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 Approvals of the NDA's for dipyrone drug products were withdrawn on June 27, 1977 (see the Federal Register of June 17, 1977 (42 FR 30893)). Withdrawn from the Canadian market in 1963.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Approved, Investigational, Withdrawn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
Thumb
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
TargetActionsOrganism
UProstaglandin G/H synthase 1Not AvailableHumans
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.
DrugInteraction
AbacavirMetamizole may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Metamizole is combined with Abciximab.
AbirateroneThe metabolism of Abiraterone can be increased when combined with Metamizole.
AcalabrutinibThe metabolism of Acalabrutinib can be increased when combined with Metamizole.
AcarboseMetamizole may decrease the excretion rate of Acarbose which could result in a higher serum level.
AcebutololMetamizole may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Metamizole is combined with Aceclofenac.
AcemetacinThe risk or severity of adverse effects can be increased when Metamizole is combined with Acemetacin.
AcenocoumarolThe metabolism of Acenocoumarol can be increased when combined with Metamizole.
AcetaminophenThe risk or severity of adverse effects can be increased when Acetaminophen is combined with Metamizole.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

Products

Product Ingredients
IngredientUNIICASInChI Key
Metamizole magnesiumMS156427256150-97-6NHMUJYOBLYTIKO-UHFFFAOYSA-L
Metamizole sodiumVSU62Z74ON68-89-3DJGAAPFSPWAYTJ-UHFFFAOYSA-M
Metamizole sodium monohydrate6429L0L52Y5907-38-0UNZIDPIPYUMVPA-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
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
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
PhaseStatusPurposeConditionsCount
4CompletedTreatmentBack Pain Lower Back Chronic1
4CompletedTreatmentCesarean Section / Pain, Neuropathic / Postoperative pain1
4CompletedTreatmentFever1
4CompletedTreatmentInadequate or Impaired Respiratory Function / Pain1
4CompletedTreatmentPain1
4CompletedTreatmentSub-acute Back Pain1
4RecruitingPreventionAnaesthesia therapy / Hip Fracture1
4RecruitingTreatmentBack Pain Lower Back1
4RecruitingTreatmentPostoperative pain1
4TerminatedTreatmentPain1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Zhejiang Haisen Pharmaceutical Co. Ltd.
Dosage Forms
FormRouteStrength
Injection1 gr/2ml
Injection2.5 gr/5ml
Syrup250 mg/5ml
Injection, solutionParenteral1000 mg
SyrupOral50 mg/mL
SolutionOral30 mg
Tablet, film coatedOral30 mg
Tablet500 mg/1
Suppository1000 MG
SolutionIntramuscular; Intravenous2.5 g
Tablet, coatedOral30 mg
Tablet10 mg
Capsule25 mg
Injection, solutionIntramuscular; Intravenous1 g/2ml
TabletOral500 mg
SolutionIntramuscular; Intravenous1 g/2ml
TabletOral30 mg
Tablet, coatedOral500 mg
SolutionIntramuscular; Intravenous2 g
SolutionIntramuscular; Intravenous1 g
TabletOral0.5 g
Capsule, coatedOral350 mg
SolutionOral333.4 mg
Injection, solutionIntramuscular; Intravenous1000 mg/2ml
InjectionIntravenous1 g/2ml
Injection, solutionParenteral1.0 g
Solution / drops500 mg/ml
Tablet500 MG
SolutionOral500 MG/ML
Injection, solutionParenteral500 mg/ml
Tablet, film coatedOral500 MG
Injection, solutionParenteral7.5 mg
Injection
Tablet
SolutionOral300 mg
InjectionIntramuscular; Intravenous1 gr/2ml
Ointment50 g
Injection, solutionIntramuscular; Intravenous1 gr/2ml
Suppository300 mg
SyrupOral
Injection, solutionParenteral2.5 G
Syrup250 mg/ml
Injection, solution1 G/2ML
Solution / dropsOral500 MG/ML
Suppository1 G
SuppositoryRectal300 mg
SolutionOral500 MG
Injection, solutionParenteral1 G/2ML
InjectionIntramuscular; Intravenous1 g/2ml
Tablet, film coatedOral
Tablet, coatedOral850 mg
Injection1 g
Injection2 g
Tablet5 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.53 mg/mLALOGPS
logP-0.4ALOGPS
logP-0.82ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)-1.4ChemAxon
pKa (Strongest Basic)-0.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area81.16 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity80.04 m3·mol-1ChemAxon
Polarizability31.41 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7868
Blood Brain Barrier+0.8896
Caco-2 permeable-0.5869
P-glycoprotein substrateNon-substrate0.8148
P-glycoprotein inhibitor INon-inhibitor0.828
P-glycoprotein inhibitor IINon-inhibitor0.8107
Renal organic cation transporterNon-inhibitor0.921
CYP450 2C9 substrateNon-substrate0.8588
CYP450 2D6 substrateNon-substrate0.7959
CYP450 3A4 substrateSubstrate0.6035
CYP450 1A2 substrateNon-inhibitor0.7153
CYP450 2C9 inhibitorNon-inhibitor0.7064
CYP450 2D6 inhibitorNon-inhibitor0.8562
CYP450 2C19 inhibitorNon-inhibitor0.6768
CYP450 3A4 inhibitorNon-inhibitor0.9297
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8506
Ames testAMES toxic0.7763
CarcinogenicityCarcinogens 0.8197
BiodegradationReady biodegradable0.7192
Rat acute toxicity2.6224 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8411
hERG inhibition (predictor II)Non-inhibitor0.6724
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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
  1. 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
  1. 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
  1. 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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