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

Stem definitionDrug idCAS RN
diuretics, piretanide derivatives 427 28395-03-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • bumetanide
  • bumethanide
  • bufenox
A sulfamyl diuretic.
  • Molecular weight: 364.42
  • Formula: C17H20N2O5S
  • CLOGP: 3.37
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 3
  • TPSA: 118.72
  • ALOGS: -4.15
  • ROTB: 8

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
1 mg O
1 mg P
1 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.10 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 45 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.46 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 90 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.16 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 2.50 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.03 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.20 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Feb. 28, 1983 FDA

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
Fluid retention 188.61 12.73 177 23660 50869 46611356
Cardiac failure congestive 188.35 12.73 233 23604 91517 46570708
Acute kidney injury 183.19 12.73 384 23453 235471 46426754
Fluid overload 163.87 12.73 125 23712 27060 46635165
Dyspnoea 160.83 12.73 601 23236 514947 46147278
Right ventricular failure 121.94 12.73 85 23752 16008 46646217
Pulmonary arterial hypertension 105.60 12.73 95 23742 25833 46636392
Oedema peripheral 95.78 12.73 235 23602 159471 46502754
Rheumatoid arthritis 93.09 12.73 8 23829 240207 46422018
Pulmonary hypertension 93.06 12.73 103 23734 35890 46626335
Oedema 90.21 12.73 139 23698 66932 46595293
Drug ineffective 88.81 12.73 131 23706 677707 45984518
Cardiac failure 86.29 12.73 150 23687 79798 46582427
Renal failure 84.46 12.73 182 23655 113412 46548813
International normalised ratio increased 71.38 12.73 103 23734 46780 46615445
Renal impairment 65.68 12.73 128 23709 74244 46587981
Off label use 55.01 12.73 68 23769 379773 46282452
Body tinea 51.48 12.73 19 23818 916 46661309
Hyperkalaemia 50.63 12.73 92 23745 50617 46611608
Atrial fibrillation 50.31 12.73 141 23696 103449 46558776
Hypotension 45.82 12.73 237 23600 232352 46429873
Pulmonary oedema 45.15 12.73 88 23749 51017 46611208
BRASH syndrome 42.25 12.73 10 23827 96 46662129
Impaired quality of life 39.19 12.73 23 23814 3219 46659006
Exposure during pregnancy 38.29 12.73 5 23832 108207 46554018
Dyspnoea exertional 37.80 12.73 81 23756 50208 46612017
Treatment failure 36.28 12.73 3 23834 93084 46569141
Infection susceptibility increased 36.04 12.73 19 23818 2160 46660065
Chronic obstructive pulmonary disease 35.73 12.73 86 23751 57547 46604678
Gastrointestinal haemorrhage 35.30 12.73 103 23734 77270 46584955
Infusion related reaction 35.04 12.73 5 23832 101203 46561022
Inhibitory drug interaction 34.72 12.73 18 23819 1977 46660248
Left ventricular failure 34.65 12.73 25 23812 4965 46657260
Cardiac failure acute 33.67 12.73 30 23807 8048 46654177
Hypoxia 32.83 12.73 78 23759 51760 46610465
Death 31.64 12.73 285 23552 335263 46326962
Transfusion 31.01 12.73 36 23801 13195 46649030
Purpura 30.14 12.73 31 23806 9927 46652298
Bradycardia 29.99 12.73 88 23749 66210 46596015
Congestive cardiomyopathy 29.51 12.73 24 23813 5689 46656536
Joint swelling 29.34 12.73 25 23812 166048 46496177
Weight increased 28.55 12.73 162 23675 164311 46497914
Dialysis 27.96 12.73 30 23807 10086 46652139
Cellulitis 27.78 12.73 89 23748 70199 46592026
Gout 26.78 12.73 31 23806 11325 46650900
Glucose tolerance impaired 26.45 12.73 21 23816 4810 46657415
Alopecia 25.69 12.73 27 23810 162387 46499838
Drug hypersensitivity 25.49 12.73 54 23783 243771 46418454
Pleural effusion 24.97 12.73 96 23741 82856 46579369
