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

pka

8.81±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

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5-(N,N-HEXAMETHYLENE)-AMILORIDE Usage And Synthesis

Description

5-(N,N-hexamethylene)-Amiloride (HMA) is a derivative of amiloride with diverse biological activities. It is an allosteric antagonist of adenosine A_2A receptors (K_i = 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.

Uses

5-(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].

Definition

ChEBI: 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 Actions

Inhibitor of Na+/H+ antiport.

in vivo

IC 50

HIV-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(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