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 Approvals of the NDA's for dipyrone drug products were withdrawn on June 27, 1977 (see the Federal Register of June 17, 1977 (42 FR 30893)). Withdrawn from the Canadian market in 1963.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Approved, Investigational, Withdrawn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
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.

Pharmacology
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Drug Discovery
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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
Medicalerrors
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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.
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.
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 risk or severity of bleeding and hemorrhage can be increased when Metamizole is combined with Acenocoumarol.
AcetaminophenThe risk or severity of adverse effects can be increased when Acetaminophen is combined with Metamizole.
AcetohexamideThe protein binding of Acetohexamide can be decreased when combined with Metamizole.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Metamizole is combined with Acetylsalicylic acid.
AclidiniumMetamizole may decrease the excretion rate of Aclidinium which could result in a higher serum level.
Interactions
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Food Interactions
Not Available

Products

Products
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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
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ANTIALGINA®Metamizole sodium (300 mg) + Caffeine (30 mg) + Isometheptene mucate (30 mg)Tablet, film coatedOralTECNOQUIMICAS S.A.2007-04-24Not applicableColombia flag
ANTIALGINA�Metamizole sodium (300 mg) + Caffeine (30 mg) + Isometheptene (50 mg)SolutionOralTECNOFAR TQ S.A.S2007-03-062015-02-27Colombia flag
CAFETRIN �Metamizole (300 mg) + Caffeine (30 mg) + Isometheptene mucate (30 mg)Tablet, coatedOralLABORATORIOS RICH MONDS S.A.S2018-05-11Not applicableColombia flag
DIPIRONA 300 MG + ISOMETEPTENO 50 MG + CAFEINA 30 MG GOTASMetamizole sodium monohydrate (300 mg) + Caffeine (30 mg) + Isometheptene (50 mg)SolutionOralSANOFI-AVENTIS DE COLOMBIA S.A.2018-07-062019-04-22Colombia flag
DIPIRONA SODICA / ISOMETEPTENO MUCATO/CAFEINA 300 MG / 30 MG/30MG TABLETA RECUBIERTAMetamizole sodium (300 mg) + Caffeine (30 mg) + Isometheptene mucate (30 mg)Tablet, coatedOralLABORATORIO FRANCO COLOMBIANO LAFRANCOL S.A.S.2013-07-09Not applicableColombia flag
DIPIRONA SODICA 300 MG/ ISOMETEPTENO CLORHIDRATO 50 MG / CAFEINA 30 MG GOTASMetamizole sodium (300 mg) + Caffeine (30 mg) + Isometheptene (50 mg)SolutionOralLABORATORIO FRANCO COLOMBIANO LAFRANCOL S.A.S.2013-08-30Not applicableColombia flag
DOSALDIN® GOTASMetamizole sodium (300 mg) + Caffeine (30 mg) + Isometheptene (50 mg)SolutionOralSERVICIO TECNICO GONHER FARMACEUTICA LTDA.2010-05-10Not applicableColombia flag
ESPASMOBIL� GOTASMetamizole (333.4 mg) + Butylscopolamine bromide (6.67 mg)SolutionOralFARMACOL CHINOIN S.A.S..2006-11-102021-10-01Colombia flag
ESPASMOBIL�SOLUCION INYECTABLEMetamizole sodium (2.5 g) + Butylscopolamine bromide (20 mg)SolutionIntramuscular; IntravenousLABORATORIOS RYAN DE COLOMBIA S. EN C.2006-11-102019-08-05Colombia flag
HIOSCINA 20 MG + DIPIRONA 2.5 GMetamizole sodium (2.5 g) + Butylscopolamine (20 mg)SolutionIntramuscular; IntravenousLABORATORIOS RYAN DE COLOMBIA S.A.S.2006-11-10Not applicableColombia flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
NOVOPYRINE 1 GR/2 ML 10 AMPULMetamizole sodium (1 g/2ml)InjectionIntramuscular; IntravenousOSEL İLAÇ SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag

Categories

ATC Codes
N02BB72 — Metamizole sodium, combinations with psycholepticsN02BB02 — Metamizole sodiumN02BB52 — Metamizole sodium, combinations excl. psycholeptics
Drug Categories
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
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
4CompletedSupportive CareBeta-endorphin / Dipyrone / Hernia Surgery / Pain1
4CompletedTreatmentBack Pain Lower Back Chronic1
4CompletedTreatmentCesarean Sections / Neuropathic Pain / Postoperative pain1
4CompletedTreatmentFever1
4CompletedTreatmentInadequate or Impaired Respiratory Function / Pain1
4CompletedTreatmentPain1
4CompletedTreatmentPostoperative pain1
4CompletedTreatmentSub-acute Back Pain1
4RecruitingPreventionAnaesthesia therapy / Hip Fracture1
4RecruitingTreatmentBack Pain Lower Back1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Zhejiang Haisen Pharmaceutical Co. Ltd.
Dosage Forms
FormRouteStrength
Injection, solution
Injection, solutionParenteral1000 mg
TabletOral500 mg/1
SuppositoryRectal1000 MG
SuppositoryRectal
SolutionIntramuscular; Intravenous
SyrupOral3 g
SolutionIntramuscular; Intravenous
SolutionParenteral2.5 g
InjectionParenteral1 g
SolutionIntramuscular1 g
Tablet, coatedOral500 mg
SolutionOral500 mg
SolutionParenteral2000 mg
InjectionIntramuscular; Intravenous2 g
SolutionIntramuscular; Intravenous2 g
SolutionParenteral
Tablet, coatedOral
SolutionParenteral1 g
SolutionIntramuscular; Intravenous1 g
SolutionIntramuscular; Intravenous; Subcutaneous2.5 g
InjectionIntramuscular; Intravenous2500 mg
TabletOral0.5 g
SolutionParenteral2 g
TabletOral
SolutionOral
InjectionParenteral
Capsule, coatedOral
InjectionIntravenous
SolutionOral0.5 g
SolutionIntramuscular2.5 g
SolutionIntravenous; Parenteral2.5 g
Tablet, film coatedOral500 mg
Injection, solutionParenteral
TabletOral
Solution / dropsOral
SolutionOral500 MG/ML
Injection, solutionParenteral7.5 mg
Injection
TabletOral5 mg
SolutionOral300 mg
SolutionOral96 mg
Tablet
Tablet; tablet, film coatedOral
InjectionIntramuscular; Intravenous
Solution / drops; suspension / drops
Ointment
SuppositoryRectal300 mg
SyrupOral
Injection, solutionIntramuscular; Intravenous
Injection, solutionParenteral2.5 G
Tablet, film coatedOral
SuppositoryRectal
SuppositoryRectal1 G
TabletOral500 MG
SolutionIntramuscular; Intravenous2.5 g
Injection, solutionParenteral1 G/2ML
Tablet, coatedOral850 mg
Tablet, film coatedOral
Tablet, sugar coatedOral
SolutionIntravenous
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

Drugtargets
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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
  1. 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
  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. [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
  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. [Article]

Drug created on September 11, 2007 20:09 / Updated on July 29, 2021 04:17