Blood potassium decreased 24.88 12.73 58 23779 38005 46624220
Acute respiratory failure 24.31 12.73 49 23788 29089 46633136
Blood creatinine increased 24.30 12.73 90 23747 76313 46585912
Epistaxis 24.13 12.73 80 23757 64225 46598000
Respiratory failure 24.00 12.73 104 23733 94712 46567513
Pain in jaw 23.49 12.73 57 23780 38315 46623910
Haemoglobin decreased 23.02 12.73 128 23709 128821 46533404
Drug intolerance 22.64 12.73 25 23812 147024 46515201
Drug abuse 22.26 12.73 3 23834 63405 46598820
Genital infection female 21.52 12.73 6 23831 115 46662110
Cardiorenal syndrome 21.45 12.73 9 23828 611 46661614
Therapeutic product effect decreased 20.90 12.73 8 23829 82593 46579632
Oxygen saturation decreased 20.78 12.73 80 23757 69084 46593141
Intentional overdose 20.72 12.73 4 23833 64940 46597285
Rectal haemorrhage 20.47 12.73 54 23783 38201 46624024
Dehydration 20.16 12.73 145 23692 159395 46502830
Chronic left ventricular failure 19.62 12.73 7 23830 306 46661919
Therapeutic product effect incomplete 19.07 12.73 8 23829 78145 46584080
Orthopnoea 19.06 12.73 19 23818 5861 46656364
Arthralgia 18.94 12.73 109 23728 364494 46297731
Torsade de pointes 18.92 12.73 27 23810 12127 46650098
Arteriosclerosis coronary artery 18.79 12.73 22 23815 8134 46654091
Unevaluable event 18.72 12.73 59 23778 46116 46616109
Suicide attempt 18.40 12.73 3 23834 55033 46607192
Atrial flutter 18.34 12.73 23 23814 9125 46653100
Abdominal distension 18.21 12.73 80 23757 73271 46588954
Blood urea increased 18.09 12.73 40 23797 25312 46636913
Product use in unapproved indication 17.97 12.73 12 23825 90261 46571964
Paracentesis 17.82 12.73 9 23828 936 46661289
Contraindicated product administered 16.77 12.73 10 23827 79937 46582288
Injection site pain 16.73 12.73 18 23819 107134 46555091
Pneumonia 16.62 12.73 277 23560 376043 46286182
Cardiomegaly 16.53 12.73 31 23806 17451 46644774
Hospitalisation 16.40 12.73 70 23767 63315 46598910
Chronic kidney disease 16.37 12.73 52 23785 40819 46621406
Urine output decreased 16.32 12.73 24 23813 11073 46651152
Pemphigoid 15.94 12.73 17 23820 5674 46656551
Blood potassium increased 15.94 12.73 30 23807 16937 46645288
Arthropathy 15.88 12.73 12 23825 84688 46577537
Musculoskeletal stiffness 15.82 12.73 16 23821 97977 46564248
Seizure 15.76 12.73 24 23813 123030 46539195
Packed red blood cell transfusion 15.39 12.73 11 23826 2152 46660073
Confusional state 15.11 12.73 136 23701 159756 46502469
Brain natriuretic peptide increased 15.03 12.73 15 23822 4635 46657590
Hepatic enzyme increased 14.81 12.73 12 23825 81775 46580450
Anaemia 14.68 12.73 197 23640 255582 46406643
Injection site erythema 14.67 12.73 10 23827 74417 46587808
Lung transplant 14.62 12.73 12 23825 2880 46659345
Drug monitoring procedure not performed 14.47 12.73 6 23831 395 46661830
Urosepsis 14.24 12.73 27 23810 15326 46646899
Claudication of jaw muscles 14.23 12.73 4 23833 79 46662146
Subacute cutaneous lupus erythematosus 14.23 12.73 10 23827 1905 46660320
Generalised oedema 14.20 12.73 26 23811 14373 46647852
Blood sodium decreased 14.08 12.73 33 23804 21693 46640532
Oxygen consumption increased 14.08 12.73 13 23824 3650 46658575
Right ventricular dysfunction 13.85 12.73 9 23828 1509 46660716
Compartment syndrome 13.84 12.73 10 23827 1989 46660236
Malignant neoplasm progression 13.79 12.73 8 23829 64918 46597307
Asthenia 13.72 12.73 229 23608 310846 46351379
Hypoaesthesia 13.55 12.73 25 23812 118844 46543381
Diaphragmatic disorder 13.22 12.73 6 23831 492 46661733
Incarcerated umbilical hernia 13.05 12.73 3 23834 25 46662200
Diuretic therapy 13.01 12.73 4 23833 109 46662116
Brain stem stroke 12.99 12.73 5 23832 271 46661954
Blood aldosterone abnormal 12.85 12.73 3 23834 27 46662198
Bone density decreased 12.79 12.73 20 23817 9732 46652493

