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
Cardiac failure congestive 217.26 12.95 241 24605 92516 53231704
Acute kidney injury 211.07 12.95 403 24443 253465 53070755
Fluid retention 200.72 12.95 181 24665 54220 53270000
Fluid overload 180.65 12.95 129 24717 27702 53296518
Dyspnoea 165.66 12.95 622 24224 585610 52738610
Right ventricular failure 125.51 12.95 85 24761 16758 53307462
Rheumatoid arthritis 115.61 12.95 8 24838 314523 53009697
Pulmonary arterial hypertension 111.48 12.95 96 24750 27026 53297194
Pulmonary hypertension 106.96 12.95 108 24738 37162 53287058
Oedema peripheral 106.23 12.95 241 24605 170546 53153674
Drug ineffective 99.77 12.95 142 24704 817103 52507117
Renal failure 94.36 12.95 185 24661 118267 53205953
Oedema 93.26 12.95 142 24704 74204 53250016
Cardiac failure 91.23 12.95 152 24694 85692 53238528
Body tinea 78.25 12.95 27 24819 1174 53323046
International normalised ratio increased 77.24 12.95 103 24743 47658 53276562
Renal impairment 71.06 12.95 134 24712 83184 53241036
Off label use 65.75 12.95 74 24772 472138 52852082
Atrial fibrillation 65.41 12.95 154 24692 111498 53212722
Infection susceptibility increased 58.68 12.95 27 24819 2510 53321710
Inhibitory drug interaction 58.12 12.95 26 24820 2264 53321956
Hyperkalaemia 54.86 12.95 94 24752 54162 53270058
Pulmonary oedema 54.22 12.95 93 24753 53630 53270590
Impaired quality of life 52.35 12.95 31 24815 4840 53319380
Hypotension 50.50 12.95 243 24603 253833 53070387
Treatment failure 47.89 12.95 3 24843 128400 53195820
Infusion related reaction 47.07 12.95 8 24838 155949 53168271
Purpura 45.77 12.95 39 24807 10814 53313406
Glucose tolerance impaired 44.83 12.95 29 24817 5291 53318929
Joint swelling 43.28 12.95 28 24818 234610 53089610
Death 43.01 12.95 299 24547 356933 52967287
Exposure during pregnancy 40.94 12.95 5 24841 124855 53199365
Gastrointestinal haemorrhage 40.86 12.95 105 24741 80225 53243995
Alopecia 40.60 12.95 30 24816 234553 53089667
Dyspnoea exertional 40.26 12.95 83 24763 54917 53269303
Cellulitis 39.35 12.95 100 24746 75889 53248331
Chronic obstructive pulmonary disease 38.78 12.95 87 24759 60986 53263234
Bradycardia 37.30 12.95 94 24752 70962 53253258
BRASH syndrome 37.11 12.95 10 24836 185 53324035
Cardiac failure acute 36.97 12.95 32 24814 9060 53315160
Hypoxia 36.12 12.95 80 24766 55600 53268620
Drug intolerance 35.92 12.95 26 24820 205467 53118753
Left ventricular failure 35.22 12.95 25 24821 5308 53318912
Contraindicated product administered 34.79 12.95 10 24836 135619 53188601
Therapeutic product effect decreased 34.65 12.95 8 24838 125647 53198573
Transfusion 32.72 12.95 36 24810 13651 53310569
Arthropathy 31.84 12.95 13 24833 141440 53182780
Congestive cardiomyopathy 29.93 12.95 24 24822 6114 53318106
Pleural effusion 29.87 12.95 100 24746 88479 53235741
Dialysis 29.70 12.95 30 24816 10312 53313908
Blood creatinine increased 29.37 12.95 95 24751 82567 53241653
Haemoglobin decreased 28.44 12.95 133 24713 137174 53187046
Respiratory failure 28.34 12.95 107 24739 100405 53223815
Epistaxis 28.16 12.95 83 24763 68627 53255593
Hepatic enzyme increased 27.75 12.95 12 24834 126183 53198037
Gout 26.88 12.95 31 24815 12368 53311852
Weight increased 26.20 12.95 174 24672 204393 53119827
Blood potassium decreased 26.08 12.95 58 24788 40402 53283818
Pain in jaw 25.88 12.95 58 24788 40611 53283609
Drug hypersensitivity 25.78 12.95 53 24793 265189 53059031
Acute respiratory failure 25.05 12.95 49 24797 31209 53293011
Pneumonia 24.77 12.95 294 24552 406875 52917345
Bone density decreased 24.56 12.95 28 24818 11036 53313184
Arthralgia 23.61 12.95 115 24731 439668 52884552
Dehydration 22.62 12.95 145 24701 168265 53155955
Genital infection female 22.06 12.95 6 24840 115 53324105
