Norphenazone (CED0003432)

Record Information
Version1.0
Creation Date2016-05-19 04:49:51 UTC
Update Date2026-08-17 21:19:14 UTC
Accession NumberCHEM015387
Identification
Common NameNorphenazone
ClassSmall Molecule
Description
Norphenazone is an organic compound with the formula C10H10N2O and an average molecular weight of 174.20 g/mol. Norphenazone belongs to the pyrazolines, a subclass of azolines within the organic compounds. Industrially, this organoheterocyclic compound is utilized as a dye. The substance has been identified in 16 recorded sources across various sectors. In the category of electrical and electronic equipment, it is found in electrodes, gas filled discharge tubes with solid cathode, colour television systems, electrically stimulated smoking devices, and conductors or conductive bodies characterised by the conductive materials, among three other sources. Within household cleaning and consumer products, it appears in soap detergents, perfumes within detergents and soaps, tobacco smoke filters, and non electric simulated smoking devices. Its presence is also recorded in food preservation within the food, food processing and cookware sector, in floors under building and construction, and in drinking water. Regarding healthcare, pharmaceuticals and veterinary products, norphenazone is categorized as an unclassified nervous system drug. Recorded exposure routes for the compound include oral and intravenous administration. At the molecular level, norphenazone acts as an upregulator of the apoptosis regulator Bcl-2 (BCL2).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
1-Phenyl-3-methyl-5-oxo-2-pyrazolineChEBI
2,4-Dihydro-5-methyl-2-phenyl-3H-pyrazol-3-oneChEBI
3-Methyl-1-phenyl-2-pyrazolin-5-oneChEBI
3-Methyl-1-phenyl-5-pyrazoloneChEBI
3-Methyl-1-phenylpyrazol-5-oneChEBI
C.I. developer 1ChEBI
Developer ZChEBI
MethylphenylpyrazoloneChEBI
NorphenazoneChEBI
Phenyl methyl pyrazoloneChEBI
PhenylmethylpyrazoloneChEBI
RadicutChEBI
RadicavaKegg
1-Phenyl-3-methyl-5-pyrazoloneMeSH
MCI 186MeSH
MCI-186MeSH
EdaraboneMeSH
NorantipyrineMeSH
1 Phenyl 3 methyl 5 pyrazoloneMeSH
3 Methyl 1 phenyl 2 pyrazolin 5 oneMeSH
Chemical FormulaC10H10N2O
Average Molecular Mass174.203 g/mol
Monoisotopic Mass174.079 g/mol
CAS Registry Number89-25-8
IUPAC Name3-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-5-one
Traditional Nameedaravone
SMILESCC1=NN(C(=O)C1)C1=CC=CC=C1
InChI IdentifierInChI=1S/C10H10N2O/c1-8-7-10(13)12(11-8)9-5-3-2-4-6-9/h2-6H,7H2,1H3
InChI KeyQELUYTUMUWHWMC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrazolones. Pyrazolones are compounds containing a pyrazole ring which bears a ketone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolines
Sub ClassPyrazolines
Direct ParentPyrazolones
Alternative Parents
Substituents
  • Benzenoid
  • Pyrazolinone
  • Monocyclic benzene moiety
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • 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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.94 g/LALOGPS
logP0.53ALOGPS
logP1.53ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)13.45ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.67 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.49 m³·mol⁻¹ChemAxon
Polarizability18.61 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-000x-7900000000-1b63674e9e61b0415592Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-1900000000-9c17dd936441a10926dcNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-1900000000-9c17dd936441a10926dcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0900000000-e9a7118da8dd61cf703dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-1900000000-96343e3befaa9cf0a207Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9100000000-aeca339c7e738592814aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-f624c623e550dc22aaa3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-1900000000-2012f697925d920763a6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9100000000-d2d3b4076db8592d0461Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0900000000-99e013a33d61f5b2babbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0900000000-f092173f0b19729a2e6dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9200000000-344f8ae11a95707342e4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-eb2d5882d0b284199cabNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-4d7edbfa19219b7402adNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0axu-9700000000-576a3531c2b1f5164af3Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1463.0Log mg/kg[820:2600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
