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Merck
CN

SML2039

SAK3

≥98% (HPLC)

Synonym(s):

8′-Methyl-2′,4-dioxo-2-(1-piperidinyl)-spiro[2-cyclopentene-1,3′(2′H)-imidazo[1,2-a]pyridine]-3-carboxylic acid ethyl ester, Ethyl 8′-methyl-2′,4-dioxo-2-(piperidin-1-yl)-2′H-spiro[cyclopent[2]ene-1,3′-imidazo[1,2-a]pyridine]-3-carboxylate

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About This Item

Empirical Formula (Hill Notation):
C20H23N3O4
CAS Number:
1256269-87-0
Molecular Weight:
369.41
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Product Name

SAK3, ≥98% (HPLC)

InChI key

WZHBYTVHUFURPY-UHFFFAOYSA-N

SMILES string

O=C(OCC)C1=C(C2(CC1=O)N3C=CC=C(C3=NC2=O)C)N4CCCCC4

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Related Categories

Biochem/physiol Actions

Potent and orally active Cav3.1 & Cav3.3 T-type voltage-gated Ca2+ channel (T-VGCC) enhancer with in vivo cognitive deficits-improving efficacy.
SAK3 is a potent and orally active spiroimidazopyridine derivative that enhances Cav3.1 and Cav3.3, but not Cav3.2, T-type voltage-gated Ca2+ channel (T-VGCC) activity (∼20% peak current increase with 0.1 nM SAK3 by whole-cell patch-clamp using human Cav3.1 or Cav3.3 transfected neuro2A; no effect up to 10 nM using Cav3.2 transfectant). Acute SAK3 oral administration (0.5 mg/kg) significantly enhances hippocampal CA1 region acetylcholine (ACh) release in naïve mice, as well as increases hippocampal ACh levels and improves memory deficits among olfactory-bulbectomized (OBX) mice. Daily SAK3 oral administration 24 hrs following hypothyroidism induction by methimazole (MMI) is efficacious against MMI-induced medial septum (MS) cholinergic neurons loss (0.5-1 mg/kg/day) and cognitive deficits (1 mg/kg/day).

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000446012
0000446012
0000320697
0000320697
0000239307

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Husain Noreen et al.
Neurochemistry international, 108, 91-99 (2017-03-11)
Methimazole (MMI) is a first-line therapy used to manage hyperthyroidism and Graves' disease. Despite its therapeutic benefit, chronic MMI administration can lead to hypothyroidism and perturb brain homeostasis in patients, resulting in neuropsychiatric disorders such as depression and cognitive dysfunction.
Yasushi Yabuki et al.
Neuropharmacology, 117, 1-13 (2017-01-18)
T-type voltage-gated Ca
Chinnasamy Dhanalakshmi et al.
Neurobiology of disease, 149, 105224-105224 (2020-12-29)
The TATA-box binding protein associated factor 1 (TAF1) is part of the TFIID complex that plays a key role during the initiation of transcription. Variants of TAF1 are associated with neurodevelopmental disorders. Previously, we found that CRISPR/Cas9 based editing of
Udaiyappan Janakiraman et al.
Neurobiology of disease, 143, 105006-105006 (2020-07-06)
T-type calcium channels, in the central nervous system, are involved in the pathogenesis of many neurodegenerative diseases, including TAF1 intellectual disability syndrome (TAF1 ID syndrome). Here, we evaluated the efficacy of a novel T-type Ca2+ channel enhancer, SAK3 (ethyl 8'-methyl-2'

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