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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Ouabain European Pharmacopoeia (EP) Reference Standard

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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
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
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
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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