity were studied in selected tissues of Channa punctatus Bloch during individual and combined exposures of carbaryl and phenthoate. The total lipid levels decreased with elevated levels of free fatty acids and lipase activity during all exposures, suggesting increased lipid hydrolysis to derive energy as an attempt to face the pesticide toxic stress. The cholesterol levels showed an elevated trend. ... The effect produced by carbaryl + phenthoate treatment remained higher than either of the pesticides alone, suggesting the manifestation of an additive effect.
Some phenothiazines may antagonize & some may potentiate the toxic anticholinesterase effects of ... /organophosphorus insecticides/. /Organophosphate cholinesterase inhibitors/
For more Interactions (Complete) data for PHENTHOATE (7 total), please visit the HSDB record page.
Non-Human Toxicity Values
LD50 MOUSE ORAL 350-400 MG/KG /TECHNICAL PRODUCT/
LD50 RAT ORAL 300-400 MG/KG /TECHNICAL PRODUCT/
LD50 Rat oral 77.7 mg/kg
LD50 Rat oral 118 mg/kg
For more Non-Human Toxicity Values (Complete) data for PHENTHOATE (10 total), please visit the HSDB record page.
References

[1]. Fatal Poisoning With Both Dichlorvos and Phenthoate. J Forensic Sci. 2018 Nov;63(6):1928-1931.

[2]. Elucidating the Potential Neurotoxicity of Chiral Phenthoate: Molecular Insight From Experimental and Computational Studies. Chemosphere. 2020 Sep;255:127007.

Additional Infomation
Phenthoate is an organic thiophosphate that is ethyl mandelate in which the hydroxy group has been replaced by a (dimethoxyphosphorothioyl)sulfanediyl group. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an acaricide and an agrochemical. It is an organic thiophosphate, an organothiophosphate insecticide and an ethyl ester.
Phenthoate is a synthetic organic thiophosphate compound and organophosphate acetylcholinesterase inhibitor that is used as a pesticide. It is characterized as a colorless crystalline solid with an aromatic odor, and exposure occurs by inhalation, ingestion, or contact.
Mechanism of Action
Cholinesterase inhibitor.
The cardiovascular actions of anticholinesterase agents are complex, since they reflect both ganglionic and postganglionic effects of accumulated ACh on the heart and blood vessels. The predominant effect on the heart from the peripheral action of accumulated ACh is bradycardia, resulting in a fall in cardiac output. Higher doses usually cause a fall in blood pressure, often as a consequence of effects of anticholinesterase agents on the medullary vasomotor centers of the CNS. /Anticholinesterase agents/
Organophosphorus derivatives act by combining with and inactivating the enzyme acetylcholinesterase. ... The inactivation of cholinesterase by cholinesterase inhibitor pesticides allows the accumulation of large amounts of acetylcholine, with resultant widespread effects that may be ... separated into 4 categories: (1) Potentiation of postganglionic parasympathetic activity. ... (2) Persistent depolarization of skeletal muscle ... (3) Initial stimulation following depression of cells of central nervous system ... (4) Variable ganglionic stimulation or blockade ... /Cholinesterase inhibitor pesticides/
The main feature of the toxic mechanism of organophosphorus pesticides is inhibition of the esterase enzyme activity, in particular of cholinesterase, which plays an important physiological part. Organophosphorus pesticides can also indirectly interact with the biochemical receptors of acetylcholine. /Organophosphorus pesticides/
For more Mechanism of Action (Complete) data for PHENTHOATE (7 total), please visit the HSDB record page.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H17O4PS2
Molecular Weight
320.36
Exact Mass
320.03
CAS #
2597-03-7
PubChem CID
17435
Appearance
Colorless to light yellow liquid
Density
1.3±0.1 g/cm3
Boiling Point
379.5±52.0 °C at 760 mmHg
Melting Point
156ºC
Flash Point
183.3±30.7 °C
Vapour Pressure
0.0±0.9 mmHg at 25°C
Index of Refraction
1.564
LogP
3.96
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
8
Heavy Atom Count
19
Complexity
324
Defined Atom Stereocenter Count
0
SMILES
CCOC(=O)C(C1=CC=CC=C1)SP(=S)(OC)OC
InChi Key
XAMUDJHXFNRLCY-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H17O4PS2/c1-4-16-12(13)11(10-8-6-5-7-9-10)19-17(18,14-2)15-3/h5-9,11H,4H2,1-3H3
Chemical Name
ethyl 2-dimethoxyphosphinothioylsulfanyl-2-phenylacetate
Synonyms
Dimephenthioate; Phenthoate; Phenthoate
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 Data
Solubility (In Vitro)
DMSO : ~250 mg/mL (~780.37 mM)
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.1215 mL 15.6074 mL 31.2149 mL
5 mM 0.6243 mL 3.1215 mL 6.2430 mL
10 mM 0.3121 mL 1.5607 mL 3.1215 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.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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