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| Other Sizes |
| ADME/Pharmacokinetics |
Metabolism / Metabolites
Organophosphate metabolism primarily occurs through oxidation, esterase hydrolysis, and reactions with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphate pesticides can produce moderately toxic products. Generally, thiophosphates themselves are not directly toxic and require oxidative metabolism to be converted into proximal toxins. Products produced by glutathione transferase reactions are generally less toxic. Paraoxygenase (PON1) is a key enzyme in organophosphate metabolism. PON1 can inactivate certain organophosphates through hydrolysis. PON1 hydrolyzes active metabolites in various organophosphate pesticides and nerve agents such as soman, sarin, and VX. The existence of PON1 polymorphism leads to differences in the enzyme level and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effects of organophosphate exposure. |
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| Toxicity/Toxicokinetics |
Toxicity Summary
Azathioprine is a cholinesterase, or acetylcholinesterase (AChE) inhibitor. Cholinesterase inhibitors (or "anticholinesterases") inhibit the activity of acetylcholinesterase. Because acetylcholinesterase plays a vital physiological role, chemicals that interfere with its activity are potent neurotoxins; even low doses can cause excessive salivation and lacrimation, followed by muscle spasms and ultimately death. Substances used in nerve gases and many pesticides have been shown to exert their effects by binding to serine residues at the active site of acetylcholinesterase, thus completely inhibiting the enzyme's activity. Acetylcholinesterase breaks down the neurotransmitter acetylcholine, which is released at the neuromuscular junction, causing muscle or organ relaxation. The mechanism of action of acetylcholinesterase inhibitors is to allow acetylcholine to accumulate and exert its sustained effect, ensuring the continuous transmission of nerve impulses and preventing muscle contraction from ceasing. The most common acetylcholinesterase inhibitors are phosphorus-containing compounds designed to bind to the enzyme's active site. Its structural requirements include a phosphorus atom with two lipophilic groups, a leaving group (such as a halogen or thiocyanate group), and a terminal oxygen atom. |
| Additional Infomation |
Thiomethylphosphide is an organothiophosphate insecticide, organochlorine insecticide, and organochlorine acaricide. It is an EC 3.1.1.7 (acetylcholinesterase) inhibitor and also an agricultural chemical. Its structure is similar to that of oxazolo[4,5-b]pyridine-2(3H)-one. Thiomethylphosphide is a synthetic organothiophosphate compound, an organophosphate acetylcholinesterase inhibitor, mutagen, and neurotoxin used as an insecticide. It is a water-soluble, colorless to gray or orange-yellow solid that can be exposed to air, through inhalation, ingestion, or contact. Thiomethylphosphide is an organophosphate insecticide whose mechanism of action is through the inhibition of cholinesterase activity. In veterinary medicine, it is used in aquaculture to control ectoparasites in Atlantic salmon. It exhibits moderate acute oral toxicity in mammals but high acute oral toxicity in birds.
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| Molecular Formula |
C9H10CLN2O5PS
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|---|---|
| Molecular Weight |
324.6779
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| Exact Mass |
323.973
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| CAS # |
35575-96-3
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| PubChem CID |
71482
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| Appearance |
White to off-white solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
428.8±55.0 °C at 760 mmHg
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| Melting Point |
88-93°C
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| Flash Point |
213.1±31.5 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.589
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| LogP |
0.82
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
19
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| Complexity |
393
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| Defined Atom Stereocenter Count |
0
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| SMILES |
ClC1C([H])=NC2=C(C=1[H])OC(N2C([H])([H])SP(=O)(OC([H])([H])[H])OC([H])([H])[H])=O
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| InChi Key |
VNKBTWQZTQIWDV-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H10ClN2O5PS/c1-15-18(14,16-2)19-5-12-8-7(17-9(12)13)3-6(10)4-11-8/h3-4H,5H2,1-2H3
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| Chemical Name |
6-chloro-3-(dimethoxyphosphorylsulfanylmethyl)-[1,3]oxazolo[4,5-b]pyridin-2-one
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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) |
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 | 3.0800 mL | 15.3998 mL | 30.7996 mL | |
| 5 mM | 0.6160 mL | 3.0800 mL | 6.1599 mL | |
| 10 mM | 0.3080 mL | 1.5400 mL | 3.0800 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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