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Details

Stereochemistry ACHIRAL
Molecular Formula C17H20N2O5S
Molecular Weight 364.416
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Bumetanide

SMILES

CCCCNC1=C(OC2=CC=CC=C2)C(=CC(=C1)C(O)=O)S(N)(=O)=O

InChI

InChIKey=MAEIEVLCKWDQJH-UHFFFAOYSA-N
InChI=1S/C17H20N2O5S/c1-2-3-9-19-14-10-12(17(20)21)11-15(25(18,22)23)16(14)24-13-7-5-4-6-8-13/h4-8,10-11,19H,2-3,9H2,1H3,(H,20,21)(H2,18,22,23)

HIDE SMILES / InChI

Molecular Formula C17H20N2O5S
Molecular Weight 364.416
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: http://www.rxlist.com/bumex-drug/side-effects-interactions.htm https://www.drugs.com/cdi/bumetanide.html http://www.wikidoc.org/index.php/Bumetanide_(oral)

Bumetanide is indicated for the treatment of edema associated with congestive heart failure, hepatic and renal disease, including the nephrotic syndrome. It blocks the reabsorption of sodium and fluid from the kidney's tubules. The most frequent clinical adverse reactions considered probably or possibly related to bumetanide are muscle cramps (seen in 1.1% of treated patients), dizziness (1.1%), hypotension (0.8%), headache (0.6%), nausea (0.6%) and encephalopathy (in patients with preexisting liver disease) (0.6%). One or more of these adverse reactions have been reported in approximately 4.1% of patients treated with Bumex (bumetanide). Lithium should generally not be given with diuretics (such as Bumex (bumetanide)) because they reduce its renal clearance and add a high risk of lithium toxicity. Bumex (bumetanide) may potentiate the effect of various antihypertensive drugs, necessitating a reduction in the dosage of these drugs.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.0 µM [IC50]
Target ID: Q9UP95|||O60632
Gene ID: 6560.0
Gene Symbol: SLC12A4
Target Organism: Homo sapiens (Human)
60.0 µM [IC50]
Target ID: Q9H2X9
Gene ID: 57468.0
Gene Symbol: SLC12A5
Target Organism: Homo sapiens (Human)
55.0 µM [IC50]
Target ID: Q13621
Gene ID: 6557.0
Gene Symbol: SLC12A1
Target Organism: Homo sapiens (Human)
4.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BUMEX

Approved Use

Bumetanide Injection is indicated for the treatment of edema associated with congestive heart failure, hepatic and renal disease, including the nephrotic syndrome. Almost equal diuretic response occurs after oral and parenteral administration of bumetanide. Therefore, if impaired gastrointestinal absorption is suspected or oral administration is not practical, bumetanide should be given by the intramuscular or intravenous route. Successful treatment with bumetanide following instances of allergic reactions to furosemide suggests a lack of cross-sensitivity.

Launch Date

1983
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
111.38 ng/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUMETANIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
42 ng/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUMETANIDE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
258 ng × h/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUMETANIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
167.34 ng × h/mL
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUMETANIDE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.88 h
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUMETANIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
3%
BUMETANIDE serum
Homo sapiens
population: HEALTHY
age: NEWBORN
sex: UNKNOWN
food status: UNKNOWN
5%
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUMETANIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
2 mg 2 times / day multiple, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2 mg, 2 times / day
Sources:
unhealthy, 14–18
Health Status: unhealthy
Age Group: 14–18
Sex: M+F
Sources:
Disc. AE: Hypokalemia, Anorexia...
AEs leading to
discontinuation/dose reduction:
Hypokalemia (moderate, 14.3%)
Anorexia (moderate)
Fatigue (moderate)
Polyuria (moderate, 4.8%)
Sources:
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 22-72
Health Status: unhealthy
Age Group: 22-72
Sex: M+F
Sources:
AEs

AEs

AESignificanceDosePopulation
Hypokalemia moderate, 14.3%
Disc. AE
2 mg 2 times / day multiple, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2 mg, 2 times / day
Sources:
unhealthy, 14–18
Health Status: unhealthy
Age Group: 14–18
Sex: M+F
Sources:
Polyuria moderate, 4.8%
Disc. AE
2 mg 2 times / day multiple, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2 mg, 2 times / day
Sources:
unhealthy, 14–18
Health Status: unhealthy
Age Group: 14–18
Sex: M+F
Sources:
Anorexia moderate
Disc. AE
2 mg 2 times / day multiple, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2 mg, 2 times / day
Sources:
unhealthy, 14–18
Health Status: unhealthy
Age Group: 14–18
Sex: M+F
Sources:
Fatigue moderate
Disc. AE
2 mg 2 times / day multiple, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2 mg, 2 times / day
Sources:
unhealthy, 14–18
Health Status: unhealthy
Age Group: 14–18
Sex: M+F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer










Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
modest [IC50 348 uM]
yes [IC50 0.75 uM]
yes [IC50 7.6 uM]
yes [IC50 77.5 uM]
Drug as victim
PubMed

PubMed

TitleDatePubMed
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.
1999 May 7
Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta.
2000 Feb 11
Functional comparison of the K+-Cl- cotransporters KCC1 and KCC4.
2000 Sep 29
Effect of chloride channel blockers on anti-IgE-stimulated histamine and IL-4/IL-13 release from human basophils.
2001 Apr
Differential roles of the sodium-calcium exchanger in renin secretion and renal vascular resistance.
2001 Aug
Effects of thiazide- and loop-diuretics, alone or in combination, on calcitropic hormones and biochemical bone markers: a randomized controlled study.
2001 Aug
Bumetanide annihilation of amphotericin B-induced apoptosis and cytotoxicity is due to its effect on cellular K+ flux.
2001 Dec
Growth factors stimulate the Na-K-2Cl cotransporter NKCC1 through a novel Cl(-)-dependent mechanism.
2001 Dec
Adrenergic receptor activated ion transport in human fetal retinal pigment epithelium.
2001 Jan
Vasopressin regulates water flow in a rat cortical collecting duct cell line not containing known aquaporins.
2001 Jan 1
The effect of serotonin on airway transepithelial sodium ion pathways.
2001 Jan 26
Liquid and ion transport by fetal airway and lung epithelia of mice deficient in sodium-potassium-2-chloride transporter.
2001 Jul
Na+-K+-Cl- cotransporter in rat focal cerebral ischemia.
2001 Jun
Two further British families with the 'cryohydrocytosis' form of hereditary stomatocytosis.
2001 Jun
Endogenous and exogenous Na-K-Cl cotransporter expression in a low K-resistant mutant MDCK cell line.
2001 Jun
K(+) transport in red blood cells from human umbilical cord.
2001 Jun 6
Optical imaging reveals cation--Cl(-) cotransporter-mediated transient rapid decrease in intracellular Cl(-) concentration induced by oxygen--glucose deprivation in rat neocortical slices.
2001 Mar
HCO3- potentiates the cAMP-dependent secretory response of the human distal colon through a DIDS-sensitive pathway.
2001 May
Vacuolation induced by VacA toxin of Helicobacter pylori requires the intracellular accumulation of membrane permeant bases, Cl(-) and water.
2001 Nov 23
Ion transport and ligand binding by the Na-K-Cl cotransporter, structure-function studies.
2001 Oct
Ionic mechanisms of GABA-induced long-term potentiation in the rat superior colliculus.
2001 Oct
Contribution of the Na(+)-K(+)-2Cl(-) cotransporter (NKCC1) to transepithelial transport of H(+), NH(4)(+), K(+), and Na(+) in rat outer medullary collecting duct.
2002 Apr
Activation of NKCC1 by hyperosmotic stress in human tracheal epithelial cells involves PKC-delta and ERK.
2002 Feb 13
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Parenteral Administration: The usual initial dose is 0.5 to 1 mg intravenously or intramuscularly. Intravenous administration should be given over a period of 1 to 2 minutes. If the response to an initial dose is deemed insufficient, a second or third dose may be given at intervals of 2 to 3 hours, but should not exceed a daily dosage of 10 mg.
The usual total daily dosage of Bumetanide is 0.5 mg to 2 mg and in most patients is given as a single dose.
Route of Administration: Other
10 uM of bumetanide reduced amplitude and frequency of ictal-like events (ILE) induced by 8.5 mM K(+), but it increased the frequency of ILE induced by 1 microM kainate.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:56:05 GMT 2025
Edited
by admin
on Mon Mar 31 17:56:05 GMT 2025
Record UNII
0Y2S3XUQ5H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Bumetanide
EP   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
Bumex
Preferred Name English
3-(Butylamino)-4-phenoxy-5-sulfamoylbenzoic acid
Systematic Name English
Bumetanide [MI]
Common Name English
Bumetanide [EP MONOGRAPH]
Common Name English
RO10-6338
Code English
Bumetanide [VANDF]
Common Name English
RO-10-6338
Code English
S-95008.
Code English
Bumetanide [USP-RS]
Common Name English
Bumetanide [ORANGE BOOK]
Common Name English
Benzoic acid, 3-(aminosulfonyl)-5-(butylamino)-4-phenoxy-
Systematic Name English
Bumetanide [USAN]
Common Name English
Bumetanide [EP IMPURITY]
Common Name English
S95008.
Code English
PF-1593
Code English
RO-106338
Code English
Bumetanide [WHO-DD]
Common Name English
Bumetanide [INN]
Common Name English
PF1593
Code English
Bumetanide [MART.]
Common Name English
Bumetanide [USP MONOGRAPH]
Common Name English
Bumetanide [JAN]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175590
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
NDF-RT N0000175366
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
WHO-VATC QC03EB02
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
NCI_THESAURUS C49184
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
LIVERTOX 126
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
WHO-ATC C03CB02
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
WHO-VATC QC03CA02
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
WHO-ATC C03CA02
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
WHO-VATC QC03CB02
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
WHO-ATC C03EB02
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
Code System Code Type Description
MERCK INDEX
m2759
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
249-004-6
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
PRIMARY
EPA CompTox
DTXSID5022699
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
PRIMARY
MESH
D002034
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
PRIMARY
WIKIPEDIA
BUMETANIDE
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
PRIMARY
EVMPD
SUB05971MIG
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
PRIMARY
RXCUI
1808
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
PRIMARY RxNorm
IUPHAR
4837
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
PRIMARY
LACTMED
Bumetanide
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
PRIMARY
DRUG BANK
DB00887
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
PRIMARY
NCI_THESAURUS
C28875
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
PRIMARY
RS_ITEM_NUM
1078303
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
PRIMARY
CAS
28395-03-1
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
PRIMARY
DRUG CENTRAL
427
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
PRIMARY
CHEBI
3213
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
PRIMARY
INN
2943
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
PRIMARY
PUBCHEM
2471
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
PRIMARY
ChEMBL
CHEMBL1072
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
PRIMARY
FDA UNII
0Y2S3XUQ5H
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
PRIMARY
DAILYMED
0Y2S3XUQ5H
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
PRIMARY
SMS_ID
100000088443
Created by admin on Mon Mar 31 17:56:05 GMT 2025 , Edited by admin on Mon Mar 31 17:56:05 GMT 2025
PRIMARY
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DERIVATIVE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
POTENCY
BINDER->LIGAND
BINDING
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IMPURITY -> PARENT
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EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
USP
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Name Property Type Amount Referenced Substance Defining Parameters References
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