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Merck

492031

NS8593

≥98% (HPLC), aminobenzimidazole derivative, powder

Synonym(s):

NS8593, (R)-N-(Benzimidazol-2-yl)-1,2,3,4-tetrahydro-1-naphthylamine

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About This Item

Empirical Formula (Hill Notation):
C17H17N3
CAS Number:
875755-39-8
Molecular Weight:
263.34
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD32671885

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Product Name

NS8593, An aminobenzimidazole derivative that selectively and reversibly blocks small conductance Ca2+-activated K+ channels in a Ca2+-dependent manner.

InChI key

XZIZUQSOFMLIIR-CQSZACIVSA-N

SMILES string

C1(NC(N[C@@H]2CCCC3=C2C=CC=C3)=N4)=C4C=CC=C1

assay

≥98% (HPLC)

form

powder

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

white

solubility

DMSO: 100 mg/mL

shipped in

wet ice

storage temp.

2-8°C

Quality Level

100

Related Categories

Disclaimer

Toxicity: Standard Handling (A)

General description

An aminobenzimidazole derivative that selectively and reversibly blocks small conductance Ca2+-activated K+ channels (SK1-3; Kd = 420 nM, 600 nM, and 730 nM for SK1, SK2, SK3, respectively) in a Ca2+-dependent manner. It mediates channel gating by interacting with gating structures deep within the inner pore vestibule where Ser507 and Ala532 are deemed to be important for inhibition. Interacts at a site that is distinct from the apamin binding site in SK channels. Can access high-affinity binding sites from both the inside and outside of the cell membrane. Does not affect QT intervals, but prolongs the atrial effective refractive period and prevents acetylcholine-induced atrial fibrillations in ex vivo and in vivo models. Also shown to reversibly block TRPM7 channel (IC50 = 1.6 mM) in smooth muscle cells, primary podocytes, HEK293 cells expressing TRPM7, and ventricular myocytes in a Mg2+-dependent manner and blocks the motility of cells in culture.

Other Notes

Chubanov, V., et al. 2012. Brit. Journ. Pharm.166, 1357.
Jenkins, D., et al. 2011. Hypertension.57, 1129.
Jenkins, D., et al. 2011. Mol. Pharm.79, 899.
Jenkins, D., et al. 2011. Mol. Pharm.79, 899.
Lasse, S., et al. 2011. J. Cardiov. Pharm.57, 672.
Diness, J., et al. 2010. Circ Arrhythm Electrophusiol.3, 380.
Ji, H., et al. 2009. Eur. J. Neurosci.9, 1883.
Strobaek, D., et al. 2006. Mol. Pharm.70, 1771.

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk

WGK 2

Certificates of Analysis (COA)

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