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Details

Stereochemistry ACHIRAL
Molecular Formula 2C16H15N2O3S.Mg
Molecular Weight 655.039
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FEBUXOSTAT MAGNESIUM

SMILES

[Mg++].CC(C)COC1=C(C=C(C=C1)C2=NC(C)=C(S2)C([O-])=O)C#N.CC(C)COC3=C(C=C(C=C3)C4=NC(C)=C(S4)C([O-])=O)C#N

InChI

InChIKey=BNABHEFFEDHWIR-UHFFFAOYSA-L
InChI=1S/2C16H16N2O3S.Mg/c2*1-9(2)8-21-13-5-4-11(6-12(13)7-17)15-18-10(3)14(22-15)16(19)20;/h2*4-6,9H,8H2,1-3H3,(H,19,20);/q;;+2/p-2

HIDE SMILES / InChI
Molecular Formula C16H15N2O3S
Molecular Weight 315.367
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula Mg
Molecular Weight 24.305
Charge 2
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.

Originator

Approval Year

2009
364
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 1.26 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/16884320
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/16884320
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/16884320
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%
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/16884320
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252
inducer
440

substrate
1193

inhibitor
2438
inhibitor
2507

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
2153

CYP2C19
2057
CYP1A2
1197

CYP2C8
810

CYP1A1
389

UGT1A1
479

UGT1A3
470

UGT1A9
423

UGT2B7
456

P-gp
2052
CYP1A
59

CYP2B6
669

CYP2C19
329

CYP3A4/5
133
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A
122
 low
CYP2B6
1160
 low
CYP2C19
2141
 low
CYP2C9
2497
 low
CYP3A4/5
357
 low
CYP2D6
2546
 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
CYP1A2
2333
 no [Ki >100 uM]
CYP2C19
2141
 no [Ki >100 uM]
CYP2C9
2497
 no [Ki >100 uM]
CYP3A4
2633
 no [Ki >100 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
2052
 inconclusive
CYP1A1
389
 yes
CYP1A2
1197
 yes
CYP2C8
810
 yes
UGT1A1
479
 yes
UGT1A3
470
 yes
UGT1A9
423
 yes
UGT2B7
456
 yes
CYP2C9
1193
 yes
no (co-administration study)
Comment: warfarin: no effect at steady-state
Page: 12,20,38
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:31596
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31596
ChemicalBook
CB22508843
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB22508843
ChemicalBook
CB4841564
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4841564
eMolecules
6719182
https://www.emolecules.com/cgi-bin/more?vid=6719182
MolPort
MolPort-005-940-740
https://www.molport.com/shop/molecule-link/MolPort-005-940-740
Selleck Chemicals
Febuxostat(Uloric)
http://www.selleckchem.com/products/Febuxostat(Uloric).html
ZINC
ZINC000000005423
http://zinc15.docking.org/substances/ZINC000000005423
PubMed

PubMed

TitleDatePubMed
Update on gout and hyperuricemia.
2010-02
Update on gout: new therapeutic strategies and options.
2010-01
Approach to the treatment of hyperuricemia.
2009-11
[Crystal-induced activation of the inflammasome: gout and pseudogout].
2009-11
Febuxostat for the treatment of hyperuricaemia in people with gout: a single technology appraisal.
2009-10
Gout Study Group: update on hyperuricemia and gout.
2009-07
Gout--what are the treatment options?
2009-06
Clinical efficacy and safety of successful longterm urate lowering with febuxostat or allopurinol in subjects with gout.
2009-06
Febuxostat (Uloric) for chronic treatment of gout.
2009-05-18
New drugs: Febuxostat, lacosamide, and rufinamide.
2009-05-16
Febuxostat: a new treatment for hyperuricaemia in gout.
2009-05
Nickel-catalyzed biaryl coupling of heteroarenes and aryl halides/triflates.
2009-04-16
New gout treatment approved.
2009-04-01
Febuxostat: new drug. Hyperuricaemia: risk of gout attacks.
2009-04
Gateways to clinical trials.
2009-04
Febuxostat: a new agent for lowering serum urate.
2009-04
A critical reappraisal of allopurinol dosing, safety, and efficacy for hyperuricemia in gout.
2009-04
Update on emerging urate-lowering therapies.
2009-03
Febuxostat.
2009-03
Febuxostat in the treatment of gout: 5-yr findings of the FOCUS efficacy and safety study.
2009-02
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 in the management of hyperuricemia and chronic gout: a review.
2008-12
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.
2008-11-15
Gout management: let's get it right this time.
2008-11-15
Xanthine oxidase inhibition with febuxostat attenuates systolic overload-induced left ventricular hypertrophy and dysfunction in mice.
2008-11
Gateways to clinical trials.
2008-10
The effect of age and gender on pharmacokinetics, pharmacodynamics, and safety of febuxostat, a novel nonpurine selective inhibitor of xanthine oxidase.
2008-09
Determinants of the clinical outcomes of gout during the first year of urate-lowering therapy.
2008-06
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.
2008-05
Gateways to clinical trials.
2008-04
[New antihyperuricemic medicine: febuxostat, Puricase, etc].
2008-04
[Inhibitors of xanthine oxidoreductase].
2008-04
Effects of febuxostat on metabolic and renal alterations in rats with fructose-induced metabolic syndrome.
2008-04
Treatment with the xanthine oxidase inhibitor febuxostat lowers uric acid and alleviates systemic and glomerular hypertension in experimental hyperuricaemia.
2008-04
Refractory gout: what is it and what to do about it?
2008-03
Effect of food or antacid on pharmacokinetics and pharmacodynamics of febuxostat in healthy subjects.
2008-03
Chronic xanthine oxidase inhibition following myocardial infarction in rabbits: effects of early versus delayed treatment.
2008-02-27
Crystal structures of mammalian xanthine oxidoreductase bound with various inhibitors: allopurinol, febuxostat, and FYX-051.
2008-02
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.
2007-12
Febuxostat: a novel non-purine selective inhibitor of xanthine oxidase for the treatment of hyperuricemia in gout.
2007-02
Patents

Patents

20060252808
5
20080038242
3
20080096904
3
20080145846
3

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 Wed Apr 02 00:03:12 GMT 2025
Edited
by admin
on Wed Apr 02 00:03:12 GMT 2025
Record UNII
4UB2J8Q7HG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FEBUXOSTAT MAGNESIUM
Common Name English
5-THIAZOLECARBOXYLIC ACID, 2-(3-CYANO-4-(2-METHYLPROPOXY)PHENYL)-4-METHYL-, MAGNESIUM SALT (2:1)
Preferred Name English
Code System Code Type Description
PUBCHEM
141336381
Created by admin on Wed Apr 02 00:03:12 GMT 2025 , Edited by admin on Wed Apr 02 00:03:12 GMT 2025
PRIMARY
CAS
1456533-39-3
Created by admin on Wed Apr 02 00:03:12 GMT 2025 , Edited by admin on Wed Apr 02 00:03:12 GMT 2025
PRIMARY
FDA UNII
4UB2J8Q7HG
Created by admin on Wed Apr 02 00:03:12 GMT 2025 , Edited by admin on Wed Apr 02 00:03:12 GMT 2025
PRIMARY
Related Record Type Details
Structure of Febuxostat
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of Febuxostat
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
NIH
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