Oxygen saturation decreased 21.89 12.95 82 24764 76643 53247577
Cardiorenal syndrome 21.71 12.95 9 24837 650 53323570
Therapeutic product effect incomplete 21.36 12.95 8 24838 91776 53232444
Rectal haemorrhage 20.85 12.95 54 24792 41427 53282793
Drug abuse 20.57 12.95 3 24843 65523 53258697
Anaemia 20.57 12.95 208 24638 276510 53047710
Hospitalisation 20.35 12.95 76 24770 70936 53253284
Hyperlipidaemia 19.96 12.95 34 24812 19481 53304739
Orthopnoea 19.94 12.95 19 24827 6085 53318135
Chronic left ventricular failure 19.84 12.95 7 24839 325 53323895
Arteriosclerosis coronary artery 19.80 12.95 22 24824 8432 53315788
Musculoskeletal stiffness 19.79 12.95 17 24829 123351 53200869
Blood urea increased 19.68 12.95 40 24806 26191 53298029
Unevaluable event 19.53 12.95 59 24787 49439 53274781
Blood potassium increased 19.47 12.95 32 24814 17809 53306411
Torsade de pointes 19.42 12.95 27 24819 12978 53311242
Atrial flutter 19.17 12.95 23 24823 9568 53314652
Intentional overdose 19.09 12.95 4 24842 67201 53257019
Poor quality sleep 18.81 12.95 31 24815 17292 53306928
Abdominal distension 18.54 12.95 80 24766 79710 53244510
Paracentesis 18.43 12.95 9 24837 955 53323265
Chronic kidney disease 18.35 12.95 53 24793 43317 53280903
Cardiomegaly 18.19 12.95 31 24815 17769 53306451
Suicide attempt 17.50 12.95 3 24843 58165 53266055
Skin disorder 17.48 12.95 37 24809 24921 53299299
Urine output decreased 17.16 12.95 24 24822 11599 53312621
Asthenia 17.03 12.95 239 24607 343351 52980869
Blood aldosterone abnormal 16.69 12.95 4 24842 45 53324175
Diaphragmatic disorder 16.66 12.95 7 24839 523 53323697
Impaired work ability 16.37 12.95 26 24820 14064 53310156
Generalised oedema 16.37 12.95 27 24819 15072 53309148
Packed red blood cell transfusion 16.12 12.95 11 24835 2192 53322028
Pemphigoid 15.49 12.95 17 24829 6427 53317793
Brain natriuretic peptide increased 15.47 12.95 15 24831 4910 53319310
Wound 15.45 12.95 12 24834 91545 53232675
Lactic acidosis 15.25 12.95 45 24801 37208 53287012
Lung transplant 15.09 12.95 12 24834 3022 53321198
Liver function test abnormal 15.08 12.95 53 24793 48018 53276202
Oxygen consumption increased 14.87 12.95 13 24833 3728 53320492
Blood sodium decreased 14.74 12.95 33 24813 23083 53301137
Claudication of jaw muscles 14.60 12.95 4 24842 79 53324141
Urosepsis 14.49 12.95 27 24819 16583 53307637
Sinusitis 14.47 12.95 36 24810 168528 53155692
Injection site pain 14.41 12.95 19 24827 113372 53210848
Compartment syndrome 14.40 12.95 10 24836 2051 53322169
Discomfort 14.30 12.95 14 24832 95458 53228762
Product use in unapproved indication 14.08 12.95 19 24827 112270 53211950
Right ventricular dysfunction 14.07 12.95 9 24837 1610 53322610
Malignant neoplasm progression 13.92 12.95 8 24838 71533 53252687
Abdominal discomfort 13.52 12.95 55 24791 221007 53103213
Product use issue 13.45 12.95 28 24818 139556 53184664
Diuretic therapy 13.38 12.95 4 24842 109 53324111
Brain stem stroke 13.35 12.95 5 24841 276 53323944
Incarcerated umbilical hernia 13.33 12.95 3 24843 25 53324195
Seizure 13.32 12.95 25 24821 129484 53194736
Drug monitoring procedure not performed 13.30 12.95 6 24840 533 53323687
Injection site erythema 13.19 12.95 10 24836 77239 53246981
Pain 13.16 12.95 194 24652 588204 52736016
Subacute cutaneous lupus erythematosus 13.15 12.95 10 24836 2358 53321862
Hypersensitivity 13.14 12.95 52 24794 210613 53113607

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 208.04 13.32 513 19374 292955 32200684
Cardiac failure congestive 172.66 13.32 235 19652 84617 32409022
Cardiac failure 136.12 13.32 219 19668 91454 32402185
Fluid retention 113.08 13.32 108 19779 26442 32467197
Dyspnoea 110.58 13.32 475 19412 361570 32132069
Pulmonary hypertension 82.79 13.32 81 19806 20413 32473226
