febuxostat Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
xanthine oxydase and xanthine dehydrogenase inhibitor 1137 144060-53-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • februxostat
  • febuxostat
  • feburic
  • uloric
  • adenuric
A thiazole derivative and inhibitor of XANTHINE OXIDASE that is used for the treatment of HYPERURICEMIA in patients with chronic GOUT.
  • Molecular weight: 316.38
  • Formula: C16H16N2O3S
  • CLOGP: 4.10
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 1
  • TPSA: 83.21
  • ALOGS: -4.24
  • ROTB: 5

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
80 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.01 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 3 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 3.61 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
Feb. 26, 2015 EMA
Feb. 13, 2009 FDA TAKEDA PHARMS USA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Rash 243.48 37.03 95 748 59463 2297779
Acute kidney injury 237.22 37.03 77 766 28045 2329197
Gout 157.78 37.03 31 812 1424 2355818
Diarrhoea 67.73 37.03 45 798 83519 2273723
Pruritus 65.66 37.03 35 808 43305 2313937
Urinary retention 65.19 37.03 18 825 3649 2353593
Pneumonia aspiration 64.83 37.03 18 825 3724 2353518
Blood creatinine increased 61.22 37.03 22 821 10511 2346731
Head injury 58.99 37.03 17 826 4017 2353225
Blood uric acid increased 53.15 37.03 11 832 650 2356592
Nausea 47.43 37.03 41 802 112148 2245094
Acute coronary syndrome 43.62 37.03 11 832 1566 2355676
Troponin increased 42.52 37.03 10 833 1064 2356178
Fall 41.93 37.03 27 816 47072 2310170
Renal failure 40.97 37.03 19 824 17330 2339912
Vomiting 40.34 37.03 31 812 71571 2285671
Angina unstable 40.13 37.03 10 833 1356 2355886

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Gout 480.26 34.25 107 1703 2509 1742462
Rash 327.32 34.25 150 1660 38543 1706428
Acute kidney injury 130.75 34.25 79 1731 34865 1710106
Pruritus 109.21 34.25 61 1749 23161 1721810
Hyperkalaemia 106.79 34.25 44 1766 8503 1736468
Blood uric acid increased 104.16 34.25 26 1784 983 1743988
Rhabdomyolysis 102.10 34.25 46 1764 11044 1733927
Blood creatinine increased 101.03 34.25 49 1761 13897 1731074
Cardiac failure 78.53 34.25 40 1770 12562 1732409
Liver function test abnormal 76.64 34.25 31 1779 5695 1739276
Hepatic enzyme increased 75.62 34.25 32 1778 6589 1738382
Renal failure 68.77 34.25 43 1767 19974 1724997
Nausea 65.73 34.25 61 1749 51135 1693836
Arthralgia 64.94 34.25 44 1766 23400 1721571
Dizziness 58.22 34.25 48 1762 34313 1710658
Myalgia 57.19 34.25 35 1775 15623 1729348
Renal impairment 54.04 34.25 31 1779 12283 1732688
Agranulocytosis 53.52 34.25 21 1789 3555 1741416
Gouty tophus 52.28 34.25 9 1801 48 1744923
Hypocalcaemia 48.87 34.25 19 1791 3137 1741834
Pyrexia 47.67 34.25 49 1761 46351 1698620
Alanine aminotransferase increased 46.22 34.25 28 1782 12250 1732721
Procedural failure 43.48 34.25 6 1804 3 1744968
Drug interaction 43.04 34.25 37 1773 27921 1717050
Pancytopenia 40.44 34.25 25 1785 11332 1733639
Gamma-glutamyltransferase increased 40.10 34.25 19 1791 5079 1739892
Lactic acidosis 39.99 34.25 19 1791 5110 1739861
Hepatic function abnormal 39.80 34.25 21 1789 7053 1737918
Interstitial lung disease 38.78 34.25 23 1787 9673 1735298
Eosinophilia 36.77 34.25 16 1794 3511 1741460

Pharmacologic Action:

SourceCodeDescription
ATC M04AA03 MUSCULO-SKELETAL SYSTEM
ANTIGOUT PREPARATIONS
ANTIGOUT PREPARATIONS
Preparations inhibiting uric acid production
MeSH PA D018501 Antirheumatic Agents
MeSH PA D006074 Gout Suppressants
FDA EPC N0000175698 Xanthine Oxidase Inhibitor
FDA MoA N0000000206 Xanthine Oxidase Inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hyperuricemia indication 35885006 DOID:1920
Gout Prevention indication
Myocardial infarction contraindication 22298006 DOID:5844
Liver function tests abnormal contraindication 166603001
Cerebrovascular accident contraindication 230690007
Thromboembolic disorder contraindication 371039008

