ChemicalBook CAS DataBase List 1428-95-1

1428-95-1

Name	5-(N,N-HEXAMETHYLENE)-AMILORIDE
CAS	1428-95-1
Molecular Formula	C12H18ClN7O
MDL Number	MFCD00069211
Molecular Weight	311.77
MOL File	1428-95-1.mol

Synonyms

hma Amilo 5-HMA HMA-5 amipromizide Hexamethyleneamiloride 5-(N,N-HEXAMETHYLENE)-AMILORIDE AMILORIDE,5-(N,N-HEXAMETHYLENE)- HMA (5-(N,N-Hexamethylene)amiloride) 5-(N,N-HEXAMETHYLENE)-AMILORIDE USP/EP/BP 5-(N,N-Hexamethylene)amiloride Solution, 100ppm AMILORIDE, 5-(N,N-HEXAMETHYLENE) >93% NA +/H+ ANTIPORTER INH 3-amino-5-(azepan-1-yl)-6-chloro-N-(diaminomethylene)pyrazinamide 3-amino-5-(azepan-1-yl)-6-chloro-N-(diaminomethylidene)pyrazine-2-carboxamide N-(Diaminomethylene)-3-amino-5-(hexamethyleneamino)-6-chloropyrazine-2-carboxamide 3-azanyl-5-(azepan-1-yl)-N-[bis(azanyl)methylidene]-6-chloro-pyrazine-2-carboxamide 3-Amino-5-(1-azacycloheptane-1-yl)-6-chloro-N-(aminoiminomethyl)pyrazine-2-carboxamide 3-AMINO-N-(AMINOIMINOMETHYL)-6-CHLORO-5-(HEXAHYDRO-1H-AZEPIN-1-YL)-PYRAZINE-CARBOXAMIDE 3-Amino-5-(hexahydro-1H-azepin-1-yl)-6-chloro-N-(aminoiminomethyl)-2-pyrazinecarboxamide 6-Chloro-3-amino-5-[(hexahydro-1H-azepin)-1-yl]-N-(diaminomethylene)-2-pyrazinecarboxamide 2-Pyrazinecarboxamide, 3-amino-N-(aminoiminomethyl)-6-chloro-5-(hexahydro-1H-azepin-1-yl)-

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
InChI	1S/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)
InChIKey	RQQJJXVETXFINY-UHFFFAOYSA-N
SMILES	N\C(N)=N\C(=O)c1nc(Cl)c(nc1N)N2CCCCCC2

Safety Data

Hazard Codes	T
Risk Statements	23/24/25 less more
Safety Statements	22-36/37/39-45 less more
RIDADR	2811
WGK Germany	3
HazardClass	6.1(b)
PackingGroup	III
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Dermal Acute Tox. 3 Inhalation Acute Tox. 3 Oral

Hazard Information

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

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.

	t_1/2 (h)	Plasma CL_int (mL/min/kg)	Plasma V_ss (L/kg)	Plasma AUC_0-inf (h·μM)	B/P ratio	Blood CL (mL/min/kg)	Blood V_ss (L/kg)
Female Balb/c mice	0.62	86	2.0	1.5	1.5	59	1.4
Sprague Dawley rats	3.2	83.5	5.3	1.6	1.8	46.2	2.9
	% IV dose excreted in urine (0-24 h)	Renal Blood CL (mL/min/kg)	Non-Renal Blood CL (mL/min/kg)
Sprague Dawley rats	0.5	0.2	46.0

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 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

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