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Compound Detail

CHEMBL1164729

FEBUXOSTAT
💊 Approved Drug
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💊 Approved Drug
Cc1nc(-c2ccc(OCC(C)C)c(C#N)c2)sc1C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1164729
Name FEBUXOSTAT
Phase Approved
Structure Type MOL
InChI Key BQSJTQLCZDPROO-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Adenuric Febuxostat Febuxostat krka Febuxostat mylan Febuxostat viatris (previously febuxostat mylan) NSC-758874 TMX-67 Uloric
9
Targets
46
Activities
3
Assay Types
11
PK Parameters
20
Publications
8
Known Names
10
Indications
1
Mechanisms

Molecular Properties

316.4
MW (Da)
3.72
ALogP
5
HBA
1
HBD
83.2
PSA (Ų)
0.91
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2008
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -stat
USAN Year 2002

Extended Properties

Molecular Formula C16H16N2O3S
MW 316.38
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -1.73

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Xanthine dehydrogenase inhibitor INHIBITOR Xanthine dehydrogenase/oxidase ✓ ✓

Indications

Arthritis, Gouty Gout Hyperuricemia Cardiovascular Diseases Tumor Lysis Syndrome Angina, Stable Hypertension Kidney Calculi Kidney Diseases Non-alcoholic Fatty Liver Disease

ATC Classification

M04AA03
febuxostat
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIGOUT PREPARATIONS

