Bumetanide

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 Search

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)

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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018225s024lbl.pdf
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	Potency
Solute carrier family 12 member 2 3 Target ID: P55011 Gene ID: 6558.0 Gene Symbol: SLC12A2 Target Organism: Homo sapiens (Human) Sources: http://www.drugbank.ca/drugs/DB00887 \| https://www.ncbi.nlm.nih.gov/pubmed/16022677 \| https://www.ncbi.nlm.nih.gov/pubmed/11882915/	Inhibitor 8504	3.0 µM [IC50]
Solute carrier family 12 member 4 2 Target ID: Q9UP95\|\|\|O60632 Gene ID: 6560.0 Gene Symbol: SLC12A4 Target Organism: Homo sapiens (Human) Sources: http://www.drugbank.ca/drugs/DB00887 \| https://www.ncbi.nlm.nih.gov/pubmed/16807348	Blocker 555	60.0 µM [IC50]
Solute carrier family 12 member 5 2 Target ID: Q9H2X9 Gene ID: 57468.0 Gene Symbol: SLC12A5 Target Organism: Homo sapiens (Human) Sources: http://www.drugbank.ca/drugs/DB00887 \| https://www.ncbi.nlm.nih.gov/pubmed/16807348	Blocker 555	55.0 µM [IC50]
Solute carrier family 12 member 1 2 Target ID: Q13621 Gene ID: 6557.0 Gene Symbol: SLC12A1 Target Organism: Homo sapiens (Human) Sources: http://www.drugbank.ca/drugs/DB00887 \| https://www.ncbi.nlm.nih.gov/pubmed/26101812	Blocker 555	4.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Edema 23 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018225s024lbl.pdf	Primary		Approved 8583	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

C_max

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

T_1/2

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

F_unbound

Value	Dose	Co-administered	Analyte	Population
3% DRUG LABEL https://nctr-crs.fda.gov/fdalabel/services/spl/set-ids/9bd7a71e-0e78-dae7-e053-2995a90ad110/spl-doc?hl=bumetanide			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: https://pubmed.ncbi.nlm.nih.gov/28291262	unhealthy, 14–18 Health Status: unhealthy Age Group: 14–18 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/28291262	Disc. AE: Hypokalemia, Anorexia... AEs leading to discontinuation/dose reduction: Hypokalemia (moderate, 14.3%) Anorexia (moderate) Fatigue (moderate) Polyuria (moderate, 4.8%) Sources: https://pubmed.ncbi.nlm.nih.gov/28291262
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: https://pubmed.ncbi.nlm.nih.gov/7040493	unhealthy, 22-72 Health Status: unhealthy Age Group: 22-72 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/7040493	Sources: https://pubmed.ncbi.nlm.nih.gov/7040493

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: https://pubmed.ncbi.nlm.nih.gov/28291262	unhealthy, 14–18 Health Status: unhealthy Age Group: 14–18 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/28291262
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: https://pubmed.ncbi.nlm.nih.gov/28291262	unhealthy, 14–18 Health Status: unhealthy Age Group: 14–18 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/28291262
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: https://pubmed.ncbi.nlm.nih.gov/28291262	unhealthy, 14–18 Health Status: unhealthy Age Group: 14–18 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/28291262
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: https://pubmed.ncbi.nlm.nih.gov/28291262	unhealthy, 14–18 Health Status: unhealthy Age Group: 14–18 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/28291262

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 725 OAT3 747 OAT4 150 OAT2 153	MRP4 91 OAT3 391 OATP2 11 P-gp 2052 OAT4 93 OAT2 125

Drug as perpetrator

Target	Modality	Activity
OAT4 150	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/14610216/	modest [IC50 348 uM]
OAT3 749	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/14610216/	yes [IC50 0.75 uM]
OAT1 730	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/14610216/	yes [IC50 7.6 uM]
OAT2 155	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/14610216/	yes [IC50 77.5 uM]

