ArticleBioorganic & medicinal chemistry2012
Novel bioactive metabolites of dipyrone (metamizol).
Article in Bioorganic & medicinal chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 36 papers, 4 of them syntheses that pooled it.
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Who cites it
36 citing papers in PubMed, 4 syntheses or guidelines pooled it, 129 citations in OpenAlex.
- Effects of major analgesics on male fertility: A systematic literature review.JBRA assisted reproduction · 2024Pooled it
- Non-steroidal anti-inflammatory drugs in the pathophysiology of vasospasms and delayed cerebral ischemia following subarachnoid hemorrhage: a critical review.Neurosurgical review · 2021Pooled it
- Nonsteroidal anti-inflammatory drugs and pain in cancer patients: a systematic review and reappraisal of the evidence.British journal of anaesthesia · 2019Pooled it
- [Pediatric perioperative systemic pain therapy: Austrian interdisciplinary recommendations on pediatric perioperative pain management].Schmerz (Berlin, Germany) · 2014Guideline
- Ampyrone is a direct agonist of human tyrosinase and a potential therapeutic for hypopigmentation disorders.JCI insight · 2026Article
- Cannabinoid Effects of Metamizol/Dipyrone: A Possible Second Life in Pediatric Anesthesia for a Vintage Drug.Biomedicines · 2026Review
- Evaluating the analgesic effect of metamizole in the mouse model for DSS-induced acute colitis.Frontiers in physiology · 2026Article
- Mannich Bases: Promising Scaffolds for the Treatment of Infectious Diseases.Current medicinal chemistry · 2025Review
- Metamizole does not affect fracture healing in a murine ischemia model.Frontiers in physiology · 2025Article
- Pharmacological Pain Treatment in Older Persons.Drugs & aging · 2024Review
- Opioid versus non-opioid postoperative pain management in otolaryngology.BMC anesthesiology · 2023Article
- 2-Arylpropionic Acid Pyrazolamides as Cannabinoid CB2 Receptor Inverse Agonists Endowed with Anti-Inflammatory Properties.Pharmaceuticals (Basel, Switzerland) · 2022Article
- 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
- Pharmacokinetics of metamizole (dipyrone) as an add-on in calves undergoing umbilical surgery.PloS one · 2022Article
- Comparative Effects of Metamizole (Dipyrone) and Naproxen on Renal Function and Prostacyclin Synthesis in Salt-Depleted Healthy Subjects - A Randomized Controlled Parallel Group Study.Frontiers in pharmacology · 2021Article
- Non-opioid Analgesics and the Endocannabinoid SystemBalkan medical journal · 2020Article
- Metamizole relieves pain by influencing cytokine levels in dorsal root ganglia in a rat model of neuropathic pain.Pharmacological reports : PR · 2020Article
- CBBritish journal of pharmacology · 2020Article
- A Guide to Targeting the Endocannabinoid System in Drug Design.International journal of molecular sciences · 2020Review
- Acute intermittent porphyria: analgesia can be dangerous.BMJ case reports · 2019Article
Corrections and comments
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Authors and funding
11 authors at 4 institutions in 3 countries.
Funding
Abstract
Dipyrone is a common antipyretic drug and the most popular non-opioid analgesic in many countries. In spite of its long and widespread use, molecular details of its fate in the body are not fully known. We administered dipyrone orally to mice. Two unknown metabolites were found, viz. the arachidonoyl amides of the known major dipyrone metabolites, 4-methylaminoantipyrine (2) and 4-aminoantipyrine (3). They were identified by ESI-LC-MS/MS after extraction from the CNS, and comparison with reference substances prepared synthetically. The arachidonoyl amides were positively tested for cannabis receptor binding (CB(1) and CB(2)) and cyclooxygenase inhibition (COX-1 and COX-2 in tissues and as isolated enzymes), suggesting that the endogenous cannabinoid system may play a role in the effects of dipyrone against pain.
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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.