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
Enthesopathy 146.78 17.26 53 12432 4637 46668940
Cardiac failure 133.83 17.26 134 12351 79814 46593763
Renal impairment 132.55 17.26 129 12356 74243 46599334
Blood parathyroid hormone decreased 124.09 17.26 46 12439 4335 46669242
Tenosynovitis 122.55 17.26 53 12432 7462 46666115
Acute kidney injury 121.45 17.26 222 12263 235633 46437944
Panniculitis 119.16 17.26 48 12437 5656 46667921
Granuloma skin 115.31 17.26 41 12444 3429 46670148
Red blood cell sedimentation rate 111.79 17.26 34 12451 1739 46671838
Tongue disorder 108.32 17.26 48 12437 7162 46666415
Skin necrosis 103.26 17.26 49 12436 8555 46665022
Gout 98.84 17.26 52 12433 11304 46662273
Rheumatoid nodule 95.06 17.26 47 12438 8973 46664604
Drug eruption 94.16 17.26 63 12422 21266 46652311
Hypercalcaemia 83.03 17.26 58 12427 20988 46652589
Anaemia 77.28 17.26 194 12291 255585 46417992
Tendonitis 74.88 17.26 47 12438 14230 46659347
Aspartate aminotransferase increased 72.49 17.26 97 12388 78603 46594974
Hyperkalaemia 66.99 17.26 75 12410 50634 46622943
Ulcer 64.13 17.26 46 12439 17346 46656231
C-reactive protein abnormal 62.28 17.26 49 12436 21221 46652356
Blood creatinine increased 59.66 17.26 87 12398 76316 46597261
Hepatic function abnormal 58.06 17.26 58 12427 34363 46639214
Basal cell carcinoma 57.42 17.26 46 12439 20441 46653136
Alanine aminotransferase increased 54.10 17.26 90 12395 88361 46585216
Platelet count decreased 53.62 17.26 96 12389 99928 46573649
Skin ulcer 53.47 17.26 54 12431 32404 46641173
Hyperuricaemia 50.95 17.26 25 12460 4692 46668885
Alanine aminotransferase abnormal 41.77 17.26 18 12467 2509 46671068
Blood uric acid increased 41.63 17.26 21 12464 4180 46669397
Rash pruritic 39.91 17.26 54 12431 44161 46629416
C-reactive protein increased 39.04 17.26 62 12423 58528 46615049
Rash 38.84 17.26 193 12292 356319 46317258
Drug ineffective 38.79 17.26 77 12408 677761 45995816
Inflammation 38.71 17.26 56 12429 48725 46624852
Psoriatic arthropathy 38.40 17.26 48 12437 36331 46637246
Loss of personal independence in daily activities 36.03 17.26 59 12426 57124 46616453
Neutrophil count decreased 34.67 17.26 50 12435 43376 46630201
Red blood cell sedimentation rate increased 33.94 17.26 36 12449 22853 46650724
Fear of injection 33.29 17.26 18 12467 4129 46669448
Tumour lysis syndrome 31.02 17.26 21 12464 7215 46666362
Chronic kidney disease 26.87 17.26 43 12442 40828 46632749
Synovitis 25.77 17.26 53 12432 61022 46612555
Renal failure 25.08 17.26 77 12408 113517 46560060
Cardiac failure chronic 24.73 17.26 14 12471 3510 46670067
Toxicity to various agents 24.58 17.26 13 12472 211753 46461824
Fatigue 23.46 17.26 84 12401 608613 46064964
Myoglobin blood increased 22.98 17.26 10 12475 1426 46672151
Anaemia vitamin B12 deficiency 22.52 17.26 7 12478 385 46673192
Cardiac failure acute 22.33 17.26 18 12467 8060 46665517
Hyperferritinaemia 21.76 17.26 5 12480 84 46673493
Tubulointerstitial nephritis 21.46 17.26 23 12462 14765 46658812
Blood urea increased 21.42 17.26 30 12455 25322 46648255
Anxiety 19.91 17.26 12 12473 181945 46491632
Anaemia macrocytic 19.87 17.26 11 12474 2642 46670935
Upper respiratory tract inflammation 19.33 17.26 11 12474 2784 46670793
Haematoma muscle 19.28 17.26 7 12478 621 46672956
Haematochezia 18.81 17.26 35 12450 37458 46636119
Hypocalcaemia 18.74 17.26 29 12456 26756 46646821
Drug tolerance decreased 18.41 17.26 11 12474 3048 46670529
Transfusion 18.19 17.26 20 12465 13211 46660366
Renal disorder 17.43 17.26 28 12457 26658 46646919
Erythema 17.41 17.26 80 12405 142740 46530837
Mesenteric vein thrombosis 17.40 17.26 7 12478 821 46672756
Nasal mucosal erosion 17.37 17.26 4 12481 68 46673509
Interstitial lung disease 17.34 17.26 42 12443 53907 46619670