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.3 acidic
pKa2 0.46 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
40MG ULORIC TAKEDA PHARMS USA N021856 Feb. 13, 2009 RX TABLET ORAL 8372872 Sept. 8, 2031 USE OF FEBUXOSTAT FOR THE MANAGEMENT OF HYPERURICEMIA IN PATIENTS SUFFERING FROM GOUT AND, WHEN USED WITH THEOPHYLLINE WITHOUT THE NEED FOR DOSE ADJUSTMENT OF THEOPHYLLINE
40MG ULORIC TAKEDA PHARMS USA N021856 Feb. 13, 2009 RX TABLET ORAL 9107912 Sept. 8, 2031 USE OF FEBUXOSTAT FOR THE MANAGEMENT OF HYPERURICEMIA IN PATIENTS SUFFERING FROM GOUT AND, WHEN USED WITH THEOPHYLLINE WITHOUT THE NEED FOR DOSE ADJUSTMENT OF THEOPHYLLINE
80MG ULORIC TAKEDA PHARMS USA N021856 Feb. 13, 2009 RX TABLET ORAL 8372872 Sept. 8, 2031 USE OF FEBUXOSTAT FOR THE MANAGEMENT OF HYPERURICEMIA IN PATIENTS SUFFERING FROM GOUT AND, WHEN USED WITH THEOPHYLLINE WITHOUT THE NEED FOR DOSE ADJUSTMENT OF THEOPHYLLINE
80MG ULORIC TAKEDA PHARMS USA N021856 Feb. 13, 2009 RX TABLET ORAL 9107912 Sept. 8, 2031 USE OF FEBUXOSTAT FOR THE MANAGEMENT OF HYPERURICEMIA IN PATIENTS SUFFERING FROM GOUT AND, WHEN USED WITH THEOPHYLLINE WITHOUT THE NEED FOR DOSE ADJUSTMENT OF THEOPHYLLINE

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
40MG ULORIC TAKEDA PHARMS USA N021856 Feb. 13, 2009 RX TABLET ORAL Aug. 15, 2020 INFORMATION ADDED TO THE LABELING REGARDING RANDOMIZED, MULTICENTER, DOUBLE-BLIND, PLACEBO-CONTROLLED STUDIES ON PATIENTS WITH SEVERE RENAL IMPAIRMENT
80MG ULORIC TAKEDA PHARMS USA N021856 Feb. 13, 2009 RX TABLET ORAL Aug. 15, 2020 INFORMATION ADDED TO THE LABELING REGARDING RANDOMIZED, MULTICENTER, DOUBLE-BLIND, PLACEBO-CONTROLLED STUDIES ON PATIENTS WITH SEVERE RENAL IMPAIRMENT

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Xanthine dehydrogenase/oxidase Enzyme INHIBITOR Ki 9.22 WOMBAT-PK CHEMBL
Potassium voltage-gated channel subfamily H member 2 Ion channel EC50 7.44 WOMBAT-PK
Xanthine dehydrogenase/oxidase Enzyme IC50 8.52 CHEMBL
Xanthine dehydrogenase/oxidase Enzyme IC50 8.40 CHEMBL

External reference:

IDSource
D000069465 MESH_DESCRIPTOR_UI
4025245 VUID
N0000179385 NUI
C0249529 UMLSCUI
D01206 KEGG_DRUG
101V0R1N2E UNII
8140 INN_ID
441610003 SNOMEDCT_US
232999 MMSL
4025245 VANDF
73689 RXNORM
26212 MMSL
d07397 MMSL
441743008 SNOMEDCT_US
012966 NDDF
CHEMBL1164729 ChEMBL_ID
DB04854 DRUGBANK_ID
CHEBI:31596 CHEBI
134018 PUBCHEM_CID
6817 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 0054-0413 TABLET 40 mg ORAL ANDA 19 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 0054-0414 TABLET 80 mg ORAL ANDA 19 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 0378-3925 TABLET, FILM COATED 40 mg ORAL ANDA 19 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 0378-3926 TABLET, FILM COATED 80 mg ORAL ANDA 19 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 14445-156 TABLET, FILM COATED 40 mg ORAL ANDA 18 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 14445-157 TABLET, FILM COATED 80 mg ORAL ANDA 18 sections
ULORIC HUMAN PRESCRIPTION DRUG LABEL 1 21695-516 TABLET 80 mg ORAL NDA 17 sections
ULORIC HUMAN PRESCRIPTION DRUG LABEL 1 43353-305 TABLET 40 mg ORAL NDA 19 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 46708-190 TABLET, COATED 40 mg ORAL ANDA 19 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 46708-191 TABLET, COATED 80 mg ORAL ANDA 19 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 47335-721 TABLET, FILM COATED 40 mg ORAL ANDA 19 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 47335-722 TABLET, FILM COATED 80 mg ORAL ANDA 19 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 51407-293 TABLET 40 mg ORAL ANDA 19 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 51407-294 TABLET 80 mg ORAL ANDA 19 sections
ULORIC HUMAN PRESCRIPTION DRUG LABEL 1 55154-5158 TABLET 40 mg ORAL NDA 19 sections
ULORIC HUMAN PRESCRIPTION DRUG LABEL 1 55154-5159 TABLET 80 mg ORAL NDA 19 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 62332-190 TABLET, COATED 40 mg ORAL ANDA 19 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 62332-191 TABLET, COATED 80 mg ORAL ANDA 19 sections
ULORIC HUMAN PRESCRIPTION DRUG LABEL 1 64764-677 TABLET 80 mg ORAL NDA 19 sections
ULORIC HUMAN PRESCRIPTION DRUG LABEL 1 64764-918 TABLET 40 mg ORAL NDA 19 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 69539-035 TABLET, FILM COATED 40 mg ORAL ANDA 19 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 69539-036 TABLET, FILM COATED 80 mg ORAL ANDA 19 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 71610-386 TABLET 40 mg ORAL ANDA 20 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 71610-411 TABLET, FILM COATED 40 mg ORAL ANDA 19 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 72205-028 TABLET, FILM COATED 40 mg ORAL ANDA 19 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 72205-029 TABLET, FILM COATED 80 mg ORAL ANDA 19 sections