Metamizole

Summary

Metamizole (CHEMBL461522) is an approved small-molecule antirheumatic drug.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• Clinical trials: 35
• Chemistry: 311.36 Da · C13H17N3O4S

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL461522
Name	Metamizole
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	3111
ChEBI	CHEBI:62088
Molecular formula	C13H17N3O4S
Molecular weight	311.36
InChIKey	LVWZTYCIRDMTEY-UHFFFAOYSA-N

SMILES: CC1=C(C(=O)N(N1C)C2=CC=CC=C2)N(C)CS(=O)(=O)O

IUPAC name: [(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)-methylamino]methanesulfonic acid

ChEBI definition: A pyrazole that is antiipyrine substituted at C-4 by a methyl(sulfomethyl)amino group, the sodium salt of which, metamizole sodium, was widely used as a powerful analgesic and antipyretic, but withdrawn from many markets from the 1970s due to a risk of causing risk of causing agranulocytosis.

Pharmacological roles (ChEBI): antipyretic, antirheumatic drug, non-narcotic analgesic, peripheral nervous system drug, prodrug, cyclooxygenase 3 inhibitor, anti-inflammatory agent.

Also known as: Dipyrone free acid anhydrous, Metamizole, Methamizole-, Methamizole, Dipyrone, METAMIZOLE SODIUM, DIPYRONE, metamizole, METAMIZOLE

Parent form; salt/anhydrous children: CHEMBL487894, CHEMBL3989803

Patent coverage: 1,604 distinct patent families (4,322 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 1 (assay-derived). Sample: Prostaglandin G/H synthase 1.

Bioactivity

ChEMBL activities: 1 potent at pChembl ≥ 5 of 1 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
PTGS1	5.44	AC50	3661	nM	CHEMBL_ACT_25206720

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

0 indications (0 at ChEMBL trial phase 4).

Clinical trials

Total trials: 35.

Phase distribution

Phase	Trials
Not specified	12
PHASE4	11
PHASE3	5
PHASE2	5
PHASE1	2

Top trials by phase / activity

NCT	Phase	Status	Title
NCT06950840	PHASE4	NOT_YET_RECRUITING	Antipyretic Treatment for Intrapartum Fever: Dipyrone vs Acetaminophen (RCT)
NCT01359020	PHASE4	COMPLETED	Ibuprofen, Acetaminophen and Dipyrone to Fever Control in Children
NCT02181920	PHASE4	TERMINATED	Metamizol for the Treatment of Neoplastic Chronic Pain
NCT02184260	PHASE4	TERMINATED	Efficacy and Safety of Metamizole Versus Placebo as Antithermic Therapy in the Acute Phase of Ischemic Stroke
NCT02686021	PHASE4	COMPLETED	Potential Benefit of the Combination of Metamizole and Ibuprofen After Third Lower Molar Extraction
NCT02689024	PHASE4	TERMINATED	Delirium in Elderly Patients With Trauma of the Hip
NCT03404908	PHASE4	COMPLETED	TAP vs QLB in Patients After Cesarean Delivery
NCT03622489	PHASE4	UNKNOWN	Comparing Protocols for Analgesia Following Elective Cesarean Section
NCT04111315	PHASE4	UNKNOWN	Efficacy of Metamizole Versus Ibuprofen and a Short Educational Intervention Versus Standard Care in Acute Low Back Pain
NCT04595877	PHASE4	COMPLETED	Double-blind, Randomized Controlled Study to Assess the Analgesic Effect of 2 g of Magnesium Dipyrone (Metamizol) and Changes in Plasma Beta-endorphin Immunoreactivity Values in Patients Undergoing Elective Inguinal Herniorrhaphy Under Epidural Anesthesia.
NCT04691726	PHASE4	COMPLETED	Impact of Intra- and Postoperative Continuous Infusion of Lidocaine on Analgesia in Vascular Anaesthesia
NCT06237231	PHASE3	NOT_YET_RECRUITING	Efficacy and Safety of DIT112 in the Treatment of Moderate to Severe Pain After Dental Surgery for the Extraction of Impacted Third Molars
NCT02662660	PHASE3	COMPLETED	Analgesia iv vs Epidural Analgesia vs Port-sites Infiltration After Laparoscopic Sleeve Gastrectomy
NCT02711241	PHASE3	TERMINATED	Optimal Analgesia in Acute Gastroenteritis
NCT04641338	PHASE3	COMPLETED	Fixed Combination of Dipyrone and Codeine for Controlling Pain After Pelvic-abdominal Surgery
NCT04972292	PHASE3	COMPLETED	Fixed Dose Combination of COdeine + DIpyrone to Mitigate Moderate to Intense Pain Post-impacted Third Lower Molar Extraction
NCT00841841	PHASE2	COMPLETED	Dipyrone Versus Acetaminophen in the Control of Postoperative Pain
NCT01858402	PHASE2	COMPLETED	Paracetamol Versus Dipyrone After Pediatric Lower Abdominal Surgery in Children With Spinal Anesthesia
NCT02660177	PHASE2	COMPLETED	Pharmacokinetics of Intravenous Metamizole in Children Less Than 6 Years Old
NCT04593329	PHASE2	WITHDRAWN	Efficacy and Safety of Tiradentes Association in the Treatment of Acute Pain
NCT05125978	PHASE2	WITHDRAWN	Efficacy and Safety of Canadá Association in the Treatment of Chronic Pain
NCT01995006	PHASE1	COMPLETED	Effect of Metamizole (Dipyrone) on Renal Function in Salt-depleted Healthy Subjects
NCT03990129	PHASE1	COMPLETED	Pharmacokinetic Interactions of Metamizole (Dipyrone) in Healthy Subjects
NCT07384013	Not specified	RECRUITING	Study Protocol: Impact of Metamizole (Optalgin®) on Anti-Xa Concentrations in Oncology Patients Receiving DOACs
NCT00763997	Not specified	COMPLETED	Study of the Effect of Dipyrone, Ibuprofen, Paracetamol and Parecoxib on the Platelet Aggregation in Analgetic Dosages
NCT01263652	Not specified	WITHDRAWN	Patient Preferences, Analgesic Delivery Method and Pain Reduction in Spine Patients
NCT02814279	Not specified	COMPLETED	Comparison of Two Flaps for Root Coverage
NCT02817763	Not specified	COMPLETED	A New Surgical-restorative Approach to Treat Gingival Recessions Associated With Non-carious Cervical Lesions (NCCL)
NCT03389243	Not specified	COMPLETED	Paracetamol and Metamizole With SPI-guided Anaesthesia for VRS
NCT03594513	Not specified	UNKNOWN	Mucoderm® Versus CTG in the Treatment of Multiple Gingival Recessions Associated With Non-carious Cervical Lesion.
NCT04082728	Not specified	COMPLETED	Evaluation of the Added Value of Metamizole to Standard Post-operative Treatment After Ambulant Surgery
NCT04703257	Not specified	COMPLETED	Evaluation of the Added Value of Metamizole to Standard Postoperative Treatment After Ambulant Shoulder Surgery
NCT04720248	Not specified	COMPLETED	Postoperative Pain in Scheduled Craniotomy
NCT05916716	Not specified	UNKNOWN	Use of a Novel Volume-stable Collagen Matrix (VCMX) in the Treatment of Single Gingival Recession Associated With Non-carious Cervical Lesion Partially Restored
NCT05916742	Not specified	UNKNOWN	Biofunctionalization of a Volume-stable Collagen Matrix (VCMX) for the Treatment of Single Gingival Recession

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).