Chemical Component Summary

Name2-(3-CYANO-4-ISOBUTOXY-PHENYL)-4-METHYL-5-THIAZOLE-CARBOXYLIC ACID
Identifiers2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid
FormulaC16 H16 N2 O3 S
Molecular Weight316.375
TypeNON-POLYMER
Isomeric SMILESCc1c(sc(n1)c2ccc(c(c2)C#N)OCC(C)C)C(=O)O
InChIInChI=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)
InChIKeyBQSJTQLCZDPROO-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count38
Chiral Atom Count0
Bond Count39
Aromatic Bond Count12

Drug Info: DrugBank

DrugBank IDDB04854 
NameFebuxostat
Groups approved
DescriptionFebuxostat is a non-purine xanthine oxidase (XO) inhibitor.[A39743] In early 2008, febuxostat was granted marketing authorization by the European Commission for the treatment of chronic hyperuricemia and gout.[A230548] In the following year, the FDA for approved febuxostat for use in the chronic management of hyperuricemia in adult patients with gout who have an inadequate response or intolerance to [allopurinol].[L32238] Gout is a form of arthritis that is caused by the accumulation of uric acid crystal in or around a joint, leading to inflammation and further deposition of uric acid crystal deposition in bones, joints, tissues, and other organs in the long term. Gout is closely associated with hyperuricemia. Febuxostat works by inhibiting the activity of an enzyme that is responsible for the synthesis of uric acid, thereby reducing serum uric acid levels.[A230548] In February 2019, a black box warning for febuxostat was added, based on the findings of a post-market clinical study (the CARES trial) where there was an increased risk of cardiovascular (CV) fatal outcomes in patients with gout and known cardiovascular disease treated with febuxostat, when compared to those treated with allopurinol. The manufacturer and the FDA advise health professionals to limit the use of febuxostat to second-line therapy in patients who have inadequate response or intolerance to allopurinol, and to avoid the use of febuxostat in patients with cardiovascular diseases.[A2742, L13056]
Synonyms
  • Febuxostat
  • Febuxostat hemihydrate
  • Fébuxostat
  • Febuxostatum
  • 2-(3-cyano-4-isobutoxyphenyl)-4-methyl- 1,3-thiazole-5-carboxylic acid
Brand Names
  • Febuxostat Mylan
  • Adenuric
  • Uloric
  • Mar-febuxostat
  • Auro-febuxostat
IndicationFebuxostat is indicated for the chronic management of hyperuricemia in adult patients with gout who have an inadequate response to a maximally titrated dose of [allopurinol], who are intolerant to allopurinol, or for whom treatment with allopurinol is not advisable.[L46073] It is not recommended for the treatment of asymptomatic hyperuricemia [L32238] or secondary hyperuricemia.[A230583]
Categories
  • Antigout Preparations
  • Antirheumatic Agents
  • BCRP/ABCG2 Inhibitors
  • Cytochrome P-450 CYP1A2 Substrates
  • Cytochrome P-450 CYP2C8 Substrates
ATC-CodeM04AA03
CAS number144060-53-7

Drug Targets

NameTarget SequencePharmacological ActionActions
Xanthine dehydrogenase/oxidaseMTADKLVFFVNGRKVVEKNADPETTLLAYLRRKLGLSGTKLGCGEGGCGA...unknowninhibitor
UDP-glucuronosyltransferase 1-1MAVESQGGRPLVLGLLLCVLGPVVSHAGKILLIPVDGSHWLSMLGAIQQL...unknownsubstrate
UDP-glucuronosyltransferase 1-3MATGLQVPLPWLATGLLLLLSVQPWAESGKVLVVPIDGSHWLSMREVLRE...unknownsubstrate
UDP-glucuronosyltransferase 1-9MACTGWTSPLPLCVCLLLTCGFAEAGKLLVVPMDGSHWFTMRSVVEKLIL...unknownsubstrate
UDP-glucuronosyltransferase 2B7MSVKWTSVILLIQLSFCFSSGNCGKVLVWAAEYSHWMNIKTILDELIQRG...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1164729
PubChem 134018
ChEMBL CHEMBL1164729
ChEBI CHEBI:31596
CCDC/CSD HIQQEF, UREQOY01, BUVBEC, XULRUT, RUNSUR, UREQOY, HIQQAB02, XULRUT01, OYADAV, PUHGUV, HIQQIJ, HIQQAB, QEFDEO, QEDNUM