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Merck
CN

SML2333

VU0463271

≥98% (HPLC), KCC2 inhibitor, powder

Synonym(s):

N-Cyclopropyl-N-(4-methyl-2-thiazolyl)-2-[(6-phenyl-3-pyridazinyl)thio]-acetamide, N-Cyclopropyl-N-(4-methyl-2-thiazolyl)-2-[(6-phenyl-3-pyridazinyl)thio]acetamide, N-Cyclopropyl-N-(4-methylthiazol-2-yl)-2-(6-phenylpyridazin-3-ylthio)acetamide

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About This Item

Empirical Formula (Hill Notation):
C19H18N4OS2
CAS Number:
1391737-01-1
Molecular Weight:
382.50
MDL number:
MFCD30182240
UNSPSC Code:
12352200
NACRES:
NA.21

Key Documents

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Product Name

VU0463271, ≥98% (HPLC)

Assay

≥98% (HPLC)

form

powder

color

off-white to blue-gray

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

[s]1c(nc(c1)C)N(C4CC4)C(=O)CSc2nnc(cc2)c3ccccc3

InChI

1S/C19H18N4OS2/c1-13-11-26-19(20-13)23(15-7-8-15)18(24)12-25-17-10-9-16(21-22-17)14-5-3-2-4-6-14/h2-6,9-11,15H,7-8,12H2,1H3

InChI key

DPONSKCACOZTGN-UHFFFAOYSA-N

Related Categories

Biochem/physiol Actions

Potent and selective potassium-chloride cotransporter KCC2 inhibitor with greatly enhanced potency than its structural analogs VU0255011/ML077 & VU0240511.
VU0463271 is a potent and selective potassium-chloride cotransporter 2 (KCC2) inhibitor that displays greatly enhanced potency than its structural analogs VU0255011 (ML077) & VU0240511 (IC50 = 61, 537, and 568 nM, respectively). VU0463271 exhibits much reduced efficacy against the related Na-K-2Cl cotransporter 1 (NKCC1 inhibition max ~37% at 100 μM) and little affinity toward a panel of 68 GPCRs, ion channels, and transporters. Although VU0463271 is reported to exhibit affinity toward mitochondrial translocator protein TSPO (IC50 of 204 nM against PK11195 binding; rat heart) and inhibitory potency against α1B adrenergic receptor (IC50 of 364.7 nM; human α1B CHO transfectants), these proteins are not known to affect chloride homeostasis.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000472143
0000472137
0000472137
0000361935
0000361936

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D Subramanian et al.
Translational psychiatry, 8(1), 16-16 (2018-01-11)
Autism spectrum disorder (ASD) and temporal lobe epilepsy exhibit remarkable comorbidity, but for reasons not clearly understood. To reveal a common pathophysiological mechanism, we here describe and characterize an in vitro epileptiform activity in the rat hippocampus that exhibits common
Hannah Alfonsa et al.
Nature communications, 7, 13495-13495 (2016-11-18)
Chloride regulation affects brain function in many ways, for instance, by dictating the GABAergic reversal potential, and thereby influencing neuronal excitability and spike timing. Consistent with this, there is increasing evidence implicating chloride in a range of neurological conditions. Investigations
Eric Delpire et al.
Bioorganic & medicinal chemistry letters, 22(14), 4532-4535 (2012-06-26)
Further chemical optimization of the MLSCN/MLPCN probe ML077 (KCC2 IC(50)=537 nM) proved to be challenging as the effort was characterized by steep SAR. However, a multi-dimensional iterative parallel synthesis approach proved productive. Herein we report the discovery and SAR of
Peter M Klein et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 38(5), 1232-1248 (2017-12-24)
Maintenance of a low intracellular Cl- concentration ([Cl-]i) is critical for enabling inhibitory neuronal responses to GABAA receptor-mediated signaling. Cl- transporters, including KCC2, and extracellular impermeant anions ([A]o) of the extracellular matrix are both proposed to be important regulators of
Matthew R Kelley et al.
Neuropharmacology, 108, 103-110 (2016-04-26)
Impaired neuronal inhibition has long been associated with the increased probability of seizure occurrence and heightened seizure severity. Fast synaptic inhibition in the brain is primarily mediated by the type A γ-aminobutyric acid receptors (GABAARs), ligand-gated ion channels that can
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