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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 Approvals of the NDA’s for dipyrone drug products were withdrawn on June 27, 1977 (see the Federal Register of June 17, 1977 (42 FR 30893)). Withdrawn from the Canadian market in 1963.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
Dipyrone
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
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
Salts
Name/CASStructureProperties
Metamizole sodium
68-89-3
Thumb
  • InChI Key: DJGAAPFSPWAYTJ-UHFFFAOYSA-M
  • Monoisotopic Mass: 333.07592138
  • Average Mass: 333.339
DBSALT000332
Categories
UNII934T64RMNJ
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassPyrazoles
Direct ParentPhenylpyrazoles
Alternative Parents
Substituents
  • Phenylpyrazole
  • Dialkylarylamine
  • Benzenoid
  • Pyrazolinone
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous amide
  • Alkanesulfonic acid
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonic acid
  • Tertiary amine
  • Lactam
  • Azacycle
  • Hydrocarbon derivative
  • Organic alkali metal salt
  • Organic sodium salt
  • Organic salt
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic zwitterion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
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 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.8 mg/mLALOGPS
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 Area83.99 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity78.92 m3·mol-1ChemAxon
Polarizability31.11 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesN02BB02N02BB52N02BB72
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AldesleukinThe risk or severity of adverse effects can be increased when Metamizole is combined with Aldesleukin.
AlemtuzumabThe risk or severity of adverse effects can be increased when Metamizole is combined with Alemtuzumab.
AltretamineThe risk or severity of adverse effects can be increased when Metamizole is combined with Altretamine.
AmsacrineThe risk or severity of adverse effects can be increased when Metamizole is combined with Amsacrine.
Arsenic trioxideThe risk or severity of adverse effects can be increased when Metamizole is combined with Arsenic trioxide.
AzacitidineThe risk or severity of adverse effects can be increased when Metamizole is combined with Azacitidine.
BelinostatThe risk or severity of adverse effects can be increased when Metamizole is combined with Belinostat.
BendamustineThe risk or severity of adverse effects can be increased when Metamizole is combined with Bendamustine.
BevacizumabThe risk or severity of adverse effects can be increased when Metamizole is combined with Bevacizumab.
BexaroteneThe risk or severity of adverse effects can be increased when Metamizole is combined with Bexarotene.
BlinatumomabThe risk or severity of adverse effects can be increased when Metamizole is combined with Blinatumomab.
BortezomibThe risk or severity of adverse effects can be increased when Metamizole is combined with Bortezomib.
BosutinibThe risk or severity of adverse effects can be increased when Metamizole is combined with Bosutinib.
BusulfanThe risk or severity of adverse effects can be increased when Metamizole is combined with Busulfan.
CabazitaxelThe risk or severity of adverse effects can be increased when Metamizole is combined with Cabazitaxel.
CapecitabineThe risk or severity of adverse effects can be increased when Metamizole is combined with Capecitabine.
CarbamazepineThe risk or severity of adverse effects can be increased when Metamizole is combined with Carbamazepine.
CarboplatinThe risk or severity of adverse effects can be increased when Metamizole is combined with Carboplatin.
CarfilzomibThe risk or severity of adverse effects can be increased when Metamizole is combined with Carfilzomib.
CarmustineThe risk or severity of adverse effects can be increased when Metamizole is combined with Carmustine.
ChlorambucilThe risk or severity of adverse effects can be increased when Metamizole is combined with Chlorambucil.
ChloramphenicolThe risk or severity of adverse effects can be increased when Metamizole is combined with Chloramphenicol.
CisplatinThe risk or severity of adverse effects can be increased when Metamizole is combined with Cisplatin.
CladribineThe risk or severity of adverse effects can be increased when Metamizole is combined with Cladribine.
ClofarabineThe risk or severity of adverse effects can be increased when Metamizole is combined with Clofarabine.
CyclophosphamideThe risk or severity of adverse effects can be increased when Metamizole is combined with Cyclophosphamide.
CytarabineThe risk or severity of adverse effects can be increased when Metamizole is combined with Cytarabine.
DacarbazineThe risk or severity of adverse effects can be increased when Metamizole is combined with Dacarbazine.
DactinomycinThe risk or severity of adverse effects can be increased when Metamizole is combined with Dactinomycin.
