3-amino-6-chloro-N-(diaminomethylidene)-5-[ethyl(propan-2-yl)amino]pyrazine-2-carboxamide

• ChemBase ID: 168621
• Molecular Formular: C11H18ClN7O
• Molecular Mass: 299.75992
• Monoisotopic Mass: 299.12613591
• SMILES: c1(c(nc(c(n1)N)C(=O)N=C(N)N)Cl)N(C(C)C)CC
• Canonical SMILES: CCN(c1nc(N)c(nc1Cl)C(=O)N=C(N)N)C(C)C
• InChI: InChI=1S/C11H18ClN7O/c1-4-19(5(2)3)9-7(12)16-6(8(13)17-9)10(20)18-11(14)15/h5H,4H2,1-3H3,(H2,13,17)(H4,14,15,18,20)
• InChIKey: QDERNBXNXJCIQK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-amino-6-chloro-N-(diaminomethylidene)-5-[ethyl(propan-2-yl)amino]pyrazine-2-carboxamide
• IUPAC Traditional name: 3-amino-6-chloro-N-(diaminomethylidene)-5-[ethyl(isopropyl)amino]pyrazine-2-carboxamide
• Synonyms: 3-Amino-N-(aminoiminomethyl)-6-chloro-5-[ethyl(1-methylethyl)amino]-2-pyrazinecarboxamide; EIPA; Ethylisopropylamiloride; L 593754; MH 12-43; 5-(N-Ethyl-N-isopropyl) Amiloride

Database IDs

• CAS Number: 1154-25-2
• PubChem SID: 162262753
• PubChem CID: 1795

CALCULATED PROPERTIES

• Acid pKa: 16.80904
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 1.173963
• LogD (pH = 7.4): 1.1767559
• Log P: 1.1767917
• Molar Refractivity: 80.3326 cm^3
• Polarizability: 28.819124 Å^3
• Polar Surface Area: 136.51 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: dil aq. Acid; DMSO; Methanol (30.7 mg/ml)
• Apperance: Yellow Solid
• Melting Point: 201-202°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E921500

Selective Na+/H+ antiporter inhibitor. Selectively enhances the excretion of sodium ions without causing an increase in excretion of potassium ions.

REFERENCES

• Gupta, et al.: J. Pharmacol. Exp. Ther., 248(3)
• 991 (1989)