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MedKoo Cat#: 597013 | Name: Acetaminophen mercapturate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Paracetamol Mercapturate is a metabolite of Acetaminophen. 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.

Chemical Structure

Acetaminophen mercapturate
Acetaminophen mercapturate
CAS#52372-86-8

Theoretical Analysis

MedKoo Cat#: 597013

Name: Acetaminophen mercapturate

CAS#: 52372-86-8

Chemical Formula: C13H16N2O5S

Exact Mass: 312.0780

Molecular Weight: 312.34

Elemental Analysis: C, 49.99; H, 5.16; N, 8.97; O, 25.61; S, 10.26

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Acetaminophen mercapturate;
IUPAC/Chemical Name
S-(5-acetamido-2-hydroxyphenyl)-N-acetyl-L-cysteine
InChi Key
DVPRQNKJGQEICH-JTQLQIEISA-N
InChi Code
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
SMILES Code
O=C(O)[C@H](CSC1=CC(NC(C)=O)=CC=C1O)NC(C)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 312.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: van der Hooft JJJ, Wandy J, Young F, Padmanabhan S, Gerasimidis K, Burgess KEV, Barrett MP, Rogers S. Unsupervised Discovery and Comparison of Structural Families Across Multiple Samples in Untargeted Metabolomics. Anal Chem. 2017 Jul 18;89(14):7569-7577. doi: 10.1021/acs.analchem.7b01391. Epub 2017 Jul 5. PubMed PMID: 28621528; PubMed Central PMCID: PMC5524435. 2: Ganetsky M, Böhlke M, Pereira L, Williams D, LeDuc B, Guatam S, Salhanick SD. Effect of excipients on acetaminophen metabolism and its implications for prevention of liver injury. J Clin Pharmacol. 2013 Apr;53(4):413-20. doi: 10.1002/jcph.24. Epub 2013 Feb 22. PubMed PMID: 23436315; PubMed Central PMCID: PMC4383763. 3: Reith D, Medlicott NJ, Kumara De Silva R, Yang L, Hickling J, Zacharias M. Simultaneous modelling of the Michaelis-Menten kinetics of paracetamol sulphation and glucuronidation. Clin Exp Pharmacol Physiol. 2009 Jan;36(1):35-42. doi: 10.1111/j.1440-1681.2008.05029.x. Epub 2008 Aug 26. PubMed PMID: 18759860. 4: Koling S, Hempel G, Lanvers C, Boos J, Würthwein G. Monitoring paracetamol metabolism after single and repeated administration in pediatric patients with neoplastic diseases. Int J Clin Pharmacol Ther. 2007 Sep;45(9):496-503. PubMed PMID: 17907592. 5: Yim HK, Jung YS, Kim SY, Kim YC. Contrasting changes in phase I and phase II metabolism of acetaminophen in male mice pretreated with carbon tetrachloride. Basic Clin Pharmacol Toxicol. 2006 Feb;98(2):225-30. PubMed PMID: 16445600. 6: Slitt AM, Dominick PK, Roberts JC, Cohen SD. Effect of ribose cysteine pretreatment on hepatic and renal acetaminophen metabolite formation and glutathione depletion. Basic Clin Pharmacol Toxicol. 2005 Jun;96(6):487-94. PubMed PMID: 15910414. 7: Martin U, Temple RM, Winney RJ, Prescott LF. The disposition of paracetamol and its conjugates during multiple dosing in patients with end-stage renal failure maintained on haemodialysis. Eur J Clin Pharmacol. 1993;45(2):141-5. PubMed PMID: 8223835. 8: Hoffmann KJ, Baillie TA. The use of alkoxycarbonyl derivatives for the mass spectral analysis of drug-thioether metabolites. Studies with the cysteine, mercapturic acid and glutathione conjugates of acetaminophen. Biomed Environ Mass Spectrom. 1988 Jun 15;15(12):637-47. PubMed PMID: 3416089. 9: Jørgensen L, Thomsen P, Poulsen HE. Disulfiram prevents acetaminophen hepatotoxicity in rats. Pharmacol Toxicol. 1988 May;62(5):267-71. PubMed PMID: 3413028. 10: Vendemiale G, Altomare E, Trizio T, Leandro G, Manghisi OG, Albano O. Effect of acute and chronic cimetidine administration on acetaminophen metabolism in humans. Am J Gastroenterol. 1987 Oct;82(10):1031-4. PubMed PMID: 3661511. 11: Price VF, Miller MG, Jollow DJ. Mechanisms of fasting-induced potentiation of acetaminophen hepatotoxicity in the rat. Biochem Pharmacol. 1987 Feb 15;36(4):427-33. PubMed PMID: 3827934. 12: Miller MG, Jollow DJ. Acetaminophen hepatotoxicity: studies on the mechanism of cysteamine protection. Toxicol Appl Pharmacol. 1986 Mar 30;83(1):115-25. PubMed PMID: 3952741. 13: Miller MG, Price VF, Jollow DJ. Anomalous susceptibility of the fasted hamster to acetaminophen hepatotoxicity. Biochem Pharmacol. 1986 Mar 1;35(5):817-25. PubMed PMID: 3754139. 14: Galinsky RE, Corcoran GB. Influence of advanced age on the formation and elimination of acetaminophen metabolites by male rats. Pharmacology. 1986;32(6):313-20. PubMed PMID: 3755243. 15: Poulsen HE, Lerche A, Pedersen NT. Potentiated hepatotoxicity from concurrent administration of acetaminophen and allyl alcohol to rats. Biochem Pharmacol. 1985 Mar 15;34(6):727-31. PubMed PMID: 3977950. 16: Poulsen HE, Lerche A, Pedersen NT. Phenobarbital induction does not potentiate hepatotoxicity but accelerates liver cell necrosis from acetaminophen overdose in the rat. Pharmacology. 1985;30(2):100-8. PubMed PMID: 3975258. 17: Miller MG, Jollow DJ. Effect of L-ascorbic acid on acetaminophen-induced hepatotoxicity and covalent binding in hamsters. Evidence that in vitro covalent binding differs from that in vivo. Drug Metab Dispos. 1984 May-Jun;12(3):271-9. PubMed PMID: 6145552. 18: Price VF, Jollow DJ. Mechanism of ketone-induced protection from acetaminophen hepatotoxicity in the rat. Drug Metab Dispos. 1983 Sep-Oct;11(5):451-7. PubMed PMID: 6138230.