Acetaminophen mercapturate
Catalog Number: BT-257089
CAS Number: 52372-86-8
Molecular Formula: C13H16N2O5S
Molecular Weight: 312.34 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
Product Introduction
Description
Acetaminophen mercapturate is a metabolite of acetaminophen, a widely used analgesic and antipyretic drug. It is formed in the liver by the conjugation of acetaminophen with glutathione, a tripeptide composed of cysteine, glycine, and glutamate. Acetaminophen mercapturate has been the subject of extensive research due to its potential therapeutic and toxic effects, as well as its role in drug development, environmental pollution, and industrial processes.
Properties
CAS Number
52372-86-8
Product Name
Acetaminophen mercapturate
IUPAC Name
(2R)-2-acetamido-3-(5-acetamido-2-hydroxyphenyl)sulfanylpropanoic acid
Molecular Formula
C13H16N2O5S
Molecular Weight
312.34 g/mol
InChI
InChI=1S/C13H16N2O5S/c1-7(16)14-9-3-4-11(18)12(5-9)21-6-10(13(19)20)15-8(2)17/h3-5,10,18H,6H2,1-2H3,(H,14,16)(H,15,17)(H,19,20)/t10-/m0/s1
InChI Key
DVPRQNKJGQEICH-JTQLQIEISA-N
SMILES
CC(=O)NC1=CC(=C(C=C1)O)SCC(C(=O)O)NC(=O)C
Solubility
Soluble in DMSO
Synonyms
acetaminophen mercapturate
acetaminophen mercapturate monopotassium salt
paracetamol mercapturate
acetaminophen mercapturate monopotassium salt
paracetamol mercapturate
Canonical SMILES
CC(=O)NC1=CC(=C(C=C1)O)SCC(C(=O)O)NC(=O)C
Isomeric SMILES
CC(=O)NC1=CC(=C(C=C1)O)SC[C@@H](C(=O)O)NC(=O)C
Method of Synthesis or Extraction
The synthesis of acetaminophen mercapturate involves the reaction of acetaminophen with glutathione in the presence of glutathione S-transferase, an enzyme that catalyzes the conjugation reaction. The efficiency and yield of this method depend on various factors, such as the concentration of reactants, pH, temperature, and enzyme activity. Alternative methods, such as chemical synthesis and biosynthesis using microbial or plant sources, have also been explored. However, these methods have lower yields and require more complex purification steps. Environmental and safety considerations of acetaminophen mercapturate synthesis include the use of hazardous chemicals, waste disposal, and potential exposure to toxic intermediates.
Chemical Structure and Biological Activity
Acetaminophen mercapturate has a molecular weight of 338.4 g/mol and a chemical formula of C14H19N3O8S. It is a conjugate of acetaminophen and glutathione, with a thiol group (-SH) attached to the phenolic ring of acetaminophen. The mechanism of action of acetaminophen mercapturate involves the detoxification of acetaminophen by binding to reactive metabolites and preventing their interaction with cellular macromolecules. Acetaminophen mercapturate has been shown to have antioxidant and anti-inflammatory properties, as well as modulating the immune response and cell proliferation.
Biological Effects
Acetaminophen mercapturate affects various cellular functions and signal transduction pathways. It has been shown to inhibit the activity of cyclooxygenase enzymes, which are involved in the synthesis of prostaglandins and other inflammatory mediators. Acetaminophen mercapturate also modulates the expression of genes involved in oxidative stress, apoptosis, and cell cycle regulation. The potential therapeutic effects of acetaminophen mercapturate include the prevention and treatment of acetaminophen-induced liver injury, inflammation, and cancer. However, high doses or prolonged exposure to acetaminophen mercapturate may lead to adverse effects, such as nephrotoxicity, immunosuppression, and carcinogenesis.
Applications
Acetaminophen mercapturate has various applications in medical, environmental, and industrial research. In medical research, acetaminophen mercapturate plays a crucial role in drug development, as it is a major metabolite of acetaminophen and a biomarker of its toxicity. Clinical trials have shown that acetaminophen mercapturate levels can predict the risk of liver injury and other adverse effects of acetaminophen. In environmental research, acetaminophen mercapturate is used as an indicator of environmental pollution, as it is excreted in urine and can be detected in wastewater and soil samples. Acetaminophen mercapturate also has potential applications in pollution management and sustainability, as it can be used as a bioremediation agent for the degradation of organic pollutants. In industrial research, acetaminophen mercapturate is used in manufacturing processes, such as the production of glutathione and other thiol-containing compounds. Acetaminophen mercapturate also has implications for improving product quality and efficiency, as it can be used as a marker of product purity and stability. Health and safety considerations of acetaminophen mercapturate in industrial settings include the risk of exposure to toxic intermediates and the need for proper waste disposal.
Future Perspectives and Challenges
Despite the significant progress in the study of acetaminophen mercapturate, there are still several limitations and challenges that need to be addressed. One of the main challenges is the lack of standardized methods for the measurement of acetaminophen mercapturate levels in biological and environmental samples. This hinders the comparison of results across studies and the establishment of reference values. Another challenge is the need for more comprehensive studies on the long-term effects of acetaminophen mercapturate on human health and the environment. This requires the integration of various disciplines, such as toxicology, pharmacology, and environmental science. Future trends and prospects in the application of acetaminophen mercapturate in scientific research include the development of new analytical methods, the identification of novel therapeutic targets, and the exploration of its potential in personalized medicine and precision agriculture.
Conclusion:
Acetaminophen mercapturate is a metabolite of acetaminophen that has significant implications for human health, environmental pollution, and industrial processes. Its chemical structure, biological activity, and applications have been extensively studied, but there are still several challenges and limitations that need to be addressed. The future of acetaminophen mercapturate research lies in the integration of various disciplines and the development of innovative approaches to its measurement, characterization, and application.
Conclusion:
Acetaminophen mercapturate is a metabolite of acetaminophen that has significant implications for human health, environmental pollution, and industrial processes. Its chemical structure, biological activity, and applications have been extensively studied, but there are still several challenges and limitations that need to be addressed. The future of acetaminophen mercapturate research lies in the integration of various disciplines and the development of innovative approaches to its measurement, characterization, and application.
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