| Size | Price | Stock | Qty |
|---|---|---|---|
| 250g |
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| Other Sizes |
| Targets |
2-Pyrazinecarboxylic acid targets urate retention pathways in the kidney, making it a very potent urate-retaining drug. As the active metabolite of pyrazinamide, it also targets the mycobacterial enzyme responsible for pyrazinamide's antibacterial activity. The compound's mechanism involves inhibition of urate excretion in the kidney, leading to increased serum urate levels. In the context of tuberculosis treatment, pyrazinoic acid (the active form) disrupts mycobacterial membrane energetics and inhibits fatty acid synthesis. The compound's nitrogen-containing heterocyclic structure enables interactions with various biological targets through hydrogen bonding and π-stacking.
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|---|---|
| ln Vitro |
Pyrazinecarboxylic acid is pyrazinamide's active metabolite. An agent that fights tuberculosis is pyrazinamide. Probenecid decreased the urine excretion of pyrazinecarboxylic acid in this model used to evaluate the effects of uricosuric medications, suggesting an inverse link between urate and pyrazinecarboxylic acid excretion. In vitro experiments have shown that pyrazinecarboxylic acid stimulation of vesicles in the rat kidney's brush border membrane promotes urate absorption, which is prevented by uricosuric medications. Plant cells use PZA (pyrazinamide) to convert it to POA (pyrazinecarboxylic acid), which inhibits the action of 1-aminocyclopropane-1-carboxylic acid oxidase (ACO), the enzyme that catalyzes the last step in the production of ethylene.
In vitro studies have demonstrated that 2-pyrazinecarboxylic acid exhibits potent urate-retaining activity, making it a valuable tool for studying urate homeostasis. The compound also shows antimicrobial activity as the active metabolite of pyrazinamide. In cell-based assays, pyrazinoic acid inhibits mycobacterial growth through disruption of membrane energetics. The compound has been studied for its potential antimicrobial and anti-inflammatory properties. Its activity is dependent on the conversion of pyrazinamide to pyrazinoic acid by the bacterial enzyme pyrazinamidase. |
| ln Vivo |
In vivo studies have established 2-pyrazinecarboxylic acid as the active metabolite responsible for the antibacterial activity of pyrazinamide. Following administration of pyrazinamide, the compound is converted to pyrazinoic acid in vivo, which then exerts its antibacterial effects. The compound's urate-retaining activity has been characterized in animal models and humans, where it effectively reduces urate excretion. Its role as a metabolite of an approved antibacterial agent makes it an important compound for understanding drug metabolism and mechanism of action.
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| Enzyme Assay |
Cell-free biochemical assays for 2-pyrazinecarboxylic acid typically measure inhibition of target enzymes or binding to relevant proteins. For studying its role as a pyrazinamide metabolite, assays may involve measuring conversion of pyrazinamide to pyrazinoic acid by pyrazinamidase using HPLC or spectrophotometric methods. For urate retention studies, the compound's effects on urate transporters can be assessed using membrane preparations. IC₅₀ or Ki values are determined from dose-response curves using nonlinear regression analysis. The compound's purity (typically ≥99%) is verified by HPLC. Assays are performed in triplicate with appropriate positive and negative controls.
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| Cell Assay |
Cellular assays for 2-pyrazinecarboxylic acid typically use mycobacterial cultures to assess antibacterial activity or kidney cell lines to study urate transport. A standard protocol for antibacterial testing involves culturing Mycobacterium tuberculosis or other mycobacterial species in appropriate media, treating with varying concentrations of the compound (1-100 μg/mL) for 7-14 days, and measuring growth inhibition by colony counting or optical density. For urate transport studies, kidney epithelial cells are treated with the compound and urate uptake or efflux is measured using radiolabeled urate. Cell viability is assessed to confirm that observed effects are not due to cytotoxicity.