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
Acute kidney injury 211.10 13.46 497 17986 273345 29660650
Cardiac failure congestive 166.04 13.46 231 18252 84176 29849819
Cardiac failure 127.64 13.46 203 18280 83215 29850780
Fluid retention 106.30 13.46 102 18381 24896 29909099
Dyspnoea 104.13 13.46 443 18040 332852 29601143
Pulmonary hypertension 79.64 13.46 77 18406 18959 29915036
Fluid overload 64.83 13.46 69 18414 19023 29914972
Pulmonary arterial hypertension 45.39 13.46 41 18442 9260 29924735
Oedema peripheral 44.50 13.46 155 18328 105677 29828318
Drug ineffective 44.16 13.46 90 18393 340297 29593698
Renal failure 41.16 13.46 173 18310 128793 29805202
Right ventricular failure 40.35 13.46 36 18447 8000 29925995
Blood ketone body increased 39.64 13.46 13 18470 361 29933634
Oedema 39.43 13.46 84 18399 42909 29891086
Toxicity to various agents 34.62 13.46 35 18448 177148 29756847
Hypotension 32.93 13.46 224 18259 200341 29733654
International normalised ratio increased 32.51 13.46 83 18400 47656 29886339
Completed suicide 31.55 13.46 11 18472 99481 29834514
Renal impairment 30.88 13.46 118 18365 84066 29849929
Hyperkalaemia 30.64 13.46 100 18383 65910 29868085
Peripheral swelling 29.69 13.46 94 18389 60980 29873015
Gastrointestinal haemorrhage 29.00 13.46 115 18368 83331 29850664
Atrial fibrillation 25.59 13.46 133 18350 107991 29826004
Ventricular tachycardia 24.67 13.46 49 18434 23813 29910182
Dyspnoea exertional 24.53 13.46 62 18421 35368 29898627
Pulmonary oedema 24.48 13.46 71 18412 43904 29890091
Off label use 23.70 13.46 77 18406 249213 29684782
Cardiac failure chronic 23.17 13.46 23 18460 5840 29928155
Pulmonary renal syndrome 22.35 13.46 7 18476 167 29933828
Febrile neutropenia 22.07 13.46 20 18463 106673 29827322
Blood creatinine increased 22.03 13.46 113 18370 91262 29842733
Pyrexia 21.58 13.46 101 18382 294388 29639607
Orthostatic hypotension 21.00 13.46 46 18437 23933 29910062
Cardiac failure acute 20.77 13.46 27 18456 9182 29924813
Hepatic cirrhosis 20.47 13.46 36 18447 15963 29918032
Neutropenia 20.22 13.46 30 18453 128510 29805485
Anti-neutrophil cytoplasmic antibody positive vasculitis 19.77 13.46 9 18474 614 29933381
Chronic kidney disease 19.08 13.46 59 18424 37779 29896216
Venous pressure jugular increased 18.63 13.46 9 18474 702 29933293
Weight increased 18.30 13.46 93 18390 74820 29859175
Weight bearing difficulty 16.86 13.46 9 18474 866 29933129
Packed red blood cell transfusion 16.76 13.46 11 18472 1549 29932446
Reaction to excipient 16.73 13.46 7 18476 389 29933606
Orthopnoea 16.46 13.46 17 18466 4523 29929472
Hypovolaemia 16.03 13.46 23 18460 8582 29925413
Rheumatoid arthritis 16.02 13.46 3 18480 41194 29892801
Polyuria 15.83 13.46 21 18462 7285 29926710
Amyloidosis 15.81 13.46 12 18471 2127 29931868
Ascites 15.39 13.46 53 18430 35868 29898127
Bradycardia 15.06 13.46 80 18403 65446 29868549
Dyspnoea paroxysmal nocturnal 14.47 13.46 9 18474 1156 29932839
Hepatic function abnormal 14.43 13.46 4 18479 41941 29892054
Hungry bone syndrome 14.33 13.46 4 18479 63 29933932
Transitional cell carcinoma 14.32 13.46 11 18472 1984 29932011
Blood potassium increased 14.08 13.46 31 18452 16182 29917813
Abdominal cavity drainage 14.07 13.46 6 18477 350 29933645
Incarcerated hernia 14.04 13.46 5 18478 179 29933816
Intra-abdominal haemorrhage 13.82 13.46 11 18472 2091 29931904
Faeces discoloured 13.65 13.46 28 18455 13918 29920077
Suicide attempt 13.59 13.46 3 18480 36694 29897301
Vasculitic rash 13.55 13.46 8 18475 935 29933060

