CAS 64889-81-2

3-(Glutathion-S-yl)acetaminophen

Description:

3-(Glutathion-S-yl)acetaminophen, also known as a conjugate of acetaminophen and glutathione, is a chemical compound that plays a significant role in the detoxification processes within biological systems. It is formed when acetaminophen, a widely used analgesic and antipyretic, undergoes conjugation with glutathione, a tripeptide that acts as an important antioxidant. This compound is characterized by its ability to mitigate the toxic effects of acetaminophen overdose, as it facilitates the excretion of harmful metabolites. The presence of the glutathione moiety enhances its solubility in water, promoting renal clearance. In terms of structure, it features a thiol group from glutathione, which is crucial for its reactivity and interaction with cellular components. The compound is typically studied in the context of pharmacology and toxicology, particularly regarding its role in protecting liver cells from oxidative stress and damage. Understanding its characteristics is essential for developing therapeutic strategies to counteract acetaminophen toxicity.

Formula: C₁₈H₂₄N₄O₈S

InChI: InChI=1S/C18H24N4O8S/c1-9(23)21-10-2-4-13(24)14(6-10)31-8-12(17(28)20-7-16(26)27)22-15(25)5-3-11(19)18(29)30/h2,4,6,11-12,24H,3,5,7-8,19H2,1H3,(H,20,28)(H,21,23)(H,22,25)(H,26,27)(H,29,30)/t11-,12-/m0/s1

InChI key: InChIKey=VFNAXGMNFCUWCI-RYUDHWBXSA-N

SMILES: S(C[C@H](NC(CC[C@@H](C(O)=O)N)=O)C(NCC(O)=O)=O)C1=CC(NC(C)=O)=CC=C1O

Synonyms:

• L-γ-Glutamyl-S-[5-(acetylamino)-2-hydroxyphenyl]-L-cysteinylglycine
• Glycine, N-[S-[5-(acetylamino)-2-hydroxyphenyl]-N-L-γ-glutamyl-L-cysteinyl]-
• 3-(Glutathion-S-yl)acetaminophen
• Glycine, L-γ-glutamyl-S-[5-(acetylamino)-2-hydroxyphenyl]-L-cysteinyl-
• Acetaminophen-glutathione adduct

Acetaminophen glutathione disodium salt

CAS: 64889-81-2

Molecular weight: 500.43

Ref: 7W-GM8542

Acetaminophen Impurity 3 Disodium Salt

CAS: 64889-81-2

Formula: C₁₈H₂₂N₄O₈S·2Na

Molecular weight: 454.46 2*22.99

Ref: 4Z-A-0226

Acetaminophen Glutathione-d3 Disodium Salt (~90%)

Controlled Product

CAS: 64889-81-2

Formula: C₁₈H₁₉D₃N₄Na₂O₈S

Purity: ~90%

Color and Shape: Off-White To Dark Brown

Molecular weight: 503.45

Ref: TR-A161226

Acetaminophen Glutathione Disodium Salt

CAS: 64889-81-2, 79032-41-0

Applications Acetaminophen Glutathione Disodium Salt is a metabolite of Acetaminophen (A161220), an analgesic and antipyretic agent used as a pain reliever to treat headache, muscle aches, and arthritis (1,2,3,4).
References (1) Chen, C., et al.: Xenobiotica, 30, 1019 (2000) (2) Ikeda, H., et al.: Biochem. J., 364, 563 (2002) (3) Aleksunes, L., et al.: Toxicol. Sci., 83, 44 (2005) (4) Elsby, R., et al.: J. Biol. Chem., 278, 22243 (2003)

Formula: C₁₈H₂₂N₄Na₂O₈S

Color and Shape: White To Brown

Molecular weight: 500.43

Ref: TR-A161223

Acetaminophen Glutathione-13C2,15N Disodium Salt

Controlled Product

CAS: 64889-81-2, 874462-73-4

Formula: C₂C₁₆H₂₂₁₅NN₃Na₂O₈S

Color and Shape: Neat

Molecular weight: 502.405

Ref: TR-A161224

Acetaminophen Glutathione

CAS: 64889-81-2

Formula: C₁₈H₂₄N₄O₈S

Color and Shape: Neat

Molecular weight: 456.47

Ref: TR-A298535

Acetaminophen glutathione disodium salt

CAS: 64889-81-2

Acetaminophen glutathione disodium salt is a prodrug of acetaminophen, which is a non-opioid analgesic and antipyretic drug. It has been shown to be protective against cisplatin-induced nephrotoxicity in cell culture and in CD-1 mice. Acetaminophen glutathione disodium salt inhibits mitochondrial enzyme activities, including dehydroascorbate reductase, which reduces the formation of reactive oxygen species. Acetaminophen glutathione disodium salt also blocks proximal tubule reabsorption and increases the excretion of drugs or their metabolites by increasing the second-order rate constant.

Formula: C₁₈H₂₂N₄Na₂O₈S

Purity: Min. 95%

Molecular weight: 500.43 g/mol

Ref: 3D-FA16945