Metamizole
Identification
- Name
- Metamizole
- Accession Number
- DB04817
- Description
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 Approvals of the NDA's for dipyrone drug products were withdrawn on June 27, 1977 (see the Federal Register of June 17, 1977 (42 FR 30893)). Withdrawn from the Canadian market in 1963.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- Approved, Investigational, Withdrawn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
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:Accelerate your drug discovery research with our fully connected ADMET dataset- Indication
Used in the past as a powerful painkiller and fever reducer.
- Associated Conditions
- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- 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
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- 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. 
Improve patient outcomesBuild effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.Learn more - Food Interactions
- Not Available
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- 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 2007-04-24 Not applicable Colombia 
ANTIALGINA® Metamizole sodium (300 mg) + Caffeine (30 mg) + Isometheptene (50 mg) Solution Oral 2007-03-06 2015-02-27 Colombia CAFETRIN ® Metamizole (300 mg) + Caffeine (30 mg) + Isometheptene mucate (30 mg) Tablet, coated Oral 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 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 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 2013-08-30 Not applicable Colombia DOSALDIN® GOTAS Metamizole sodium (300 mg) + Caffeine (30 mg) + Isometheptene (50 mg) Solution Oral 2010-05-10 Not applicable Colombia ESPASMOBIL®SOLUCION INYECTABLE Metamizole sodium (2.5 g) + Butylscopolamine bromide (20 mg) Solution Intramuscular; Intravenous 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 2006-11-10 Not applicable Colombia MIGRINON® TABLETAS RECUBIERTAS Metamizole (300 mg) + Caffeine (30 mg) + Isometheptene mucate (30 mg) Tablet, coated Oral 2009-11-19 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
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 Back Pain Lower Back Chronic 1 4 Completed Treatment Cesarean Section / Neuropathic Pain / Postoperative pain 1 4 Completed Treatment Fever 1 4 Completed Treatment Inadequate or Impaired Respiratory Function / Pain 1 4 Completed Treatment 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 4 Recruiting Treatment Postoperative pain 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Zhejiang Haisen Pharmaceutical Co. Ltd.
- Dosage Forms
Form Route Strength Injection, solution Solution Oral Tablet, film coated Oral Suppository Rectal Suppository Rectal Solution Intramuscular; Intravenous Tablet, coated Oral Syrup Oral Injection Parenteral Tablet Oral Tablet, coated Oral Solution Parenteral Injection Intramuscular; Intravenous Solution Parenteral Solution Intramuscular; Intravenous Solution Intramuscular; Intravenous; Subcutaneous Injection Parenteral Capsule, coated Oral Injection Intravenous Solution Intramuscular Solution Intravenous; Parenteral Injection, solution Parenteral Tablet Oral Solution / drops Oral Injection Solution Oral Tablet Tablet; tablet, film coated Oral Solution / drops; suspension / drops Ointment Injection, solution Intramuscular; Intravenous Tablet, film coated Oral Suppository Rectal 1 G Tablet Oral 500 MG Solution Intramuscular; Intravenous 2.5 g 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. [PubMed:11752352]
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. [PubMed:17344806]
- 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. [PubMed:17344806]
Drug created on September 11, 2007 20:09 / Updated on April 20, 2021 23:20