metamizole
Trade name: Novalgin
Small moleculeexperimental
Metamizole or dipyrone is a painkiller, spasm reliever, and fever reliever drug. It is most commonly given by mouth or by intravenous infusion. It belongs to the ampyrone sulfonate family of medicines and was patented in 1922. Metamizole is marketed under various trade names. It was first used medically in Germany under the brand name "Novalgin", later becoming widely known in Slavic nations and India under the name "Analgin". — Wikipedia
Clinical trial activity
55 trials · 42 clinical orgs · 0 marketing orgs
Phase 1
3
Phase 2
17
Phase 3
12
Phase 4
20
Earliest trial started Oct 1, 1998 (NCT02183220)
Timeline
Indications
Approved for
Studied for
- Acupuncture, Ear · Phase 3
- Acute Pain · Phase 4
- Analgesics, Opioid · Phase 4
- Anesthesia · Phase 4
- Anesthesia, Spinal · Phase 4
- Aorta · Phase 4
- Aortic Aneurysm, Abdominal · Phase 4
- Arthroplasty, Replacement, Hip · Phase 4
- beta-Endorphin · Phase 4
- Cesarean Section · Phase 4
- Child · Phase 2
- Chorioamnionitis · Phase 4
- Chronic Pain · Phase 3
- Dipyrone · Phase 4
- Drug Interactions · Phase 1
- Episiotomy · Phase 3
- Fever · Phase 4
- Gastroenteritis · Phase 3
- Gastroenterology · Phase 4
- General Surgery · Phase 4
- Healthy Volunteers · Phase 1
- Hip Fractures · Phase 4
- Labor Pain · Phase 3
- Low Back Pain · Phase 4
- Lung Diseases · Phase 4
- Mandibular Diseases · Phase 4
- Migraine Disorders · Phase 3
- Neuralgia · Phase 4
- Pain · Phase 4
- Pain Management · Phase 4
- Pancreatic Diseases · Phase 4
- Pancreatitis · Phase 4
- Pediatrics · Phase 4
- Postoperative Pain · Phase 4
- Renal Colic · Phase 4
- Sepsis · Phase 3
- Spinal Cord Injuries · Phase 3
- Stroke · Phase 4
- Temporomandibular Joint Disorders · Phase 4
Mechanism of action
- CyclooxygenaseINHIBITOR
Cyclooxygenase inhibitor
The pharmacologically active dipyrone metabolite, 4-methylamino-antipyrine (MAA), targets the initiation of the catalytic reaction of both COX isoforms by reducing the higher oxidation states of COX or sequestering activating peroxides. It does not compete with arachidonic acid for the catalytic site of COX. Instead it binds to the Fe3+ in the haem. In the next step, the Fe3+ is reduced and an MAA radical is formed.
Chemistry & pharmacology
Loading structure…
SMILES
Cc1c(N(C)CS(=O)(=O)[O-])c(=O)n(-c2ccccc2)n1C.O.[Na+]- Mol. weight
- 351.36 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Achiral Molecule
- Inorganic
- No
- Polymer
- No
Oral
No
Parenteral
No
Topical
No
Sources
- ChEMBLCHEMBL3989803 ↗
- WikipediaMetamizole ↗
- ChEMBLCHEMBL487894 ↗
- ChEMBLCHEMBL461522 ↗
- ChEMBLCHEMBL278519 ↗
Also known as
- acetaminophen mixture with caffeine and dipyrone
- algocalmin
- algocalmin
- algocalmin
- algocalmin
- algocalmin
- algocalmin
- dipirone
- diprofarn
- diprofarn
- dipyrone
- dipyrone
- dipyrone
- dipyrone
- dipyrone
- dipyrone
- dipyrone monohydrate
- dipyrone sodium
- dypiron
- dypirone
- magnesium metamizol
- metamizol
- metamizol
- metamizol
- metamizole
- metamizole
- metamizole
- metamizole
- metamizole
- metamizole calcium
- metamizole magnesium
- metamizole sodium
- metamizole sodium
- metamizole sodium
- metapyrin
- methampyrone
- methampyrone
