Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C17H20N2O5S |
| Molecular Weight | 364.4178 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCNc1cc(cc(c1Oc2ccccc2)S(=O)(=O)N)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 Date4.1523839E11 |
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 |
|
| Effect of chloride channel blockers on anti-IgE-stimulated histamine and IL-4/IL-13 release from human basophils. | 2001 Apr |
|
| Alternatively spliced isoform of apical Na(+)-K(+)-Cl(-) cotransporter gene encodes a furosemide-sensitive Na(+)-Cl(-)cotransporter. | 2001 Apr |
|
| Insulin increases the turnover rate of Na+-K+-ATPase in human fibroblasts. | 2001 Apr |
|
| "Avian-type" renal medullary tubule organization causes immaturity of urine-concentrating ability in neonates. | 2001 Aug |
|
| Alterations in airway ion transport in NKCC1-deficient mice. | 2001 Aug |
|
| Contractile regulation of the Na(+)-K(+)-2Cl(-) cotransporter in vascular smooth muscle. | 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 |
|
| Effect of short-term treatment with bumetanide, quinapril and low-sodium diet on dogs with moderate congestive heart failure. | 2001 Feb |
|
| HCO3- transport in relation to mucus secretion from submucosal glands. | 2001 Jul |
|
| Epinephrine-induced increases in [Ca2+](in) and KCl-coupled fluid absorption in bovine RPE. | 2001 Jul |
|
| Na+-K+-Cl- cotransporter in rat focal cerebral ischemia. | 2001 Jun |
|
| cAMP-dependent fluid secretion in rat inner medullary collecting ducts. | 2001 Jun |
|
| 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 |
|
| Pharmacokinetics and pharmacodynamics of intravenous bumetanide in mutant Nagase analbuminemic rats: importance of globulin binding for the pharmacodynamic effects. | 2001 May |
|
| HCO3- potentiates the cAMP-dependent secretory response of the human distal colon through a DIDS-sensitive pathway. | 2001 May |
|
| Role of renocortical cyclooxygenase-2 for renal vascular resistance and macula densa control of renin secretion. | 2001 May |
|
| Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. | 2001 May |
|
| Ethanol-induced swelling in neonatal rat primary astrocyte cultures. | 2001 May 11 |
|
| 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 |
|
| Quantitative determination of the loop diuretic bumetanide in urine and pharmaceuticals by high-performance liquid chromatography with amperometric detection. | 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 |
|
| Mechanism of substance P-induced liquid secretion across bronchial epithelium. | 2001 Sep |
|
| 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 |
|
| 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 |
|
| 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
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| Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175590
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NDF-RT |
N0000175366
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WHO-VATC |
QC03EB02
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NCI_THESAURUS |
C49184
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LIVERTOX |
126
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WHO-ATC |
C03CB02
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WHO-VATC |
QC03CA02
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WHO-ATC |
C03CA02
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WHO-VATC |
QC03CB02
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WHO-ATC |
C03EB02
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M2759
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249-004-6
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28395-03-1
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D002034
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BUMETANIDE
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SUB05971MIG
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1808
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4837
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Bumetanide
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DB00887
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C28875
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1078303
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28395-03-1
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427
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2943
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2471
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CHEMBL1072
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0Y2S3XUQ5H
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