Drug Warnings

Black Box Warning
cardiotoxicity
Country: United States

Activity Summary

IC50 36 meas. best 8.9
Ki 8 meas. best 10.0
Kd 2 meas. best 5.79

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Xanthine dehydrogenase/oxidase
CHEMBL1929
 Ki 10.0 9.4325 0.1 4
Xanthine dehydrogenase/oxidase
CHEMBL3649
 Ki 9.92 9.175 0.1 4
Xanthine dehydrogenase/oxidase
CHEMBL1929
 IC50 8.9 7.6182 1.3 11
Xanthine dehydrogenase/oxidase
CHEMBL3649
 IC50 8.56 7.9367 2.8 18
Unchecked
CHEMBL612545
 IC50 8.51 8.51 3.1 2
Xanthine dehydrogenase/oxidase
CHEMBL1075246
 IC50 8.4 8.4 4.0 1
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 IC50 7.57 7.57 27.0 1
Histone deacetylase 6
CHEMBL1865
 IC50 7.26 7.26 55.4 1
Flavin reductase (NADPH)
CHEMBL5019
 Kd 5.79 5.79 1621.8 2
ATP-binding cassette sub-family C member 4
CHEMBL1743128
 IC50 5.72 5.72 1900.0 1
Bile salt export pump
CHEMBL6020
 IC50 4.37 4.37 42900.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 61510.0 ng.hr.mL-1 Rattus norvegicus
AUC 7941.14 ng.hr.mL-1 Homo sapiens
AUC 478018.54 ng.hr.mL-1 Sapajus apella
CL 3.0 mL.min-1.g-1 Homo sapiens
CL 7.0 uL.min-1.(10^6cells)-1 Homo sapiens
CL 12.73 uL.min-1.(10^6cells)-1 Rattus norvegicus
Cmax 51741.58 nM Rattus norvegicus
T1/2 2.9 hr Rattus norvegicus
T1/2 2.9 hr Rattus norvegicus
T1/2 10.8 hr Homo sapiens
Tmax 1.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Xanthine dehydrogenase/oxidase Ki = 0.1 nM 10.0 Non-competitive inhibition of human xanthine oxidase 28478180
Xanthine dehydrogenase/oxidase Ki = 0.1 nM 10.0 Mixed-type inhibition of xanthine oxidase (unknown origin) assessed as inhibitor... 34992040
Xanthine dehydrogenase/oxidase Ki = 0.12 nM 9.92 Mixed-type inhibition of bovine xanthine oxidase 25060641
Xanthine dehydrogenase/oxidase Ki = 0.6 nM 9.22 Inhibition of xanthine oxidase (unknown origin) 30769179
Xanthine dehydrogenase/oxidase Ki = 0.6 nM 9.22 Binding affinity to bovine milk XO using xanthine as substrate assessed as inhib... 36758304
Xanthine dehydrogenase/oxidase Ki = 0.9 nM 9.05 Mixed-type inhibition of bovine xanthine oxidase assessed as enzyme-inhibitor co... 25060641
Xanthine dehydrogenase/oxidase IC50 = 1.259 nM 8.9 Inhibition of C-terminally FLAG-tagged human xanthine oxidase (amino acid 1 to 1... 24508129
Xanthine dehydrogenase/oxidase IC50 = 2.78 nM 8.56 Inhibition of Bovine milk XO using xanthine as substrate assessed as decrease in... 37974965
Xanthine dehydrogenase/oxidase IC50 = 2.92 nM 8.54 Inhibition of xanthine oxidase (unknown origin) measured by spectrophotometric a... 35063733
Xanthine dehydrogenase/oxidase IC50 = 3.0 nM 8.52 Inhibition of bovine xanthine oxidase by spectrophotometry 20189693
Xanthine dehydrogenase/oxidase Ki = 3.1 nM 8.51 Inhibition of xanthine dehydrogenase (unknown origin) 30769179
Xanthine dehydrogenase/oxidase Ki = 3.1 nM 8.51 Binding affinity to bovine milk XO using xanthine as substrate assessed as inhib... 36758304
Unchecked IC50 = 3.1 nM 8.51 Inhibition of butter milk Xanthine oxidase using xanthine as substrate preincuba... 25704891
Unchecked IC50 = 3.1 nM 8.51 Inhibition of butter milk xanthine oxidase (unknown origin) assessed as initial ... 26774578
Xanthine dehydrogenase/oxidase IC50 = 3.981 nM 8.4 Inhibition of rat xanthine oxidase 24508129
Xanthine dehydrogenase/oxidase IC50 = 4.8 nM 8.32 Inhibition of bovine milk xanthine oxidase using xanthine as substrate preincuba... 30630716
Xanthine dehydrogenase/oxidase IC50 = 5.2 nM 8.28 Inhibition of bovine milk xanthine oxidoreductase pre-incubated for 3 mins follo... 28918097
Xanthine dehydrogenase/oxidase IC50 = 6.91 nM 8.16 Inhibition of XOR (unknown origin) using xanthine as substrate incubated for 3 m... 36462435
Xanthine dehydrogenase/oxidase IC50 = 7.0 nM 8.15 Inhibition of bovine xanthine oxidase assessed as reduction in uric acid formati... 31761385
Xanthine dehydrogenase/oxidase IC50 = 8.0 nM 8.1 Inhibition of XOR (unknown origin) using xanthine as substrate measured for 10 m... 38663283

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 63
39108024 10.1021/acs.jmedchem.4c01480 Sapajus apella 6
34957824 10.1021/acs.jmedchem.1c01664 Flavin reductase (NADPH) 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
- 10.6019/CHEMBL3301361 ADMET 4
- 10.6019/CHEMBL4808148 Histone deacetylase 6 4
26363870 10.1016/j.ejmech.2015.08.056 Xanthine dehydrogenase/oxidase 3
34992040 10.1016/j.ejmech.2021.114086 Xanthine dehydrogenase/oxidase 3
30769179 10.1016/j.ejmech.2019.01.043 ADMET 3
25131536 10.1016/j.bmcl.2014.07.058 MDA-MB-231 3
24508129 10.1016/j.bmcl.2014.01.050 Xanthine dehydrogenase/oxidase 2
23956101 10.1093/toxsci/kft176 Homo sapiens 2
23956101 10.1093/toxsci/kft176 Unchecked 2
25704891 10.1016/j.bmcl.2015.01.055 Rattus norvegicus 2
25060641 10.1021/np500320g Xanthine dehydrogenase/oxidase 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
24508129 10.1016/j.bmcl.2014.01.050 Rattus norvegicus 2
23122864 10.1016/j.bmcl.2012.10.029 Rattus norvegicus 2
30630716 10.1016/j.bmcl.2019.01.005 Xanthine dehydrogenase/oxidase 2

Data from ChEMBL 36 via Core Engine