5-(N,N-HEXAMETHYLENE)-AMILORIDE

5-(N,N-HEXAMETHYLENE)-AMILORIDE Basic information
Product Name:5-(N,N-HEXAMETHYLENE)-AMILORIDE
Synonyms:5-(N,N-HEXAMETHYLENE)-AMILORIDE;AMILORIDE,5-(N,N-HEXAMETHYLENE)-;3-AMINO-N-(AMINOIMINOMETHYL)-6-CHLORO-5-(HEXAHYDRO-1H-AZEPIN-1-YL)-PYRAZINE-CARBOXAMIDE;AMILORIDE, 5-(N,N-HEXAMETHYLENE) >93% NA +/H+ ANTIPORTER INH;hma;amipromizide;3-Amino-5-(1-azacycloheptane-1-yl)-6-chloro-N-(aminoiminomethyl)pyrazine-2-carboxamide;3-Amino-5-(hexahydro-1H-azepin-1-yl)-6-chloro-N-(aminoiminomethyl)-2-pyrazinecarboxamide
CAS:1428-95-1
MF:C12H18ClN7O
MW:311.77
EINECS:
Product Categories:
Mol File:1428-95-1.mol
5-(N,N-HEXAMETHYLENE)-AMILORIDE Structure
5-(N,N-HEXAMETHYLENE)-AMILORIDE Chemical Properties
Melting point 224-225 °C
density 1.63±0.1 g/cm3(Predicted)
storage temp. 2-8°C
solubility DMF: 3mg/mL; DMSO: 10mg/mL; DMSO:PBS (pH 7.2) (1:4): 0.2mg/mL
form A crystalline solid
pka8.81±0.46(Predicted)
Safety Information
Hazard Codes T
Risk Statements 23/24/25
Safety Statements 22-36/37/39-45
RIDADR 2811
WGK Germany 3
HazardClass 6.1(b)
PackingGroup III
MSDS Information
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SigmaAldrich English
5-(N,N-HEXAMETHYLENE)-AMILORIDE Usage And Synthesis
Description5-(N,N-hexamethylene)-Amiloride (HMA) is a derivative of amiloride with diverse biological activities. It is an allosteric antagonist of adenosine A2A receptors (Ki = 3.3 μM). HMA inhibits the cation-selective ion channel formed by the HIV-1 viral protein Vpu when used at a concentration of 50 μM, as well as budding of virus-like particles in HeLa cells expressing the HIV-1 proteins Gag and Vpu when used at a concentration of 10 μM. It also blocks the cation-selective ion channels formed by the hepatitis C virus (HCV) protein p7. HMA (40 μM) induces necrosis in and reduces the viability of MCF-7, MDA-MB-231, T47D, SK-BR-3, Met-1, and NDL breast cancer cells but not cardiomyocytes or uterine, pulmonary, and renal epithelial cells. HMA protects against post-ischemic contractile dysfunction and reduces coronary effluent creatine phosphokinase activity in a model of ischemia-reperfusion injury using isolated rat right ventricular free walls.
DefinitionChEBI: A member of the class of pyrazines that is amiloride in which the two amino hydrogens at position N-5 are replaced by a hexamethylene moiety, resulting in the formation of an azepane ring.
Biochem/physiol ActionsInhibitor of Na+/H+ antiport.
5-(N,N-HEXAMETHYLENE)-AMILORIDE Preparation Products And Raw materials
Torasemide Labetalol PHENAMIL METHANESULFONATE 3' 4'-DICHLOROBENZAMIL EIPA 5-(N-Ethyl-N-isopropyl)amiloridehydrochloride PHENAMIL Amiloride hydrochloride AMILORIDE AMILORIDE MONOHYDROCHLORIDE DIHYDRATE BENZAMIL HYDROCHLORIDE MIA 3',4'-DICHLOROBENZAMIL HYDROCHLORIDE 5-(N,N-HEXAMETHYLENE)-AMILORIDE Amiloride hydrochloride dihydrate

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