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=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)
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 |
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 |
---|---|---|---|---|
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 |
|
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 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
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 |
---|---|---|---|---|
3% |
BUMETANIDE serum | Homo sapiens population: HEALTHY age: NEWBORN sex: UNKNOWN food status: UNKNOWN |
||
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 |
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: |
unhealthy, 14–18 |
Disc. AE: Hypokalemia, Anorexia... AEs leading to discontinuation/dose reduction: Hypokalemia (moderate, 14.3%) Sources: Anorexia (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: |
unhealthy, 22-72 |
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: |
unhealthy, 14–18 |
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 |
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 |
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 |
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 |
---|---|---|
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
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.
Substance Class |
Chemical
Created
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on
Edited
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Record UNII |
0Y2S3XUQ5H
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Record Status |
Validated (UNII)
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NDF-RT |
N0000175590
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NDF-RT |
N0000175366
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QC03EB02
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NCI_THESAURUS |
C49184
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LIVERTOX |
126
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C03CB02
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QC03CA02
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C03EB02
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Related Record | Type | Details | ||
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DERIVATIVE -> PARENT |
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> INHIBITOR |
POTENCY
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (TLC)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (TLC)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (TLC)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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