Drug as victim

Target	Modality	Activity
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/28192112/	no
MRP4 91	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25449033/	yes
OAT2 125	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15901346/	yes
OAT3 391	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25449033/	yes
OAT4 93	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/14610216/	yes
OATP2 11	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25449033/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3213	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3213
ChemicalBook	CB9382992	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9382992
eMolecules	535080	https://www.emolecules.com/cgi-bin/more?vid=535080
MolPort	MolPort-003-666-390	https://www.molport.com/shop/molecule-link/MolPort-003-666-390
Selleck Chemicals	Bumetanide	http://www.selleckchem.com/products/Bumetanide.html
ZINC	ZINC000003813061	http://zinc15.docking.org/substances/ZINC000003813061

PubMed

Title	Date	PubMed
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.	1999 May 7	10224140
Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta.	2000 Feb 11	10660625
Functional comparison of the K+-Cl- cotransporters KCC1 and KCC4.	2000 Sep 29	10913127
Effect of chloride channel blockers on anti-IgE-stimulated histamine and IL-4/IL-13 release from human basophils.	2001 Apr	11411600
Differential roles of the sodium-calcium exchanger in renin secretion and renal vascular resistance.	2001 Aug	11512025
Effects of thiazide- and loop-diuretics, alone or in combination, on calcitropic hormones and biochemical bone markers: a randomized controlled study.	2001 Aug	11489064
Bumetanide annihilation of amphotericin B-induced apoptosis and cytotoxicity is due to its effect on cellular K+ flux.	2001 Dec	11733461
Growth factors stimulate the Na-K-2Cl cotransporter NKCC1 through a novel Cl(-)-dependent mechanism.	2001 Dec	11698253
Adrenergic receptor activated ion transport in human fetal retinal pigment epithelium.	2001 Jan	11133877
Vasopressin regulates water flow in a rat cortical collecting duct cell line not containing known aquaporins.	2001 Jan 1	11155210
The effect of serotonin on airway transepithelial sodium ion pathways.	2001 Jan 26	11165222
Liquid and ion transport by fetal airway and lung epithelia of mice deficient in sodium-potassium-2-chloride transporter.	2001 Jul	11472970
Na+-K+-Cl- cotransporter in rat focal cerebral ischemia.	2001 Jun	11488540
Two further British families with the 'cryohydrocytosis' form of hereditary stomatocytosis.	2001 Jun	11442486
Endogenous and exogenous Na-K-Cl cotransporter expression in a low K-resistant mutant MDCK cell line.	2001 Jun	11350756
K(+) transport in red blood cells from human umbilical cord.	2001 Jun 6	11406100
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	11248366
HCO3- potentiates the cAMP-dependent secretory response of the human distal colon through a DIDS-sensitive pathway.	2001 May	11417223
Vacuolation induced by VacA toxin of Helicobacter pylori requires the intracellular accumulation of membrane permeant bases, Cl(-) and water.	2001 Nov 23	11728476
Ion transport and ligand binding by the Na-K-Cl cotransporter, structure-function studies.	2001 Oct	11913460
Ionic mechanisms of GABA-induced long-term potentiation in the rat superior colliculus.	2001 Oct	11685402
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	11912241
Activation of NKCC1 by hyperosmotic stress in human tracheal epithelial cells involves PKC-delta and ERK.	2002 Feb 13	11909643

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Mon Mar 31 17:56:05 GMT 2025` Edited by `admin` on `Mon Mar 31 17:56:05 GMT 2025`
Record UNII	0Y2S3XUQ5H
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

Bumetanide

Official Name

English

Bumex

Preferred Name

English

3-(Butylamino)-4-phenoxy-5-sulfamoylbenzoic acid

Systematic Name

English

Bumetanide [MI]

Common Name

English

Bumetanide [EP MONOGRAPH]

Common Name

English

RO10-6338

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-

Systematic Name

English

Bumetanide [USAN]

Common Name

English

Bumetanide [EP IMPURITY]

Common Name

English

S95008.

Code

English

PF-1593

Code

English

RO-106338

Code

English

Bumetanide [WHO-DD]

Common Name

English

Bumetanide [INN]

Common Name

English

PF1593

Code

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