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B3023

Sigma-Aldrich

Bumetanide

≥98% (TLC), powder, Na⁺/K⁺/Cl⁻ cotransporter inhibitor

Synonym(s):

3-(Aminosulfonyl)-5-(butylamino)-4-phenoxybenzoic acid

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About This Item

Empirical Formula (Hill Notation):
C17H20N2O5S
CAS Number:
28395-03-1
Molecular Weight:
364.42
EC Number:
249-004-6
MDL number:
MFCD00078949
UNSPSC Code:
12352200
PubChem Substance ID:
24278265
NACRES:
NA.77

product name

Bumetanide, ≥98%

assay

≥98%

form

powder

originator

Roche

SMILES string

CCCCNc1cc(cc(c1Oc2ccccc2)S(N)(=O)=O)C(O)=O

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)

InChI key

MAEIEVLCKWDQJH-UHFFFAOYSA-N

Gene Information

human ... SLC12A1(6557)

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Biochem/physiol Actions

Inhibitor of Na+/K+/Cl- cotransporter.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Roche. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Wolfgang Löscher et al.
Neuropharmacology, 69, 62-74 (2012-06-19)
In cortical and hippocampal neurons, cation-chloride cotransporters (CCCs) control the reversal potential (EGABA) of GABAA receptor-mediated current and voltage responses and, consequently, they modulate the efficacy of GABAergic inhibition. Two members of the CCC family, KCC2 (the major neuron-specific K-Cl
Mark H Pitcher et al.
The journal of pain : official journal of the American Pain Society, 14(1), 57-65 (2012-12-04)
Stimulation of peripheral nociceptors results in increased c-Fos labeling in spinal cord regions associated with nociceptive processing. Accordingly, intracolonic capsaicin, which generates robust secondary (referred) allodynia on the abdomen of mice, also causes an increased spinal c-Fos labeling. In naïve
Jiajie Shan et al.
The Journal of physiology, 590(21), 5273-5297 (2012-07-11)
Anion and fluid secretion are both defective in cystic fibrosis (CF); however, the transport mechanisms are not well understood. In this study, Cl(-) and HCO(3)(-) secretion was measured using genetically matched CF transmembrane conductance regulator (CFTR)-deficient and CFTR-expressing cell lines
Jun Wang et al.
Journal of neuroinflammation, 19(1), 91-91 (2022-04-14)
The mechanisms underlying dysfunction of choroid plexus (ChP) blood-cerebrospinal fluid (CSF) barrier and lymphocyte invasion in neuroinflammatory responses to stroke are not well understood. In this study, we investigated whether stroke damaged the blood-CSF barrier integrity due to dysregulation of
Ernesto Vargas et al.
The Journal of physiology, 591(1), 57-65 (2012-09-26)
The expression of Na(+)-K(+)-2Cl(-) cotransporter (NKCC1) is responsible for high intracellular Cl(-) resulting in the excitatory action of GABA(A) receptor activation in the developing brain. Giant depolarizing potentials (GDPs) are spontaneous network oscillations that involve GABA(A) receptors and are thought
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