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
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)
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 |
DescriptionSources: http://www.drugbank.ca/drugs/DB04854Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/uloric.html
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 |
---|---|---|---|
Target ID: CHEMBL1929 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24508129 |
1.26 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Uloric Approved UseUloric is a xanthine oxidase (XO) inhibitor indicated for the chronic management of hyperuricemia in patients with gout. Launch Date2009 |
Cmax
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 |
T1/2
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 |
Funbound
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 |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Drug as victim
PubMed
Title | Date | PubMed |
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[Development antihyperuricemic candidates]. | 2003 Jan |
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Gateways to clinical trials. | 2003 Jan-Feb |
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PK/PD and safety of a single dose of TMX-67 (febuxostat) in subjects with mild and moderate renal impairment. | 2004 Oct |
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Recent advances in the management of gout and hyperuricemia. | 2005 May |
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Recent developments in our understanding of the renal basis of hyperuricemia and the development of novel antihyperuricemic therapeutics. | 2006 |
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Gateways to clinical trials. | 2006 Apr |
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[Gout]. | 2006 Jan 11 |
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Gout's not just for the gluttonous. | 2006 Jun |
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Hyperuricemia and gout: new insights into pathogenesis and treatment. | 2007 |
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Gateways to clinical trials. | 2007 Dec |
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Assessment of outcome in clinical trials of gout--a review of current measures. | 2007 Dec |
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[Crystal-induced arthritis--old but important]. | 2007 Jul |
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Uricase and other novel agents for the management of patients with treatment-failure gout. | 2007 Jun |
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Rasburicase represents a new tool for hyperuricemia in tumor lysis syndrome and in gout. | 2007 Mar 2 |
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Febuxostat: a viewpoint by H. Ralph Schumacher Jr and Lan X. Chen. | 2008 |
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A benefit-risk assessment of benzbromarone in the treatment of gout. Was its withdrawal from the market in the best interest of patients? | 2008 |
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Effect of febuxostat on the progression of renal disease in 5/6 nephrectomy rats with and without hyperuricemia. | 2008 |
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Treatment with the xanthine oxidase inhibitor febuxostat lowers uric acid and alleviates systemic and glomerular hypertension in experimental hyperuricaemia. | 2008 Apr |
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Chronic xanthine oxidase inhibition following myocardial infarction in rabbits: effects of early versus delayed treatment. | 2008 Feb 27 |
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Effect of food or antacid on pharmacokinetics and pharmacodynamics of febuxostat in healthy subjects. | 2008 Mar |
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Xanthine oxidase inhibition with febuxostat attenuates systolic overload-induced left ventricular hypertrophy and dysfunction in mice. | 2008 Nov |
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The role of urate and xanthine oxidase in vascular oxidative stress: future directions. | 2009 |
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Update on emerging urate-lowering therapies. | 2009 Mar |
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Febuxostat for the treatment of hyperuricaemia in people with gout: a single technology appraisal. | 2009 Oct |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/uloric.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24686534
Febuxostat (200uM) inhibited cholesterol crystal-induced ROS formation and inflammatory cytokine release in murine macrophages.
Substance Class |
Chemical
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Record UNII |
101V0R1N2E
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Validated (UNII)
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LIVERTOX |
NBK548645
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WHO-VATC |
QM04AA03
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EMA ASSESSMENT REPORTS |
ADENURIC (AUTHORIZED: GOUT)
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WHO-ATC |
M04AA03
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NDF-RT |
N0000175698
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NDF-RT |
N0000000206
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NCI_THESAURUS |
C1637
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NCI_THESAURUS |
C921
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Febuxostat
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DB04854
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C65629
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OO-12
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73689
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100000089380
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m5253
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CHEMBL1164729
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6817
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134018
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758874
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Related Record | Type | Details | ||
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EXCRETED UNCHANGED |
AMOUNT EXCRETED
URINE
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METABOLIC ENZYME -> SUBSTRATE | |||
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BINDER->LIGAND |
BINDING
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EXCRETED UNCHANGED |
AMOUNT EXCRETED
FECAL
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METABOLIC ENZYME -> SUBSTRATE | |||
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TARGET -> INHIBITOR |
Ki
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METABOLIC ENZYME -> SUBSTRATE | |||
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SOLVATE->ANHYDROUS |
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> INHIBITOR |
Ki
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METABOLIC ENZYME -> SUBSTRATE |
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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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
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METABOLITE ACTIVE -> PARENT |
URINE
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METABOLITE ACTIVE -> PARENT |
MAJOR
URINE
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METABOLITE ACTIVE -> PARENT |
MAJOR
FECAL
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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
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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
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METABOLITE ACTIVE -> PARENT |
MAJOR
URINE
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CI file
USP
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IMPURITY -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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HIGH-FAT MEAL |
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Biological Half-life | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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