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| Targets |
Pyridine-3,5-dicarboxylic acid acts as a competitive inhibitor of butyrobetaine hydroxylase. Butyrobetaine hydroxylase is an enzyme involved in the biosynthesis of carnitine, a molecule essential for fatty acid transport into mitochondria. By inhibiting this enzyme, the compound can affect fatty acid metabolism and energy production. The pyridine dicarboxylic acid scaffold also enables metal chelation, which may contribute to its biological effects through modulation of metal-dependent enzymes. The compound's rigid structure and carboxylic acid groups facilitate interactions with enzyme active sites.
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| ln Vitro |
In vitro, pyridine-3,5-dicarboxylic acid exhibits competitive inhibition of butyrobetaine hydroxylase. This enzyme inhibition suggests potential applications in studying carnitine biosynthesis and fatty acid metabolism. The compound is also used as a building block for the synthesis of coordination compounds, pharmaceuticals, and agrochemicals. Its metal-chelating properties make it useful in the preparation of metal-organic frameworks (MOFs) and catalysts. In cell-based assays, the compound itself is not typically tested for pharmacological activity, but its metal complexes may be evaluated for biological properties.
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| ln Vivo |
Pyridine-3,5-dicarboxylic acid is not a pharmacologically active drug and does not exhibit in vivo therapeutic activity as a standalone compound. It has not been evaluated in animal models for efficacy against any disease. The compound is primarily used as a chemical intermediate and research reagent. Any in vivo activity would be associated with drug candidates or metal complexes synthesized from this intermediate, not with the compound itself. The compound is not administered to animals in standard pharmacological studies. Its role is strictly chemical—providing a versatile dicarboxylic acid scaffold.
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| Enzyme Assay |
In vitro enzyme inhibition assays for pyridine-3,5-dicarboxylic acid typically involve butyrobetaine hydroxylase inhibition studies. A standard protocol uses purified enzyme incubated with the substrate butyrobetaine and cofactors (α-ketoglutarate, Fe²⁺, ascorbate) in the presence of varying concentrations of the test compound. Product formation (carnitine) is measured by HPLC or radiometric methods. IC₅₀ values are calculated from dose-response curves. For metal chelation studies, the compound is titrated with metal ions (e.g., Cu²⁺, Zn²⁺, Fe³⁺) and complex formation is monitored by UV-Vis spectroscopy or potentiometry.
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| Cell Assay |
In vitro cell culture experiments with pyridine-3,5-dicarboxylic acid are not standard as the compound is primarily a chemical reagent. When the compound is used to synthesize drug candidates or metal complexes, those products may be tested in cell culture using standard protocols. Typically, compounds are dissolved in DMSO and diluted in culture medium to achieve desired concentrations (typically 0.1-100 µM). Cells are incubated for 24-72 hours, and effects on cell viability, proliferation, or specific signaling pathways are measured using appropriate assays. The intermediate itself is not evaluated in cellular systems.
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| Animal Protocol |
In vivo animal studies are not conducted with pyridine-3,5-dicarboxylic acid, as it is a research reagent for chemical synthesis. When the compound is used to synthesize drug candidates, those final products undergo standard preclinical evaluation. Typical protocols for drug candidates include pharmacokinetic studies in rodents (oral or intravenous administration, blood sampling for LC-MS/MS analysis), efficacy studies in disease models, and toxicology studies (acute and repeated-dose toxicity, histopathology). These studies evaluate the safety and efficacy of the final drug molecules, not the synthetic intermediate.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of pyridine-3,5-dicarboxylic acid are not characterized as it is not a drug substance. Based on its physicochemical properties (molecular weight 167.12, moderate water solubility, logP approximately -0.5), the compound would be expected to have low oral bioavailability due to its polar nature and poor membrane permeability. It would likely be distributed primarily in extracellular fluid and rapidly cleared via renal excretion. The compound may be metabolized via conjugation reactions. However, the compound is not intended for human exposure and has not been evaluated in formal pharmacokinetic studies.
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| Toxicity/Toxicokinetics |
Toxicological data for pyridine-3,5-dicarboxylic acid are limited as it is a research reagent. Standard laboratory safety precautions should be followed when handling this compound, including the use of gloves, safety glasses, and working in a fume hood. The compound may be a skin and eye irritant. No acute toxicity data are available. The compound is not intended for drug, household, or other uses. It should be stored in a cool, dry place away from moisture and strong oxidizing agents.
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| Additional Infomation |
Dinicotinic acid is a pyridine dicarboxylic acid. It is the conjugate acid of dinicotinic acid (1-).
Pyridine-3,5-dicarboxylic acid is a versatile building block in coordination chemistry and materials science for the synthesis of metal-organic frameworks (MOFs) and catalysts. It is also used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. The compound is a competitive inhibitor of butyrobetaine hydroxylase, making it useful for studying carnitine biosynthesis. It is also known as dinicotinic acid and 5-carboxynicotinic acid. The compound has not undergone clinical trials and is not approved as a pharmaceutical. Its mechanism of action is chemical—serving as a chelating agent and enzyme inhibitor. |
| Molecular Formula |
C7H5NO4
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|---|---|
| Molecular Weight |
167.12
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| Exact Mass |
167.021
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| CAS # |
499-81-0
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| PubChem CID |
10366
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| Appearance |
White to off-white solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
463.7±30.0 °C at 760 mmHg
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| Melting Point |
>300 °C(lit.)
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| Flash Point |
234.3±24.6 °C
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| Vapour Pressure |
0.0±1.2 mmHg at 25°C
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| Index of Refraction |
1.628
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| LogP |
-0.34
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
12
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| Complexity |
184
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| Defined Atom Stereocenter Count |
0
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| SMILES |
N1C=C(C(O)=O)C=C(C(O)=O)C=1
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| InChi Key |
MPFLRYZEEAQMLQ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H5NO4/c9-6(10)4-1-5(7(11)12)3-8-2-4/h1-3H,(H,9,10)(H,11,12)
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| Chemical Name |
pyridine-3,5-dicarboxylic 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 | 5.9837 mL | 29.9186 mL | 59.8372 mL | |
| 5 mM | 1.1967 mL | 5.9837 mL | 11.9674 mL | |
| 10 mM | 0.5984 mL | 2.9919 mL | 5.9837 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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