ChemicalBook > CAS DataBase List > 5-(N,N-HEXAMETHYLENE)-AMILORIDE

5-(N,N-HEXAMETHYLENE)-AMILORIDE

Product Name
5-(N,N-HEXAMETHYLENE)-AMILORIDE
CAS No.
1428-95-1
Chemical Name
5-(N,N-HEXAMETHYLENE)-AMILORIDE
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
CBNumber
CB8418632
Molecular Formula
C12H18ClN7O
Formula Weight
311.77
MOL File
1428-95-1.mol
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5-(N,N-HEXAMETHYLENE)-AMILORIDE Property

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
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
A9561
Product name
5-(N,N-Hexamethylene)amiloride
Packaging
25mg
Price
$113
Updated
2024/03/01
Sigma-Aldrich
Product number
A9561
Product name
5-(N,N-Hexamethylene)amiloride
Packaging
100mg
Price
$151.2
Updated
2024/03/01
Cayman Chemical
Product number
29788
Product name
5-(N,N-hexamethylene)-Amiloride
Packaging
10mg
Price
$72
Updated
2024/03/01
Cayman Chemical
Product number
29788
Product name
5-(N,N-hexamethylene)-Amiloride
Packaging
25mg
Price
$109
Updated
2024/03/01
Cayman Chemical
Product number
29788
Product name
5-(N,N-hexamethylene)-Amiloride
Purity
≥98%
Packaging
100mg
Price
$290
Updated
2021/12/16
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5-(N,N-HEXAMETHYLENE)-AMILORIDE Chemical Properties,Usage,Production

Description

5-(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.

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.

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 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 Preparation Products And Raw materials

Raw materials

Preparation Products

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

China 44 Germany 1 Switzerland 1 United Kingdom 1 United States 10 Global 57
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View Lastest Price from 5-(N,N-HEXAMETHYLENE)-AMILORIDE manufacturers

Dideu Industries Group Limited
Product
5-(N,N-HEXAMETHYLENE)-AMILORIDE 1428-95-1
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons Min
Release date
2021-07-08

1428-95-1, 5-(N,N-HEXAMETHYLENE)-AMILORIDERelated Search:

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

  • 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
  • 6-Chloro-3-amino-5-[(hexahydro-1H-azepin)-1-yl]-N-(diaminomethylene)-2-pyrazinecarboxamide
  • Hexamethyleneamiloride
  • N-(Diaminomethylene)-3-amino-5-(hexamethyleneamino)-6-chloropyrazine-2-carboxamide
  • 3-amino-5-(azepan-1-yl)-6-chloro-N-(diaminomethylene)pyrazinamide
  • 3-amino-5-(azepan-1-yl)-6-chloro-N-(diaminomethylidene)pyrazine-2-carboxamide
  • 3-azanyl-5-(azepan-1-yl)-N-[bis(azanyl)methylidene]-6-chloro-pyrazine-2-carboxamide
  • HMA (5-(N,N-Hexamethylene)amiloride)
  • 5-(N,N-Hexamethylene)amiloride Solution, 100ppm
  • Amilo
  • 5-HMA
  • HMA-5
  • 2-Pyrazinecarboxamide, 3-amino-N-(aminoiminomethyl)-6-chloro-5-(hexahydro-1H-azepin-1-yl)-
  • 5-(N,N-HEXAMETHYLENE)-AMILORIDE USP/EP/BP
  • 1428-95-1
  • C12H18ClN7O
  • Cell Biology
  • Cell Signaling and Neuroscience
  • Amiloride and Derivatives
  • BioChemical
  • Monovalent Ion Channels
  • Ion Channels
  • Sodium Channel Modulators
  • Voltage-gated Ion Channels