Oedema peripheral 67.46 13.32 187 19700 113904 32379735
Fluid overload 67.30 13.32 71 19816 19550 32474089
Pulmonary arterial hypertension 45.72 13.32 42 19845 9779 32483860
Drug ineffective 45.59 13.32 105 19782 383372 32110267
Oedema 44.05 13.32 90 19797 45057 32448582
Venous pressure jugular increased 43.73 13.32 17 19870 787 32492852
Right ventricular failure 40.97 13.32 37 19850 8426 32485213
Renal failure 39.59 13.32 175 19712 134303 32359336
Blood ketone body increased 37.94 13.32 13 19874 418 32493221
Glomerular filtration rate decreased 36.38 13.32 42 19845 12769 32480870
Blood potassium increased 36.29 13.32 48 19839 16756 32476883
International normalised ratio increased 33.61 13.32 85 19802 48950 32444689
Toxicity to various agents 33.19 13.32 36 19851 178005 32315634
Hyperkalaemia 31.43 13.32 104 19783 69646 32423993
Hypotension 30.38 13.32 231 19656 215879 32277760
Renal impairment 30.38 13.32 124 19763 91848 32401791
Venous pressure jugular decreased 29.68 13.32 7 19880 54 32493585
Peripheral swelling 29.11 13.32 100 19787 68245 32425394
Hepatic cytolysis 28.29 13.32 30 19857 8303 32485336
Cardiac failure chronic 28.08 13.32 28 19859 7212 32486427
Gastrointestinal haemorrhage 27.79 13.32 116 19771 86766 32406873
Ventricular tachycardia 27.38 13.32 53 19834 25503 32468136
Off label use 27.38 13.32 96 19791 306224 32187415
Febrile neutropenia 27.27 13.32 20 19867 119546 32374093
Completed suicide 26.03 13.32 12 19875 92505 32401134
Pyrexia 25.54 13.32 105 19782 319863 32173776
Pulmonary oedema 25.48 13.32 74 19813 46193 32447446
Blood pressure systolic decreased 25.43 13.32 21 19866 4242 32489397
Dyspnoea paroxysmal nocturnal 24.93 13.32 14 19873 1503 32492136
Blood creatinine increased 24.50 13.32 120 19767 96012 32397627
Orthopnoea 24.15 13.32 22 19865 5065 32488574
Atrial fibrillation 23.15 13.32 136 19751 116568 32377071
Dyspnoea exertional 23.10 13.32 64 19823 38897 32454742
Neutropenia 22.06 13.32 33 19854 142142 32351497
Pulmonary renal syndrome 21.88 13.32 7 19880 181 32493458
Weight increased 21.72 13.32 105 19782 83558 32410081
Vasculitic rash 21.69 13.32 11 19876 961 32492678
Orthostatic hypotension 21.39 13.32 48 19839 25602 32468037
Dizziness 20.53 13.32 207 19680 209411 32284228
Cardiac failure acute 20.32 13.32 28 19859 10156 32483483
Hepatic cirrhosis 19.41 13.32 36 19851 16773 32476866
Packed red blood cell transfusion 18.69 13.32 12 19875 1642 32491997
Chronic kidney disease 18.34 13.32 60 19827 39915 32453724
Anti-neutrophil cytoplasmic antibody positive vasculitis 18.22 13.32 9 19878 744 32492895
Rheumatoid arthritis 17.64 13.32 3 19884 44541 32449098
Amyloidosis 17.49 13.32 13 19874 2253 32491386
Weight bearing difficulty 16.58 13.32 9 19878 904 32492735
Transitional cell carcinoma 15.97 13.32 12 19875 2115 32491524
Reaction to excipient 15.93 13.32 7 19880 443 32493196
Bradycardia 15.90 13.32 86 19801 71476 32422163
Hypovolaemia 15.64 13.32 23 19864 8854 32484785
Death 15.00 13.32 322 19565 382195 32111444
Treatment failure 14.73 13.32 3 19884 39160 32454479
Hospitalisation 14.57 13.32 64 19823 48907 32444732
Polyuria 14.52 13.32 21 19866 7964 32485675
Suicide attempt 14.24 13.32 3 19884 38241 32455398
Brain natriuretic peptide abnormal 14.07 13.32 6 19881 353 32493286
Sinus bradycardia 14.06 13.32 27 19860 12911 32480728
Abdominal cavity drainage 14.02 13.32 6 19881 356 32493283
Hepatic function abnormal 13.93 13.32 5 19882 44835 32448804
Ascites 13.90 13.32 55 19832 40136 32453503
Haemoglobin decreased 13.58 13.32 122 19765 119549 32374090
Blood urea increased 13.53 13.32 47 19840 32226 32461413
Neutrophil count decreased 13.43 13.32 6 19881 47133 32446506

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

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