| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
2-Amino-5-methylpyrazine targets DprE1 (decaprenylphosphoryl-β-D-ribose 2'-epimerase), a key enzyme involved in the biosynthesis of the mycobacterial cell wall. DprE1 is an essential enzyme for the survival of Mycobacterium tuberculosis and is a validated target for antitubercular drug discovery. By inhibiting DprE1, compounds derived from 2-amino-5-methylpyrazine disrupt cell wall synthesis, leading to bacterial death. The compound's pyrazine ring and amino group enable interactions with the DprE1 active site through hydrogen bonding and hydrophobic contacts. DprE1 inhibitors are being developed as novel therapies for tuberculosis, including drug-resistant strains.
|
|---|---|
| ln Vitro |
In vitro studies have demonstrated that 2-amino-5-methylpyrazine derivatives exhibit potent antimycobacterial activities as DprE1 inhibitors. The compound's derivatives show activity against Mycobacterium tuberculosis, including drug-sensitive and drug-resistant strains. In cell-based assays using mycobacterial cultures, these compounds inhibit bacterial growth with minimum inhibitory concentrations (MICs) in the low micromolar range. The compound's pyrazine core is a privileged scaffold for antitubercular drug discovery. Structure-activity relationship studies have identified key functional groups that enhance potency against DprE1.
|
| ln Vivo |
In vivo activity data for 2-amino-5-methylpyrazine derivatives has been generated in animal models of tuberculosis. DprE1 inhibitors containing the pyrazine scaffold have shown efficacy in mouse models of TB infection, reducing bacterial burden in lungs and spleen. The compound's derivatives are being evaluated for their potential as novel antitubercular agents, particularly for the treatment of drug-resistant TB. However, comprehensive in vivo studies for the parent compound itself are limited, as the compound is primarily used as a building block for more advanced derivatives.
|
| Enzyme Assay |
Cell-free biochemical assays for 2-amino-5-methylpyrazine derivatives typically measure inhibition of DprE1 enzyme activity. A standard protocol involves incubating recombinant DprE1 with varying concentrations of the test compound (0.001-100 μM), the substrate decaprenylphosphoryl-ribose (DPR), and appropriate cofactors in assay buffer at 37°C. Enzyme activity is measured by detecting the conversion of substrate to product using HPLC or radiometric methods. IC₅₀ values are determined from dose-response curves using nonlinear regression analysis. Assays are performed in triplicate with appropriate positive and negative controls.
|
| Cell Assay |
Cellular assays for 2-amino-5-methylpyrazine derivatives typically use mycobacterial cultures to assess antibacterial activity. A standard protocol involves culturing Mycobacterium tuberculosis H37Rv or clinical isolates in Middlebrook 7H9 broth or on 7H10 agar plates, treating with varying concentrations of the test compound (0.01-100 μg/mL) for 7-14 days, and measuring growth inhibition by resazurin reduction assay, colony counting, or optical density. MIC values are determined as the lowest concentration that inhibits visible growth. Cytotoxicity is assessed in mammalian cell lines to evaluate selectivity.
|
| Animal Protocol |
In vivo studies for 2-amino-5-methylpyrazine derivatives are typically conducted in mouse models of tuberculosis. A standard protocol involves infecting immunocompetent mice (e.g., BALB/c or C3HeB/FeJ) with Mycobacterium tuberculosis via aerosol or intravenous injection. After infection establishment (typically 2-4 weeks), mice are treated with the test compound administered orally or intraperitoneally at doses of 10-100 mg/kg daily for 4-8 weeks. Bacterial burden in lungs and spleen is assessed by colony counting at study termination. Body weight and survival are monitored for toxicity assessment.
|
| ADME/Pharmacokinetics |
Pharmacokinetic data for 2-amino-5-methylpyrazine derivatives is being generated as part of antitubercular drug development programs. The compound's molecular weight is 109.13 g/mol, suggesting good oral bioavailability potential. For derivatives, PK parameters including oral bioavailability, half-life, and clearance are determined in preclinical species. The pyrazine core generally confers favorable physicochemical properties for drug development, including moderate polarity and potential for blood-brain barrier penetration.
|
| Toxicity/Toxicokinetics |
Toxicological data specific to 2-amino-5-methylpyrazine is limited, as the compound is primarily a research chemical. For derivatives being developed as antitubercular agents, comprehensive toxicological evaluation is conducted as part of preclinical development, including acute and repeat-dose toxicity studies in rodents and non-rodents, genotoxicity assays, and safety pharmacology assessments. The compound's safety profile in the context of DprE1 inhibition is being established through ongoing research. Standard laboratory safety precautions should be observed when handling this compound.
|
| Additional Infomation |
2-Amino-5-methylpyrazine is a research compound that serves as a key building block for the synthesis of DprE1 inhibitors with potent antimycobacterial activities. DprE1 is a validated target for tuberculosis drug discovery, and inhibitors of this enzyme are being developed as novel therapies for TB, including drug-resistant strains. The compound is commercially available from various suppliers for research purposes only. No clinical trials or regulatory approvals exist for the parent compound itself. Its primary value lies in its utility as a scaffold for antitubercular drug discovery and as a biochemical reagent for biomedical research.
|
| Molecular Formula |
C5H7N3
|
|---|---|
| Molecular Weight |
109.13
|
| Exact Mass |
109.063
|
| CAS # |
5521-58-4
|
| PubChem CID |
313215
|
| Appearance |
Light brown to yellow solid powder
|
| Density |
1.2±0.1 g/cm3
|
| Boiling Point |
244.3±35.0 °C at 760 mmHg
|
| Melting Point |
117 °C
|
| Flash Point |
124.8±13.1 °C
|
| Vapour Pressure |
0.0±0.5 mmHg at 25°C
|
| Index of Refraction |
1.582
|
| LogP |
0.61
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
0
|
| Heavy Atom Count |
8
|
| Complexity |
74.1
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
CC1=CN=C(C=N1)N
|
| InChi Key |
ZNQOALAKPLGUPH-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C5H7N3/c1-4-2-8-5(6)3-7-4/h2-3H,1H3,(H2,6,8)
|
| Chemical Name |
5-methylpyrazin-2-amine
|
| 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 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)
|
| 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
|
|---|---|
| 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 | 9.1634 mL | 45.8169 mL | 91.6338 mL | |
| 5 mM | 1.8327 mL | 9.1634 mL | 18.3268 mL | |
| 10 mM | 0.9163 mL | 4.5817 mL | 9.1634 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
