U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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=CC(=CC(=C1OC2=CC=CC=C2)S(N)(=O)=O)C(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
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
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
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
3%
BUMETANIDE serum
Homo sapiens
population: HEALTHY
age: NEWBORN
sex: UNKNOWN
food status: UNKNOWN
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: Page: p.4
unhealthy, 14–18
n = 21
Health Status: unhealthy
Condition: Autism spectrum disorders
Age Group: 14–18
Sex: M+F
Population Size: 21
Sources: Page: p.4
Disc. AE: Hypokalemia, Anorexia...
AEs leading to
discontinuation/dose reduction:
Hypokalemia (moderate, 14.3%)
Anorexia (moderate)
Fatigue (moderate)
Polyuria (moderate, 4.8%)
Sources: Page: p.4
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: Page: p.597
unhealthy, 22-72
n = 18
Health Status: unhealthy
Condition: Renal edema
Age Group: 22-72
Sex: M+F
Population Size: 18
Sources: Page: p.597
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: Page: p.4
unhealthy, 14–18
n = 21
Health Status: unhealthy
Condition: Autism spectrum disorders
Age Group: 14–18
Sex: M+F
Population Size: 21
Sources: Page: p.4
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: Page: p.4
unhealthy, 14–18
n = 21
Health Status: unhealthy
Condition: Autism spectrum disorders
Age Group: 14–18
Sex: M+F
Population Size: 21
Sources: Page: p.4
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: Page: p.4
unhealthy, 14–18
n = 21
Health Status: unhealthy
Condition: Autism spectrum disorders
Age Group: 14–18
Sex: M+F
Population Size: 21
Sources: Page: p.4
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: Page: p.4
unhealthy, 14–18
n = 21
Health Status: unhealthy
Condition: Autism spectrum disorders
Age Group: 14–18
Sex: M+F
Population Size: 21
Sources: Page: p.4
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
External Cl(-)-dependent formation of watery vacuoles by long-term hypotonic shock in 3T3-L1 cells.
2001
Diuretic therapy and resistance in congestive heart failure.
2001
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
Loop diuretics and in vitro relaxation of human fetal and newborn mouse airways.
2001 Aug
"Avian-type" renal medullary tubule organization causes immaturity of urine-concentrating ability in neonates.
2001 Aug
Protection of ischemic myocardium in diabetics by inhibition of electroneutral Na+-K+-2Cl- cotransporter.
2001 Aug
Insulin-independent, MAPK-dependent stimulation of NKCC activity in skeletal muscle.
2001 Aug
Alterations in airway ion transport in NKCC1-deficient mice.
2001 Aug
Regional differences in ciliary epithelial cell transport properties.
2001 Aug 1
Contribution of the Na-K-Cl cotransporter on GABA(A) receptor-mediated presynaptic depolarization in excitatory nerve terminals.
2001 Aug 15
Cisplatin-induced apoptosis of mesothelioma cells is affected by potassium ion flux modulator amphotericin B and bumetanide.
2001 Aug 15
Potentiation of urinary atrial natriuretic peptide interferes with macula densa function.
2001 Aug 15
An integrative, in situ approach to examining K+ flux in resting skeletal muscle.
2001 Dec
Neurotransmitter-stimulated ion transport across cultured bovine mammary epithelial cell monolayers.
2001 Dec
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
HCO3- transport in relation to mucus secretion from submucosal glands.
2001 Jul
Liquid and ion transport by fetal airway and lung epithelia of mice deficient in sodium-potassium-2-chloride transporter.
2001 Jul
Effects of the potassium channel blocker barium on sodium and potassium transport in the rat loop of Henle in vivo.
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
Pharmacokinetics and pharmacodynamics of intravenous bumetanide in mutant Nagase analbuminemic rats: importance of globulin binding for the pharmacodynamic effects.
2001 May
Localization of a Na(+)-K(+)-2Cl(-) cotransporter in the rabbit lens.
2001 Nov
Role of Cl- current in endothelin-1-induced contraction in rabbit basilar artery.
2001 Nov
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
Mechanism(s) of chloride transport in human distal colonic apical membrane vesicles.
2001 Oct
Quantitative determination of the loop diuretic bumetanide in urine and pharmaceuticals by high-performance liquid chromatography with amperometric detection.
2001 Oct
Indirectly gated Cl(-)-dependent Cl(-) channels sense physiological changes of extracellular chloride in the leech.
2001 Oct
Ion transport by sheep distal airways in a miniature chamber.
