3-amino-N-carbamimidoyl-6-chloro-5-[methyl(2-methylpropyl)amino]pyrazine-2-carboxamide

• ChemBase ID: 132882
• Molecular Formular: C11H18ClN7O
• Molecular Mass: 299.75992
• Monoisotopic Mass: 299.12613591
• SMILES: CC(C)CN(C)c1c(nc(c(n1)N)C(=O)NC(=N)N)Cl
• Canonical SMILES: CC(CN(c1nc(N)c(nc1Cl)C(=O)NC(=N)N)C)C
• InChI: InChI=1S/C11H18ClN7O/c1-5(2)4-19(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: RVIUMPLAOXSSGN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-amino-N-carbamimidoyl-6-chloro-5-[methyl(2-methylpropyl)amino]pyrazine-2-carboxamide
• IUPAC Traditional name: 3-amino-N-carbamimidoyl-6-chloro-5-[methyl(2-methylpropyl)amino]pyrazine-2-carboxamide
• Synonyms: MIA; 5-(N-Methyl-N-isobutyl)-amiloride

Database IDs

• CAS Number: 96861-65-3
• MDL Number: MFCD00078567
• PubChem SID: 162227159; 24278228
• PubChem CID: 73314

CALCULATED PROPERTIES

• Acid pKa: 11.395542
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 1.5185543
• LogD (pH = 7.4): 1.6832356
• Log P: 1.6858405
• Molar Refractivity: 90.6536 cm^3
• Polarizability: 28.63766 Å^3
• Polar Surface Area: 134.01 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• 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)

Product Information

• Purity: ≥98% (TLC)

DETAILS

Sigma Aldrich - A5585

Biochem/physiol Actions
Potent blocker of the Na+/H+ antiport. Possible antitumor agent.
Application
5-(N-Methyl-N-isobutyl)-amiloride is a potent blocker of the Na2/H+ antiport. 5-(N-Methyl-N-isobutyl)-amiloride has been used to study early cellular response to acidosis.