Pharmacologic Action:

SourceCodeDescription
ATC C03CA02 CARDIOVASCULAR SYSTEM
DIURETICS
HIGH-CEILING DIURETICS
Sulfonamides, plain
ATC C03CB02 CARDIOVASCULAR SYSTEM
DIURETICS
HIGH-CEILING DIURETICS
Sulfonamides and potassium in combination
ATC C03EB02 CARDIOVASCULAR SYSTEM
DIURETICS
DIURETICS AND POTASSIUM-SPARING AGENTS IN COMBINATION
High-ceiling diuretics and potassium-sparing agents
FDA PE N0000175366 Increased Diuresis at Loop of Henle
FDA EPC N0000175590 Loop Diuretic
CHEBI has role CHEBI:35498 diuretics
CHEBI has role CHEBI:131770 cystic fibrosis transmembrane conductance regulator inhibitors
MeSH PA D004232 Diuretics
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D045283 Natriuretic Agents
MeSH PA D049994 Sodium Potassium Chloride Symporter Inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Edema indication 267038008
Edema due to Hepatic Cirrhosis indication
Peripheral Edema due to Chronic Heart Failure indication
Renal Disease with Edema indication
Pulmonary Edema due to Chronic Heart Failure indication
Hypertensive disorder off-label use 38341003 DOID:10763
Hypercalcemia off-label use 66931009 DOID:12678
Decompensated cardiac failure off-label use 195111005
Anuria contraindication 2472002 DOID:2983
Hypocalcemia contraindication 5291005
Hypovolemia contraindication 28560003
Hyperuricemia contraindication 35885006 DOID:1920
Hypokalemia contraindication 43339004
Hepatic coma contraindication 72836002 DOID:12550
Diabetes mellitus contraindication 73211009 DOID:9351
Oliguria contraindication 83128009
Hearing disorder contraindication 128540005
Hypomagnesemia contraindication 190855004
Disease of liver contraindication 235856003 DOID:409
Thrombocytopenic disorder contraindication 302215000 DOID:1588

