Tifenazoxide

Modify Date: 2024-01-15 11:43:48

Tifenazoxide Structure
Tifenazoxide structure
Common Name Tifenazoxide
CAS Number 279215-43-9 Molecular Weight 291.77800
Density N/A Boiling Point N/A
Molecular Formula C9H10ClN3O2S2 Melting Point N/A
MSDS Chinese USA Flash Point N/A

 Use of Tifenazoxide


Tifenazoxide (NN414) is a potent, orally active and SUR1/Kir6.2 selective KATP channels opener. Tifenazoxide has antidiabetic effect, can inhibit glucose stimulated insulin release in vitro and in vivo, and has a beneficial effect on glucose homeostasis[1][2].

 Names

Name 2H-Thieno(3,2-E)-1,2,4-thiadiazin-3-amine, 6-chloro-N-(1-methylcyclopropyl)-, 1,1-dioxide

 Tifenazoxide Biological Activity

Description Tifenazoxide (NN414) is a potent, orally active and SUR1/Kir6.2 selective KATP channels opener. Tifenazoxide has antidiabetic effect, can inhibit glucose stimulated insulin release in vitro and in vivo, and has a beneficial effect on glucose homeostasis[1][2].
Related Catalog
Target

KATP channels[1][2]

In Vitro Tifenazoxide (NN414) hyperpolarises βTC3 cell membranes, and inhibits insulin release from βTC6, from isolated rat islets and from human islets at least a 100-fold more potent than Diazoxide[2]. The EC50 values for Tifenazoxide and diazoxide are 0.45 and 31 µM, respectively in the patch-clamp assay. Tifenazoxide (100 µM) activates Kir6.2/SUR1 channels, but not Kir6.2/SUR2A or Kir6.2/SUR2 channels, expressed in Xenopus oocytes both in whole-cell and inside-out macropatch recordings[2]. Tifenazoxide is a potent inhibitor of glucose stimulated insulin release from βTC6 cells (IC50 = 0.15 µM)[1].
In Vivo Tifenazoxide (NN414; 1.5 mg/kg; oral administration; twice daily; for 3 weeks; male VDF Zucker (fa/fa) rat) treatment for 3 weeks in VDF rats reduces basal hyperglycemia, improves glucose tolerance, and reduces hyperinsulinemia during an oral glucose tolerance test (OGTT) and improves insulin secretory responsiveness ex vivo[1]. Animal Model: Male Vancouver diabetic fatty (VDF) Zucker rat[1] Dosage: 1.5 mg/kg Administration: Oral administration; twice daily; for 3 weeks Result: Basal glucose was significantly reduced with the fall averaging 0.64 mM after 3 weeks of treatment.
References

[1]. Carr RD, et al. NN414, a SUR1/Kir6.2-selective potassium channel opener, reduces blood glucose and improves glucose tolerance in the VDF Zucker rat. Diabetes. 2003 Oct;52(10):2513-8.

[2]. Hansen JB. Towards selective Kir6.2/SUR1 potassium channel openers, medicinal chemistry and therapeutic perspectives. Curr Med Chem. 2006;13(4):361-76.

 Chemical & Physical Properties

Molecular Formula C9H10ClN3O2S2
Molecular Weight 291.77800
Exact Mass 290.99000
PSA 107.18000
LogP 3.05910
Vapour Pressure 3.22E-08mmHg at 25°C

 Safety Information

RIDADR NONH for all modes of transport

 Articles1

More Articles
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Diabetologia 55 , 2432-44, (2012)

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 hyp...

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