| Identification | Back Directory | [Name]
8-chloro-N-(1-methylcyclopropyl)-2,2-dioxo-2$l^{6},9-dithia-3,5-diazab icyclo[4.3.0]nona-3,7,10-trien-4-amine | [CAS]
279215-43-9 | [Synonyms]
NN414
tifenazoxide
NN414 >=98% (HPLC)
NN 414 - Tifenazoxide
6-Chloro-3-[[1-methylcyclopropyl]amino]-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide
2H-Thieno[3,2-e]-1,2,4-thiadiazin-3-amine, 6-chloro-N-(1-methylcyclopropyl)-, 1,1-dioxide
8-chloro-N-(1-methylcyclopropyl)-2,2-dioxo-2$l^{6},9-dithia-3,5-diazab icyclo[4.3.0]nona-3,7,10-trien-4-amine | [Molecular Formula]
C9H10ClN3O2S2 | [MDL Number]
MFCD18711369 | [MOL File]
279215-43-9.mol | [Molecular Weight]
291.78 |
| Chemical Properties | Back Directory | [Melting point ]
251-252 °C (decomp)(Solv: methanol (67-56-1); water (7732-18-5)) | [Boiling point ]
448.0±55.0 °C(Predicted) | [density ]
1.88±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: soluble15mg/mL, clear | [form ]
powder | [pka]
-6.81±0.20(Predicted) | [color ]
white to beige | [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) | [InChIKey]
KYSFUHHFTIGRJN-UHFFFAOYSA-N | [SMILES]
CC1(CC1)NC2=NS(=O)(=O)c3sc(Cl)cc3N2 |
| Hazard Information | Back Directory | [Uses]
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]. | [Biological Activity]
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 restreducing the workload of the beta cell which is thought may prove beneficial for patients with type 2 diabetes. A recent study found th at 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 Parkinsonμs disease. | [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.
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| [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. DOI:10.2337/diabetes.52.10.2513
[2] Hansen JB. Towards selective Kir6.2/SUR1 potassium channel openers, medicinal chemistry and therapeutic perspectives. Curr Med Chem. 2006;13(4):361-76. DOI:10.2174/092986706775527947 |
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