Acetaminophen inhibits prostanoid synthesis by scavenging the PGHS‐activator peroxynitrite
Open accessAbstract
The primary pharmacological target of acetaminophen is prostaglandin endoperoxide H 2 syn‐thase (PGHS). The enzymatic catalytic mechanism is radical‐based, initiated, and maintained by the persistent presence of peroxides, particularly peroxynitrite, which is termed “peroxide tone”. Whereas the prevailing concept assumes a direct reduction of the active, oxidized enzyme by acetaminophen, here we show that acetaminophen is a potent scavenger of peroxynitrite (peroxynitrite‐mediated phenol nitration, IC 50 ≈72μM; Sin‐1‐mediated DHR123 oxidation, IC 50 ≈11μM) and thus inhibits PGHS by eliminating the peroxide tone. Nanomolar concentrations of peroxynitrite increased the activity of isolated PGHS and prostacyclin formation by aortic endothelial cells. This elevated activity was efficiently inhibited by pharmacologically relevant concentrations of acetaminophen (IC 50 ≈10μM for 6‐keto‐PGF 1α ) and other free radical scavengers. However, when the peroxide tone was provided by H 2 O 2 or tert‐butyl‐OOH, acetaminophen had only negligible inhibitory effects. Our concept could help to explain the efficacy of acetaminophen to inhibit PGHS in cell types with moderate oxidant formation. However, high levels of peroxynitrite or other peroxides such as lipid peroxides formed at inflammatory sites might overwhelm the ability of acetaminophen to decrease PGHS activation. The concept presented herein provides a molecular basis to explain the excellent analgesic and antipyretic properties of acetaminophen together with its minimal anti‐inflammatory effects.— Schildknecht, S., Daiber, A., Ghisla, S., Cohen, R. A., Bachschmid, M. M. Acetaminophen inhibits prostanoid synthesis by scavenging the PGHS‐activator peroxynitrite. FASEB J. 22, 215–224 (2008)
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Paracetamol, as a reducing agent, reduces hydroperoxide tone and thus inactivates COX.
“Paracetamol, as reducing agent,26 reduces the hydroperoxide tone and thus inactivates COX.27–30”
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Love, L. C. (2015) · doi:10.1002/9781118912997.ch6
Sterling, K. (2020) · York University Digital Library (York University)
Samtidig bruk av warfarin og smertestillende legemidler
Pettersen, M. H. (2008) · NORA - Norwegian Open Research Archives
- Authors
- Schildknecht, S., Daiber, A., Ghisla, S., Cohen, R. A., & Bachschmid, M. M.
- Affiliations
- Boston University (US)
- Johannes Gutenberg University Mainz (DE)
- University of Konstanz (DE)
- Venue
- The FASEB Journal
- Publisher
- Wiley
- Published
- 2007-08-27
- Volume
- 22
- Issue
- 1
- Pages
- 215-224
- ISSN
- 0892-6638 (ISSN-L)
- 1530-6860
- OpenAlex
- W2112145177
- Cited by
- 57
- References
- 44
- Citations by year
- 2026: 2 · 2025: 1 · 2024: 4 · 2023: 2 · 2022: 3 · 2021: 6 · 2020: 3 · 2018: 3 · 2017: 1 · 2015: 3 · 2014: 2 · 2013: 5 · 2012: 2
- FWCI
- 4.01
- Type
- journal article
- Language
- en
- Open access
- green
- nbn-resolving.de
- Licence
- Locations
- The FASEB Journal (publishedVersion)
- PubMed (publishedVersion)
- KOPS (University of Konstanz) (submittedVersion, cc-by-nc-nd)
- Funders
- National Institutes of Health (P01 HL 68758, R01 AG027080, P01 HL081738)
- Topics
- Health Sciences › Medicine › Pharmacology › Inflammatory mediators and NSAID effects
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Eicosanoids and Hypertension Pharmacology
- Keywords
- paracetamol, peroxynitrite, free radical scavenging, prostacyclin, aortic endothelial cells, 6-keto-PGF1 alpha, anti-inflammatory activity
- MeSH terms
- Acetaminophen, Animals, Cattle, Cells, Cultured, Chromatography, High Pressure Liquid, Male, Prostaglandins, Sheep, Spectrometry, Fluorescence, Free Radical Scavengers, Enzyme Activators, Peroxynitrous Acid, Cyclooxygenase 1
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