5- (N, N-Hexamethylene) -amiloride

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].

Product Specifications

CAS Number

[1428-95-1]

Product Name Alternative

Hexamethylene amiloride; HMA

UNSPSC

12352005

Hazard Statement

H301+H311+H331

Target

Apoptosis; HIV; Sodium Channel

Type

Reference compound

Related Pathways

Anti-infection; Apoptosis; Membrane Transporter/Ion Channel

Applications

Cancer-programmed cell death

Field of Research

Cancer; Infection

Assay Protocol

https://www.medchemexpress.com/5-n-n-hexamethylene-amiloride.html

Concentration

10mM

Purity

99.14

Solubility

DMSO : 100 mg/mL (ultrasonic)

Smiles

O=C(C1=NC(Cl)=C(N2CCCCCC2)N=C1N)NC(N)=N

Molecular Formula

C12H18ClN7O

Molecular Weight

311.77

Precautions

H301+H311+H331

References & Citations

[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.|[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.|[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.