Reactome | Acetaminophen oxidised to N-acetylbenzoquinoneimine (NAPQI)

Acetaminophen oxidised to N-acetylbenzoquinoneimine (NAPQI)

Stable Identifier

R-HSA-76397

Type

Reaction [transition]

Species

Homo sapiens

Compartment

endoplasmic reticulum lumen, endoplasmic reticulum membrane

ReviewStatus

5/5

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Metabolism (Homo sapiens)

- Biological oxidations (Homo sapiens)
  - Phase I - Functionalization of compounds (Homo sapiens)
    - Cytochrome P450 - arranged by substrate type (Homo sapiens)
      - Xenobiotics (Homo sapiens)
        
        CYP2E1 reactions (Homo sapiens)
        
        Acetaminophen oxidised to N-acetylbenzoquinoneimine (NAPQI) (Homo sapiens)

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Acetaminophen oxidised to N-acetylbenzoquinoneimine (NAPQI)

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N-acetyl-p-benzoquinone imine (NAPQI) is the reactive intermediate of the analgesic and antipyretic, acetaminophen (INN, paracetamol). At usual doses, NAPQI is quickly detoxified by conjugation but in overdose situations, NAPQI is extremely toxic to liver tissue.

Literature References

PubMed ID	Title	Journal	Year
10741631	Contribution of CYP2E1 and CYP3A to acetaminophen reactive metabolite formation Manyike, PT, Kharasch, ED, Kalhorn, TF, Slattery, JT	Clin Pharmacol Ther	2000