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| Animal Protocol |
In vivo studies for 2-pyrazinecarboxylic acid are typically conducted in mouse models of tuberculosis or in rodent models of urate metabolism. For antibacterial studies, mice are infected with Mycobacterium tuberculosis and treated with pyrazinamide (which is converted to the active acid in vivo) at doses of 100-300 mg/kg daily for several weeks. Bacterial burden in lungs and spleen is assessed by colony counting. For urate retention studies, rodents are administered the compound and serum urate levels are measured over time. Pharmacodynamic effects are assessed through appropriate biomarkers.
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| ADME/Pharmacokinetics |
Pharmacokinetic studies of 2-pyrazinecarboxylic acid have been conducted as part of pyrazinamide research. Following administration of pyrazinamide, pyrazinoic acid is produced and exhibits a half-life that allows for once-daily dosing in tuberculosis treatment. The compound's molecular weight is 124.10 g/mol, and it is water-soluble, which facilitates absorption and distribution. The compound is primarily excreted renally. Its role as an active metabolite means its PK profile is closely linked to that of the parent drug pyrazinamide.
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| Toxicity/Toxicokinetics |
Toxicological data for 2-pyrazinecarboxylic acid is available from pyrazinamide studies, where it is the active metabolite. The compound's safety profile has been established through clinical use of pyrazinamide. Common adverse effects associated with pyrazinamide therapy include hepatotoxicity, hyperuricemia (due to the urate-retaining activity of pyrazinoic acid), and gastrointestinal disturbances. The urate-retaining effect can lead to gout in susceptible individuals. The compound should be used with caution in patients with hepatic impairment or pre-existing gout. Comprehensive toxicology assessments have been conducted to support clinical use.
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| Additional Infomation |
Pyrazine-2-carboxylic acid is the parent compound of the pyrazine carboxylic acid class of compounds, i.e., a pyrazine with a single carboxyl substituent. It is the active metabolite of the anti-tuberculosis drug pyrazinamide. It is both a drug metabolite and an anti-tuberculosis agent. It is the conjugate acid of pyrazine-2-carboxylic acid salt. Pyrazine acid is present in or produced by Escherichia coli (K12 strain, MG1655 strain). Pyrazine-2-carboxylic acid has also been reported to exist in Trypanosoma brevicornu, and relevant data are available.
2-Pyrazinecarboxylic acid is a pharmacologically active compound as the metabolite of the antibacterial agent pyrazinamide (P840600). Pyrazinamide is approved for the treatment of tuberculosis and is a critical component of first-line anti-TB therapy. The conversion of pyrazinamide to pyrazinoic acid by mycobacterial pyrazinamidase is essential for its antibacterial activity. The compound's urate-retaining properties are responsible for the hyperuricemia observed as a side effect of pyrazinamide therapy. 2-Pyrazinecarboxylic acid is also studied for its potential antimicrobial and anti-inflammatory properties. It is commercially available for research purposes. |
| Molecular Formula |
C5H4N2O2
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|---|---|
| Molecular Weight |
124.10
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| Exact Mass |
124.027
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| CAS # |
98-97-5
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| Related CAS # |
Pyrazinecarboxylic acid-d3;1794791-32-4
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| PubChem CID |
1047
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
313.1±22.0 °C at 760 mmHg
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| Melting Point |
222-225 °C (dec.)(lit.)
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| Flash Point |
143.1±22.3 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.579
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| LogP |
-1.36
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
9
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| Complexity |
116
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O([H])C(C1C([H])=NC([H])=C([H])N=1)=O
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| InChi Key |
NIPZZXUFJPQHNH-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C5H4N2O2/c8-5(9)4-3-6-1-2-7-4/h1-3H,(H,8,9)
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| Chemical Name |
pyrazine-2-carboxylic acid
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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 | 8.0580 mL | 40.2901 mL | 80.5802 mL | |
| 5 mM | 1.6116 mL | 8.0580 mL | 16.1160 mL | |
| 10 mM | 0.8058 mL | 4.0290 mL | 8.0580 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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