- methampyrone
- nolotil
- noramidopyrine methanesulfonate sodium
- noramidopyrine methanesulfonate sodium
- novaldin
- novaldin
- optalgin
- sodium dipyrone
- sulpyrine
- sulpyrine
- sulpyrine
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT05125978 | Phase 2 | Sep 30, 2026 | EMS S/A |
| NCT07024199 | Phase 4 | Sep 30, 2025 | Medical University of Warsaw |
| NCT06950840 | Phase 4 | Aug 1, 2025 | Tel Aviv University |
| NCT06878014 | Phase 4 | Mar 4, 2025 | Silesian University of Medicine |
| NCT06237231 | Phase 3 | Feb 15, 2025 | EMS S/A |
| NCT05916716 | N/A | Aug 1, 2022 | Sao Paulo State University |
| NCT04972292 | Phase 3 | Jul 31, 2022 | Eurofarma Laboratorios S.A. |
| NCT05916742 | N/A | Apr 15, 2022 | Sao Paulo State University |
| NCT05270434 | N/A | Mar 1, 2022 | Changhai Hospital |
| NCT04641338 | Phase 3 | Jan 31, 2022 | Brainfarma Industria Química e Farmacêutica S/A, Brazilian Clinical Research Institute |
| NCT04593329 | Phase 2 | Oct 31, 2021 | EMS S/A |
| NCT04703257 | N/A | Feb 26, 2021 | Hasselt University |
| NCT04621253 | Phase 1 | Apr 29, 2020 | University of Basel |
| NCT04082728 | N/A | Nov 1, 2019 | Hasselt University |
| NCT04111315 | Phase 4 | Oct 31, 2019 | University of Bern |
| NCT04148846 | N/A | Sep 20, 2019 | University of Sao Paulo |
| NCT04691726 | Phase 4 | Jan 29, 2019 | Medical University of Silesia, Silesian University of Medicine |
| NCT03990129 | Phase 1 | Sep 4, 2018 | University of Basel |
| NCT03639389 | Phase 3 | Sep 1, 2018 | Karolinska Institute |
| NCT03594513 | N/A | Jul 2, 2018 | Fundação de Amparo à Pesquisa do Estado de São Paulo, Sao Paulo State University |
Showing 20 of 55 trials
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Organizations
Research & Development (42)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Sao Paulo State University | Academic/Hospital | 5 | 5 | 1 | 2014 |
| Silesian University of Medicine | Academic/Hospital | 5 | 4 | 2 | 2016 |
| Boehringer Ingelheim | For profit | 4 | 4 | 2 | 1998 |
| EMS S/A | For profit | 3 | 3 | 2 | 2021 |
| Medical University of Lublin | Academic/Hospital | 3 | 3 | 1 | 2016 |
| Tel Aviv University | Academic/Hospital | 3 | 3 | 1 | 2017 |
| University of Basel | Academic/Hospital | 3 | 3 | 2 | 2016 |
| University of Bern | Academic/Hospital | 3 | 3 | 2 | 2014 |
| Hasselt University | Academic/Hospital | 2 | 2 | 1 | 2019 |
| Hebrew University | Academic/Hospital | 2 | 1 | 1 | 2010 |
| Miguel Hernández University | Academic/Hospital | 2 | 2 | 1 | 2012 |
| University of Sao Paulo | Academic/Hospital | 2 | 1 | 2 | 2006 |
| Ache Laboratorios Farmaceuticos S.A. | For profit | 1 | 1 | 1 | 2017 |
| Barzilai Medical Center | Academic/Hospital | 1 | 1 | 1 | 2010 |
| Baskent University | Academic/Hospital | 1 | 1 | 1 | 2009 |
| Brainfarma Industria Química e Farmacêutica S/A | For profit | 1 | 0 | 1 | 2022 |
| Brazilian Clinical Research Institute | Academic/Hospital | 1 | 1 | 1 | 2022 |
| Changhai Hospital | Academic/Hospital | 1 | 1 | 1 | 2022 |
| Emek Medical Center | Academic/Hospital | 1 | 1 | 1 | 2011 |
| Eurofarma Laboratorios S.A. | For profit | 1 | 1 | 1 | 2022 |
42 organizations
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