CAS 52372-86-8

Acetaminophen mercapturate

Description:

Acetaminophen mercapturate, also known as N-acetyl-p-aminophenol mercapturate, is a metabolite of acetaminophen (paracetamol) formed through the conjugation of acetaminophen with glutathione. This compound is primarily associated with the detoxification process of acetaminophen in the liver, particularly in cases of overdose where the liver's capacity to process the drug is overwhelmed. The mercapturate pathway is a significant route for the elimination of toxic metabolites, helping to prevent cellular damage. Acetaminophen mercapturate is characterized by its thiol group, which contributes to its reactivity and solubility in water. It is typically analyzed in biological samples to assess acetaminophen exposure and potential toxicity. The compound is not commonly used therapeutically but serves as an important biomarker in toxicology studies. Its CAS number, 52372-86-8, is used for identification in chemical databases and regulatory contexts. Overall, acetaminophen mercapturate plays a crucial role in understanding the metabolism and safety profile of acetaminophen.

Formula: C₁₃H₁₆N₂O₅S

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: InChIKey=DVPRQNKJGQEICH-JTQLQIEISA-N

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

Synonyms:

• 3-[(5-Acetamido-2-hydroxyphenyl)thio]-N-acetylalanine
• <span class="text-smallcaps">L</span>-Cysteine, N-acetyl-S-[5-(acetylamino)-2-hydroxyphenyl]-
• Acetaminophen mercapturate
• N-Acetyl-2-(N-acetyl-<span class="text-smallcaps">L</span>-cysteinyl)-4-aminophenol
• N-Acetyl-S-[5-(acetylamino)-2-hydroxyphenyl]-<span class="text-smallcaps">L</span>-cysteine
• Paracetamol mercapturate
• Pcm-M
• l-Cysteine, N-acetyl-S-[5-(acetylamino)-2-hydroxyphenyl]-
• N-Acetyl-S-[5-(acetylamino)-2-hydroxyphenyl]-L-cysteine

Acetaminophen Mercapturate

CAS: 52372-86-8

Formula: C₁₃H₁₆N₂O₅S

Color and Shape: White To Off-White Solid

Molecular weight: 312.34

Ref: 4Z-A-025

3-(N-Acetyl-L-cystein-S-yl) acetaminophen sodium salt

CAS: 52372-86-8

Formula: C₁₃H₁₆N₂O₅S

Purity: ≥ 95.0%

Color and Shape: Off-white to grey solid

Molecular weight: 334.32

Ref: 7W-GM9067

Acetaminophen-d3 mercapturate

CAS: 52372-86-8

Formula: C₁₁H₁₁D₃N₂O₄S

Molecular weight: 273.33

Ref: 4Z-A-026

3-(N-Acetyl-L-cystein-S-yl) Acetaminophen

Controlled Product

CAS: 52372-86-8

Stability Very Hygroscopic
Applications Paracetamol Mercapturate is a metabolite of Acetaminophen (A161220) (1,2). Acetaminophen is a widely used analgesic and antipyretic drug. It can also be used in biological study of urinary antihypertensive drug metabolite screening using molecular networking coupled to high-resolution mass spectrometry fragmentation.
References (1) Trettin, A., et al.: J. Chromatogr. B., 963, 105 (2014) (2) Pickering, G., et al.: Clin. Pharmacol. Ther., 90, 707 (2011)

Formula: C₁₃H₁₆N₂O₅S

Color and Shape: Neat

Molecular weight: 312.34

Ref: TR-P191100

rac-Acetaminophen Mercapturate-d5 (Major)

Controlled Product

CAS: 52372-86-8

Applications rac-Acetaminophen Mercapturate-d5 (Major), is a labeled analogue and free acid of 3-(N-Acetyl-L-cystein-S-yl) Acetaminophen Disodium Salt (A172100), which is a metabolite of Acetaminophen (A161220). Acetaminophen is an analgesic and antipyretic agent used as a pain reliever to treat headache, muscle aches, and arthritis (1,2,3).
References van der Hooft, J.,et al.: Metabolomics, 12, 1 (2016)

Formula: C₁₃H₁₁D₅N₂O₅S

Color and Shape: Neat

Molecular weight: 317.37

Ref: TR-A172101

Acetaminophen mercapturate

CAS: 52372-86-8

Paracetamol Mercapturate is a metabolite of Acetaminophen. It can also be used in the biological study of urinary antihypertensive drugs.

Formula: C₁₃H₁₆N₂O₅S

Purity: 98%

Color and Shape: Solid

Molecular weight: 312.34

Ref: TM-T20215

3-(N-Acetyl-L-cystein-S-yl) Acetaminophen

Controlled Product

CAS: 52372-86-8

3-(N-Acetyl-L-cystein-S-yl) Acetaminophen is a metabolite of acetaminophen and has been shown to be associated with the development of hepatotoxicity. It is produced by CYP2E1 and can be detected in urine, serum, and plasma. 3-(N-Acetyl-L-cystein-S-yl) Acetaminophen may be used as a biomarker for liver injury caused by acetaminophen overdose. It has also been linked to an increased risk of cardiovascular events such as myocardial infarction and stroke. 3-(N-Acetyl-L-cystein-S-yl) Acetaminophen is not considered to be toxic or carcinogenic in humans.

Formula: C₁₃H₁₆N₂O₅S

Purity: Min. 95%

Molecular weight: 312.34 g/mol

Ref: 3D-CCA37286

Acetaminophen Mercapturate

CAS: 52372-86-8

Formula: C₁₃H₁₆N₂O₅S

Molecular weight: 312.34

Ref: ST-EA-CP-A7034