3,5-diamino-N-carbamimidoyl-6-chloropyrazine-2-carboxamide hydrochloride

• ChemBase ID: 72807
• Molecular Formular: C6H9Cl2N7O
• Molecular Mass: 266.08796
• Monoisotopic Mass: 265.0245633
• SMILES: c1(c(nc(c(n1)C(=O)NC(=N)N)N)N)Cl.Cl
• Canonical SMILES: NC(=N)NC(=O)c1nc(Cl)c(nc1N)N.Cl
• InChI: InChI=1S/C6H8ClN7O.ClH/c7-2-4(9)13-3(8)1(12-2)5(15)14-6(10)11;/h(H4,8,9,13)(H4,10,11,14,15);1H
• InChIKey: ACHKKGDWZVCSNH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5-diamino-N-carbamimidoyl-6-chloropyrazine-2-carboxamide hydrochloride
• IUPAC Traditional name: amiloride hydrochloride; amilorida hydrochloride; 3,5-diamino-N-carbamimidoyl-6-chloropyrazine-2-carboxamide hydrochloride
• Synonyms: Midamor; Colectril; Amipramizide; Amiloride hydrochloride; 3,5-diamino-N-carbamimidoyl-6-chloropyrazine-2-carboxamide hydrochloride; Amipramidin; Amipramizid; Amiprazidine; Guanamprazin; Guanamprazine; Amiloride hydrochloride; 3,5-Diamino-N-(aminoiminomethyl)-6-chloro-2-pyrazinecarboxamide Hydrochloride; 3,5-Diamino-N-(aminomethyl)-6-chloropyrazinecarboxamide; N-Amidino-3,5-diamino-6-chloropyrazinecarboxamide hydrochloride; AMILORIDE; N-Amidino-3,5-diamino-6-chlorocyrazinecarboxamide Monohydrochloride; N-Amidino-3,5-diamino-6-chloropyrazinamide Hydrochloride; Amipramidine; Amiprazide; Nilurid

Database IDs

• CAS Number: 2016-88-8
• EC Number: 217-958-2
• PubChem SID: 162037728
• PubChem CID: 16230

CALCULATED PROPERTIES

• Acid pKa: 11.426196
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -0.7251268
• LogD (pH = 7.4): -0.4992728
• Log P: -0.49543247
• Molar Refractivity: 67.1812 cm^3
• Polarizability: 19.563002 Å^3
• Polar Surface Area: 156.79 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 285-288°C; 295-297°C (dec.)

Safety Information

• Storage Condition: -20°C; Refrigerator, Under Inert Atmosphere; Room Temperature (15-30°C)
• RTECS: UQ2275500
• European Hazard Symbols: Harmful (Xn)
• Risk Statements: R:22
• Safety Statements: S:46-36/37/39

Pharmacology Properties

• Mechanism of Action: Amiloride exerts its potassium sparing effect through the inhibition of sodium reabsorption at the distal convoluted tubule, cortical collecting tubule and collecting duct;; Amiloride is not an aldosterone antagonist and its effects are seen even in the absence of aldosterone.; Inhibitor of sodium reabsorption in the distal convoluted tubules and collecting ducts in the kidneys by binding to the amiloride-sensitive sodium channels.; this decreases the net negative potential of the tubular lumen and reduces both potassium and hydrogen secretion and their subsequent excretion.; This promotes the loss of sodium and water from the body, but without depleting potassium.

Product Information

• Salt Data: HCl; hydrochloride
• Application(s): Potassium-sparing diuretic

DETAILS

MP Biomedicals - 02153537

Hydrochloride
A sodium ion channel inhibitor.

Selleck Chemicals - S1811

Research Area: Metabolic Disease
Biological Activity:
Amiloride hydrochloride(Midamor), a pyrazine compound inhibit sodium reabsorption through sodium channels in renal epithelial cells. This inhibition creates a negative potential in the luminal membranes of principal cells, located in the distal convoluted tubule and collecting duct. Negative potential reduces secretion of potassium and hydrogen ions. Amiloride is used in conjunction with diuretics to spare potassium loss. [1]

Toronto Research Chemicals - A578700

Sodium channel blocker. Diuretic.

REFERENCES

• http://www.drugbank.ca/drugs/DB00594
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