Febuxostat

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 Search

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
Sources: http://www.drugbank.ca/drugs/DB04854
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

Targets

Primary Target	Pharmacology	Condition	Potency
Xanthine dehydrogenase 33 Target ID: CHEMBL1929 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24508129	Inhibitor 8504		1.26 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hyperuricemia in patients with gout 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/021856s000_Lbl.pdf	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

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inducer 440 substrate 1193 inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other 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

Target	Modality	Activity	Clinical evidence
CYP1A 122	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/021856s000_ClinPharmR_P1.pdf#page=11 Page: 11.0	low
CYP2B6 1160	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/021856s000_ClinPharmR_P1.pdf#page=11 Page: 11.0	low
CYP2C19 2141	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/021856s000_ClinPharmR_P1.pdf#page=11 Page: 11.0	low
CYP2C9 2497	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/021856s000_ClinPharmR_P1.pdf#page=11 Page: 11.0	low
CYP3A4/5 357	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/021856s000_ClinPharmR_P1.pdf#page=11 Page: 11.0	low
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/021856s000_ClinPharmR_P1.pdf#page=38; https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021856s013lbl.pdf#page=13 Page: 38,13	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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/021856s000_ClinPharmR_P1.pdf#page=38; https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021856s013lbl.pdf#page=13 Page: 38,13
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/021856s000_ClinPharmR_P1.pdf#PAGE=38 Page: 38.0	no [Ki >100 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/021856s000_ClinPharmR_P1.pdf#PAGE=38 Page: 38.0	no [Ki >100 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/021856s000_ClinPharmR_P1.pdf#PAGE=38 Page: 38.0	no [Ki >100 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/021856s000_ClinPharmR_P1.pdf#PAGE=38 Page: 38.0	no [Ki >100 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/021856s000_ClinPharmR_P1.pdf#page=38 Page: 38.0	inconclusive
CYP1A1 389	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/021856s000_ClinPharmR_P1.pdf#page=38 Page: 38.0	yes
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/021856s000_ClinPharmR_P1.pdf#page=38 Page: 38.0	yes
CYP2C8 810	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/021856s000_ClinPharmR_P1.pdf#page=38 Page: 38.0	yes
UGT1A1 479	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/021856s000_ClinPharmR_P1.pdf#page=38 Page: 38.0	yes
UGT1A3 470	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/021856s000_ClinPharmR_P1.pdf#page=38 Page: 38.0	yes
UGT1A9 423	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/021856s000_ClinPharmR_P1.pdf#page=38 Page: 38.0	yes
UGT2B7 456	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/021856s000_ClinPharmR_P1.pdf#page=38 Page: 38.0	yes
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/021856s000_ClinPharmR_P1.pdf#page=12 Page: 12,20,38	yes	no (co-administration study) Comment: warfarin: no effect at steady-state Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/021856s000_ClinPharmR_P1.pdf#page=12 Page: 12,20,38

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
[Development antihyperuricemic candidates].	2003 Jan	12629719
Gateways to clinical trials.	2003 Jan-Feb	12690708
PK/PD and safety of a single dose of TMX-67 (febuxostat) in subjects with mild and moderate renal impairment.	2004 Oct	15571212
Recent advances in the management of gout and hyperuricemia.	2005 May	15838244
Recent developments in our understanding of the renal basis of hyperuricemia and the development of novel antihyperuricemic therapeutics.	2006	16820043
Gateways to clinical trials.	2006 Apr	16810345
[Gout].	2006 Jan 11	16463802
Gout's not just for the gluttonous.	2006 Jun	16795900
Hyperuricemia and gout: new insights into pathogenesis and treatment.	2007	17922673
Gateways to clinical trials.	2007 Dec	18200333
Assessment of outcome in clinical trials of gout--a review of current measures.	2007 Dec	17650521
[Crystal-induced arthritis--old but important].	2007 Jul	17562056
Uricase and other novel agents for the management of patients with treatment-failure gout.	2007 Jun	17531181
Rasburicase represents a new tool for hyperuricemia in tumor lysis syndrome and in gout.	2007 Mar 2	17396159
Febuxostat: a viewpoint by H. Ralph Schumacher Jr and Lan X. Chen.	2008	18729538
A benefit-risk assessment of benzbromarone in the treatment of gout. Was its withdrawal from the market in the best interest of patients?	2008	18636784
Effect of febuxostat on the progression of renal disease in 5/6 nephrectomy rats with and without hyperuricemia.	2008	18434753
Treatment with the xanthine oxidase inhibitor febuxostat lowers uric acid and alleviates systemic and glomerular hypertension in experimental hyperuricaemia.	2008 Apr	18048425
Chronic xanthine oxidase inhibition following myocardial infarction in rabbits: effects of early versus delayed treatment.	2008 Feb 27	18215719
Effect of food or antacid on pharmacokinetics and pharmacodynamics of febuxostat in healthy subjects.	2008 Mar	17953718
Xanthine oxidase inhibition with febuxostat attenuates systolic overload-induced left ventricular hypertrophy and dysfunction in mice.	2008 Nov	18995179
The role of urate and xanthine oxidase in vascular oxidative stress: future directions.	2009	19851527
Update on emerging urate-lowering therapies.	2009 Mar	19339925
Febuxostat for the treatment of hyperuricaemia in people with gout: a single technology appraisal.	2009 Oct	19846027

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 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

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Name

Type

Language

ADENURIC

Preferred Name

English

Febuxostat

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