Dipyrone (CHEM016300)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:26:40 UTC
Update Date2016-11-09 01:15:22 UTC
Accession NumberCHEM016300
Identification
Common NameDipyrone
ClassSmall Molecule
DescriptionMetamizole, 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 Approvals of the NDA's for Metamizole drug products were withdrawn on June 27, 1977 (see the Federal Register of June 17, 1977 (42 FR 30893)). Withdrawn from the Canadian market in 1963.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AlgocalminChEBI
Aminopyrine sodium sulfonateChEBI
AnalginChEBI
Analgin (sodium salt)ChEBI
DipyroneChEBI
Meamizol sodicoChEBI
Metamizole sodiqueChEBI
Metamizolum natricumChEBI
MethampyroneChEBI
MethylmelubrinChEBI
Mexican aspirinChEBI
NeomelurbrinChEBI
Noraminophenazone methanesulfonate sodium saltChEBI
Noraminophenazone sodium mesylateChEBI
NovalginChEBI
Sodium (antipyrinylmethylamino)methanesulfonateChEBI
Sodium methylaminoantipyrine methanesulfonateChEBI
Sodium noramidopyrine methanesulfonateChEBI
SulpyrineChEBI
VetalginChEBI
Metamizole sodiumKegg
Aminopyrine sodium sulfonic acidGenerator
Aminopyrine sodium sulphonateGenerator
Aminopyrine sodium sulphonic acidGenerator
Noraminophenazone methanesulfonic acid sodium saltGenerator
Noraminophenazone methanesulphonate sodium saltGenerator
Noraminophenazone methanesulphonic acid sodium saltGenerator
Noraminophenazone sodium mesylic acidGenerator
Sodium (antipyrinylmethylamino)methanesulfonic acidGenerator
Sodium (antipyrinylmethylamino)methanesulphonateGenerator
Sodium (antipyrinylmethylamino)methanesulphonic acidGenerator
Sodium methylaminoantipyrine methanesulfonic acidGenerator
Sodium methylaminoantipyrine methanesulphonateGenerator
Sodium methylaminoantipyrine methanesulphonic acidGenerator
Sodium noramidopyrine methanesulfonic acidGenerator
Sodium noramidopyrine methanesulphonateGenerator
Sodium noramidopyrine methanesulphonic acidGenerator
NovalgetolMeSH
NovamidazophenMeSH
BiopyrinMeSH
Methanesulfonate sodium, noramidopyrineMeSH
Methanesulfonate, noramidopyrineMeSH
Noramidopyrine methanesulfonateMeSH
NovaminsulfoneMeSH
OptalginMeSH
PyralginMeSH
DipyroniumMeSH
MethamizoleMeSH
NaroneMeSH
SulpyrinMeSH
AlgopyrinMeSH
MetamizolMeSH
Noramidopyrine methanesulfonate sodiumMeSH
NormelubrineMeSH
Chemical FormulaC13H16N3NaO4S
Average Molecular Mass333.339 g/mol
Monoisotopic Mass333.076 g/mol
CAS Registry Number68-89-3
IUPAC Namesodium [(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(methyl)amino]methanesulfonate
Traditional Namesodium metamizole(1-)
SMILES[Na+].CN(CS([O-])(=O)=O)C1=C(C)N(C)N(C1=O)C1=CC=CC=C1
InChI IdentifierInChI=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
InChI KeyDJGAAPFSPWAYTJ-UHFFFAOYSA-M
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles 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
  • Monocyclic benzene moiety
  • Pyrazolinone
  • Benzenoid
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Organosulfonic acid
  • Sulfonyl
  • Alkanesulfonic acid
  • Vinylogous amide
  • Heteroaromatic compound
  • Lactam
  • Organic alkali metal salt
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic salt
  • Organosulfur compound
  • Organic oxygen compound
  • Organic sodium salt
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.8 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 Area83.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity78.92 m³·mol⁻¹ChemAxon
Polarizability31.11 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9210000000-0afef355301fc17c2ab5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-066r-9120000000-b465330a1885c099bc73Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-3950000000-68aa296020d535c13e5aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-008a-0589000000-b2e06a3bc03abe2c7ad1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-2390000000-f96215f9805484d3d245Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9700000000-723448621b6d4d8c57adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-3903000000-2a615794737c974d93b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-2893000000-f8d185e5d45c2b2b7599Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00l6-9510000000-0f180ea4f7628f16bdbcSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB04817
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMetamizole
Chemspider IDNot Available
ChEBI ID59033
PubChem Compound ID6236
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15012736
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15137974
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15595715
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15851637
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=16752674
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=17435797
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21446784
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=25776531
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=25789542
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=3044874
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=3425858