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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2017-03-02 21:34:00 UTC
HMDB IDHMDB15503
Secondary Accession NumbersNone
Metabolite Identification
Common NameAntipyrine
DescriptionAn analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29)
Structure
Thumb
Synonyms
ValueSource
1,2-dihydro-1,5-Dimethyl-2-phenyl-3H-pyrazol-3-oneChEBI
2,3-Dimethyl-1-phenyl-5-pyrazoloneChEBI
FenazonaChEBI
PhenazoneChEBI
AnalgesineHMDB
AnodyninHMDB
AnodynineHMDB
AntipirinHMDB
AntipyrinHMDB
AntipyrinumHMDB
AzophenHMDB
AzophenumHMDB
FenazoneHMDB
PhenozoneHMDB
PyramidoneMeSH
Chemical FormulaC11H12N2O
Average Molecular Weight188.2258
Monoisotopic Molecular Weight188.094963016
IUPAC Name1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one
Traditional Nameantipyrine
CAS Registry Number60-80-0
SMILES
CN1N(C(=O)C=C1C)C1=CC=CC=C1
InChI Identifier
InChI=1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3
InChI KeyVEQOALNAAJBPNY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassAzoles
Direct ParentPhenylpyrazoles
Alternative Parents
Substituents
  • Phenylpyrazole
  • Monocyclic benzene moiety
  • Pyrazolinone
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
BiofunctionNot Available
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point114 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.74e+01 g/LNot Available
LogP0.38HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility47.4 mg/mLALOGPS
logP1.18ALOGPS
logP1.22ChemAxon
logS-0.6ALOGPS
pKa (Strongest Basic)0.37ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.55 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity56.42 m3·mol-1ChemAxon
Polarizability20.4 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001a-0900000000-94d2c7fe629bedc897b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-ebc5f64904e52ff3d68eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-602baaec0430c9c48fc7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-a3fafbc8e8baf10dba96View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-ad19708445bbe9cd2bffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-052s-2900000000-efb8c895ae384b102f76View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-4900000000-80fc3f4f0ffbc6d8c8bbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-3a2d3f4534b07f6de875View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-dbaaf801a6650b53331bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-0258999e6a4bf7041deaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-4b511d8866a35ece5abdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4s-2900000000-eea7fbb638b6e5146e90View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-4900000000-80478740d36be900a6e7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01q1-0900000000-e6dcb2d1a0ca860186fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-ae7f87ba95e0fc52493eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-1011-1900000000-a520cee151b2f2b6fcd1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-4fe0a2e33ea5e0c5c876View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01wb-0900000000-1eaec6590298997b716eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-65a45a9258dc65cd80a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Antipyrine Action PathwaySMP00692Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01435 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01435 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01435
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2121
KEGG Compound IDC13244
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenazone
NuGOwiki LinkHMDB15503
Metagene LinkHMDB15503
METLIN IDNot Available
PubChem Compound2206
PDB IDNot Available
ChEBI ID31225
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available