(2Z)-but-2-enedioic acid ethyl N-(2-amino-6-{[(4-fluorophenyl)methyl]amino}pyridin-3-yl)carbamate

• ChemBase ID: 169288
• Molecular Formular: C19H21FN4O6
• Molecular Mass: 420.3916432
• Monoisotopic Mass: 420.14451263
• SMILES: c1c(ccc(c1)CNc1ccc(c(n1)N)NC(=O)OCC)F.C(=C\C(=O)O)\C(=O)O
• Canonical SMILES: OC(=O)/C=C\C(=O)O.CCOC(=O)Nc1ccc(nc1N)NCc1ccc(cc1)F
• InChI: InChI=1S/C15H17FN4O2.C4H4O4/c1-2-22-15(21)19-12-7-8-13(20-14(12)17)18-9-10-3-5-11(16)6-4-10;5-3(6)1-2-4(7)8/h3-8H,2,9H2,1H3,(H,19,21)(H3,17,18,20);1-2H,(H,5,6)(H,7,8)/b;2-1-
• InChIKey: DPYIXBFZUMCMJM-BTJKTKAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-but-2-enedioic acid ethyl N-(2-amino-6-{[(4-fluorophenyl)methyl]amino}pyridin-3-yl)carbamate
• IUPAC Traditional name: flupirtine; maleic acid
• Synonyms: N-[2-Amino-6-[[(4-fluorophenyl)methyl]amino]-3-pyridinyl]carbamic Acid Ethyl Ester (2Z)-2-Butenedioate; 2-Amino-6-[(p-fluorobenzyl)amino]-3-pyridinecarbamic Acid Ethyl Ester Maleate; W 2964M; Flupirtine Maleate

Database IDs

• CAS Number: 75507-68-5
• PubChem SID: 162263420
• PubChem CID: 6435335

CALCULATED PROPERTIES

• Acid pKa: 12.896986
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.9672019
• LogD (pH = 7.4): 2.319763
• Log P: 2.669325
• Molar Refractivity: 85.4865 cm^3
• Polarizability: 30.264492 Å^3
• Polar Surface Area: 89.27 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 186-188°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - F598510

Analgesic. Substituted pyridine with central analgesic properties.

REFERENCES

• Vaupel, D., et al.: Eur. J. Pharmacol., 162, 447 (1989)
• Nickel, B., et al.: Arzneim.-Forsch., 40, 909 (1989)
• Lunemann, J., et al.: J. Immunol., 168, 4881 (2002).