384Unclassified nervous system drugsHealthcare, pharmaceuticals & veterinary productsNot Available
490Personal care & cosmeticsNot Available
497FloorsBuilding & ConstructionNot Available
509Colour Television SystemsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
523Gas Filled Discharge Tubes With Solid CathodeElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
533Sparking PlugsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
633Azo DyesTextiles, leather & furnishingsNot Available
639Degreasing LeatherTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureProtein RecAP9WHJ3Mycobacterium tuberculosisPredicted (SEA)39.0803
Click to view 3D structureProtein-lysine 6-oxidaseP28300HumansPredicted (SEA)1.71268
Click to view 3D structureMyosin-14Q6URW6Mus musculusPredicted (SEA)0.389246
Click to view 3D structureMyosin-7P79293Sus scrofaPredicted (SEA)0.389246
Click to view 3D structureNonmuscle myosin heavy chainQ789A4Gallus gallusPredicted (SEA)0.389246
Click to view 3D structureMyosin-2Q9TV63Sus scrofaPredicted (SEA)0.389246
LgtC structureClick to view 3D structureLgtCQ93EK7Neisseria meningitidisPredicted (SEA)2.02408
Sentrin-specific protease 8 structureClick to view 3D structureSentrin-specific protease 8Q96LD8HumansPredicted (SEA)24.8339
Click to view 3D structureDNA damage-inducible transcript 3 proteinP35639Mus musculusPredicted (SEA)131.176
X-box-binding protein 1 structureClick to view 3D structureX-box-binding protein 1P17861HumansPredicted (SEA)131.176
Click to view 3D structureGlucose-6-phosphate dehydrogenase-6-phosphogluconolactonaseQ9BHT9Plasmodium bergheiPredicted (SEA)33.0081
Regulator of G-protein signaling 8 structureClick to view 3D structureRegulator of G-protein signaling 8P57771HumansPredicted (SEA)4.82665
Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1 structureClick to view 3D structureCarboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1Q9GZU7HumansPredicted (SEA)114.75
Replicase polyprotein 1ab structureClick to view 3D structureReplicase polyprotein 1abP0DTD1SARS-CoV-2Predicted (SEA)212.217
Caspase-3 structureClick to view 3D structureCaspase-3P42574HumansPredicted (SEA)182.634
Click to view 3D structureL,D-transpeptidase 2I6Y9J2Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)Predicted (SEA)2.72472
Sulfhydryl oxidase 1 structureClick to view 3D structureSulfhydryl oxidase 1O00391HumansPredicted (SEA)2.72472
YTH domain-containing family protein 1 structureClick to view 3D structureYTH domain-containing family protein 1Q9BYJ9HumansPredicted (SEA)2.72472
Pyruvate carboxylase structureClick to view 3D structurePyruvate carboxylaseA0A0H3JRU9Staphylococcus aureus (strain Mu50 / ATCC 700699)Predicted (SEA)7.86277
Cyclin-dependent kinase 8 structureClick to view 3D structureCyclin-dependent kinase 8P49336HumansPredicted (SEA)999.506
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)2441.59
RAC-alpha serine/threonine-protein kinase structureClick to view 3D structureRAC-alpha serine/threonine-protein kinaseP31749HumansPredicted (SEA)1639.35
Ribosomal protein S6 kinase beta-1 structureClick to view 3D structureRibosomal protein S6 kinase beta-1P23443HumansPredicted (SEA)1406.74
MAP kinase-activated protein kinase 2 structureClick to view 3D structureMAP kinase-activated protein kinase 2P49137HumansPredicted (SEA)1511.68
RAC-beta serine/threonine-protein kinase structureClick to view 3D structureRAC-beta serine/threonine-protein kinaseP31751HumansPredicted (SEA)1371.7
Concentrations
Not Available
External Links
DrugBank IDDB12243
HMDB IDHMDB0251697
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEdaravone
Chemspider ID3881
ChEBI ID31530
PubChem Compound IDNot Available
Kegg Compound IDC13008
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12935312
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=14758002
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15304976
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=16545576
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=17280782
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=17997244
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=18485133
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=25348283
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=26196041
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=26778341
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=27018216
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=27037019
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=27056755
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=27116382
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=27128210