DasatinibThe risk or severity of adverse effects can be increased when Metamizole is combined with Dasatinib.
DaunorubicinThe risk or severity of adverse effects can be increased when Metamizole is combined with Daunorubicin.
DecitabineThe risk or severity of adverse effects can be increased when Metamizole is combined with Decitabine.
DexrazoxaneThe risk or severity of adverse effects can be increased when Metamizole is combined with Dexrazoxane.
DinutuximabThe risk or severity of adverse effects can be increased when Metamizole is combined with Dinutuximab.
DocetaxelThe risk or severity of adverse effects can be increased when Metamizole is combined with Docetaxel.
DoxorubicinThe risk or severity of adverse effects can be increased when Metamizole is combined with Doxorubicin.
EpirubicinThe risk or severity of adverse effects can be increased when Metamizole is combined with Epirubicin.
EribulinThe risk or severity of adverse effects can be increased when Metamizole is combined with Eribulin.
EtoposideThe risk or severity of adverse effects can be increased when Metamizole is combined with Etoposide.
EverolimusThe risk or severity of adverse effects can be increased when Metamizole is combined with Everolimus.
FloxuridineThe risk or severity of adverse effects can be increased when Metamizole is combined with Floxuridine.
FlucytosineThe risk or severity of adverse effects can be increased when Metamizole is combined with Flucytosine.
FludarabineThe risk or severity of adverse effects can be increased when Metamizole is combined with Fludarabine.
FluorouracilThe risk or severity of adverse effects can be increased when Metamizole is combined with Fluorouracil.
GemcitabineThe risk or severity of adverse effects can be increased when Metamizole is combined with Gemcitabine.
Gemtuzumab ozogamicinThe risk or severity of adverse effects can be increased when Metamizole is combined with Gemtuzumab ozogamicin.
HydroxyureaThe risk or severity of adverse effects can be increased when Metamizole is combined with Hydroxyurea.
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Metamizole is combined with Ibritumomab.
IbrutinibThe risk or severity of adverse effects can be increased when Metamizole is combined with Ibrutinib.
IdarubicinThe risk or severity of adverse effects can be increased when Metamizole is combined with Idarubicin.
IfosfamideThe risk or severity of adverse effects can be increased when Metamizole is combined with Ifosfamide.
ImatinibThe risk or severity of adverse effects can be increased when Metamizole is combined with Imatinib.
Interferon alfa-n3The risk or severity of adverse effects can be increased when Metamizole is combined with Interferon alfa-n3.
Interferon alfacon-1The risk or severity of adverse effects can be increased when Metamizole is combined with Interferon alfacon-1.
IrinotecanThe risk or severity of adverse effects can be increased when Metamizole is combined with Irinotecan.
IxabepiloneThe risk or severity of adverse effects can be increased when Metamizole is combined with Ixabepilone.
IxazomibThe risk or severity of adverse effects can be increased when Metamizole is combined with Ixazomib.
L-PhenylalanineThe risk or severity of adverse effects can be increased when Metamizole is combined with L-Phenylalanine.
LenalidomideThe risk or severity of adverse effects can be increased when Metamizole is combined with Lenalidomide.
LinezolidThe risk or severity of adverse effects can be increased when Metamizole is combined with Linezolid.
LomustineThe risk or severity of adverse effects can be increased when Metamizole is combined with Lomustine.
MechlorethamineThe risk or severity of adverse effects can be increased when Metamizole is combined with Mechlorethamine.
MelphalanThe risk or severity of adverse effects can be increased when Metamizole is combined with Melphalan.
MercaptopurineThe risk or severity of adverse effects can be increased when Metamizole is combined with Mercaptopurine.
MethimazoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Methimazole.
MethotrexateThe risk or severity of adverse effects can be increased when Methotrexate is combined with Metamizole.
MitomycinThe risk or severity of adverse effects can be increased when Metamizole is combined with Mitomycin.
MitoxantroneThe risk or severity of adverse effects can be increased when Metamizole is combined with Mitoxantrone.
NelarabineThe risk or severity of adverse effects can be increased when Metamizole is combined with Nelarabine.
NilotinibThe risk or severity of adverse effects can be increased when Metamizole is combined with Nilotinib.
