An acetaminophen-protein adduct
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Biochemicals
Amino Acids
Conjugates

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Neuroscience
Pain Research

3-Cysteinylacetaminophen (trifluoroacetate salt)

Item No. 26388

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
S-[5-(acetylamino)-2-hydroxyphenyl]-L-cysteine, trifluoroacetate salt
CAS Number
1331891-93-0
Synonyms
  • 3-(cysteine-S-yl)acetaminophen
  • APAP-Cys
Molecular Formula
C11H14N2O4S • CF3COOH
Formula Weight
384.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 0.17 mg/ml
λmax
214, 248, 302 nm
SMILES
OC1=C(SC[C@H](N)C(O)=O)C=C(NC(C)=O)C=C1.OC(C(F)(F)F)=O
InChi Code
InChI=1S/C11H14N2O4S.C2HF3O2/c1-6(14)13-7-2-3-9(15)10(4-7)18-5-8(12)11(16)17;3-2(4,5)1(6)7/h2-4,8,15H,5,12H2,1H3,(H,13,14)(H,16,17);(H,6,7)/t8-;/m0./s1
InChi Key
PDZGEXMJHANKLR-QRPNPIFTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    3-Cysteinylacetaminophen is an acetaminophen-protein adduct formed during the metabolism of acetaminophen (Item No. 10024).1,2 3-Cysteinylacetaminophen has been found in isolated human serum following therapeutic and supratherapeutic doses of acetaminophen and in the presence and absence of hepatotoxicity.3,4 In mice, 3-cysteinylacetaminophen decreases renal glutathione (GSH) levels, an effect that can be blocked by the γ-glutamyl inhibitor acivicin (Item No. 14003).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yoon, E., Babar, A., Choudhary, M., et al. Acetaminophen-induced hepatotoxicity: A comprehensive update. J. Clin. Transl. Hepatol. 4(2), 131-142 (2016).

    2. Stern, S.T., Bruno, M.K., Horton, R.A., et al. Contribution of acetaminophen-cysteine to acetaminophen nephrotoxicity II. Possible involvement of the γ-glutamyl cycle. Toxicol. Appl. Pharmacol. 202(2), 160-171 (2005).

    3. Heard, K., Green, J.L., Anderson, V., et al. Paracetamol (acetaminophen) protein adduct concentrations during therapeutic dosing. Br. J. Clin. Pharmacol. 81(3), 562-568 (2016).

    4. O'Malley, G.F., Mizrahi, F., Giraldo, P., et al. Protein-derived acetaminophen-cysteine can be detected after repeated supratherapeutic ingestion of acetaminophen in the absence of hepatotoxicity. J. Med. Toxicol. 11(3), 317-320 (2015).