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.36 acidic
pKa2 9.88 acidic
pKa3 0.86 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
Solute carrier family 12 member 1 Transporter INHIBITOR Ki 7.60 WOMBAT-PK CHEMBL
Sodium/potassium-transporting ATPase subunit alpha-1 Transporter Kd 7.52 WOMBAT-PK
Solute carrier family 12 member 2 Transporter INHIBITOR IC50 5.60 IUPHAR
G-protein coupled receptor 35 GPCR AGONIST EC50 5.54 IUPHAR

External reference:

IDSource
4017794 VUID
N0000146155 NUI
D00247 KEGG_DRUG
4017794 VANDF
C0006376 UMLSCUI
CHEBI:3213 CHEBI
CHEMBL1072 ChEMBL_ID
DB00887 DRUGBANK_ID
D002034 MESH_DESCRIPTOR_UI
2943 INN_ID
2471 PUBCHEM_CID
4837 IUPHAR_LIGAND_ID
0Y2S3XUQ5H UNII
1808 RXNORM
3606 MMSL
4304 MMSL
d00179 MMSL
002312 NDDF
387498005 SNOMEDCT_US
86647004 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 0185-0128 TABLET 0.50 mg ORAL ANDA 21 sections
Bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 0185-0129 TABLET 1 mg ORAL ANDA 21 sections
Bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 0185-0130 TABLET 2 mg ORAL ANDA 21 sections
Bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 0409-1412 INJECTION, SOLUTION 0.25 mg INTRAMUSCULAR ANDA 20 sections
bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 0615-8361 TABLET 1 mg ORAL ANDA 20 sections
bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 0615-8362 TABLET 2 mg ORAL ANDA 20 sections
Bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 0615-8393 TABLET 1 mg ORAL ANDA 21 sections
Bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 0615-8394 TABLET 2 mg ORAL ANDA 21 sections
Bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 0641-6007 INJECTION 0.25 mg INTRAMUSCULAR ANDA 22 sections
Bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 0641-6008 INJECTION 0.25 mg INTRAMUSCULAR ANDA 22 sections
Bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 0641-6161 INJECTION 0.25 mg INTRAMUSCULAR ANDA 22 sections
Bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 0641-6162 INJECTION 0.25 mg INTRAMUSCULAR ANDA 22 sections
Bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 0832-0540 TABLET 0.50 mg ORAL ANDA 22 sections
Bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 0832-0541 TABLET 1 mg ORAL ANDA 22 sections
Bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 0832-0542 TABLET 2 mg ORAL ANDA 22 sections
Bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 0904-7016 TABLET 1 mg ORAL ANDA 21 sections
bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 14539-700 TABLET 0.50 mg ORAL ANDA 19 sections
bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 14539-701 TABLET 1 mg ORAL ANDA 19 sections
bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 14539-702 TABLET 2 mg ORAL ANDA 19 sections
bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 16714-831 TABLET 0.50 mg ORAL ANDA 18 sections
bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 16714-832 TABLET 1 mg ORAL ANDA 18 sections
bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 16714-833 TABLET 2 mg ORAL ANDA 18 sections
Bumex HUMAN PRESCRIPTION DRUG LABEL 1 30698-630 TABLET 0.50 mg ORAL NDA 21 sections
Bumex HUMAN PRESCRIPTION DRUG LABEL 1 30698-631 TABLET 1 mg ORAL NDA 21 sections
Bumex HUMAN PRESCRIPTION DRUG LABEL 1 30698-632 TABLET 2 mg ORAL NDA 21 sections
Bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 33261-983 TABLET 1 mg ORAL ANDA 20 sections
Bumetanide Human Prescription Drug Label 1 42799-119 TABLET 0.50 mg ORAL NDA AUTHORIZED GENERIC 23 sections
Bumetanide Human Prescription Drug Label 1 42799-120 TABLET 1 mg ORAL NDA AUTHORIZED GENERIC 23 sections
Bumetanide Human Prescription Drug Label 1 42799-121 TABLET 2 mg ORAL NDA AUTHORIZED GENERIC 23 sections
Bumetanide HUMAN PRESCRIPTION DRUG LABEL 1 43353-288 TABLET 1 mg ORAL ANDA 21 sections