Details
Stereochemistry | ACHIRAL |
Molecular Formula | C16H16N2O3S |
Molecular Weight | 316.3765 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)COc1ccc(cc1C#N)-c2nc(C)c(C(=O)O)s2
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 | 316.3765 |
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 Date1.23439677E12 |
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 |
Doses
Dose | Population | Adverse events |
---|---|---|
300 mg 1 times / day multiple, oral Highest studied dose Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: |
healthy, adult Health Status: healthy Age Group: adult Sources: |
|
40 mg 1 times / day steady, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: |
unhealthy, adult n = 757 Health Status: unhealthy Condition: hyperuricemia | gout Age Group: adult Sex: M+F Population Size: 757 Sources: |
Disc. AE: Function liver abnormal... AEs leading to discontinuation/dose reduction: Function liver abnormal (1.8%) Sources: |
80 mg 1 times / day steady, oral Recommended Dose: 80 mg, 1 times / day Route: oral Route: steady Dose: 80 mg, 1 times / day Sources: |
unhealthy, adult n = 1279 Health Status: unhealthy Condition: hyperuricemia | gout Age Group: adult Sex: M+F Population Size: 1279 Sources: |
Disc. AE: Function liver abnormal... AEs leading to discontinuation/dose reduction: Function liver abnormal (1.2%) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Function liver abnormal | 1.8% Disc. AE |
40 mg 1 times / day steady, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: |
unhealthy, adult n = 757 Health Status: unhealthy Condition: hyperuricemia | gout Age Group: adult Sex: M+F Population Size: 757 Sources: |
Function liver abnormal | 1.2% Disc. AE |
80 mg 1 times / day steady, oral Recommended Dose: 80 mg, 1 times / day Route: oral Route: steady Dose: 80 mg, 1 times / day Sources: |
unhealthy, adult n = 1279 Health Status: unhealthy Condition: hyperuricemia | gout Age Group: adult Sex: M+F Population Size: 1279 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
PubMed
Title | Date | PubMed |
---|---|---|
Pathophysiology, clinical presentation and treatment of gout. | 2006 |
|
Pharmacokinetics, pharmacodynamics and safety of febuxostat, a non-purine selective inhibitor of xanthine oxidase, in a dose escalation study in healthy subjects. | 2006 |
|
Recent developments in our understanding of the renal basis of hyperuricemia and the development of novel antihyperuricemic therapeutics. | 2006 |
|
A concise history of gout and hyperuricemia and their treatment. | 2006 |
|
Febuxostat for prevention of gout attacks. | 2006 Aug |
|
Pharmacokinetic interactions of concomitant administration of febuxostat and NSAIDs. | 2006 Aug |
|
Febuxostat: a selective xanthine oxidase inhibitor for the treatment of hyperuricemia and gout. | 2006 Dec |
|
Gateways to clinical trials. | 2006 Jul-Aug |
|
Advances in the management of gout and hyperuricaemia. | 2006 Jul-Aug |
|
New developments in clinically relevant mechanisms and treatment of hyperuricemia. | 2006 Jun |
|
Is febuxostat a more effective treatment for hyperuricemia and gout than allopurinol? | 2006 May |
|
Acute effects of febuxostat, a nonpurine selective inhibitor of xanthine oxidase, in pacing induced heart failure. | 2006 Nov |
|
Case 8: initiation of urate-lowering therapy for standard advanced gout. | 2006 Nov |
|
Metabolic diseases: gout. | 2006 Nov-Dec |
|
[Febuxostat versus allopurinol for hyperuricemia]. | 2006 Oct |
|
Gout Assessment Questionnaire: Initial results of reliability, validity and responsiveness. | 2006 Oct |
|
Hyperuricemia and gout: new insights into pathogenesis and treatment. | 2007 |
|
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 |
|
[Crystal-induced arthritis--old but important]. | 2007 Jul |
|
Therapeutic advances in gout. | 2007 Mar |
|
Febuxostat : a viewpoint by N. Lawrence Edwards. | 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 |
|
Crystal structures of mammalian xanthine oxidoreductase bound with various inhibitors: allopurinol, febuxostat, and FYX-051. | 2008 Feb |
|
Determinants of the clinical outcomes of gout during the first year of urate-lowering therapy. | 2008 Jun |
|
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 |
|
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 |
|
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 |
|
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 |
|
Update on emerging urate-lowering therapies. | 2009 Mar |
|
[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 |
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
Created
by
admin
on
Edited
Fri Jun 25 22:09:35 UTC 2021
by
admin
on
Fri Jun 25 22:09:35 UTC 2021
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Record UNII |
101V0R1N2E
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Record Status |
Validated (UNII)
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Record Version |
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LIVERTOX |
400
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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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101V0R1N2E
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DB04854
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C65629
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C084623
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SUB25382
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M5253
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CHEMBL1164729
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6817
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134018
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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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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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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT |
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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ACTIVE MOIETY |
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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