Febuxostat (CED0004184)

Record Information
Version1.0
Creation Date2016-05-22 06:36:20 UTC
Update Date2026-08-19 15:26:56 UTC
Accession NumberCHEM019886
Identification
Common NameFebuxostat
ClassSmall Molecule
Description
Febuxostat is an organic compound with the formula C16H16N2O3S and an average molecular weight of 316.38 g/mol. Febuxostat belongs to the thiazoles, a subclass of azoles within the organic compounds. In terms of its biological activity, the compound acts as an inhibitor of the protein target xanthine dehydrogenase/oxidase (XDH). The compound is found in or released from two recorded sources: household cleaning and consumer products, specifically non electric simulated smoking devices, and healthcare, pharmaceuticals and veterinary products, specifically antigout preparations. The recorded route of exposure for this compound is oral.
Contaminant TypeNot Available
Chemical Structure
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
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 Solubility0.018 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-4090000000-636b08208913e37cf6c9Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03xr-0292000000-d8e012f875d1014fe351Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03xr-0292000000-d8e012f875d1014fe351Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-066s-4089000000-c7acf0318016cd20bec2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05fr-3091000000-70fc366c85a87b110805Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9220000000-e6f092b19cb56951c75bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0092000000-1d9268ebb0d7e9e4ca73Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0190000000-8c117b3535dd9b43783aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01b9-6390000000-029b21a0f25181f7e081Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03xr-2098000000-d7c4d373123c0fe32da1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ox-1090000000-a4e1f7032b3cedd91963Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00l6-1290000000-f8dae3e7cfb7130dd262Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0091000000-492981b99c59ea00141bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0190000000-ee6d6f385111dcd5aae3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-1390000000-27c92224dda6826d4dd3Not 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
2473.0Log mg/kg[1400:4400]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
366Antigout preparationsHealthcare, pharmaceuticals & veterinary productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
602MolluscicidesAgriculture & land managementNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
656Snap FastenersTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Febuxostat Drug Metabolism Action Pathway
Febuxostat Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureXanthine dehydrogenase/oxidaseP80457Bos taurusPredicted (SEA)0.389246
Xanthine dehydrogenase/oxidase structureClick to view 3D structureXanthine dehydrogenase/oxidaseP47989HumansPredicted (SEA)0.389246
RISC-loading complex subunit TARBP2 structureClick to view 3D structureRISC-loading complex subunit TARBP2Q15633HumansPredicted (SEA)0.0778492
Protein deacetylase HDAC6 structureClick to view 3D structureProtein deacetylase HDAC6Q9UBN7HumansPredicted (SEA)27.2472
Broad substrate specificity ATP-binding cassette transporter ABCG2 structureClick to view 3D structureBroad substrate specificity ATP-binding cassette transporter ABCG2Q9UNQ0HumansPredicted (SEA)55.8179
ATP-binding cassette sub-family C member 4 structureClick to view 3D structureATP-binding cassette sub-family C member 4O15439HumansPredicted (SEA)0.155698
Click to view 3D structureXanthine dehydrogenase/oxidaseP22985Rattus norvegicusPredicted (SEA)0.0778492
Sphingosine 1-phosphate receptor 1 structureClick to view 3D structureSphingosine 1-phosphate receptor 1P21453HumansPredicted (SEA)34.3315
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)686.319
Flavin reductase (NADPH) structureClick to view 3D structureFlavin reductase (NADPH)P30043HumansPredicted (SEA)0.0778492
Sphingosine 1-phosphate receptor 3 structureClick to view 3D structureSphingosine 1-phosphate receptor 3Q99500HumansPredicted (SEA)22.2649
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)835.945
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)702.511
AP2-associated protein kinase 1 structureClick to view 3D structureAP2-associated protein kinase 1Q2M2I8HumansPredicted (SEA)191.353
Peroxisome proliferator-activated receptor delta structureClick to view 3D structurePeroxisome proliferator-activated receptor deltaQ03181HumansPredicted (SEA)70.9985
Histone deacetylase 2 structureClick to view 3D structureHistone deacetylase 2Q92769HumansPredicted (SEA)353.747
Histone deacetylase 1 structureClick to view 3D structureHistone deacetylase 1Q13547HumansPredicted (SEA)662.73
Histone deacetylase 3 structureClick to view 3D structureHistone deacetylase 3O15379HumansPredicted (SEA)319.338
Peroxisome proliferator-activated receptor alpha structureClick to view 3D structurePeroxisome proliferator-activated receptor alphaQ07869HumansPredicted (SEA)152.818
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)1723.19
Click to view 3D structurePeroxisome proliferator-activated receptor deltaP35396Mus musculusPredicted (SEA)15.1806
Click to view 3D structurePeroxisome proliferator-activated receptor deltaQ0ZAQ8Canis lupus familiarisPredicted (SEA)21.5642
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)967.977
Peroxisome proliferator-activated receptor gamma structureClick to view 3D structurePeroxisome proliferator-activated receptor gammaP37231HumansPredicted (SEA)295.126
Free fatty acid receptor 1 structureClick to view 3D structureFree fatty acid receptor 1O14842HumansPredicted (SEA)110.857
Concentrations
Not Available
External Links
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