| Size | Price | Stock | Qty |
|---|---|---|---|
| 250mg |
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| 500mg |
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| Other Sizes |
| Targets |
Metalaxyl targets protein synthesis in fungi. It inhibits the synthesis of RNA in target fungi, effectively blocking the production of essential proteins and enzymes. It is effective against oomycetous fungi. Its mechanism involves inhibition of ribosomal RNA synthesis, leading to the disruption of protein synthesis.
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| ln Vitro |
Isolates of the Phytophthora fungus that infects potato crops are inhibited in their growth by metalaxyl (EC50s = 0.3-3.9 μg/mL) [1].
In vitro, metalaxyl inhibits the growth of potato blight (P. infestans) fungal isolates, with EC₅₀ values ranging from 0.3-3.9 μg/ml. It is a fungicide that inhibits protein synthesis in fungi. Its activity is characterized by its ability to inhibit the growth of various fungal pathogens in culture. |
| ln Vivo |
In albinos, bradycardia was the result of metalaxyl therapy, and at the highest doses (250 and 300 mg/kg), bradycardia persisted and caused abrupt cardiac arrest. In hearts and mitochondria treated with metalaxyl, methanol cholinesterase activity does not develop [2].
In vivo, metalaxyl is used as a systemic fungicide to control plant diseases caused by oomycetous fungi. It is applied to crops such as grapes to prevent fungal infections. It is absorbed by plants and provides systemic protection against fungal pathogens. It interferes with skeletal development in zebrafish embryos. |
| Enzyme Assay |
In vitro enzyme/receptor binding studies are not applicable to metalaxyl, as its target is the protein synthesis machinery in fungi. Its activity is assessed by measuring its effects on fungal growth in culture. Standard protocols involve culturing fungi in the presence of serial dilutions of metalaxyl and measuring growth inhibition by optical density or colony counting.
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| Cell Assay |
In vitro cellular assays for metalaxyl are not typically performed, as it is a fungicide. Its effects on fungal cells are assessed by measuring growth inhibition. Its effects on zebrafish embryos can be studied by exposing embryos to the compound and assessing skeletal development. Cytotoxicity in mammalian cells may be assessed using standard viability assays.
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| Animal Protocol |
In vivo animal studies for metalaxyl are primarily conducted in agricultural settings to assess its efficacy against plant pathogens. Toxicological studies in animals assess its effects on non-target organisms. Zebrafish embryo assays are used to assess its developmental toxicity. Standard protocols involve exposing embryos to the compound and assessing developmental abnormalities.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Metabolites of metalaxyl in the human body are known to include desmethylmetalaxyl, metalaxyl acid, methyl 2-[(2,6-dimethyl-3-hydroxyphenyl)(methoxyacetyl)amino]propionate, and N-(2-(hydroxymethyl)-6-methylphenyl)-N-(methoxyacetyl)-DL-alanine methyl ester. Currently, three major metabolic pathways and one minor metabolic pathway have been proposed. The major metabolic pathway involves the hydrolysis of the ether, followed by oxidation, ester hydrolysis, or N-dealkylation of the ester chain into the resulting alcohol. The second major metabolic pathway involves the oxidation of aromatic methyl groups to benzyl acid or ester hydrolysis. The third major metabolic pathway is ester hydrolysis, which sometimes produces benzyl acid. The minor metabolic pathway involves meta-hydroxylation of the benzene ring. Urinary metabolites are mainly in the bound form (glucuronide or sulfate), while fecal metabolites are mostly in the unbound form. The main metabolite in urine and feces is N-(2,6-dimethylphenyl)-N-(hydroxyacetyl)alanine. Metalaxyl is primarily excreted in urine and feces. (L918) Pharmacokinetic properties of metalaxyl include a molecular weight of 279.33. It is a systemic fungicide that is absorbed by plants. Its half-life in soil and plants varies depending on environmental conditions. It is metabolized in plants and animals. Detailed pharmacokinetic parameters are available from environmental fate studies. |
| Toxicity/Toxicokinetics |
Toxicity Summary
It binds to nAChR in the nervous system. It can also cause endocrine disorders in humans by binding to and inhibiting estrogen receptors. (T10, A590) Toxicity Data LD50: 669 mg/kg (oral, rat) (L918) LD50: 7120 mg/kg (oral, hamster) (L918) LD50: >6000 mg/kg (skin, rabbit) (L918) Toxicological data for metalaxyl indicate that it is mildly irritating to the skin and eyes. Exposure often results in nonspecific symptoms such as headache, dizziness, weakness, and nausea. It may have anti-estrogenic and anti-androgenic effects in animal studies. It is considered to have low acute toxicity to mammals but may be toxic to aquatic organisms. |
| References |
[1]. Emil Rekanović, et al. Toxicity of metalaxyl, azoxystrobin, dimethomorph, cymoxanil, zoxamide and mancozeb to Phytophthora infestans isolates from Serbia. J Environ Sci Health B. 2012;47(5):403-9.
[2]. K A Naidu, et al. Metalaxyl-induced bradycardia in rats: mediated by alpha-adrenoreceptors. J Toxicol Environ Health. 1988;23(4):495-8. |
| Additional Infomation |
N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alanine methyl ester is an alanine derivative with the structure alanine methyl ester, in which one hydrogen atom bonded to the nitrogen atom is replaced by a methoxyacetyl group, and the other hydrogen atom is replaced by a 2,6-dimethylphenyl group. It is an alanine derivative, aromatic amide, carboxamide, ether, and methyl ester. Metalaxyl has been reported to exist in Ganoderma lucidum, and relevant data are available. (±)-Methamphetamine is a systemic agricultural fungicide belonging to the cyclic peptide fungicide class. Cyclic peptide fungicides are natural or synthetic compounds whose structure contains amino and hydroxycarboxylic acid residues (usually 1-amino and 1-hydroxy acid), which are usually (but not necessarily) arranged in a regular alternation. See also: Metalaxyl-M (note moved to).
Metalaxyl is a systemic fungicide used to control fungal diseases in crops. It inhibits protein synthesis in fungi. It is effective against downy mildew and soil-borne diseases caused by Phytium and Phytophthora species. It is not approved for human therapeutic use and is intended for agricultural applications. |
| Molecular Formula |
C15H21NO4
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|---|---|
| Molecular Weight |
279.33
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| Exact Mass |
279.147
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| CAS # |
57837-19-1
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| Related CAS # |
Metalaxyl-13C6;1356199-69-3;Metalaxyl-d6
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| PubChem CID |
42586
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
394.3±42.0 °C at 760 mmHg
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| Melting Point |
72-73°C
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| Flash Point |
192.3±27.9 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.528
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| LogP |
2.15
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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 |
6
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| Heavy Atom Count |
20
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| Complexity |
335
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C[CH](N(C1=C(C)C=CC=C1C)C(COC)=O)C(OC)=O
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| InChi Key |
ZQEIXNIJLIKNTD-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C15H21NO4/c1-10-7-6-8-11(2)14(10)16(13(17)9-19-4)12(3)15(18)20-5/h6-8,12H,9H2,1-5H3
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| Chemical Name |
methyl 2-(N-(2-methoxyacetyl)-2,6-dimethylanilino)propanoate
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| Synonyms |
CGA-48988; CGA 48988; Metalaxyl
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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: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| 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 (~358.00 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.95 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 (8.95 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (8.95 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 | 3.5800 mL | 17.9000 mL | 35.7999 mL | |
| 5 mM | 0.7160 mL | 3.5800 mL | 7.1600 mL | |
| 10 mM | 0.3580 mL | 1.7900 mL | 3.5800 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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