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| Other Sizes |
| ln Vitro |
Pyridaben (0-10 µM; 3 min) combines with brain submitochondrial granules' complexes I–III of the factor receptor [1]. With malate-glutamate as the substrate, pyridaben (0–10 µM; 3 min) significantly reduces the respiratory control of brain mitochondria in a dose-dependent manner (IC50= 1.7 µM) [1]. When malate-glutamic acid is the substrate, pyridoglutaben (0–10 µM; 3 min) dramatically lowers the functional activity of mtNOS; however, this effect is not observed when succinate is the substrate [1].
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| Cell Assay |
Cell Viability Assay [1]
Cell Types: Rat Brain Cartilage Pellets Tested Concentrations: 0-10 µM Incubation Duration: 3 minutes Experimental Results: Result in decrease in NADH-cytochrome reductase activity (complex I-III), but not succinate-cytochrome c Reductase activity (complex II-III) and cytochrome oxidase activity (complex IV) did not modify cell viability assay [1] Cell Types: Rat brain mitochondria Tested Concentrations: 0-10 µM Incubation Duration: 3 minutes Experimental Results: In the presence of malate-glutamate as substrate, respiratory control shows a significant and dose-dependent decrease (IC50=1.7 µM) |
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
In a rat oral metabolism study, pyridoxine was primarily excreted in feces, with 80-97% of the administered dose being excreted regardless of dose or labeling site (pyridone or benzyl ring). Nearly 20% of the fecal residue consisted of unmetabolized parent compound, and trace amounts of glucuronide conjugates were detected in bile. Following a single low-dose (3 mg/kg) oral administration, peak plasma concentrations were reached in 2-3 hours, while peak plasma concentrations for high-dose (30 mg/kg) were reached approximately 24 hours post-administration. This is at least partly due to enterohepatic circulation, in which approximately 22-30% of the radioactive administered dose is excreted in bile within 24 hours. Residual radioactivity in most tissues reached or approached background levels after 72-168 hours. Overall, the drug appeared to distribute more extensively in adipose tissue over time, with adipose tissue appearing to retain relatively more radioactive material compared to other tissues. Metabolism/Metabolites In a rat oral metabolism study, pyridoxine was primarily excreted in feces, with 80-97% of the administered dose being excreted regardless of dose or labeling site (pyridone or benzyl ring). Nearly 20% of the fecal residue was unmetabolized parent compound, and some evidence of glucuronide conjugates was found in bile. Following a single low-dose (3 mg/kg) oral administration, peak plasma concentrations were reached in 2-3 hours, while peak plasma concentrations for high-dose (30 mg/kg) were reached approximately 24 hours post-administration, at least in part due to enterohepatic circulation, where nearly 22-30% of the administered radioactive dose is excreted in bile within 24 hours. Residual radioactivity levels in most tissues reached or approached background levels after 72-168 hours. Overall, the distribution of radioactive material appeared to increase over time in adipose tissue, with relatively higher residual radioactivity compared to other tissues. |
| Toxicity/Toxicokinetics |
Toxicity Data
LC50 (Rat) = 620 mg/m3 LD50: 161 mg/kg (Acute, Rat) (L2092) Non-human Toxicity Values LD50 Rat (Male) Oral: 1100 mg/kg LD50 Rat (Female) Oral: 570 mg/kg LD50 Mice (Male) Oral: 424 mg/kg LD50 Mice (Female) Oral: 383 mg/kg For more complete non-human toxicity data for PYRIDABEN (6 items), please visit the HSDB records page. |
| References |
[1]. Gomez C,et al. Pesticides and impairment of mitochondrial function in relation with the parkinsonian syndrome. Front Biosci. 2007 Jan 1;12:1079-93.
[2]. Namin HH, et al. Resistance to pyridaben in Canadian greenhouse populations of two-spotted spider mites, Tetranychus urticae (Koch). Pestic Biochem Physiol. 2020 Nov;170:104677. |
| Additional Infomation |
Pyridaben is a pyridazinone compound belonging to the organochlorine insecticide and organochlorine acaricide class. It functions as an inhibitor of mitochondrial NADH:ubiquinone reductase.
Pyridaben has been reported to be present in Ganoderma lucidum, and relevant data are available for reference. Pyridaben is an insecticide and acaricide effective against thrips, mites, aphids, and leafhoppers. It can be used to control pests in citrus and other orchards. Pyridaben was discovered and introduced by Nissan Chemical Industries, Ltd., and first marketed in Belgium in 1990. It has low water solubility and low volatility, and based on its chemical properties, it is not expected to seep into groundwater. It is moderately toxic to mammals, and bioaccumulation is not expected. It is highly toxic to most aquatic organisms and bees, but less toxic to earthworms and birds. (L2092) Mechanism of Action ... It has been proposed that NADH:ubiquinone oxidoreductase inhibitors (including Pyridaben) block multiple pathways that may be regulated by reactive oxygen species, which regulate ornithine decarboxylase activity. |
| Molecular Formula |
C19H25CLN2OS
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|---|---|
| Molecular Weight |
364.93
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| Exact Mass |
364.138
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| CAS # |
96489-71-3
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| Related CAS # |
Pyridaben-d13;2468638-05-1
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| PubChem CID |
91754
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| Appearance |
Colorless crystals
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| Density |
1.12 g/cm3
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| Boiling Point |
429.9ºC at 760 mmHg
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| Melting Point |
111-112ºC
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| Flash Point |
213.8ºC
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| Index of Refraction |
1.564
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| LogP |
5.241
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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 |
5
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| Heavy Atom Count |
24
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| Complexity |
535
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| Defined Atom Stereocenter Count |
0
|
| SMILES |
O=C1N(C(C)(C)C)N=CC(SCC2C=CC(C(C)(C)C)=CC=2)=C1Cl
|
| InChi Key |
DWFZBUWUXWZWKD-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C19H25ClN2OS/c1-18(2,3)14-9-7-13(8-10-14)12-24-15-11-21-22(19(4,5)6)17(23)16(15)20/h7-11H,12H2,1-6H3
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| Chemical Name |
2-tert-butyl-5-[(4-tert-butylphenyl)methylsulfanyl]-4-chloropyridazin-3-one
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| Synonyms |
Pyridaben Sanmite
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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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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) |
DMSO : ~50 mg/mL (~137.01 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.85 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. Solubility in Formulation 2: ≥ 2.5 mg/mL (6.85 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7403 mL | 13.7013 mL | 27.4025 mL | |
| 5 mM | 0.5481 mL | 2.7403 mL | 5.4805 mL | |
| 10 mM | 0.2740 mL | 1.3701 mL | 2.7403 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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