1428-95-1

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 NO: 1428-95-1
• Molecular Formula: C12H18ClN7O
• Molecular Weight: 311.77
• Mol File: 1428-95-1.mol
• Article Data: 0

Chemical Properties

• Melting Point: 224-225 °C
• Boiling Point: 638.2°Cat760mmHg
• Flash Point: 339.8°C
• Appearance: /
• Density: 1.63g/cm³
• Vapor Pressure: 3.47E-16mmHg at 25°C
• Refractive Index: 1.742
• Storage Temp.: 2-8°C
• PKA: 8.81±0.46(Predicted)
• CAS DataBase Reference: 5-(N,N-HEXAMETHYLENE)-AMILORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(N,N-HEXAMETHYLENE)-AMILORIDE(1428-95-1)
• EPA Substance Registry System: 5-(N,N-HEXAMETHYLENE)-AMILORIDE(1428-95-1)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 22-36/37/39-45
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 1428-95-1(Hazardous Substances Data)

Usage

Description

5-(N,N-HEXAMETHYLENE)-AMILORIDE, also known as HMA, is a derivative of amiloride with a wide range of biological activities. It is characterized as an allosteric antagonist of adenosine A2A receptors and exhibits potent inhibitory effects on various ion channels and cancer cells. HMA is a member of the pyrazine class, where the two amino hydrogens at position N-5 are replaced by a hexamethylene moiety, resulting in the formation of an azepane ring.

Uses

Used in Pharmaceutical Industry:
5-(N,N-HEXAMETHYLENE)-AMILORIDE is used as an allosteric antagonist for adenosine A2A receptors, playing a crucial role in the development of potential therapeutic agents targeting these receptors.
Used in Antiviral Applications:
HMA is used as an inhibitor of cation-selective ion channels formed by HIV-1 viral protein Vpu and hepatitis C virus (HCV) protein p7, making it a potential candidate for the development of antiviral drugs.
Used in Cancer Therapy:
5-(N,N-HEXAMETHYLENE)-AMILORIDE is used as a necrosis inducer and viability reducer in various breast cancer cell lines, including MCF-7, MDA-MB-231, T47D, SK-BR-3, Met-1, and NDL, without affecting cardiomyocytes or uterine, pulmonary, and renal epithelial cells. This selective toxicity makes HMA a promising agent for cancer treatment.
Used in Cardiovascular Protection:
HMA is used as a protective agent 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, highlighting its potential application in the treatment of cardiovascular diseases.

Biochem/physiol Actions

Inhibitor of Na+/H+ antiport.

InChI:InChI=1/C12H18ClN7O/c13-8-10(20-5-3-1-2-4-6-20)18-9(14)7(17-8)11(21)19-12(15)16/h1-6H2,(H2,14,18)(H4,15,16,19,21)