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| Other Sizes |
| Targets |
Isonicotinic acid targets dihydropteroate synthetase and dihydropteroate reductase in the bacterial folate synthesis pathway, competing with 4-aminobenzoic acid (PABA) for binding. As a metabolite of the anti-tuberculosis drug Isoniazid, it shares structural similarity with nicotinic acid and may interact with nicotinic acid receptors or enzymes involved in nicotinate metabolism. Isonicotinic acid has a role as a human metabolite and an algal metabolite. In bacterial systems, isonicotinic acid and its derivatives can inhibit the enzymatic conversion of pteridine and PABA to dihydropteroic acid by competing with PABA for binding to dihydrofolate synthetase, an intermediate of tetrahydrofolic acid (THF) synthesis. This mechanism underlies the antibacterial activity of sulfonamide drugs.
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| ln Vitro |
In vitro, Isonicotinic acid is primarily studied as a metabolite of Isoniazid and as a chemical building block rather than as a therapeutic agent. It is a pyridinemonocarboxylic acid with the carboxy group at position 4 of the pyridine ring. The compound exhibits mild acidity and participates in coordination chemistry, making it valuable in drug design and materials science. Isonicotinic acid has been reported to have a role as a human metabolite and an algal metabolite. Its in vitro activity is primarily related to its chemical properties rather than specific pharmacological effects. The compound is used as a precursor in the synthesis of various pharmaceuticals and coordination compounds.
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| ln Vivo |
In vivo, Isonicotinic acid is a metabolite of Isoniazid, a first-line anti-tuberculosis drug. Isoniazid is converted to Isonicotinic acid by hydrazinolysis, and the bioconversion can also be catalyzed by cytochrome P450 (CYP) enzymes such as CYP2C. As a metabolite, Isonicotinic acid is excreted in urine. It has been reported in various organisms including Aloe africana, Arabidopsis thaliana, and other organisms. The compound's presence in biological systems reflects its role in nicotinate and nicotinamide metabolism. It is not used therapeutically as a drug but serves as a metabolite marker for Isoniazid metabolism and as a chemical intermediate in pharmaceutical synthesis.
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| Enzyme Assay |
In vitro enzyme/receptor binding (non-cellular) assays for Isonicotinic acid are not standard pharmacological assays, as the compound is a metabolite and chemical building block rather than a therapeutic agent. However, binding studies may be performed to investigate its interaction with nicotinic acid receptors or enzymes involved in nicotinate metabolism. Enzyme activity assays may be conducted using purified enzymes such as nicotinate phosphoribosyltransferase or other enzymes in the NAD⁺ biosynthesis pathway. Additionally, Isonicotinic acid's ability to act as a chelating agent in coordination chemistry can be studied using spectrophotometric or potentiometric methods. These assays help characterize the compound's chemical properties and potential biological interactions.
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| Cell Assay |
In vitro cellular experiments with Isonicotinic acid are not typically performed for pharmacological evaluation, as the compound is a metabolite and chemical building block. However, cellular assays may be conducted to study its effects on nicotinate metabolism or to assess its cytotoxicity. Cell lines such as HepG2 (hepatocellular carcinoma) or Caco-2 (colorectal adenocarcinoma) are cultured in appropriate media and treated with varying concentrations of the compound. Cell viability is assessed using MTT or CellTiter-Glo assays. The compound's effects on NAD⁺ levels or other metabolic parameters may be measured using biochemical assays. Isonicotinic acid's role as a human metabolite makes it relevant to studies of nicotinate and nicotinamide metabolism.
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| Animal Protocol |
In vivo animal studies with Isonicotinic acid are not typically performed for therapeutic development, as the compound is a metabolite rather than a drug candidate. However, pharmacokinetic studies of Isoniazid metabolism in animals may detect Isonicotinic acid as a metabolite. Rodents are administered Isoniazid via oral or intravenous administration, and blood, urine, and tissue samples are collected at specific time points. Metabolites including Isonicotinic acid are identified and quantified using LC-MS or HPLC methods. These studies help establish the metabolic pathway and elimination profile of Isoniazid. Isonicotinic acid is excreted in urine and serves as a marker of Isoniazid metabolism.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of Isonicotinic acid are derived from its role as a metabolite of Isoniazid. The compound has molecular formula C₆H₅NO₂ and molecular weight 123.11. It appears as an off-white to beige-yellow powder and is very soluble in water. Isonicotinic acid is formed by the metabolism of Isoniazid and is excreted in urine. Its small molecular weight and high water solubility facilitate rapid renal clearance. Storage recommendations: powder at -20°C for 3 years or 4°C for 2 years; in solvent at -80°C for 6 months or -20°C for 1 month. The compound is soluble in DMSO at approximately 25 mg/mL. Detailed pharmacokinetic parameters are primarily relevant to Isoniazid metabolism studies.
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| Toxicity/Toxicokinetics |
Toxicological information for Isonicotinic acid indicates that the compound is generally considered to have low toxicity. It is a naturally occurring metabolite found in various organisms including Aloe africana and Arabidopsis thaliana. The compound appears as an off-white to beige-yellow powder and has a melting point of ≥300°C. Standard safety precautions for handling research chemicals apply, including use of personal protective equipment (gloves, safety goggles, lab coat) and working in a well-ventilated area. The compound should be stored in a cool, dark place at room temperature. Isonicotinic acid is for research use only and is not approved for clinical use.
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| References | |
| Additional Infomation |
Isonicotinic acid is a pyridine monocarboxylic acid with its carboxyl group located at position 4 of the pyridine ring. It is a metabolite in both humans and algae. It is the conjugate acid of isonicotinic acid esters. Isonicotinic acid has been reported to be found in African aloe vera, Arabidopsis thaliana, and other organisms with relevant data. Derivatives of 4-pyridinecarboxylic acid (isonicotinic acid) are heterocyclic acids.
Isonicotinic acid (CAS 55-22-1) is a pyridinemonocarboxylic acid with the carboxy group at position 4 of the pyridine ring. It has molecular formula C₆H₅NO₂ and molecular weight 123.11. Isonicotinic acid is a metabolite of the anti-tuberculosis drug Isoniazid, formed by hydrazinolysis or cytochrome P450 (CYP2C)-catalyzed bioconversion. It appears as an off-white to beige-yellow powder and is very soluble in water. The compound has a role as a human metabolite and an algal metabolite. It is an isomer of nicotinic acid and has been reported in various organisms including Aloe africana and Arabidopsis thaliana. Storage: powder at -20°C for 3 years or 4°C for 2 years; in solvent at -80°C for 6 months or -20°C for 1 month. |
| Molecular Formula |
C6H5NO2
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|---|---|
| Molecular Weight |
123.1094
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| Exact Mass |
123.032
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| CAS # |
55-22-1
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| Related CAS # |
Isonicotinic acid-d4;53907-55-4
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| PubChem CID |
5922
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
396.0±15.0 °C at 760 mmHg
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| Melting Point |
≥300 °C(lit.)
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| Flash Point |
193.3±20.4 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.571
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| LogP |
0.54
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
9
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| Complexity |
108
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
TWBYWOBDOCUKOW-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H5NO2/c8-6(9)5-1-3-7-4-2-5/h1-4H,(H,8,9)
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| Chemical Name |
pyridine-4-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 : ~25 mg/mL (~203.07 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (20.31 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 (20.31 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 (20.31 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 | 8.1228 mL | 40.6141 mL | 81.2282 mL | |
| 5 mM | 1.6246 mL | 8.1228 mL | 16.2456 mL | |
| 10 mM | 0.8123 mL | 4.0614 mL | 8.1228 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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