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 246.23 14.08 156 22156 17159 29913007
Enthesopathy 165.23 14.08 67 22245 2839 29927327
Tenosynovitis 156.19 14.08 68 22244 3447 29926719
Renal impairment 134.86 14.08 232 22080 83952 29846214
Tongue disorder 118.80 14.08 60 22252 4262 29925904
C-reactive protein abnormal 112.36 14.08 63 22249 5530 29924636
Cardiac failure 104.70 14.08 207 22105 83211 29846955
Hepatic function abnormal 104.50 14.08 142 22170 41803 29888363
Hyperuricaemia 101.02 14.08 65 22247 7329 29922837
Interstitial lung disease 95.13 14.08 165 22147 60032 29870134
Synovitis 91.24 14.08 68 22244 9715 29920451
Alanine aminotransferase abnormal 88.90 14.08 42 22270 2577 29927589
Hyperkalaemia 87.90 14.08 168 22144 65842 29864324
Cerebral infarction 77.68 14.08 97 22215 26276 29903890
Tendonitis 70.81 14.08 54 22258 7982 29922184
Platelet count decreased 61.32 14.08 196 22116 105933 29824233
Acute kidney injury 60.46 14.08 379 21933 273463 29656703
Aspartate aminotransferase increased 56.28 14.08 137 22175 63285 29866881
Blood uric acid increased 52.03 14.08 40 22272 5983 29924183
Loss of personal independence in daily activities 49.24 14.08 70 22242 21465 29908701
Alanine aminotransferase increased 48.29 14.08 143 22169 74133 29856033
Psoriatic arthropathy 46.44 14.08 58 22254 15703 29914463
Neutrophil count decreased 41.21 14.08 95 22217 42359 29887807
Lactic acidosis 39.73 14.08 78 22234 31135 29899031
Rash 37.00 14.08 257 22055 191632 29738534
Hypocalcaemia 36.90 14.08 61 22251 21315 29908851
Cardiac failure chronic 36.12 14.08 32 22280 5831 29924335
Blood creatinine increased 35.95 14.08 149 22163 91226 29838940
Gouty tophus 35.88 14.08 10 22302 128 29930038
Cerebral haemorrhage 34.60 14.08 76 22236 32811 29897355
Cardiac failure acute 33.93 14.08 38 22274 9171 29920995
Contraindicated product administered 33.62 14.08 52 22260 17179 29912987
Congenital diaphragmatic anomaly 32.18 14.08 7 22305 28 29930138
Orthostatic intolerance 32.10 14.08 14 22298 712 29929454
Anaemia 31.90 14.08 264 22048 207728 29722438
Drug eruption 31.58 14.08 51 22261 17475 29912691
Erythema 29.44 14.08 125 22187 77326 29852840
Gastric cancer 28.48 14.08 26 22286 4924 29925242
Death 28.18 14.08 154 22158 357129 29573037
Toxicity to various agents 28.11 14.08 56 22256 177127 29753039
Anxiety 28.10 14.08 16 22296 89855 29840311
Concomitant disease aggravated 27.69 14.08 26 22286 5103 29925063
Hyperkinetic heart syndrome 27.29 14.08 8 22304 124 29930042
Tumour lysis syndrome 26.71 14.08 40 22272 12845 29917321
Haemorrhage subcutaneous 26.51 14.08 18 22294 2219 29927947
Corneal abscess 26.17 14.08 6 22306 32 29930134
