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Details

Stereochemistry ACHIRAL
Molecular Formula C16H16N2O3S
Molecular Weight 316.375
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Febuxostat

SMILES

CC(C)COC1=C(C=C(C=C1)C2=NC(C)=C(S2)C(O)=O)C#N

InChI

InChIKey=BQSJTQLCZDPROO-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C16H16N2O3S
Molecular Weight 316.375
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/uloric.html

Febuxostat (ULORIC) is a novel, xanthine oxidase/dehydrogenase (XO/XDH) inhibitor being developed by Teijin, TAP Pharmaceuticals, and Ipsen for the treatment of gout. The currently available XO inhibitor, allopurinol, has been associated with serious instances of severe hypersensitivity, in some cases leading to fatalities. There is some suggestion that febuxostat is less prone to excacerbate systemic inflammatory events in animal studies. Febuxostat, a xanthine oxidase inhibitor, achieves its therapeutic effect by decreasing serum uric acid. Febuxostat is not expected to inhibit other enzymes involved in purine and pyrimidine synthesis and metabolism at therapeutic concentrations. Febuxostat is used for the treatment of hyperuricemia in patients with gout.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.26 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Uloric

Approved Use

Uloric is a xanthine oxidase (XO) inhibitor indicated for the chronic management of hyperuricemia in patients with gout.

Launch Date

2009
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.53 μg/mL
40 mg 1 times / day multiple, oral
dose: 40 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
FEBUXOSTAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3.98 μg × h/mL
40 mg 1 times / day multiple, oral
dose: 40 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
FEBUXOSTAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.2 h
40 mg 1 times / day multiple, oral
dose: 40 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
FEBUXOSTAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
40 mg 1 times / day multiple, oral
dose: 40 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
FEBUXOSTAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
low
low
low
low
low
moderate [Ki 40 uM]
weak (co-administration study)
Comment: competitive inhibition; Administration with desipramine resulted in an increase in Cmax (16%) and AUC (22%) of desipramine
Page: 38,13
no [Ki >100 uM]
no [Ki >100 uM]
no [Ki >100 uM]
no [Ki >100 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
inconclusive
yes
yes
yes
yes
yes
yes
yes
yes
no (co-administration study)
Comment: warfarin: no effect at steady-state
Page: 12,20,38
PubMed

PubMed

TitleDatePubMed
[Development antihyperuricemic candidates].
2003 Jan
Gateways to clinical trials.
2003 Jan-Feb
PK/PD and safety of a single dose of TMX-67 (febuxostat) in subjects with mild and moderate renal impairment.
2004 Oct
Recent advances in the management of gout and hyperuricemia.
2005 May
Recent developments in our understanding of the renal basis of hyperuricemia and the development of novel antihyperuricemic therapeutics.
2006
Gateways to clinical trials.
2006 Apr
[Gout].
2006 Jan 11
Gout's not just for the gluttonous.
2006 Jun
Hyperuricemia and gout: new insights into pathogenesis and treatment.
2007
Gateways to clinical trials.
2007 Dec
Assessment of outcome in clinical trials of gout--a review of current measures.
2007 Dec
[Crystal-induced arthritis--old but important].
2007 Jul
Uricase and other novel agents for the management of patients with treatment-failure gout.
2007 Jun
Rasburicase represents a new tool for hyperuricemia in tumor lysis syndrome and in gout.
2007 Mar 2
Febuxostat: a viewpoint by H. Ralph Schumacher Jr and Lan X. Chen.
2008
A benefit-risk assessment of benzbromarone in the treatment of gout. Was its withdrawal from the market in the best interest of patients?
2008
Effect of febuxostat on the progression of renal disease in 5/6 nephrectomy rats with and without hyperuricemia.
2008
Treatment with the xanthine oxidase inhibitor febuxostat lowers uric acid and alleviates systemic and glomerular hypertension in experimental hyperuricaemia.
2008 Apr
Chronic xanthine oxidase inhibition following myocardial infarction in rabbits: effects of early versus delayed treatment.
2008 Feb 27
Effect of food or antacid on pharmacokinetics and pharmacodynamics of febuxostat in healthy subjects.
2008 Mar
Xanthine oxidase inhibition with febuxostat attenuates systolic overload-induced left ventricular hypertrophy and dysfunction in mice.
2008 Nov
The role of urate and xanthine oxidase in vascular oxidative stress: future directions.
2009
Update on emerging urate-lowering therapies.
2009 Mar
Febuxostat for the treatment of hyperuricaemia in people with gout: a single technology appraisal.
2009 Oct
Patents

