ArticleEuropean journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences2015
Aromatic hydroxylation of salicylic acid and aspirin by human cytochromes P450.
Article in European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed, 46 citations in OpenAlex.
- Safety, tolerability, pharmacokinetics and pharmacodynamics of milvexian with aspirin and/or clopidogrel in healthy participants.Scientific reports · 2024Trial
- Microbial metabolite Enterobactin impairs mitochondrial respiration and alleviates colitis.Gut microbes · 2026Article
- Development of a Pregnancy-Specific Physiologically Based Pharmacokinetics (PBPK) Model for Aspirin.CPT: pharmacometrics & systems pharmacology · 2026Article
- Electrochemical Salicylic Acid Sensor Based on Molecularly Imprinted Polypyrrole.ACS applied materials & interfaces · 2025Article
- Aspirin-responsive gene switch regulating therapeutic protein expression.Nature communications · 2025Article
- New Insights into Aspirin's Anticancer Activity: The Predominant Role of Its Iron-Chelating Antioxidant Metabolites.Antioxidants (Basel, Switzerland) · 2024Review
- The Puzzle of Aspirin and Iron Deficiency: The Vital Missing Link of the Iron-Chelating Metabolites.International journal of molecular sciences · 2024Review
- The Colorimetric Detection of the Hydroxyl Radical.International journal of molecular sciences · 2023Article
- Radiosynthesis, Preclinical, and Clinical Positron Emission Tomography Studies of Carbon-11 Labeled Endogenous and Natural Exogenous Compounds.Chemical reviews · 2023Review
- Sodium salicylate and 5-aminosalicylic acid synergistically inhibit the growth of human colon cancer cells and mouse intestinal polyp-derived cells.Journal of clinical biochemistry and nutrition · 2022Article
- Review
- Evaluation of single and combined effects of two pharmaceuticals on the marine gastropod Phorcus lineatus enzymatic activity under two different exposure periods.Ecotoxicology (London, England) · 2021Article
- Modulation of CYP2C9 activity and hydrogen peroxide production by cytochrome bScientific reports · 2020Article
- Do Aspirin and Flavonoids Prevent Cancer through a Common Mechanism Involving Hydroxybenzoic Acids?-The Metabolite Hypothesis.Molecules (Basel, Switzerland) · 2020Review
- Article
- Gentisic Acid Stimulates Keratinocyte Proliferation through ERK1/2 Phosphorylation.International journal of medical sciences · 2020Article
- Aspirin metabolites 2,3‑DHBA and 2,5‑DHBA inhibit cancer cell growth: Implications in colorectal cancer prevention.Molecular medicine reports · 2020Article
- Small molecule IVQ, as a prodrug of gluconeogenesis inhibitor QVO, efficiently ameliorates glucose homeostasis in type 2 diabetic mice.Acta pharmacologica Sinica · 2019Article
- Worms on drugs: ecotoxicological effects of acetylsalicylic acid on the Polychaeta species Hediste diversicolor in terms of biochemical and histological alterations.Environmental science and pollution research international · 2019Article
- Propolis ethanolic extracts reduce adenosine diphosphate induced platelet aggregation determined on whole blood.Nutrition journal · 2018Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Aspirin (acetylsalicylic acid) is a well-known and widely-used analgesic. It is rapidly deacetylated to salicylic acid, which forms two hippuric acids-salicyluric acid and gentisuric acid-and two glucuronides. The oxidation of aspirin and salicylic acid has been reported with human liver microsomes, but data on individual cytochromes P450 involved in oxidation is lacking. In this study we monitored oxidation of these compounds by human liver microsomes and cytochrome P450 (P450) using UPLC with fluorescence detection. Microsomal oxidation of salicylic acid was much faster than aspirin. The two oxidation products were 2,5-dihydroxybenzoic acid (gentisic acid, documented by its UV and mass spectrum) and 2,3-dihydroxybenzoic acid. Formation of neither product was inhibited by desferrioxamine, suggesting a lack of contribution of oxygen radicals under these conditions. Although more liphophilic, aspirin was oxidized less efficiently, primarily to the 2,5-dihydroxy product. Recombinant human P450s 2C8, 2C9, 2C19, 2D6, 2E1, and 3A4 all catalyzed the 5-hydroxylation of salicylic acid. Inhibitor studies with human liver microsomes indicated that all six of the previously mentioned P450s could contribute to both the 5- and 3-hydroxylation of salicylic acid and that P450s 2A6 and 2B6 have contributions to 5-hydroxylation. Inhibitor studies indicated that the major human P450 involved in both 3- and 5-hydroxylation of salicylic acid is P450 2E1.
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Registered trials
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