Phenylbutazone (CHEM015999)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-20 16:10:14 UTC
Update Date2016-11-09 01:15:18 UTC
Accession NumberCHEM015999
Identification
Common NamePhenylbutazone
ClassSmall Molecule
DescriptionA drug that has anti-inflammatory, antipyretic, and analgesic activities. It is especially effective in the treatment of ankylosing spondylitis. It also is useful in rheumatoid arthritis and Reiter's syndrome (investigational indication). Although phenylbutazone is effective in gouty arthritis, risk/benefit considerations indicate that this drug should not be employed for this disease. (From AMA Drug Evaluations Annual, 1994, p1822)
Contaminant Sources
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 3
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,5-Dioxo-1,2-diphenyl-4-N-butylpyrazolidineChEBI
4-BUTYL-1,2-diphenyl-pyrazolidine-3,5-dioneChEBI
4-N-Butyl-1,2-diphenyl-3,5-pyrazolidinedioneChEBI
FenilbutazonaChEBI
PhenbutazoneChEBI
PhenylbutazonChEBI
PhenylbutazonumChEBI
AzolidKegg
ButacoteHMDB
ButapirazolHMDB
FenilbutazonHMDB
ButadionHMDB
ButadioneHMDB
ButapyrazoleHMDB
ButazolidinHMDB
DiphenylbutazoneHMDB
Chemical FormulaC19H20N2O2
Average Molecular Mass308.374 g/mol
Monoisotopic Mass308.152 g/mol
CAS Registry Number50-33-9
IUPAC Name4-butyl-1,2-diphenylpyrazolidine-3,5-dione
Traditional Name'esteve'
SMILESCCCCC1C(=O)N(N(C1=O)C1=CC=CC=C1)C1=CC=CC=C1
InChI IdentifierInChI=1S/C19H20N2O2/c1-2-3-14-17-18(22)20(15-10-6-4-7-11-15)21(19(17)23)16-12-8-5-9-13-16/h4-13,17H,2-3,14H2,1H3
InChI KeyVYMDGNCVAMGZFE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Pyrazolidinone
  • 1,3-dicarbonyl compound
  • Pyrazolidine
  • Carboxylic acid hydrazide
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • 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 Solubility0.14 g/LALOGPS
logP2.81ALOGPS
logP4.14ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)5.13ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.62 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity88.76 m³·mol⁻¹ChemAxon
Polarizability34.15 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-005c-9450000000-4ff37844132da56b866eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-0009000000-f8e4cda83d45cc4ca59bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-0549000000-2907029e48d9c65ae00eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-001i-2910000000-bb1ac78907a0338c7dc6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000x-6900000000-4f14a2268cc3ae06d3e5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9400000000-d5012ae523568dc8e63cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9100000000-2af914d40adc6817f026Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9000000000-1b11164dde00c44d0ffeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9000000000-3b304315d58e9e8f6984Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00kf-9000000000-b6387c41c12a5abb6d4bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0009000000-bde0ac035aafd4e337f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0092000000-e77e2c9ca9127d3ecff9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4l-0196000000-6d31987fe09f0949a98dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-016r-0190000000-6b839462a4e745d1fc0dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00vi-0290000000-c78339fd5994808afb08Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-0109000000-c3cb4b19bc15bf87c709Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03kl-2921000000-02a08606b3d2e3c8c702Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01vo-5910000000-1e1a7cd346204d8387aaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-9700000000-b87550cf5df8c862c64aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00kf-9500000000-222c301c8bf7fa8c9490Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1109000000-afb5ea69eff4404428beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aou-9276000000-d9698fa12a608213d596Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9110000000-43fc2f7c8c7d34d3c784Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0119000000-bae6357c0badde196104Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-6669000000-1cf1313cd0d66117dd0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-6a338e07dc558445ef7dSpectrum
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 IDDB00812
HMDB IDHMDB0014950
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDP1Z
Wikipedia LinkPhenylbutazone
Chemspider ID4617
ChEBI ID48574
PubChem Compound ID4781
Kegg Compound IDC07440
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11264893
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12692637
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=13010905
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=13048452
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=13747451
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19614844
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=20176071
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21668837
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22082440
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22180948
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22245664
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23369749
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23525812
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=25287371
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=26090772
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=26808199
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=3425858
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=7655439