ArticleBritish journal of pharmacology2007
Inhibition of cyclooxygenases by dipyrone.
Article in British journal of pharmacology, 2007. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 54 papers, 2 of them syntheses that pooled it.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
54 citing papers in PubMed, 2 syntheses or guidelines pooled it, 149 citations in OpenAlex.
- Safety of metamizole (dipyrone) for the treatment of mild to moderate pain-an overview of systematic reviews.Naunyn-Schmiedeberg's archives of pharmacology · 2024Pooled it
- [Pediatric perioperative systemic pain therapy: Austrian interdisciplinary recommendations on pediatric perioperative pain management].Schmerz (Berlin, Germany) · 2014Guideline
- Cytochrome P450 1A2 is the most important enzyme for hepatic metabolism of the metamizole metabolite 4-methylaminoantipyrine.British journal of clinical pharmacology · 2022Trial
- Enhancing the efficiency of achieving optical transparency in live animals using absorbing molecules.Journal of biomedical optics · 2026Article
- [Polypharmacy and nephrotoxicity].Innere Medizin (Heidelberg, Germany) · 2026Review
- Cannabinoid Effects of Metamizol/Dipyrone: A Possible Second Life in Pediatric Anesthesia for a Vintage Drug.Biomedicines · 2026Review
- Metamizole: Indications and Risks.Deutsches Arzteblatt international · 2026Review
- Comparative Evaluation of Analgesics in a Murine Bile Duct Ligation Model.Biomedicines · 2025Article
- Metamizole does not affect fracture healing in a murine ischemia model.Frontiers in physiology · 2025Article
- Pharmacological Pain Treatment in Older Persons.Drugs & aging · 2024Review
- Article
- Metamizole in the Management of Musculoskeletal Disorders: Current Concept Review.Journal of clinical medicine · 2024Review
- Metamizole outperforms meloxicam in sepsis: insights on analgesics, survival and immunomodulation in the peritoneal contamination and infection sepsis model.Frontiers in immunology · 2024Article
- Analgesia in esophagectomy: a narrative review.Journal of thoracic disease · 2023Review
- The Clinical Pharmacology and Therapeutic Evaluation of Non-Steroidal Anti-Inflammatory Drugs in Adult Horses.Animals : an open access journal from MDPI · 2023Review
- Design, synthesis and in vivo evaluation of 1,4-dioxo-2-butenyl aryl amine derivatives as a promising anti-inflammatory drug prototype.Bioorganic chemistry · 2022Article
- Mastocytosis presenting with mast cell-mediator release-associated symptoms elicited by cyclo oxygenase inhibitors: prevalence, clinical, and laboratory features.Clinical and translational allergy · 2022Article
- Pharmacokinetics of metamizole (dipyrone) as an add-on in calves undergoing umbilical surgery.PloS one · 2022Article
- Article
- [Perioperative analgesia with nonopioid analgesics : Joint interdisciplinary consensus-based recommendations of the German Pain Society, the German Society of Anaesthesiology and Intensive Care Medicine and the German Society of Surgery].Schmerz (Berlin, Germany) · 2021Review
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
6 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
background and purposeDipyrone is a potent analgesic drug that has been demonstrated to inhibit cyclooxygenase (COX). In contrast to classical COX-inhibitors, such as aspirin-like drugs, dipyrone has no anti-inflammatory effect and a low gastrointestinal toxicity, indicating a different mode of action. Here, we aimed to investigate the effects of dipyrone on COX. EXPERIMENTAL APPROACH: The four major metabolites of dipyrone, including the two pharmacologically active metabolites, 4-methyl-amino-antipyrine (MAA) and amino-antipyrine (AA), were used to characterise their binding to COX and haem as well as their effects on the biochemical properties of COX. Mass spectrometry, UV and visible photometry were used to study binding and prostaglandin production. Levels of anti-oxidant enzymes were assessed by Western blotting. KEY
resultsThe pharmacologically active metabolites of dipyrone, MAA and AA, did not inhibit COX activity in vitro like classical COX inhibitors, but instead redirected the prostaglandin synthesis, ruling out inhibition of COX through binding to its active site. We found that MAA and AA formed stable complexes with haem and reacted with hydrogen peroxide in presence of haem, ferrous ions (Fe(2+)) or COX. Moreover, MAA reduced Fe(3+) to Fe(2+) and accordingly increased lipid peroxidation and the expression of anti-oxidant enzymes in cultured cells and in vivo. CONCLUSIONS AND IMPLICATIONS: Our data suggest that the pharmacologically active metabolites of dipyrone inhibit COX activity by sequestering radicals which initiate the catalytic activity of this enzyme or through the reduction of the oxidative states of the COX protein.
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What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.