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Identification
NameMetamizole
Accession NumberDB04817
Typesmall molecule
Groupswithdrawn
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 Approvals of the NDA’s for dipyrone drug products were withdrawn on June 27, 1977 (see the Federal Register of June 17, 1977 (42 FR 30893)). Withdrawn from the Canadian market in 1963.

Structure
Thumb
Synonyms
SynonymLanguageCode
DipyroneNot AvailableNot Available
Salts
Name/CAS Structure Properties
Metamizole sodium
68-89-3
Thumb
  • InChI Key: DJGAAPFSPWAYTJ-UHFFFAOYSA-M
  • Monoisotopic Mass: 333.07592138
  • Average Mass: 333.339
DBSALT000332
Brand names
NameCompany
AlgocalminNot Available
AlgozoneNot Available
AnalginNot Available
DimethoneNot Available
DipironaNot Available
Neo-MelubrinaNot Available
NovalginNot Available
OptalginNot Available
ProtempNot Available
PyralginNot Available
Brand mixturesNot Available
Categories
CAS number50567-35-6
WeightAverage: 333.339
Monoisotopic: 333.07592138
Chemical FormulaC13H16N3NaO4S
InChI KeyInChIKey=DJGAAPFSPWAYTJ-UHFFFAOYSA-M
InChI
InChI=1S/C13H17N3O4S.Na/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);/q;+1/p-1
IUPAC Name
sodium [(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(methyl)amino]methanesulfonate
SMILES
[Na+].CN(CS([O-])(=O)=O)C1=C(C)N(C)N(C1=O)C1=CC=CC=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassAzoles
SubclassPyrazoles
Direct parentPhenylpyrazoles
Alternative parentsBenzene and Substituted Derivatives; Pyrazolones; Sulfonic Acids and Derivatives; Sulfonyls; Organic Sulfites; Tertiary Amines; Polyamines
Substituentspyrazolinone; benzene; organic sulfite; sulfonic acid derivative; sulfonyl; tertiary amine; polyamine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.
Pharmacology
IndicationUsed in the past as a powerful painkiller and fever reducer.
PharmacodynamicsDipyrone is a non-steroidal anti-inflammatory drug (NSAID), commonly used in the past as a powerful painkiller and fever reducer.
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrate Non-inhibitor 0.7064
CYP450 2D6 substrate Non-inhibitor 0.8562
CYP450 2C19 substrate Non-inhibitor 0.6768
CYP450 3A4 substrate 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
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility5.80e+00 g/lALOGPS
logP1.07ALOGPS
logP-0.82ChemAxon
logS-1.8ALOGPS
pKa (strongest acidic)-1.2ChemAxon
pKa (strongest basic)-0.44ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count6ChemAxon
hydrogen donor count0ChemAxon
polar surface area83.99ChemAxon
rotatable bond count4ChemAxon
refractivity78.92ChemAxon
polarizability31.11ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound522325
PubChem Substance46509035
ChemSpider6000
ChEBI25979
ChEMBL
Therapeutic Targets DatabaseDNC000568
WikipediaDipyrone
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Prostaglandin G/H synthase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Prostaglandin G/H synthase 1 P23219 Details

References:

  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

1. Cytochrome P450 2B6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytochrome P450 2B6 P20813 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

Comments
Drug created on September 11, 2007 14:09 / Updated on September 16, 2013 17:25