| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| 250mg | |||
| Other Sizes |
| Targets |
Pyributicarb targets the human pregnane X receptor (hPXR), a nuclear receptor that regulates the expression of drug-metabolizing enzymes. It acts as a potent activator of hPXR and a strong inducer of CYP3A4 expression. In plants, it targets 4-hydroxyphenyl-pyruvate dioxygenase (4-HPPD), an enzyme involved in tyrosine catabolism, causing bleaching. In fungi, it targets squalene-epoxidase in sterol biosynthesis. Through hPXR activation, Pyributicarb modulates the transcription of CYP3A4 and other PXR target genes.
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| ln Vitro |
Pyributicarb is a herbicide based on carbamates that has the ability to strongly activate both the human pregnane X receptor (hPXR) and the CYP3A4 gene. At concentrations of 0.1 to 1 μM, pyributracin was found to increase CYP3A4 reporter gene activity higher than the standard CYP3A4 inducer rifampicin. Pyributicarb-stimulated CYP3A4 reporter gene activity was considerably reduced in 3-1-10 cells by hPXR-siRNA expression, and endogenous CYP3A4 mRNA levels were decreased in HepG2 cells [1]. At only 10 nM, pyributracin stimulates the transcription of luciferase via hPXR. Pyributicarb has 8.6 times the relative efficacy of rifampicin (RIF) against hPXR [2].
In vitro studies have shown that Pyributicarb stimulates CYP3A4 transcription at submicromolar to nanomolar concentrations, displaying greater potency than the classical inducer rifampicin. In cellular reporter assays, its effects on CYP3A4 activation are markedly attenuated by hPXR knockdown, confirming hPXR-dependent transcriptional regulation. As a herbicide, it inhibits 4-HPPD in plants, leading to bleaching, and targets squalene-epoxidase in fungi. Its potent activation of hPXR makes it a valuable tool for studying PXR-mediated gene expression. |
| ln Vivo |
In mouse livers where hPXR was delivered via adenovirus, pyributicarb increases the activity of CYP3A4-derived reporter genes [1].
In vivo studies have demonstrated enhanced CYP3A4 reporter activity in mouse liver following hPXR expression and Pyributicarb treatment. As a herbicide, it has been studied for its selective herbicidal activity and its impact on plant metabolism, particularly in gramineous plants. Its ability to activate hPXR and induce CYP3A4 in vivo makes it a valuable tool for studying xenobiotic metabolism and drug-drug interactions. The compound's in vivo effects on PXR-mediated transcription have been confirmed in animal models. |
| Enzyme Assay |
The in vitro assay for Pyributicarb involves measuring the activation of the human pregnane X receptor (hPXR) using a reporter gene assay. Cells are co-transfected with an hPXR expression plasmid and a CYP3A4-luciferase reporter construct. Cells are treated with varying concentrations of Pyributicarb, and luciferase activity is measured to quantify hPXR activation. The compound's potency is compared to that of the classical inducer rifampicin. The assay is performed in triplicate with appropriate controls. The IC50 or EC50 values are determined from dose-response curves.
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| Cell Assay |
In vitro cellular assays for Pyributicarb are conducted using human hepatoma cells (e.g., HepG2) or other cell lines expressing hPXR. Cells are treated with varying concentrations of Pyributicarb. CYP3A4 mRNA expression is measured by qRT-PCR, and CYP3A4 protein levels are assessed by Western blotting or ELISA. The compound's ability to induce CYP3A4 expression is quantified. The involvement of hPXR is confirmed by knockdown experiments using siRNA or by using hPXR antagonists. Cell viability is assessed to ensure that the observed effects are not due to cytotoxicity.
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| Animal Protocol |
In vivo animal studies for Pyributicarb are performed in mouse models. Mice are treated with Pyributicarb via oral gavage or intraperitoneal injection. Liver tissues are collected, and CYP3A4 reporter activity or endogenous CYP3A gene expression is measured. The compound's ability to induce CYP3A4 in vivo is assessed. Standard study designs with vehicle control and positive control (e.g., rifampicin) groups are employed, with 4-6 animals per group. Tissue samples are also collected for histopathological analysis to assess potential toxicity.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Pyridine-bufo known human metabolites include pyridine-bufo metabolite 1. Pharmacokinetic data for Pyributicarb are not extensively reported in the available literature. The compound has a molecular weight of 330.44 g/mol and a molecular formula of C18H22N2O2S. As a thiocarbamate herbicide, it is lipophilic and would be expected to be absorbed after oral administration. It is metabolized by cytochrome P450 enzymes, including CYP3A4, which it induces, leading to potential auto-induction of its own metabolism. Specific pharmacokinetic parameters such as half-life, bioavailability, and tissue distribution are not provided. |
| Toxicity/Toxicokinetics |
Toxicology data for Pyributicarb are derived from its use as a herbicide. As a 4-HPPD inhibitor in plants, its toxicity in animals would be related to its effects on tyrosine metabolism. It has fungicidal activity through inhibition of squalene-epoxidase. The compound's ability to activate hPXR and induce CYP3A4 may lead to drug-drug interactions and altered metabolism of co-administered drugs. Specific toxicity data, including LD50 values and organ toxicity profiles, are not provided in the available sources. The compound is for research use only.
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| References |
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| Additional Infomation |
Pyridine carbamate is a monothiocarbamate with the structure of carbamic acid, in which the oxygen atom on the carbonyl group is replaced by a sulfur atom, the hydrogen atom on the nitrogen atom is replaced by a methyl group and a 6-methoxypyridin-2-yl group, and the hydrogen atom on the hydroxyl group is replaced by a p-tert-butylphenyl group. It possesses fungicidal and herbicidal activity and is used in rice and turf production. It is a sterol biosynthesis inhibitor, herbicide, and antifungal pesticide. It belongs to the pyridine class of compounds, aromatic ethers, and monothiocarbamates.
Pyributicarb is a carbamate-type herbicide that acts as a potent activator of the human pregnane X receptor (hPXR) and a strong inducer of CYP3A4 expression. It is a thiocarbamate herbicide with fungicidal activity. In plants, it inhibits 4-HPPD causing bleaching; in fungi, it targets squalene-epoxidase. Pyributicarb displays greater potency than rifampicin in activating CYP3A4 transcription. It is a valuable research tool for studying xenobiotic sensing, PXR-mediated transcription, and drug-metabolizing enzyme regulation. |
| Molecular Formula |
C18H22N2O2S
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|---|---|
| Molecular Weight |
330.44448
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| Exact Mass |
330.14
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| CAS # |
88678-67-5
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| PubChem CID |
93486
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| Appearance |
White to off-white solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
427.8±55.0 °C at 760 mmHg
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| Flash Point |
212.5±31.5 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.599
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| LogP |
5.21
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
23
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| Complexity |
397
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
VTRWMTJQBQJKQH-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C18H22N2O2S/c1-18(2,3)13-8-6-9-14(12-13)22-17(23)20(4)15-10-7-11-16(19-15)21-5/h6-12H,1-5H3
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| Chemical Name |
O-(3-tert-butylphenyl) N-(6-methoxypyridin-2-yl)-N-methylcarbamothioate
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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) |
DMSO : ~100 mg/mL (~302.63 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.57 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% 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 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.5 mg/mL (7.57 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (7.57 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0263 mL | 15.1313 mL | 30.2627 mL | |
| 5 mM | 0.6053 mL | 3.0263 mL | 6.0525 mL | |
| 10 mM | 0.3026 mL | 1.5131 mL | 3.0263 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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