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

• ChemBase ID: 72625
• Molecular Formular: C19H21FN4O6
• Molecular Mass: 420.3916432
• Monoisotopic Mass: 420.14451263
• SMILES: c1(ccc(cc1)CNc1nc(c(cc1)NC(=O)OCC)N)F.OC(=O)/C=C/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-WLHGVMLRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: but-2-enedioic acid ethyl N-(2-amino-6-{[(4-fluorophenyl)methyl]amino}pyridin-3-yl)carbamate; (2E)-but-2-enedioic acid ethyl N-(2-amino-6-{[(4-fluorophenyl)methyl]amino}pyridin-3-yl)carbamate
• IUPAC Traditional name: butenedioic acid; flupirtine; flupirtine; fumaric acid
• Synonyms: 2-Amino-6-[[(4-fluorophenyl)methyl]amino]-3-pyridinyl]-carbamic acid ethyl ester maleate salt; Flupirtine maleate salt; Katadolon; Flupirtine maleate

Database IDs

• CAS Number: 75507-68-5
• MDL Number: MFCD00941415
• PubChem SID: 24278445; 162037550
• PubChem CID: 6536833

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: soluble >20 mg/mL; H2O: insoluble
• Apperance: white solid

Safety Information

• Storage Condition: -20°C
• 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

• Target: Antimetabolites

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Maleate
• Empirical Formula (Hill Notation): C15H17FN4O2 · C4H4O4

DETAILS

Selleck Chemicals - S1334

Research Area

• Description: Cancer

Protocol

• Protocol: Cell Assay ^[4]
• Cell Lines: PC12 cell
• Concentrations: 1 or 5 μg/mL
• Incubation Time: 72 hours
• Methods:

  For measurement of viability and generation of reactive oxygen intermediates, PC12 cells are seeded in 24- or 96-well plates coated with poly-L-lysine at 10^5 cells/mL. Drugs are dissolved in PBS (pH 7.4), or ethanol and filtered sterile. At the end of each experiment cells are trypsinized and pelleted together with cells of the culture supernatant. After staining for 10 min with 0.2% Trypan blue solution live (unstained) and dead (Trypan blue positive) cells are counted in a hemocytometer chamber. In addition, cellular viability is evaluated by the reduction of MTT to formazan. After 2 hours incubation with MTT (0.5 mg/ml) at 37 °C, cells are lysed in DMSO. Extinction at 570 nm is determined on a plate photometer. For staining of surviving adherent cells, plates are incubated for 10 min with 0.5% crystalviolet dissolved in 20% methanol. Plates are rinsed with water and stained cells are lysed in 50% ethanol, 0.1 M sodiumcitrate before determining extinction at 550 nm.

• Protocol: Animal Study ^[7]
• Animal Models: male Wistar rats with cerebral ischemia induced by four-vessel-occlusion
• Formulation: sterile 0.9% sodium chloride solution
• Doses: 5 mg/kg
• Administration: Intraperitoneal injection either 20 min before and 50 min after occlusion or directly and 70 min after occlusion

References

• References: [1] Perovic S, et al. Eur J Pharmacol, 1994, 288(1), 27-33.
• References: [2] Rupalla K, et al. Eur J Pharmacol, 1995, 294(2-3), 469-473
• References: [3] Müller WE, et al. J Neurochem, 1997, 68(6), 2371-2377.
• References: [4] Seyfried J, et al. Eur J Pharmacol, 2000, 400(2-3):155-166.
• References: [5] Dörr J, et al. J Neuroimmunol, 2005, 167(1-2), 204-209.
• References: [6] Kornhuber J, et al. J Neural Transm, 1999, 106(9-10), 857-867.
• References: [7] Block F, et al. Brain Res, 1997, 754(1-2), 279-284.
• References: [8] Bleyer H, et al. Eur J Pharmacol, 1988, 151(2), 259-265.
• References: [9] Nickel B, et al. Arzneimittelforschung, 1990, 40(8), 909-911.

Sigma Aldrich - F8927

Biochem/physiol Actions
Non-opioid analgesic; cytoprotective versus PrP fragment 106-126

REFERENCES

• Perovic S, et al. Eur J Pharmacol, 1994, 288(1), 27-33.
• Rupalla K, et al. Eur J Pharmacol, 1995, 294(2-3), 469-473
• Müller WE, et al. J Neurochem, 1997, 68(6), 2371-2377.
• Seyfried J, et al. Eur J Pharmacol, 2000, 400(2-3):155-166.
• Dörr J, et al. J Neuroimmunol, 2005, 167(1-2), 204-209.
• Kornhuber J, et al. J Neural Transm, 1999, 106(9-10), 857-867.
• Block F, et al. Brain Res, 1997, 754(1-2), 279-284.
• Bleyer H, et al. Eur J Pharmacol, 1988, 151(2), 259-265.
• Nickel B, et al. Arzneimittelforschung, 1990, 40(8), 909-911.