kebuzone (CHEM043747)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 11:13:48 UTC
Update Date2016-11-09 01:22:59 UTC
Accession NumberCHEM043747
Identification
Common Namekebuzone
ClassSmall Molecule
DescriptionA pyrazolidine that is phenylbutazone in which the two methylene hydrogens at postion 3 on the butyl chain are replaced by an oxo group.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Diphenyl-4-(gamma-ketobutyl)-3,5-pyrazolidinedioneChEBI
4-(3-Oxobutyl)-1,2-diphenyl-3,5-pyrazolidinedioneChEBI
KebuzonumChEBI
KetophenylbutazonumChEBI
QuebuzonaChEBI
KebuzoneKegg
1,2-Diphenyl-4-(g-ketobutyl)-3,5-pyrazolidinedioneGenerator
1,2-Diphenyl-4-(γ-ketobutyl)-3,5-pyrazolidinedioneGenerator
ChebutanHMDB
PhloguronHMDB
ChetofenilbutazoneHMDB
CopireneHMDB
RachetonHMDB
ChetofenilbutazonHMDB
KetazonHMDB
KebuzonHMDB
KetophenylbutazoneChEBI
Chemical FormulaC19H18N2O3
Average Molecular Mass322.358 g/mol
Monoisotopic Mass322.132 g/mol
CAS Registry Number853-34-9
IUPAC Name4-(3-oxobutyl)-1,2-diphenylpyrazolidine-3,5-dione
Traditional Namekebuzone
SMILESCC(=O)CCC1C(=O)N(N(C1=O)C1=CC=CC=C1)C1=CC=CC=C1
InChI IdentifierInChI=1S/C19H18N2O3/c1-14(22)12-13-17-18(23)20(15-8-4-2-5-9-15)21(19(17)24)16-10-6-3-7-11-16/h2-11,17H,12-13H2,1H3
InChI KeyLGYTZKPVOAIUKX-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
  • Ketone
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • 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 Solubility0.11 g/LALOGPS
logP1.99ALOGPS
logP2.7ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)4.17ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area57.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity89.37 m³·mol⁻¹ChemAxon
Polarizability33.64 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, Positivesplash10-000x-9451000000-20f6c914fed406957207Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0019000000-c5e4c3ccd5cce60874beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0avi-4179000000-25bd6883a89d363eb632Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-9230000000-5de6d5996d83a5d16f71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0029000000-7b443a0fcd3e3a5df407Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kmi-5579000000-5ea363b653693ed3125cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-706ef9e0b02460c9ff45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-33d59492e0378fd90171Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0039000000-36491d2e363fb42d8075Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07bf-9800000000-f0dc377845da2da2132cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-c0122f56c13f37edfeb3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0umi-0194000000-144aa7f826627fd26805Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053u-9200000000-9967204f9ae136396b56Spectrum
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 IDDB08940
HMDB IDHMDB0041914
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkKebuzone
Chemspider ID3692
ChEBI ID31749
PubChem Compound ID3824
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=10758780
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=13718791
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=13912486
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=13912489
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=14089873
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=34731
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=4953937
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=5364826
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=5630939
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=5680889
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=5780934
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=5973922
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=6077826
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=8573641
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=8878255
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=909904
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=9650370
18. Zhivkova ZD, Russeva VN: Binding of kebuzone to human serum albumin studied by high performance liquid affinity chromatography. Arzneimittelforschung. 2000 Mar;50(3):272-5.
19. CUGURRA F, BRAMBILLA G: [Comparison between phenylbutazone and ketophenylbutazone]. Arch Ital Sci Farmacol. 1960 Jul;10:195-207.
20. SIBLIKOVA O, CERNA M, HAIS IM: [Contribution to the metabolism of ketophenylbutazone. II. Ketophenylbutazone metabolites in urine]. Cesk Farm. 1962 Mar;11:123-6.
21. SIBLIKOVA O, VACHEK J, CERNA M, TESAREK B, VITULOVA V: [Contribution to the metabolism of ketophenylbutazone. I]. Cesk Farm. 1962 Mar;11:118-23.
22. SALVI V: [CLINICAL EXPERIENCES WITH THE USE OF KETOPHENYLBUTAZONE]. Minerva Med. 1963 Sep 8;54:2554-6.
23. Horakova Z, Metys J, Cepelak V: [Influence of phenylbutazone and ketophenylbutazone on the gastrointestinal tract]. Therapie. 1965 May-Jun;20(3):617-30.
24. Huvar A, Sitar J, Kubistova J: [Time of onset of changes in the renographic curve following administration of ketophenylbutazone]. Vnitr Lek. 1969 Nov;15(11):1070-5.
25. Nielsen GH, Holmen-Christensen H: Plasma concentrations of monophenylbutazone, phenylbutazone and ketophenylbutazone after intravenous administration to rats and mice. Acta Pharmacol Toxicol (Copenh). 1967;25:Suppl 4:42.
26. Sitar J: [Further experiences with suppression of anginal pain with ketophenylbutazone]. Vnitr Lek. 1968 Sep;14(9):899-904.
27. Huvar A, Sitar J: [Effect of ketophenylbutazone on the renographic tracing examined with hippuran I-131]. Vnitr Lek. 1969 Apr;15(4):326-31.
28. Rejholec V: [Some new possibilities for the use of ketophenylbutazone (Ketazon-Spofa) in rheumatology]. Reumatizam. 1966;13(6):205-9.
29. Queisnerova M, Siblikova O, Veverkova M, Macek K, Nemecek O: [Biotransformation of ketophenylbutazone in vitro]. Cesk Farm. 1967 Jun;16(5):219-22.