Metamizole
Identification
- Summary
Metamizole is an antipyretic and analgesic drug used to relieve severe and persistent fever and pain.
- Generic Name
- Metamizole
- DrugBank Accession Number
- DB04817
- Background
Metamizole, formerly marketed as Dimethone tablets and injection, Protemp oral liquid, and other drug products, was associated with potentially fatal agranulocytosis. Approvals of the NDA's for dipyrone drug products were withdrawn on June 27, 1977 (see the Federal Register of June 17, 1977 (42 FR 30893)). Withdrawn from the Canadian market in 1963.
- Type
- Small Molecule
- Groups
- Approved, Investigational, Withdrawn
- Structure
Structure for Metamizole (DB04817)
- Weight
- Average: 311.36
Monoisotopic: 311.093977213 - Chemical Formula
- C13H17N3O4S
- Synonyms
- metamizol
Pharmacology
- Indication
Used in the past as a powerful painkiller and fever reducer.
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Dipyrone is a non-steroidal anti-inflammatory drug (NSAID), commonly used in the past as a powerful painkiller and fever reducer.
- Mechanism of action
Target Actions Organism UProstaglandin G/H synthase 1 Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Metamizole may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Metamizole is combined with Abciximab. Acebutolol Metamizole may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of adverse effects can be increased when Metamizole is combined with Aceclofenac. Acemetacin The risk or severity of adverse effects can be increased when Metamizole is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding and hemorrhage can be increased when Metamizole is combined with Acenocoumarol. Acetaminophen The risk or severity of adverse effects can be increased when Acetaminophen is combined with Metamizole. Acetohexamide The protein binding of Acetohexamide can be decreased when combined with Metamizole. Acetylsalicylic acid The risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Metamizole. Aclidinium Metamizole may decrease the excretion rate of Aclidinium which could result in a higher serum level. 
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- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Metamizole magnesium MS15642725 6150-97-6 NHMUJYOBLYTIKO-UHFFFAOYSA-L Metamizole sodium VSU62Z74ON 68-89-3 DJGAAPFSPWAYTJ-UHFFFAOYSA-M Metamizole sodium monohydrate 6429L0L52Y 5907-38-0 UNZIDPIPYUMVPA-UHFFFAOYSA-M - International/Other Brands
- Algocalmin / Algozone / Analgin / Dimethone / Dipirona / Neo-Melubrina / Novalgin / Optalgin / Protemp / Pyralgin
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ANTIALGINA® Metamizole sodium (300 mg) + Caffeine (30 mg) + Isometheptene mucate (30 mg) Tablet, film coated Oral TECNOQUIMICAS S.A. 2007-04-24 Not applicable Colombia 
ANTIALGINA® Metamizole sodium (300 mg) + Caffeine (30 mg) + Isometheptene (50 mg) Solution Oral TECNOFAR TQ S.A.S 2007-03-06 2015-02-27 Colombia CAFETRIN ® Metamizole (300 mg) + Caffeine (30 mg) + Isometheptene mucate (30 mg) Tablet, coated Oral LABORATORIOS RICH MONDS S.A.S 2018-05-11 Not applicable Colombia DIPIRONA 300 MG + ISOMETEPTENO 50 MG + CAFEINA 30 MG GOTAS Metamizole sodium monohydrate (300 mg) + Caffeine (30 mg) + Isometheptene (50 mg) Solution Oral SANOFI-AVENTIS DE COLOMBIA S.A. 2018-07-06 2019-04-22 Colombia DIPIRONA SODICA / ISOMETEPTENO MUCATO/CAFEINA 300 MG / 30 MG/30MG TABLETA RECUBIERTA Metamizole sodium (300 mg) + Caffeine (30 mg) + Isometheptene mucate (30 mg) Tablet, coated Oral LABORATORIO FRANCO COLOMBIANO - LAFRANCOL S.A.S. 2013-07-09 Not applicable Colombia DIPIRONA SODICA 300 MG/ ISOMETEPTENO CLORHIDRATO 50 MG / CAFEINA 30 MG GOTAS Metamizole sodium (300 mg) + Caffeine (30 mg) + Isometheptene (50 mg) Solution Oral LABORATORIO FRANCO COLOMBIANO - LAFRANCOL S.A.S. 2013-08-30 Not applicable Colombia DOSALDIN® GOTAS Metamizole sodium (300 mg) + Caffeine (30 mg) + Isometheptene (50 mg) Solution Oral SERVICIO TECNICO GONHER FARMACEUTICA LTDA. 2010-05-10 Not applicable Colombia ESPASMOBIL® GOTAS Metamizole (333.4 mg) + Butylscopolamine bromide (6.67 mg) Solution Oral FARMACOL CHINOIN S.A.S.. 2006-11-10 2021-10-01 Colombia ESPASMOBIL®SOLUCION INYECTABLE Metamizole sodium (2.5 g) + Butylscopolamine bromide (20 mg) Solution Intramuscular; Intravenous LABORATORIOS RYAN DE COLOMBIA S. EN C. 2006-11-10 2019-08-05 Colombia HIOSCINA 20 MG + DIPIRONA 2.5 G Metamizole sodium (2.5 g) + Butylscopolamine (20 mg) Solution Intramuscular; Intravenous LABORATORIOS RYAN DE COLOMBIA S.A.S. 2006-11-10 Not applicable Colombia - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image NOVOPYRINE 1 GR/2 ML 10 AMPUL Metamizole sodium (1 g/2ml) Injection Intramuscular; Intravenous OSEL İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey 
Categories
- ATC Codes
- N02BB72 — Metamizole sodium, combinations with psycholepticsN02BB02 — Metamizole sodiumN02BB52 — Metamizole sodium, combinations excl. psycholeptics
- Drug Categories
- Agents causing hyperkalemia
- Agents that produce hypertension
- Aminopyrine
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Antipyretics
- Central Nervous System Agents
- Cytochrome P-450 CYP2B6 Inducers
- Cytochrome P-450 CYP2B6 Inducers (strength unknown)
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- Nephrotoxic agents
- Nervous System
- Non COX-2 selective NSAIDS
- Peripheral Nervous System Agents
- Pyrazoles
- Pyrazolones
- Sensory System Agents
- Classification
- Not classified
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 934T64RMNJ
- CAS number
- 50567-35-6
- InChI Key
- LVWZTYCIRDMTEY-UHFFFAOYSA-N
- InChI
- InChI=1S/C13H17N3O4S/c1-10-12(14(2)9-21(18,19)20)13(17)16(15(10)3)11-7-5-4-6-8-11/h4-8H,9H2,1-3H3,(H,18,19,20)
- IUPAC Name
- [(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(methyl)amino]methanesulfonic acid
- SMILES
- CN(CS(O)(=O)=O)C1=C(C)N(C)N(C1=O)C1=CC=CC=C1
References
- General References
- Not Available
- External Links
- KEGG Drug
- D08188
- PubChem Compound
- 522325
- PubChem Substance
- 46509035
- ChemSpider
- 3000
- BindingDB
- 235671
- ChEBI
- 62088
- ChEMBL
- CHEMBL461522
- ZINC
- ZINC000001782155
- Therapeutic Targets Database
- DNC000568
- PharmGKB
- PA166128206
- Wikipedia
- Metamizole
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Supportive Care Beta-endorphin / Dipyrone / Hernia Surgery / Pain 1 4 Completed Treatment Cesarean Sections / Neuropathic Pain / Postoperative pain 1 4 Completed Treatment Chronic Lower Back Pain (CLBP) 1 4 Completed Treatment Fever 1 4 Completed Treatment Inadequate or Impaired Respiratory Function / Pain 1 4 Completed Treatment Pain 1 4 Completed Treatment Postoperative pain 1 4 Completed Treatment Sub-acute Back Pain 1 4 Recruiting Prevention Anaesthesia therapy / Hip Fracture 1 4 Recruiting Treatment Back Pain Lower Back 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Zhejiang Haisen Pharmaceutical Co. Ltd.
