| Definition | Glutathione, also known as 5-L-glutamyl-L-cysteinylglycine or reduced glutathione, is a member of the class of compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. Glutathione is practically insoluble (in water) and a moderately acidic compound (based on its pKa). Glutathione can be found in dill, which makes glutathione a potential biomarker for the consumption of this food product. Glutathione can be found primarily in most biofluids, including urine, cellular cytoplasm, blood, and cerebrospinal fluid (CSF), as well as throughout all human tissues. Glutathione exists in all living species, ranging from bacteria to humans. In humans, glutathione is involved in several metabolic pathways, some of which include mefenamic acid action pathway, salicylic acid action pathway, ketoprofen action pathway, and antipyrine action pathway. Glutathione is also involved in several metabolic disorders, some of which include hyperinsulinism-hyperammonemia syndrome, leukotriene C4 synthesis deficiency, 5-Oxoprolinuria, and gamma-glutamyl-transpeptidase deficiency. Moreover, glutathione is found to be associated with traumatic brain injury, canavan disease, schizophrenia, and multiple sclerosis. Glutathione is a non-carcinogenic (not listed by IARC) potentially toxic compound. Glutathione is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalanc. Glutathione (GSH) is an important antioxidant in plants, animals, fungi, and some bacteria and archaea. Glutathione is capable of preventing damage to important cellular components caused by reactive oxygen species such as free radicals, peroxides, lipid peroxides, and heavy metals. It is a tripeptide with a gamma peptide linkage between the carboxyl group of the glutamate side chain and the amine group of cysteine, and the carboxyl group of cysteine is attached by normal peptide linkage to a glycine . ORL-MUS LD50 5000 mg/kg, IPR-MUS LD50 4020 mg/kg, SCU-MUS LD50 5000 mg/kg, IVN-RBT LD50 > 2000 mg/kg, IMS-MUS LD50 4000 mg/kg (DrugBank). Glutathione (GSH) participates in leukotriene synthesis and is a cofactor for the enzyme glutathione peroxidase. It is also important as a hydrophilic molecule that is added to lipophilic toxins and waste in the liver during biotransformation before they can become part of the bile. Glutathione is also needed for the detoxification of methylglyoxal, a toxin produced as a by-product of metabolism. This detoxification reaction is carried out by the glyoxalase system. Glyoxalase I catalyzes the conversion of methylglyoxal and reduced glutathione to S-D-Lactoyl-glutathione. Glyoxalase II catalyzes the conversion of S-D-Lactoyl Glutathione to Reduced Glutathione and D-lactate. GSH is known as a cofactor in both conjugation reactions and reduction reactions, catalyzed by glutathione S-transferase enzymes in cytosol, microsomes, and mitochondria. However, it is capable of participating in non-enzymatic conjugation with some chemicals, as it is hypothesized to do to a significant extent with n-acetyl-p-benzoquinone imine (NAPQI), the reactive cytochrome P450 reactive metabolite formed by toxic overdose of acetaminophen. Glutathione in this capacity binds to NAPQI as a suicide substrate and in the process detoxifies it, taking the place of cellular protein sulfhydryl groups which would otherwise be toxically adducted. The preferred medical treatment to an overdose of this nature, whose efficacy has been consistently supported in literature, is the administration (usually in atomized form) of N-acetylcysteine, which is used by cells to replace spent GSSG and allow a usable GSH pool (T3DB). |
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| Structure | N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O)C(O)=O InChI=1S/C10H17N3O6S/c11-5(10(18)19)1-2-7(14)13-6(4-20)9(17)12-3-8(15)16/h5-6,20H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1 |
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| InChI Identifier | InChI=1S/C10H17N3O6S/c11-5(10(18)19)1-2-7(14)13-6(4-20)9(17)12-3-8(15)16/h5-6,20H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1 |
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