3,5-diamino-6-chloro-N-(N-phenylcarbamimidoyl)pyrazine-2-carboxamide; methanesulfonic acid

• ChemBase ID: 133563
• Molecular Formular: C13H16ClN7O4S
• Molecular Mass: 401.82864
• Monoisotopic Mass: 401.06730071
• SMILES: CS(=O)(=O)O.c1ccc(cc1)NC(=N)NC(=O)c1c(nc(c(n1)Cl)N)N
• Canonical SMILES: CS(=O)(=O)O.N=C(NC(=O)c1nc(Cl)c(nc1N)N)Nc1ccccc1
• InChI: InChI=1S/C12H12ClN7O.CH4O3S/c13-8-10(15)19-9(14)7(18-8)11(21)20-12(16)17-6-4-2-1-3-5-6;1-5(2,3)4/h1-5H,(H4,14,15,19)(H3,16,17,20,21);1H3,(H,2,3,4)
• InChIKey: MHPIZTURFVSLTJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5-diamino-6-chloro-N-(N-phenylcarbamimidoyl)pyrazine-2-carboxamide; methanesulfonic acid
• IUPAC Traditional name: 3,5-diamino-6-chloro-N-(N-phenylcarbamimidoyl)pyrazine-2-carboxamide; methanesulfonic acid
• Synonyms: 3,5-Diamino-6-chloro-N-[imino(phenylamino)methyl]pyrazinecarboxamide methanesulfonate salt; Phenamil methanesulfonate salt

Database IDs

• CAS Number: 1161-94-0
• MDL Number: MFCD00274070
• PubChem SID: 162227840; 24277869
• PubChem CID: 9604979

CALCULATED PROPERTIES

• Acid pKa: 11.387998
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 1.6785749
• LogD (pH = 7.4): 1.6884776
• Log P: 1.6886454
• Molar Refractivity: 93.5142 cm^3
• Polarizability: 29.000818 Å^3
• Polar Surface Area: 142.8 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: insoluble; 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble2.5 mg/mL; DMSO: >4 mg/mL; H2O: insoluble
• Apperance: yellow solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... SCNN1A(6337), SCNN1B(6338), SCNN1D(6339), SCNN1G(6340)mouse ... Scnn1a(20276), Scnn1b(20277), Scnn1d(140501), Scnn1g(20278)rat ... Scnn1a(25122), Scnn1b(24767), Scnn1g(24768)

DETAILS

Sigma Aldrich - P203

Biochem/physiol Actions
Irreversible inhibitor of amiloride-sensitive Na+ channels; derivative of amiloride.