Febuxostat (CHEM019886)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:36:20 UTC
Update Date2016-11-09 01:16:05 UTC
Accession NumberCHEM019886
Identification
Common NameFebuxostat
ClassSmall Molecule
DescriptionFebuxostat is a xanathine oxidase (XO) inhibitor indicated in patients with gout suffering from hyperuricemia and is used in its chronic management. Febuxostat is not recommended for the treatment of asymptomatic hyperuricemia. Febuxostat is marketed under the trade name Febuxostat by Takeda Pharmaceuticals America, Inc., and was approved by the FDA in February 2009.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(3-Cyano-4-isobutoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylic acidChEBI
AdenuricChEBI
DonifoxateChEBI
FebudayChEBI
FeburicChEBI
FebuxostatumChEBI
GoturicChEBI
GoutexChEBI
TEI 6720ChEBI
TEI-6720ChEBI
TMX 67ChEBI
TMX-67ChEBI
UloricChEBI
ZurigChEBI
2-(3-Cyano-4-isobutoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylateGenerator
Donifoxic acidGenerator
2-(3-cyano-4-Isobutoxyphenyl)-4-methyl-5-thiazolecarboxylic acidMeSH
6720, TEIMeSH
2-[3-Cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylateGenerator
Chemical FormulaC16H16N2O3S
Average Molecular Mass316.375 g/mol
Monoisotopic Mass316.088 g/mol
CAS Registry Number144060-53-7
IUPAC Name2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid
Traditional Namefebuxostat
SMILESCC(C)COC1=C(C=C(C=C1)C1=NC(C)=C(S1)C(O)=O)C#N
InChI IdentifierInChI=1S/C16H16N2O3S/c1-9(2)8-21-13-5-4-11(6-12(13)7-17)15-18-10(3)14(22-15)16(19)20/h4-6,9H,8H2,1-3H3,(H,19,20)
InChI KeyBQSJTQLCZDPROO-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as thiazolecarboxylic acids and derivatives. These are heterocyclic compounds containing a thiazole ring which bears a carboxylic acid group (or a derivative thereof).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassThiazoles
Direct ParentThiazolecarboxylic acids and derivatives
Alternative Parents
Substituents
  • 2,4,5-trisubstituted 1,3-thiazole
  • Phenoxy compound
  • Benzonitrile
  • Thiazolecarboxylic acid or derivatives
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Azacycle
  • Carboxylic acid
  • Ether
  • Nitrile
  • Carbonitrile
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • 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 Solubility0.018 g/LALOGPS
logP3.8ALOGPS
logP3.52ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)3.08ChemAxon
pKa (Strongest Basic)0.39ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.21 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity93.93 m³·mol⁻¹ChemAxon
Polarizability33.88 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-0006-4090000000-636b08208913e37cf6c9Spectrum
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 - LC-ESI-qTof , Positivesplash10-03xr-0292000000-d8e012f875d1014fe351Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03xr-0292000000-d8e012f875d1014fe351Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066s-4089000000-c7acf0318016cd20bec2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-3091000000-70fc366c85a87b110805Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9220000000-e6f092b19cb56951c75bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0092000000-1d9268ebb0d7e9e4ca73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0190000000-8c117b3535dd9b43783aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01b9-6390000000-029b21a0f25181f7e081Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xr-2098000000-d7c4d373123c0fe32da1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-1090000000-a4e1f7032b3cedd91963Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l6-1290000000-f8dae3e7cfb7130dd262Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0091000000-492981b99c59ea00141bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0190000000-ee6d6f385111dcd5aae3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1390000000-27c92224dda6826d4dd3Spectrum
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 IDDB04854
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFebuxostat
Chemspider IDNot Available
ChEBI ID31596
PubChem Compound ID134018
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=25724536
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=30844048
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=30919894
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=31267805
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=31332638
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=31335677
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=31378626
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=31447893
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=31449565
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=31499267
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=31531831
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=31560952