- Dosage Forms
Form Route Strength Injection, solution Injection, solution Parenteral 1000 mg Tablet Oral 500 mg/1 Suppository Rectal 1000 MG Suppository Rectal Solution Intramuscular; Intravenous Syrup Oral 3 g Solution Intramuscular; Intravenous Solution Parenteral 2.5 g Injection Parenteral 1 g Solution Intramuscular 1 g Tablet, coated Oral 500 mg Solution Oral 500 mg Solution Parenteral 2000 mg Injection Intramuscular; Intravenous 2 g Solution Intramuscular; Intravenous 2 g Solution Parenteral Solution Parenteral 1 g Solution Intramuscular; Intravenous 1 g Solution Intramuscular; Intravenous; Subcutaneous 2.5 g Injection Intramuscular; Intravenous 2500 mg Tablet Oral 0.5 g Solution Parenteral 2 g Tablet Oral Injection Parenteral Capsule, coated Oral Solution Oral Tablet, coated Oral Injection Intravenous Solution Oral 0.5 g Solution Intramuscular 2.5 g Solution Intravenous; Parenteral 2.5 g Tablet, film coated Oral 500 mg Injection, solution Parenteral Tablet Oral Solution / drops Oral Solution Oral 500 MG/ML Injection, solution Parenteral 7.5 mg Injection Tablet Oral 5 mg Solution Oral 300 mg Solution Oral 96 mg Tablet Tablet; tablet, film coated Oral Injection Intramuscular; Intravenous Solution / drops; suspension / drops Ointment Syrup Oral Injection, solution Intramuscular; Intravenous Injection, solution Parenteral 2.5 G Tablet, film coated Oral Injection, solution Intramuscular; Intravenous 1 G/2ML Solution / drops Oral 500 MG/ML Suppository Rectal 1 G Suppository Rectal 300 mg Tablet Oral 500 MG Solution Intramuscular; Intravenous 2.5 g Injection, solution Parenteral 1 G/2ML Tablet, coated Oral 850 mg Tablet, film coated Oral Tablet, sugar coated Oral Solution Intravenous - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 2.53 mg/mL ALOGPS logP -0.4 ALOGPS logP -0.82 ChemAxon logS -2.1 ALOGPS pKa (Strongest Acidic) -1.4 ChemAxon pKa (Strongest Basic) -0.54 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 81.16 Å2 ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 80.04 m3·mol-1 ChemAxon Polarizability 31.41 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.7868 Blood Brain Barrier + 0.8896 Caco-2 permeable - 0.5869 P-glycoprotein substrate Non-substrate 0.8148 P-glycoprotein inhibitor I Non-inhibitor 0.828 P-glycoprotein inhibitor II Non-inhibitor 0.8107 Renal organic cation transporter Non-inhibitor 0.921 CYP450 2C9 substrate Non-substrate 0.8588 CYP450 2D6 substrate Non-substrate 0.7959 CYP450 3A4 substrate Substrate 0.6035 CYP450 1A2 substrate Non-inhibitor 0.7153 CYP450 2C9 inhibitor Non-inhibitor 0.7064 CYP450 2D6 inhibitor Non-inhibitor 0.8562 CYP450 2C19 inhibitor Non-inhibitor 0.6768 CYP450 3A4 inhibitor Non-inhibitor 0.9297 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8506 Ames test AMES toxic 0.7763 Carcinogenicity Carcinogens 0.8197 Biodegradation Ready biodegradable 0.7192 Rat acute toxicity 2.6224 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8411 hERG inhibition (predictor II) Non-inhibitor 0.6724
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
- Gene Name
- PTGS1
- Uniprot ID
- P23219
- Uniprot Name
- Prostaglandin G/H synthase 1
- Molecular Weight
- 68685.82 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Saussele T, Burk O, Blievernicht JK, Klein K, Nussler A, Nussler N, Hengstler JG, Eichelbaum M, Schwab M, Zanger UM: Selective induction of human hepatic cytochromes P450 2B6 and 3A4 by metamizole. Clin Pharmacol Ther. 2007 Sep;82(3):265-74. doi: 10.1038/sj.clpt.6100138. Epub 2007 Mar 7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Saussele T, Burk O, Blievernicht JK, Klein K, Nussler A, Nussler N, Hengstler JG, Eichelbaum M, Schwab M, Zanger UM: Selective induction of human hepatic cytochromes P450 2B6 and 3A4 by metamizole. Clin Pharmacol Ther. 2007 Sep;82(3):265-74. doi: 10.1038/sj.clpt.6100138. Epub 2007 Mar 7. [Article]
Drug created on September 11, 2007 20:09 / Updated on September 19, 2021 18:03