B3023

Bumetanide

Name: Bumetanide
Brand: SIGMA

≥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

NACRES:

NA.77

PubChem Substance ID:

24278265

UNSPSC Code:

12352200

EC Number:

249-004-6

MDL number:

MFCD00078949

Product Name

Bumetanide, ≥98%

Quality Level

100

InChI key

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)

SMILES string

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

assay

≥98%

form

powder

originator

Roche

Gene Information

human ... SLC12A1(6557)

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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Stimulation of cutaneous low threshold mechanoreceptors in mice after intracolonic capsaicin increases spinal c-Fos labeling in an NKCC1-dependent fashion.

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

Cation-chloride cotransporters NKCC1 and KCC2 as potential targets for novel antiepileptic and antiepileptogenic treatments.

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

Bicarbonate-dependent chloride transport drives fluid secretion by the human airway epithelial cell line Calu-3.

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

Role of SPAK-NKCC1 signaling cascade in the choroid plexus blood-CSF barrier damage after stroke.

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

Genetic and pharmacological modulation of giant depolarizing potentials in the neonatal hippocampus associates with increased seizure susceptibility.

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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