Blood lactic acid 25.93 14.08 10 22302 370 29929796
Treatment failure 25.66 14.08 70 22242 34609 29895557
Renal failure 25.56 14.08 174 22138 128792 29801374
Shock haemorrhagic 25.45 14.08 34 22278 9831 29920335
Liver disorder 25.06 14.08 63 22249 29659 29900507
Conjunctival ulcer 22.42 14.08 5 22307 23 29930143
Fulminant type 1 diabetes mellitus 22.38 14.08 10 22302 539 29929627
Procedural failure 22.28 14.08 6 22306 67 29930099
Pneumonia bacterial 22.13 14.08 31 22281 9372 29920794
Rhabdomyolysis 21.42 14.08 99 22213 63481 29866685
Thirst 21.15 14.08 26 22286 6923 29923243
Transformation to acute myeloid leukaemia 20.82 14.08 10 22302 636 29929530
Asthenia 20.50 14.08 90 22222 221200 29708966
Chronic kidney disease 20.11 14.08 68 22244 37770 29892396
Blood urea increased 19.96 14.08 60 22252 31321 29898845
General physical health deterioration 19.88 14.08 135 22177 99809 29830357
Renal ischaemia 19.30 14.08 9 22303 536 29929630
Fatigue 19.26 14.08 150 22162 320523 29609643
Cytomegalovirus nephritis 19.09 14.08 6 22306 119 29930047
Hepatic enzyme increased 18.51 14.08 61 22251 33433 29896733
Pemphigoid 17.98 14.08 25 22287 7503 29922663
Cardiac arrest 17.77 14.08 26 22286 92824 29837342
Suicide attempt 17.72 14.08 3 22309 36694 29893472
Hypovolaemic shock 17.69 14.08 23 22289 6477 29923689
Brain natriuretic peptide increased 17.23 14.08 18 22294 4017 29926149
C-reactive protein increased 17.15 14.08 71 22241 43402 29886764
Blood uric acid decreased 16.88 14.08 7 22305 314 29929852
Echocardiogram abnormal 16.78 14.08 9 22303 723 29929443
Pseudohyponatraemia 16.31 14.08 5 22307 91 29930075
Decreased appetite 16.29 14.08 177 22135 149733 29780433
Nephrogenic anaemia 15.89 14.08 13 22299 2126 29928040
Product prescribing error 15.74 14.08 37 22275 16696 29913470
Depression 15.72 14.08 27 22285 90410 29839756
Skin weeping 15.64 14.08 5 22307 105 29930061
Puncture site infection 15.53 14.08 4 22308 37 29930129
Subarachnoid haemorrhage 15.45 14.08 27 22285 9859 29920307
Arrhythmia 15.38 14.08 57 22255 33112 29897054
Suicidal ideation 15.29 14.08 4 22308 36110 29894056
Nephrotic syndrome 15.17 14.08 22 22290 6863 29923303
Stress cardiomyopathy 14.96 14.08 11 22301 1538 29928628
Confusional state 14.93 14.08 51 22261 134783 29795383
Procedural haemorrhage 14.88 14.08 13 22299 2325 29927841
Thalamus haemorrhage 14.53 14.08 9 22303 949 29929217
Altered state of consciousness 14.52 14.08 40 22272 19879 29910287
Pulmonary alveolar haemorrhage 14.46 14.08 21 22291 6560 29923606
Cerebral ventricular rupture 14.28 14.08 5 22307 140 29930026
Keratoconus 14.16 14.08 4 22308 54 29930112
Drug intolerance 14.13 14.08 69 22243 45222 29884944

