N-carbamimidoyl-5-(5-fluoro-2-methylphenyl)furan-2-carboxamide

• ChemBase ID: 154026
• Molecular Formular: C13H12FN3O2
• Molecular Mass: 261.2516832
• Monoisotopic Mass: 261.09135486
• SMILES: Cc1ccc(cc1c1ccc(o1)C(=O)NC(=N)N)F
• Canonical SMILES: NC(=N)NC(=O)c1ccc(o1)c1cc(F)ccc1C
• InChI: InChI=1S/C13H12FN3O2/c1-7-2-3-8(14)6-9(7)10-4-5-11(19-10)12(18)17-13(15)16/h2-6H,1H3,(H4,15,16,17,18)
• InChIKey: DTLDHYBZLVASJQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-carbamimidoyl-5-(5-fluoro-2-methylphenyl)furan-2-carboxamide
• IUPAC Traditional name: N-carbamimidoyl-5-(5-fluoro-2-methylphenyl)furan-2-carboxamide
• Synonyms: [5-(2-Methyl-5-fluorophenyl)furan-2-ylcarbonyl]guanidine; KR-32568

Database IDs

• CAS Number: 852146-73-7
• MDL Number: MFCD08705324
• PubChem SID: 24724522; 162248165
• PubChem CID: 11368995

CALCULATED PROPERTIES

• Acid pKa: 11.714763
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 1.7736691
• LogD (pH = 7.4): 1.8315638
• Log P: 1.8323735
• Molar Refractivity: 78.6353 cm^3
• Polarizability: 26.136581 Å^3
• Polar Surface Area: 92.11 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ~10 mg/mL
• Apperance: white solid

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... SLC9A1(6548)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C13H12FN3O2

DETAILS

Sigma Aldrich - K4389

Biochem/physiol Actions
Sodium/hydrogen exchanger-1 (NHE-1) inhibitor; IC50 = 0.23 μM; inhibited NHE-1-mediated rabbit platelet swelling; in anesthetized rats, reduced infarct size from 67% (control) to 43% (at 0.1 mg/kg) and 24% (at 1.0 mg/kg); reduced number of ventricular premature beats from 530 to 266 (at 0.1 mg/kg) and 115 (at 1.0 mg/kg); reduced ventricular fibrillation incidence from 17 to 8 (0.1 mg/kg) and 0 (1.0 mg/kg); implications for research and treatment of myocardial ischemic diseases.