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144060-53-7 molecular structure
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2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid

ChemBase ID: 72735
Molecular Formular: C16H16N2O3S
Molecular Mass: 316.37484
Monoisotopic Mass: 316.08816338
SMILES and InChIs

SMILES:
c1(c(ccc(c1)c1sc(c(n1)C)C(=O)O)OCC(C)C)C#N
Canonical SMILES:
N#Cc1cc(ccc1OCC(C)C)c1nc(c(s1)C(=O)O)C
InChI:
InChI=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)
InChIKey:
BQSJTQLCZDPROO-UHFFFAOYSA-N

Cite this record

CBID:72735 http://www.chembase.cn/molecule-72735.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid
IUPAC Traditional name
febuxostat
Brand Name
Adenuric, Uloric , Febutaz
Synonyms
2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid
2-[3-Cyano-4-(2-methylpropoxy)phenyl]-4-methyl-5-thiazolecarboxylic Acid
2-(3-Cyano-4-isobutyloxyphenyl)-4-methyl-5-thiazolecarboxylic Acid
TEI 6720
TMX 67
TMX-67
Adenuric
Uloric
Febuxostat
2-(3-Cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylic acid
CAS Number
144060-53-7
MDL Number
MFCD00871598
PubChem SID
162037656
PubChem CID
134018
ATC CODE
M04AA03
CHEMBL
1164729
Chemspider ID
118173
KEGG ID
D01206
Unique Ingredient Identifier
101V0R1N2E
Wikipedia Title
Febuxostat
Medline Plus
a609020

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.078274  H Acceptors
H Donor LogD (pH = 5.5) 1.1251484 
LogD (pH = 7.4) 0.055648725  Log P 3.5209293 
Molar Refractivity 93.9288 cm3 Polarizability 32.385162 Å3
Polar Surface Area 83.21 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Methanol expand Show data source
Apperance
Off-White Solid expand Show data source
Melting Point
208-209°(dec.) expand Show data source
Hydrophobicity(logP)
4.097 expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
MSDS Link
Download expand Show data source
Target
XAO expand Show data source
Admin Routes
oral expand Show data source
Bioavailability
~49% absorbed expand Show data source
Excretion
urine (~49% mostly as metabolites, 3% as unchanged drug); feces (~45% mostly as metabolites, 12% as unchanged drug) expand Show data source
Half Life
~5-8 hours expand Show data source
Metabolism
via CYP1A2, 2C8, 2C9, UGT1A1, 1A3, 1A9, 2B7 expand Show data source
Protein Bound
~99% to albumin expand Show data source
Legal Status
Rx-only (US) expand Show data source
Pregnancy Category
C expand Show data source
US Licence
Febuxostat expand Show data source
EU Licence
Adenuric expand Show data source
Purity
95% expand Show data source
95+% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia TRC TRC
Selleck Chemicals - S1547 external link
Research Area: Metabolic Disease
Biological Activity:
Febuxostat (Uloric) is a non-purine selective XAO inhibitor with IC50 of 114 -210 nM.It works by non-competitively blocking the channel leading to the active site on xanthine oxidase. [1] Xanthine oxidase is needed to successively oxidize both hypoxanthine and xanthine to uric acid. Hence, febuxostat inhibits xanthine oxidase, therefore reducing production of uric acid. [2][3]
Toronto Research Chemicals - F229000 external link
Xanthine oxidase/xanthine dehydrogenase inhibitor. Used for treatment of hyperuricemia and chronic gout.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • •  Gaffo AL et al. Core Evid. 2010 Jun 15;4:25-36
  • • Tomlinson, B., et al.: Curr. Opin. Invest. Drugs, 6, 1168 (1993)
  • • Osada, Y., et al.: Eur. J. Pharmacol., 241, 183 (1993)
  • • Okamoto, K., et al.: J. Biol. Chem., 278, 1848 (1993)
  • • Mayer, M.D., et al.: Am. J. Therap., 12, 22 (1993)
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PATENTS

PATENTS

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INTERNET

INTERNET

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