Pharmacologic Action:

SourceCodeDescription
ATC M04AA03 MUSCULO-SKELETAL SYSTEM
ANTIGOUT PREPARATIONS
ANTIGOUT PREPARATIONS
Preparations inhibiting uric acid production
FDA MoA N0000000206 Xanthine Oxidase Inhibitors
FDA EPC N0000175698 Xanthine Oxidase Inhibitor
MeSH PA D018501 Antirheumatic Agents
MeSH PA D006074 Gout Suppressants
CHEBI has role CHEBI:35634 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)

None

Orange Book exclusivity data (new drug applications)

None

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
4025245 VUID
N0000179385 NUI
D01206 KEGG_DRUG
4025245 VANDF
C2683462 UMLSCUI
CHEBI:31596 CHEBI
TEI PDB_CHEM_ID
CHEMBL1164729 ChEMBL_ID
134018 PUBCHEM_CID
DB04854 DRUGBANK_ID
D000069465 MESH_DESCRIPTOR_UI
6817 IUPHAR_LIGAND_ID
8140 INN_ID
101V0R1N2E UNII
73689 RXNORM
161190 MMSL
232999 MMSL
26212 MMSL
d07397 MMSL
012966 NDDF
441610003 SNOMEDCT_US
441743008 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 0054-0413 TABLET 40 mg ORAL ANDA 29 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 0054-0414 TABLET 80 mg ORAL ANDA 29 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 0378-3925 TABLET, FILM COATED 40 mg ORAL ANDA 29 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 0378-3926 TABLET, FILM COATED 80 mg ORAL ANDA 29 sections
Febuxostat Human Prescription Drug Label 1 14445-156 TABLET, FILM COATED 40 mg ORAL ANDA 27 sections
Febuxostat Human Prescription Drug Label 1 14445-157 TABLET, FILM COATED 80 mg ORAL ANDA 27 sections
Febuxostat Human Prescription Drug Label 1 16714-059 TABLET, FILM COATED 40 mg ORAL ANDA 31 sections
Febuxostat Human Prescription Drug Label 1 16714-060 TABLET, FILM COATED 80 mg ORAL ANDA 31 sections
ULORIC HUMAN PRESCRIPTION DRUG LABEL 1 21695-516 TABLET 80 mg ORAL NDA 29 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 27808-206 TABLET 40 mg ORAL ANDA 32 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 27808-207 TABLET 80 mg ORAL ANDA 32 sections
ULORIC HUMAN PRESCRIPTION DRUG LABEL 1 43353-305 TABLET 40 mg ORAL NDA 29 sections
Febuxostat Human Prescription Drug Label 1 46708-190 TABLET, COATED 40 mg ORAL ANDA 29 sections
Febuxostat Human Prescription Drug Label 1 46708-191 TABLET, COATED 80 mg ORAL ANDA 29 sections
Febuxostat Human Prescription Drug Label 1 47335-721 TABLET, FILM COATED 40 mg ORAL ANDA 31 sections
Febuxostat Human Prescription Drug Label 1 47335-722 TABLET, FILM COATED 80 mg ORAL ANDA 31 sections
FEBUXOSTAT HUMAN PRESCRIPTION DRUG LABEL 1 48792-7905 TABLET 40 mg ORAL ANDA 32 sections
FEBUXOSTAT HUMAN PRESCRIPTION DRUG LABEL 1 48792-7906 TABLET 80 mg ORAL ANDA 32 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 51407-293 TABLET 40 mg ORAL ANDA 29 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 51407-294 TABLET 80 mg ORAL ANDA 29 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 55111-796 TABLET 40 mg ORAL ANDA 29 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 55111-797 TABLET 80 mg ORAL ANDA 29 sections
ULORIC HUMAN PRESCRIPTION DRUG LABEL 1 55154-5158 TABLET 40 mg ORAL NDA 32 sections
ULORIC HUMAN PRESCRIPTION DRUG LABEL 1 55154-5159 TABLET 80 mg ORAL NDA 32 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 60687-538 TABLET, FILM COATED 40 mg ORAL ANDA 31 sections
Febuxostat Human Prescription Drug Label 1 62332-190 TABLET, COATED 40 mg ORAL ANDA 29 sections
Febuxostat Human Prescription Drug Label 1 62332-191 TABLET, COATED 80 mg ORAL ANDA 29 sections
ULORIC HUMAN PRESCRIPTION DRUG LABEL 1 64764-677 TABLET 80 mg ORAL NDA 32 sections
ULORIC HUMAN PRESCRIPTION DRUG LABEL 1 64764-918 TABLET 40 mg ORAL NDA 32 sections
Febuxostat HUMAN PRESCRIPTION DRUG LABEL 1 68071-5271 TABLET, FILM COATED 40 mg ORAL ANDA 27 sections