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SML0553

Sigma-Aldrich

NN414

≥98% (HPLC)

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Synonym(s):
6-Chloro-3-[[1-methylcyclopropyl]amino]-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide, Tifenazoxide
Empirical Formula (Hill Notation):
C9H10ClN3O2S2
CAS Number:
279215-43-9
Molecular Weight:
291.78
MDL number:
MFCD18711369
UNSPSC Code:
12352200
PubChem Substance ID:
329825549
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 15 mg/mL, clear

storage temp.

2-8°C

SMILES string

CC1(CC1)NC2=NS(=O)(=O)c3sc(Cl)cc3N2

InChI

1S/C9H10ClN3O2S2/c1-9(2-3-9)12-8-11-5-4-6(10)16-7(5)17(14,15)13-8/h4H,2-3H2,1H3,(H2,11,12,13)

InChI key

KYSFUHHFTIGRJN-UHFFFAOYSA-N

Biochem/physiol Actions

NN414 is a potent Kir6.2/SUR1 selective K-ATP channel opener. Activation of the pancreatic Kir6.2/SUR KATP channels inhibits insulin release to induce beta cell rest, reducing the workload of the beta cell which is thought may prove beneficial for patients with type 2 diabetes. A recent study found that NN414 also triggered burst-like discharges in substantia nigra dopamine neurons. These K-ATP channel enabled burst-like discharges are associated with novelty-dependent exploratory behavior and may also have relevance to Parkinson′s disease.

Features and Benefits

This compound is featured on the Potassium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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C Beall et al.
Diabetologia, 55(9), 2432-2444 (2012-07-05)
Hypothalamic glucose-excited (GE) neurons contribute to whole-body glucose homeostasis and participate in the detection of hypoglycaemia. This system appears defective in type 1 diabetes, in which hypoglycaemia commonly occurs. Unfortunately, it is at present unclear which molecular components required for
Jelena Sikimic et al.
Frontiers in endocrinology, 11, 545638-545638 (2020-11-17)
Congenital hyperinsulinism (CHI) is a rare disease characterized by persistent hypoglycemia as a result of inappropriate insulin secretion, which can lead to irreversible neurological defects in infants. Poor efficacy and strong adverse effects of the current medications impede successful treatment.
Elizabeth Haythorne et al.
Neuropharmacology, 111, 212-222 (2016-09-14)
Individuals with Type 1 diabetes (T1D) are often exposed to recurrent episodes of hypoglycaemia. This reduces hormonal and behavioural responses that normally counteract low glucose in order to maintain glucose homeostasis, with altered responsiveness of glucose sensing hypothalamic neurons implicated.

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