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
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)
DescriptionCurator'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)
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P55011 Gene ID: 6558.0 Gene Symbol: SLC12A2 Target Organism: Homo sapiens (Human) |
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
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | BUMEX Approved UseBumetanide 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 Date1983 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
42 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8312869 |
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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22475517 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
167.34 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8312869 |
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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22475517 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.88 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22475517 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5% EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22475517 |
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
Dose | Population | Adverse 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%) Sources: Page: p.4Anorexia (moderate) Fatigue (moderate) Polyuria (moderate, 4.8%) |
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
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
modest [IC50 348 uM] | ||||
yes [IC50 0.75 uM] | ||||
yes [IC50 7.6 uM] | ||||
yes [IC50 77.5 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
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 |
|
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 |
|
Na+-K+-Cl- cotransporter in rat focal cerebral ischemia. | 2001 Jun |
|
Application of multiple response optimization technique to extended release formulations design. | 2001 Jun 15 |
|
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 |
|
Spontaneous water secretion in T84 cells: effects of STa enterotoxin, bumetanide, VIP, forskolin, and A-23187. | 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 |
|
Chloride transport in rabbit esophageal epithelial cells. | 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 |
|
Interleukin-13 induces a hypersecretory ion transport phenotype in human bronchial epithelial cells. | 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 |
|
Tonic and spillover inhibition of granule cells control information flow through cerebellar cortex. | 2002 Feb 14 |
|
Basolateral PAR-2 receptors mediate KCl secretion and inhibition of Na+ absorption in the mouse distal colon. | 2002 Feb 15 |
|
Effects of butyrate on active sodium and chloride transport in rat and rabbit distal colon. | 2002 Feb 15 |
|
Cyclic AMP-dependent Cl secretion is regulated by multiple phosphodiesterase subtypes in human colonic epithelial cells. | 2002 Jan 15 |
|
Rat NKCC2/NKCC1 cotransporter selectivity for loop diuretic drugs. | 2002 Mar |
|
The flavonol quercetin activates basolateral K(+) channels in rat distal colon epithelium. | 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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17681355
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.
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)