2001 Oct
Prostanoids stimulate K secretion and Cl secretion in guinea pig distal colon via distinct pathways.
2001 Oct
Selective inhibition of Cl(-) conductance in toad skin by blockers of Cl(-) channels and transporters.
2001 Oct
Loop diuretics alter the diurnal rhythm of endogenous parathyroid hormone secretion. A randomized-controlled study on the effects of loop- and thiazide-diuretics on the diurnal rhythms of calcitropic hormones and biochemical bone markers in postmenopausal women.
2001 Sep
Apoptosis in post-streptococcal glomerulonephritis.
2001 Sep
Mechanism of substance P-induced liquid secretion across bronchial epithelium.
2001 Sep
Thermogenesis induced by intravenous infusion of hypertonic solutions in the rat.
2001 Sep 1
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
Renal Na-K-Cl cotransporter NKCC2 in Dahl salt-sensitive rats.
2002 Apr
NKCC2: a drug target in hypertension.
2002 Apr
Steroids modulate transepithelial resistance and Na(+) absorption across cultured porcine vas deferens epithelia.
2002 Apr
Manipulation of chloride flux affects histamine-induced contraction in rabbit basilar artery.
2002 Apr
cAMP regulation of Cl(-) and HCO(-)(3) secretion across rat fetal distal lung epithelial cells.
2002 Apr
Na(+)/K(+)/Cl(-) cotransporter activates mitogen-activated protein kinase in fibroblasts and lymphocytes.
2002 Feb
Activation of ion secretion via proteinase-activated receptor-2 in human colon.
2002 Feb
Intrinsic optical signals in the rat optic nerve: role for K(+) uptake via NKCC1 and swelling of astrocytes.
2002 Feb
Activation of NKCC1 by hyperosmotic stress in human tracheal epithelial cells involves PKC-delta and ERK.
2002 Feb 13
Rat NKCC2/NKCC1 cotransporter selectivity for loop diuretic drugs.
2002 Mar
Functional properties of the apical Na+-K+-2Cl- cotransporter isoforms.
2002 Mar 29
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 Fri Dec 15 15:23:24 GMT 2023
Edited
by admin
on Fri Dec 15 15:23:24 GMT 2023
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
3-(BUTYLAMINO)-4-PHENOXY-5-SULFAMOYLBENZOIC ACID.
Common Name English
BUMETANIDE [MI]
Common Name English
BUMETANIDE [EP MONOGRAPH]
Common Name English
RO 10-6338
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-
Common Name English
BUMETANIDE [USAN]
Common Name English
BUMETANIDE [EP IMPURITY]
Common Name English
S95008.
Code English
RO-106338
Code English
BUMEX
Brand Name English
Bumetanide [WHO-DD]
Common Name English
bumetanide [INN]
Common Name 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 Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
NDF-RT N0000175366
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
WHO-VATC QC03EB02
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
NCI_THESAURUS C49184
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
LIVERTOX 126
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
WHO-ATC C03CB02
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
WHO-VATC QC03CA02
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
WHO-ATC C03CA02
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
WHO-VATC QC03CB02
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
WHO-ATC C03EB02
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
Code System Code Type Description
MERCK INDEX
m2759
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
249-004-6
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID5022699
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
PRIMARY
MESH
D002034
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
PRIMARY
WIKIPEDIA
BUMETANIDE
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
PRIMARY
EVMPD
SUB05971MIG
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
PRIMARY
RXCUI
1808
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
PRIMARY RxNorm
IUPHAR
4837
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
PRIMARY
LACTMED
Bumetanide
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
PRIMARY
DRUG BANK
DB00887
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
PRIMARY
NCI_THESAURUS
C28875
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
PRIMARY
RS_ITEM_NUM
1078303
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
PRIMARY
CAS
28395-03-1
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
PRIMARY
DRUG CENTRAL
427
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
PRIMARY
CHEBI
3213
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
PRIMARY
INN
2943
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
PRIMARY
PUBCHEM
2471
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
PRIMARY
ChEMBL
CHEMBL1072
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
PRIMARY
FDA UNII
0Y2S3XUQ5H
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
PRIMARY
DAILYMED
0Y2S3XUQ5H
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
PRIMARY
SMS_ID
100000088443
Created by admin on Fri Dec 15 15:23:24 GMT 2023 , Edited by admin on Fri Dec 15 15:23:24 GMT 2023
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
DERIVATIVE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
TARGET -> INHIBITOR
POTENCY
BINDER->LIGAND
BINDING
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
USP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC