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| Other Sizes |
| Targets |
5-Hydroxypyrazine-2-Carboxylic Acid is a metabolite and does not have a direct pharmacological target. As a metabolite of pyrazinamide, it is used as a biomarker for pyrazinamide metabolism and elimination. The compound is formed through the oxidation of pyrazinoic acid, which is itself a metabolite of pyrazinamide. The compound is excreted in the urine and can be measured to assess drug exposure, metabolism, and patient compliance. While the compound itself does not exert significant pharmacological activity, its concentration in biological fluids reflects the activity of pyrazinamide-metabolizing enzymes and can be used to monitor treatment efficacy and toxicity.
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| ln Vitro |
In vitro, 5-Hydroxypyrazine-2-Carboxylic Acid is used as a standard in analytical chemistry for the quantification of pyrazinamide metabolites. It can be measured in cell culture media, tissue extracts, and biological fluids using HPLC, LC-MS, or other analytical techniques. The compound is not typically used for biological activity assays, as it is a metabolite rather than a pharmacologically active compound. However, it can be used to study the metabolism of pyrazinamide in cell culture models, where the conversion of pyrazinamide to 5-hydroxypyrazine-2-carboxylic acid can be monitored. The compound's stability in various conditions should be evaluated for each specific application.
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| ln Vivo |
In vivo, 5-Hydroxypyrazine-2-Carboxylic Acid is present in plasma and urine as a metabolite of pyrazinamide. Its concentration reflects pyrazinamide metabolism and can be used to monitor drug exposure, treatment compliance, and metabolic capacity. The compound is excreted in the urine and can be measured to assess the rate of pyrazinamide elimination. In patients with tuberculosis, the measurement of 5-hydroxypyrazine-2-carboxylic acid levels can provide valuable information for optimizing dosing regimens and predicting treatment outcomes. The compound's concentration may also be affected by genetic polymorphisms in metabolizing enzymes, drug interactions, and renal function.
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| Enzyme Assay |
For non-cellular assays, 5-Hydroxypyrazine-2-Carboxylic Acid is used as a standard for analytical method development and validation. It can be used in enzyme assays to measure the activity of enzymes involved in pyrazinamide metabolism, such as xanthine oxidase or aldehyde oxidase, which are responsible for the oxidation of pyrazinoic acid to 5-hydroxypyrazine-2-carboxylic acid. The compound's purity and identity can be confirmed using analytical techniques such as HPLC, NMR, and mass spectrometry. The compound can also be used as a reference standard in the development of quality control methods for pyrazinamide formulations.
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| Cell Assay |
For in vitro cell-based assays, 5-Hydroxypyrazine-2-Carboxylic Acid is not typically used as a test compound. However, it can be measured in cell culture media as a marker of pyrazinamide metabolism in hepatocyte or other cell culture models. The compound's stability in cell culture conditions should be evaluated for each specific application.
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| Animal Protocol |
For in vivo animal studies, 5-Hydroxypyrazine-2-Carboxylic Acid levels can be measured in plasma and urine to assess pyrazinamide metabolism. Animal models of tuberculosis or of pyrazinamide pharmacokinetics can be used to study the formation and elimination of the metabolite. The effects of various factors, such as drug interactions, genetic polymorphisms, and disease states, on pyrazinamide metabolism can be assessed by measuring 5-hydroxypyrazine-2-carboxylic acid levels.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of 5-Hydroxypyrazine-2-Carboxylic Acid include a molecular weight of 140.1 and a molecular formula of C₅H₄N₂O₃. The compound is an off-white to light brown solid powder with a melting point of >295°C (dec.). It has a LogP of -1.71, indicating high hydrophilicity. The compound is soluble in DMSO at ~50 mg/mL (~356.89 mM) and in water at ~4 mg/mL (~28.55 mM). For in vivo administration, the compound can be formulated in 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% saline at ≥2.5 mg/mL. The powder should be stored at -20°C for 3 years and at 4°C for 2 years; in solvent, it is stable at -80°C for 6 months and at -20°C for 1 month. The compound is stable at ambient temperature for a few days during shipping.
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| Toxicity/Toxicokinetics |
As a metabolite of pyrazinamide, 5-Hydroxypyrazine-2-Carboxylic Acid is generally considered safe at the concentrations typically encountered during pyrazinamide therapy. However, the compound's own toxicological profile has not been extensively studied. In high concentrations, the compound may contribute to the side effects of pyrazinamide, particularly hepatotoxicity and hyperuricemia. The compound is intended for research use only and is not for human use.
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| References |
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| Additional Infomation |
5-Hydroxypyrazine-2-Carboxylic Acid is a metabolite of the anti-tuberculosis drug pyrazinamide (PZA). It is formed by the oxidation of pyrazinoic acid and is excreted in the urine. The compound serves as a valuable biomarker for monitoring pyrazinamide metabolism and patient compliance in tuberculosis treatment. It is used as a standard in analytical chemistry for the quantification of pyrazinamide metabolites. The compound is also known as 6-oxo-1H-pyrazine-3-carboxylic acid. It is not currently approved for clinical use and is available only for research purposes.
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| Molecular Formula |
C5H4N2O3
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|---|---|
| Molecular Weight |
140.0969
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| Exact Mass |
140.022
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| CAS # |
34604-60-9
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| PubChem CID |
161825
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| Appearance |
Off-white to light brown solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
608.5ºC at 760 mmHg
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| Melting Point |
>295°C (dec.)
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| Flash Point |
321.8ºC
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| Index of Refraction |
1.662
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| LogP |
-1.71
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
10
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| Complexity |
241
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
CGQFCIHUUCMACC-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C5H4N2O3/c8-4-2-6-3(1-7-4)5(9)10/h1-2H,(H,7,8)(H,9,10)
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| Chemical Name |
6-oxo-1H-pyrazine-3-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) |
DMSO : ~50 mg/mL (~356.89 mM)
H2O : ~4 mg/mL (~28.55 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (17.84 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 (17.84 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 (17.84 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 | 7.1378 mL | 35.6888 mL | 71.3776 mL | |
| 5 mM | 1.4276 mL | 7.1378 mL | 14.2755 mL | |
| 10 mM | 0.7138 mL | 3.5689 mL | 7.1378 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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