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 Approvals of the NDA's for dipyrone drug products were withdrawn on June 27, 1977 (see the Federal Register of June 17, 1977 (42 FR 30893)). Withdrawn from the Canadian market in 1963.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- Approved, Investigational, Withdrawn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
- Indication
Used in the past as a powerful painkiller and fever reducer.
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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
Learn about our commercial Adverse Effects data.
Learn More- 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 Unlock Additional DataAbacavir 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. Abiraterone The metabolism of Abiraterone can be increased when combined with Metamizole. Acalabrutinib The metabolism of Acalabrutinib can be increased when combined with Metamizole. Acarbose Metamizole may decrease the excretion rate of Acarbose which could result in a higher serum level. 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 metabolism of Acenocoumarol can be increased when combined with Metamizole. Acetaminophen The risk or severity of adverse effects can be increased when Acetaminophen is combined with Metamizole. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
- 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
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 Treatment Back Pain Lower Back Chronic 1 4 Completed Treatment Cesarean Section / Pain, Neuropathic / 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 4 Terminated Treatment Pain 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Zhejiang Haisen Pharmaceutical Co. Ltd.
- Dosage Forms
Form Route Strength Injection 1 gr/2ml Injection 2.5 gr/5ml Syrup 250 mg/5ml Injection, solution Parenteral 1000 mg Syrup Oral 50 mg/mL Solution Oral 30 mg Tablet, film coated Oral 30 mg Tablet 500 mg/1 Suppository 1000 MG Solution Intramuscular; Intravenous 2.5 g Tablet, coated Oral 30 mg Tablet 10 mg Capsule 25 mg Injection, solution Intramuscular; Intravenous 1 g/2ml Tablet Oral 500 mg Solution Intramuscular; Intravenous 1 g/2ml Tablet Oral 30 mg Tablet, coated Oral 500 mg Solution Intramuscular; Intravenous 2 g Solution Intramuscular; Intravenous 1 g Tablet Oral 0.5 g Capsule, coated Oral 350 mg Solution Oral 333.4 mg Injection, solution Intramuscular; Intravenous 1000 mg/2ml Injection Intravenous 1 g/2ml Injection, solution Parenteral 1.0 g Solution / drops 500 mg/ml Tablet 500 MG Solution Oral 500 MG/ML Injection, solution Parenteral 500 mg/ml Tablet, film coated Oral 500 MG Injection, solution Parenteral 7.5 mg Injection Tablet Solution Oral 300 mg Injection Intramuscular; Intravenous 1 gr/2ml Ointment 50 g Injection, solution Intramuscular; Intravenous 1 gr/2ml Suppository 300 mg Syrup Oral Injection, solution Parenteral 2.5 G Syrup 250 mg/ml Injection, solution 1 G/2ML Solution / drops Oral 500 MG/ML Suppository 1 G Suppository Rectal 300 mg Solution Oral 500 MG Injection, solution Parenteral 1 G/2ML Injection Intramuscular; Intravenous 1 g/2ml Tablet, film coated Oral Tablet, coated Oral 850 mg Injection 1 g Injection 2 g Tablet 5 mg - 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
- 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 14:09 / Updated on October 21, 2020 00:56
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