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ChemicalBook > Product Catalog >API >Urinary System Drugs >Diuretics Drugs >5-(N,N-HEXAMETHYLENE)-AMILORIDE

5-(N,N-HEXAMETHYLENE)-AMILORIDE

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Company Name: Shenzhen Excellent Biotech Co., Ltd.
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Products Intro: Product Name:Amilo
CAS:1428-95-1
Purity:0.99 Package:5KG;1KG Remarks:Large package please cotact us according to customer demand
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Products Intro: Product Name:amiloride
CAS:1428-95-1
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Products Intro: Product Name:5-(N,N-HEXAMETHYLENE)-AMILORIDE
CAS:1428-95-1
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Products Intro: Product Name:5-(N,N-Hexamethylene)-amiloride
CAS:1428-95-1
Purity:98% Package:100mg Remarks:V32884
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Products Intro: Product Name:5-(N,N-Hexamethylene)-amiloride;5-HMA;Hexamethylene amiloride;HMA-5;5-(N,N-Hexamethylene)amiloride
CAS:1428-95-1
Package:10 mg;5 mg;50 mg Remarks:REAGENT;FOR LABORATORY USE ONLY

5-(N,N-HEXAMETHYLENE)-AMILORIDE manufacturers

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)
color Light yellow to yellow
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
ProviderLanguage
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.
Uses5-(N,N-Hexamethylene)-amiloride (Hexamethylene amiloride) derives from an amiloride and is a potent Na+/H+ exchanger inhibitor, which decreases the intracellular pH (pHi) and induces apoptosis in leukemic cells. 5-(N,N-Hexamethylene)-amiloride (Hexamethylene amiloride) is also an inhibitor of the HIV-1 Vpu virus ion channel and inhibits mouse hepatitis virus (MHV) replication and human coronavirus 229E (HCoV229E) replication in cultured L929 cells with EC50s of 3.91 μM and 1.34 μM, respectively[1][2].
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.
in vivo

5-(N,N-Hexamethylene)-amiloride (2.5 mg/kg; i.v.; single dose) shows short half-life and lowly oral bioavailability of 4.5%[3].
In vivo pharmacokinetics in mice or rat model[3]
Dosage: 2.5 mg/kg Administration: Intravenous injection; single does; collected 10 min and 60 min after treatment.

t1/2 (h)Plasma CLint (mL/min/kg)Plasma Vss (L/kg)Plasma AUC0-inf (h·μM)B/P ratioBlood CL (mL/min/kg)Blood Vss (L/kg)
Female Balb/c mice0.62862.01.51.5591.4
Sprague Dawley rats3.283.55.31.61.846.22.9
% IV dose excreted in urine (0-24 h)Renal Blood CL (mL/min/kg)Non-Renal Blood CL (mL/min/kg)
Sprague Dawley rats0.50.246.0
Note: B/P means blood-to-plasma partitioning ratio; female Balb/c mice (17-27 g, non-fasted); male Sprague Dawley rats (238-325 g, overnight-fasted).
IC 50HIV-1
References[1] Rich IN, et al. Apoptosis of leukemic cells accompanies reduction in intracellular pH after targeted inhibition of the Na(+)/H(+) exchanger. Blood. 2000 Feb 15;95(4):1427-34. PMID:10666221
[2] Wilson L, et al. Hexamethylene amiloride blocks E protein ion channels and inhibits coronavirus replication. Virology. 2006 Sep 30;353(2):294-306. Epub 2006 Jul 3. DOI:10.1016/j.virol.2006.05.028
[3] Buckley BJ, et al. Systematic evaluation of structure-property relationships and pharmacokinetics in 6-(hetero)aryl-substituted matched pair analogs of amiloride and 5-(N,N-hexamethylene)amiloride. Bioorg Med Chem. 2021 May 1;37:116116. DOI:10.1016/j.bmc.2021.116116
5-(N,N-HEXAMETHYLENE)-AMILORIDE Preparation Products And Raw materials
Tag:5-(N,N-HEXAMETHYLENE)-AMILORIDE(1428-95-1) Related Product Information
Labetalol Torasemide Amiloride hydrochloride 5-(N,N-HEXAMETHYLENE)-AMILORIDE AMILORIDE Amiloride hydrochloride dihydrate MIA PHENAMIL METHANESULFONATE EIPA PHENAMIL BENZAMIL HYDROCHLORIDE 3' 4'-DICHLOROBENZAMIL AMILORIDE MONOHYDROCHLORIDE DIHYDRATE 5-(N-Ethyl-N-isopropyl)amiloridehydrochloride 3',4'-DICHLOROBENZAMIL HYDROCHLORIDE

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