Oxyphenbutazone (CHEM016034)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-20 16:12:00 UTC
Update Date2016-11-09 01:15:19 UTC
Accession NumberCHEM016034
Identification
Common NameOxyphenbutazone
ClassSmall Molecule
DescriptionA metabolite of phenylbutazone obtained by hydroxylation at position 4 of one of the phenyl rings. Commonly used (as its hydrate) to treat pain, swelling and stiffness associated with arthritis and gout, it was withdrawn from the market 1984 following association with blood dyscrasis and Stevens-Johnson syndrome.
Contaminant Sources
  • IARC Carcinogens Group 3
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(p-Hydroxyphenyl)-2-phenyl-4-butyl-3,5-pyrazolidinedioneChEBI
1-Phenyl-2-(p-hydroxyphenyl)-3,5-dioxo-4-butylpyrazolidineChEBI
1-Phenyl-2-(p-hydroxyphenyl)-3,5-dioxo-4-N-butylpyrazolidineChEBI
3,5-Dioxo-1-phenyl-2-(p-hydroxyphenyl)-4-N-butylpyrazolideneChEBI
4-Butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedioneChEBI
4-Butyl-1-(p-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedioneChEBI
4-Butyl-2-(4-hydroxyphenyl)-1-phenyl-3,5-dioxopyrazolidineChEBI
4-Butyl-2-(p-hydroxyphenyl)-1-phenyl-3,5-pyrazolidinedioneChEBI
HydroxyphenylbutazonChEBI
Oxi-fenibutolChEBI
OxifenbutazonaChEBI
OxifenylbutazonChEBI
OxiphenbutazonumChEBI
OxyphenbutazonumChEBI
OxyphenylbutazoneChEBI
p-HydroxyphenylbutazoneChEBI
p-OxyphenylbutazoneChEBI
ReozonKegg
TanderilMeSH
Belmac brand OF oxyphenbutazoneMeSH
DiflamilMeSH
HydroxyphenylbutazoneMeSH
Novartis ophthalmics brand OF oxyphenbutazoneMeSH
Chemical FormulaC19H20N2O3
Average Molecular Mass324.374 g/mol
Monoisotopic Mass324.147 g/mol
CAS Registry Number129-20-4
IUPAC Name4-butyl-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione
Traditional Nameoxyphenbutazone
SMILESCCCCC1C(=O)N(N(C1=O)C1=CC=C(O)C=C1)C1=CC=CC=C1
InChI IdentifierInChI=1S/C19H20N2O3/c1-2-3-9-17-18(23)20(14-7-5-4-6-8-14)21(19(17)24)15-10-12-16(22)13-11-15/h4-8,10-13,17,22H,2-3,9H2,1H3
InChI KeyHFHZKZSRXITVMK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-2-unsubstituted benzenoids
Direct Parent1-hydroxy-2-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-2-unsubstituted benzenoid
  • 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 Solubility0.26 g/LALOGPS
logP2.79ALOGPS
logP3.83ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)4.87ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area60.85 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity90.74 m³·mol⁻¹ChemAxon
Polarizability35.14 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9601000000-0e93b2309b6f4ff21792Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054k-8791000000-637b7e1dbae4d383b921Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-3920000000-8a5be556648d9ff3213bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1129000000-635a75af02145840f4c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-7396000000-7af7a18b0ccfe9a692b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9300000000-beaa3a49e9b7a30e7df1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0119000000-982c7f5b104baf102d43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dj-6698000000-2933626114d1b33aada5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4p-7900000000-77b1ac23e35e6cb8ed59Spectrum
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 IDDB03585
HMDB IDHMDB0256021
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkOxyphenbutazone
Chemspider ID4480
ChEBI ID76258
PubChem Compound IDNot Available
Kegg Compound IDC19494
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1222682
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=141661
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=14345781
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18963985
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19161668
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=20299217
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21428758
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23012453
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23983013
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=2862290
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=380595
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=501546
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=546857
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=6617711
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=6860567
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=6894379
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=7001487
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=7309664
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=7368966
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=766157
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=835859