Sample Use Guides

In Vivo Use Guide
For treatment of hyperuricemia in patients with gout, the recommended dose is 40 mg or 80 mg once daily.
Route of Administration: Oral
Febuxostat (200uM) inhibited cholesterol crystal-induced ROS formation and inflammatory cytokine release in murine macrophages.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:10:39 GMT 2025
Edited
by admin
on Mon Mar 31 18:10:39 GMT 2025
Record UNII
101V0R1N2E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ADENURIC
Preferred Name English
Febuxostat
DASH   EMA EPAR   INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
FEBUXOSTAT [VANDF]
Common Name English
TMX-67
Code English
NSC-758874
Code English
2-(3-CYANO-4-ISOBUTOXYPHENYL)-4-METHYL-1,3-THIAZOLE-5-CARBOXYLIC ACID
Systematic Name English
Febuxostat [WHO-DD]
Common Name English
FEBUXOSTAT [USAN]
Common Name English
FEBUXOSTAT [MI]
Common Name English
febuxostat [INN]
Common Name English
5-THIAZOLECARBOXYLIC ACID, 2-(3-CYANO-4-(2-METHYLPROPOXY)PHENYL)-4-METHYL-
Systematic Name English
FEBUXOSTAT [JAN]
Common Name English
FEBUXOSTAT [EMA EPAR]
Common Name English
FEBUXOSTAT [MART.]
Common Name English
ULORIC
Brand Name English
FEBUXOSTAT [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
LIVERTOX NBK548645
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
WHO-VATC QM04AA03
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
EMA ASSESSMENT REPORTS ADENURIC (AUTHORIZED: GOUT)
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
WHO-ATC M04AA03
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
NDF-RT N0000175698
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
NDF-RT N0000000206
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
NCI_THESAURUS C1637
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
NCI_THESAURUS C921
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
Code System Code Type Description
FDA UNII
101V0R1N2E
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
PRIMARY
WIKIPEDIA
Febuxostat
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
PRIMARY
DRUG BANK
DB04854
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
PRIMARY
NCI_THESAURUS
C65629
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
PRIMARY
USAN
OO-12
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
PRIMARY
MESH
C084623
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
PRIMARY
EVMPD
SUB25382
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
PRIMARY
DRUG CENTRAL
1137
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
PRIMARY
INN
8140
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
PRIMARY
CHEBI
31596
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
PRIMARY
EPA CompTox
DTXSID8048650
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
PRIMARY
DAILYMED
101V0R1N2E
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
PRIMARY
RXCUI
73689
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
PRIMARY RxNorm
SMS_ID
100000089380
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
PRIMARY
MERCK INDEX
m5253
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL1164729
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
PRIMARY
IUPHAR
6817
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
PRIMARY
CAS
144060-53-7
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
PRIMARY
PUBCHEM
134018
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
PRIMARY
NSC
758874
Created by admin on Mon Mar 31 18:10:39 GMT 2025 , Edited by admin on Mon Mar 31 18:10:39 GMT 2025
PRIMARY
Related Record Type Details
EXCRETED UNCHANGED
AMOUNT EXCRETED
URINE
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
BINDING
EXCRETED UNCHANGED
AMOUNT EXCRETED
FECAL
METABOLIC ENZYME -> SUBSTRATE
TARGET -> INHIBITOR
Ki
METABOLIC ENZYME -> SUBSTRATE
SOLVATE->ANHYDROUS
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> INHIBITOR
Ki
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE -> PARENT
67M-3, a major metabolite formed in vitro, was not detected in significant amount in vivo. 67M-3 was mainly metabolized by CYP1A1, whose level is low in healthy non-smoking
METABOLITE ACTIVE -> PARENT
URINE
METABOLITE ACTIVE -> PARENT
MAJOR
URINE
METABOLITE ACTIVE -> PARENT
MAJOR
FECAL
METABOLITE ACTIVE -> PARENT
It was reported that febuxostat is metabolized by oxidative and conjugation pathways and three major metabolites have been identified as 67M-1, 67M-2, and 67M-4
MAJOR
FECAL
METABOLITE ACTIVE -> PARENT
It was reported that febuxostat is metabolized by oxidative and conjugation pathways and three major metabolites have been iden- tified as 67M-1, 67M-2, and 67M-4
MAJOR
FECAL
METABOLITE ACTIVE -> PARENT
MAJOR
URINE
Related Record Type Details
IMPURITY -> PARENT
CI file
USP
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC HIGH-FAT MEAL

FED CONDITION

Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC