U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.26 nM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
Gateways to clinical trials.
2007 Dec
Febuxostat: a novel non-purine selective inhibitor of xanthine oxidase for the treatment of hyperuricemia in gout.
2007 Feb
Developments in the scientific and clinical understanding of gout.
2008
Febuxostat : a viewpoint by N. Lawrence Edwards.
2008
Febuxostat : a viewpoint by Naomi Schlesinger.
2008
Febuxostat: a viewpoint by H. Ralph Schumacher Jr and Lan X. Chen.
2008
Febuxostat.
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
Gateways to clinical trials.
2008 Apr
[New antihyperuricemic medicine: febuxostat, Puricase, etc].
2008 Apr
[Inhibitors of xanthine oxidoreductase].
2008 Apr
Effects of febuxostat on metabolic and renal alterations in rats with fructose-induced metabolic syndrome.
2008 Apr
Treatment with the xanthine oxidase inhibitor febuxostat lowers uric acid and alleviates systemic and glomerular hypertension in experimental hyperuricaemia.
2008 Apr
Febuxostat in the management of hyperuricemia and chronic gout: a review.
2008 Dec
Crystal structures of mammalian xanthine oxidoreductase bound with various inhibitors: allopurinol, febuxostat, and FYX-051.
2008 Feb
Chronic xanthine oxidase inhibition following myocardial infarction in rabbits: effects of early versus delayed treatment.
2008 Feb 27
Determinants of the clinical outcomes of gout during the first year of urate-lowering therapy.
2008 Jun
Refractory gout: what is it and what to do about it?
2008 Mar
Effect of food or antacid on pharmacokinetics and pharmacodynamics of febuxostat in healthy subjects.
2008 Mar
In vitro drug-drug interaction studies with febuxostat, a novel non-purine selective inhibitor of xanthine oxidase: plasma protein binding, identification of metabolic enzymes and cytochrome P450 inhibition.
2008 May
Xanthine oxidase inhibition with febuxostat attenuates systolic overload-induced left ventricular hypertrophy and dysfunction in mice.
2008 Nov
Effects of febuxostat versus allopurinol and placebo in reducing serum urate in subjects with hyperuricemia and gout: a 28-week, phase III, randomized, double-blind, parallel-group trial.
2008 Nov 15
Gout management: let's get it right this time.
2008 Nov 15
Gateways to clinical trials.
2008 Oct
The effect of age and gender on pharmacokinetics, pharmacodynamics, and safety of febuxostat, a novel nonpurine selective inhibitor of xanthine oxidase.
2008 Sep
The role of urate and xanthine oxidase in vascular oxidative stress: future directions.
2009
Gout. Hyperuricemia and cardiovascular disease: how strong is the evidence for a causal link?
2009
Gout. Novel therapies for treatment of gout and hyperuricemia.
2009
Role of urate, xanthine oxidase and the effects of allopurinol in vascular oxidative stress.
2009
Febuxostat: new drug. Hyperuricaemia: risk of gout attacks.
2009 Apr
Gateways to clinical trials.
2009 Apr
Febuxostat: a new agent for lowering serum urate.
2009 Apr
A critical reappraisal of allopurinol dosing, safety, and efficacy for hyperuricemia in gout.
2009 Apr
New gout treatment approved.
2009 Apr 1
Nickel-catalyzed biaryl coupling of heteroarenes and aryl halides/triflates.
2009 Apr 16
Febuxostat in the treatment of gout: 5-yr findings of the FOCUS efficacy and safety study.
2009 Feb
Gout Study Group: update on hyperuricemia and gout.
2009 Jul
Gout--what are the treatment options?
2009 Jun
Clinical efficacy and safety of successful longterm urate lowering with febuxostat or allopurinol in subjects with gout.
2009 Jun
Update on emerging urate-lowering therapies.
2009 Mar
Febuxostat.
2009 Mar
Febuxostat: a new treatment for hyperuricaemia in gout.
2009 May
Febuxostat (Uloric) for chronic treatment of gout.
2009 May 18
New drugs: Febuxostat, lacosamide, and rufinamide.
2009 May-Jun
Approach to the treatment of hyperuricemia.
2009 Nov
[Crystal-induced activation of the inflammasome: gout and pseudogout].
2009 Nov
Febuxostat for the treatment of hyperuricaemia in people with gout: a single technology appraisal.
2009 Oct
Update on gout and hyperuricemia.
2010 Feb
Update on gout: new therapeutic strategies and options.
2010 Jan
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
In Vitro Use Guide
Febuxostat (200uM) inhibited cholesterol crystal-induced ROS formation and inflammatory cytokine release in murine macrophages.
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:28:10 UTC 2019
Edited
by admin
on Mon Oct 21 20:28:10 UTC 2019
Record UNII
101V0R1N2E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
2-(3-CYANO-4-ISOBUTOXYPHENYL)-4-METHYL-1,3-THIAZOLE-5-CARBOXYLIC ACID
Systematic Name English
FEBUXOSTAT [USAN]
Common Name English
FEBUXOSTAT [MI]
Common Name English
FEBUXOSTAT [INN]
Common Name English
ADENURIC
Brand 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
FEBUXOSTAT [WHO-DD]
Common Name English
ULORIC
Brand Name English
FEBUXOSTAT [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
LIVERTOX 400
Created by admin on Mon Oct 21 20:28:10 UTC 2019 , Edited by admin on Mon Oct 21 20:28:10 UTC 2019
WHO-VATC QM04AA03
Created by admin on Mon Oct 21 20:28:10 UTC 2019 , Edited by admin on Mon Oct 21 20:28:10 UTC 2019
EMA ASSESSMENT REPORTS ADENURIC (AUTHORIZED: GOUT)
Created by admin on Mon Oct 21 20:28:10 UTC 2019 , Edited by admin on Mon Oct 21 20:28:10 UTC 2019
WHO-ATC M04AA03
Created by admin on Mon Oct 21 20:28:10 UTC 2019 , Edited by admin on Mon Oct 21 20:28:10 UTC 2019
NDF-RT N0000175698
Created by admin on Mon Oct 21 20:28:10 UTC 2019 , Edited by admin on Mon Oct 21 20:28:10 UTC 2019
NDF-RT N0000000206
Created by admin on Mon Oct 21 20:28:10 UTC 2019 , Edited by admin on Mon Oct 21 20:28:10 UTC 2019
NCI_THESAURUS C1637
Created by admin on Mon Oct 21 20:28:10 UTC 2019 , Edited by admin on Mon Oct 21 20:28:10 UTC 2019
NCI_THESAURUS C921
Created by admin on Mon Oct 21 20:28:10 UTC 2019 , Edited by admin on Mon Oct 21 20:28:10 UTC 2019
Code System Code Type Description
DRUG BANK
DB04854
Created by admin on Mon Oct 21 20:28:10 UTC 2019 , Edited by admin on Mon Oct 21 20:28:10 UTC 2019
PRIMARY
NCI_THESAURUS
C65629
Created by admin on Mon Oct 21 20:28:10 UTC 2019 , Edited by admin on Mon Oct 21 20:28:10 UTC 2019
PRIMARY
MESH
C084623
Created by admin on Mon Oct 21 20:28:10 UTC 2019 , Edited by admin on Mon Oct 21 20:28:10 UTC 2019
PRIMARY
EVMPD
SUB25382
Created by admin on Mon Oct 21 20:28:10 UTC 2019 , Edited by admin on Mon Oct 21 20:28:10 UTC 2019
PRIMARY
INN
8140
Created by admin on Mon Oct 21 20:28:10 UTC 2019 , Edited by admin on Mon Oct 21 20:28:10 UTC 2019
PRIMARY
EPA CompTox
144060-53-7
Created by admin on Mon Oct 21 20:28:10 UTC 2019 , Edited by admin on Mon Oct 21 20:28:10 UTC 2019
PRIMARY
RXCUI
73689
Created by admin on Mon Oct 21 20:28:10 UTC 2019 , Edited by admin on Mon Oct 21 20:28:10 UTC 2019
PRIMARY RxNorm
MERCK INDEX
M5253
Created by admin on Mon Oct 21 20:28:10 UTC 2019 , Edited by admin on Mon Oct 21 20:28:10 UTC 2019
PRIMARY Merck Index
ChEMBL
CHEMBL1164729
Created by admin on Mon Oct 21 20:28:10 UTC 2019 , Edited by admin on Mon Oct 21 20:28:10 UTC 2019
PRIMARY
IUPHAR
6817
Created by admin on Mon Oct 21 20:28:10 UTC 2019 , Edited by admin on Mon Oct 21 20:28:10 UTC 2019
PRIMARY
CAS
144060-53-7
Created by admin on Mon Oct 21 20:28:10 UTC 2019 , Edited by admin on Mon Oct 21 20:28:10 UTC 2019
PRIMARY
PUBCHEM
134018
Created by admin on Mon Oct 21 20:28:10 UTC 2019 , Edited by admin on Mon Oct 21 20:28:10 UTC 2019
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
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> INHIBITOR
Ki
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
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
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