ObinutuzumabThe risk or severity of adverse effects can be increased when Metamizole is combined with Obinutuzumab.
OlaparibThe risk or severity of adverse effects can be increased when Metamizole is combined with Olaparib.
OsimertinibThe risk or severity of adverse effects can be increased when Metamizole is combined with Osimertinib.
OxaliplatinThe risk or severity of adverse effects can be increased when Metamizole is combined with Oxaliplatin.
PaclitaxelThe risk or severity of adverse effects can be increased when Metamizole is combined with Paclitaxel.
PalbociclibThe risk or severity of adverse effects can be increased when Metamizole is combined with Palbociclib.
Peginterferon alfa-2aThe risk or severity of adverse effects can be increased when Metamizole is combined with Peginterferon alfa-2a.
Peginterferon alfa-2bThe risk or severity of adverse effects can be increased when Metamizole is combined with Peginterferon alfa-2b.
PemetrexedThe risk or severity of adverse effects can be increased when Metamizole is combined with Pemetrexed.
PentostatinThe risk or severity of adverse effects can be increased when Metamizole is combined with Pentostatin.
PomalidomideThe risk or severity of adverse effects can be increased when Metamizole is combined with Pomalidomide.
PonatinibThe risk or severity of adverse effects can be increased when Metamizole is combined with Ponatinib.
ProcarbazineThe risk or severity of adverse effects can be increased when Metamizole is combined with Procarbazine.
PropylthiouracilThe risk or severity of adverse effects can be increased when Metamizole is combined with Propylthiouracil.
RaltitrexedThe risk or severity of adverse effects can be increased when Metamizole is combined with Raltitrexed.
RituximabThe risk or severity of adverse effects can be increased when Metamizole is combined with Rituximab.
RuxolitinibThe risk or severity of adverse effects can be increased when Metamizole is combined with Ruxolitinib.
SirolimusThe risk or severity of adverse effects can be increased when Metamizole is combined with Sirolimus.
SorafenibThe risk or severity of adverse effects can be increased when Metamizole is combined with Sorafenib.
StreptozocinThe risk or severity of adverse effects can be increased when Metamizole is combined with Streptozocin.
TacrolimusThe risk or severity of adverse effects can be increased when Metamizole is combined with Tacrolimus.
Tedizolid PhosphateThe risk or severity of adverse effects can be increased when Metamizole is combined with Tedizolid Phosphate.
TemozolomideThe risk or severity of adverse effects can be increased when Metamizole is combined with Temozolomide.
TemsirolimusThe risk or severity of adverse effects can be increased when Metamizole is combined with Temsirolimus.
TeniposideThe risk or severity of adverse effects can be increased when Metamizole is combined with Teniposide.
ThalidomideThe risk or severity of adverse effects can be increased when Metamizole is combined with Thalidomide.
ThiotepaThe risk or severity of adverse effects can be increased when Metamizole is combined with Thiotepa.
TioguanineThe risk or severity of adverse effects can be increased when Metamizole is combined with Tioguanine.
TofacitinibThe risk or severity of adverse effects can be increased when Metamizole is combined with Tofacitinib.
TopotecanThe risk or severity of adverse effects can be increased when Metamizole is combined with Topotecan.
TositumomabThe risk or severity of adverse effects can be increased when Metamizole is combined with Tositumomab.
TrabectedinThe risk or severity of adverse effects can be increased when Metamizole is combined with Trabectedin.
Trastuzumab emtansineThe risk or severity of adverse effects can be increased when Metamizole is combined with ado-trastuzumab emtansine.
VinblastineThe risk or severity of adverse effects can be increased when Metamizole is combined with Vinblastine.
VindesineThe risk or severity of adverse effects can be increased when Metamizole is combined with Vindesine.
VinorelbineThe risk or severity of adverse effects can be increased when Metamizole is combined with Vinorelbine.
VorinostatThe risk or severity of adverse effects can be increased when Metamizole is combined with Vorinostat.
ZidovudineThe risk or severity of adverse effects can be increased when Metamizole is combined with Zidovudine.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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 gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the gener...
Gene Name:
PTGS1
Uniprot ID:
P23219
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
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Comments
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Drug created on September 11, 2007 14:09 / Updated on September 16, 2013 17:25