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)
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 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 |
---|---|---|
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 |
|
Diuretic therapy and resistance in congestive heart failure. | 2001 |
|
Solubilization and stability of bumetanide in vehicles for intranasal administration, a pilot study. | 2001 |
|
Effect of chloride channel blockers on anti-IgE-stimulated histamine and IL-4/IL-13 release from human basophils. | 2001 Apr |
|
Insulin increases the turnover rate of Na+-K+-ATPase in human fibroblasts. | 2001 Apr |
|
Effects of thiazide- and loop-diuretics, alone or in combination, on calcitropic hormones and biochemical bone markers: a randomized controlled study. | 2001 Aug |
|
"Avian-type" renal medullary tubule organization causes immaturity of urine-concentrating ability in neonates. | 2001 Aug |
|
Contractile regulation of the Na(+)-K(+)-2Cl(-) cotransporter in vascular smooth muscle. | 2001 Aug |
|
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 |
|
Effects of isoprostanes and prostanoids on porcine small intestine. | 2001 Feb |
|
Reduced Na-K pump but increased Na-K-2Cl cotransporter in aorta of streptozotocin-induced diabetic rat. | 2001 Feb |
|
Adrenergic receptor activated ion transport in human fetal retinal pigment epithelium. | 2001 Jan |
|
Hepatic uptake of synthetic chlorogenic acid derivatives by the organic anion transport proteins. | 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 |
|
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 |
|
Epinephrine-induced increases in [Ca2+](in) and KCl-coupled fluid absorption in bovine RPE. | 2001 Jul |
|
Endogenous and exogenous Na-K-Cl cotransporter expression in a low K-resistant mutant MDCK cell line. | 2001 Jun |
|
Application of multiple response optimization technique to extended release formulations design. | 2001 Jun 15 |
|
Na+ reabsorption in cultured rat epididymal epithelium via the Na+/nucleoside cotransporter. | 2001 Mar |
|
Corneal endothelial NKCC: molecular identification, location, and contribution to fluid transport. | 2001 Mar |
|
Gramicidin-perforated patch analysis on HCO3- secretion through a forskolin-activated anion channel in rat parotid intralobular duct cells. | 2001 Mar 1 |
|
HCO3- potentiates the cAMP-dependent secretory response of the human distal colon through a DIDS-sensitive pathway. | 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 |
|
Ion transport and ligand binding by the Na-K-Cl cotransporter, structure-function studies. | 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 |
|
Chloride transport in rabbit esophageal epithelial cells. | 2002 Apr |
|
Manipulation of chloride flux affects histamine-induced contraction in rabbit basilar artery. | 2002 Apr |
|
Na(+)/K(+)/Cl(-) cotransporter activates mitogen-activated protein kinase in fibroblasts and lymphocytes. | 2002 Feb |
|
Interleukin-13 induces a hypersecretory ion transport phenotype in human bronchial epithelial cells. | 2002 Feb |
|
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 |
|
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 16:57:56 UTC 2022
by
admin
on
Fri Dec 16 16:57:56 UTC 2022
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Record UNII |
0Y2S3XUQ5H
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000175590
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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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C03CA02
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QC03CB02
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C03EB02
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249-004-6
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D002034
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BUMETANIDE
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SUB05971MIG
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4837
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Bumetanide
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Related Record | Type | Details | ||
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TRANSPORTER -> INHIBITOR |
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DERIVATIVE -> PARENT |
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> SUBSTRATE | |||
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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 (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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