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F0778

Sigma-Aldrich

Felbamate

Synonym(s):

2-Phenyl-1,3-propanediol dicarbamate

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About This Item

Empirical Formula (Hill Notation):
C11H14N2O4
CAS Number:
25451-15-4
Molecular Weight:
238.24
EC Number:
247-001-4
MDL number:
MFCD00865296
UNSPSC Code:
12352200
PubChem Substance ID:
24277968
NACRES:
NA.77

Quality Level

200

solubility

alcohol: soluble

SMILES string

NC(=O)OCC(COC(N)=O)c1ccccc1

InChI

1S/C11H14N2O4/c12-10(14)16-6-9(7-17-11(13)15)8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H2,12,14)(H2,13,15)

InChI key

WKGXYQFOCVYPAC-UHFFFAOYSA-N

Gene Information

human ... GRIN1(2902) , GRIN2A(2903) , GRIN2B(2904) , GRIN2C(2905) , GRIN2D(2906) , GRIN3A(116443) , GRIN3B(116444)

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Biochem/physiol Actions

Anticonvulsant agent that is an allosteric antagonist at the NR2B subunit of the NMDA glutamate receptor; also has γ-aminobutyric acid (GABAA) receptor agonist properties.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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J M Rho et al.
The Journal of pharmacology and experimental therapeutics, 280(3), 1383-1391 (1997-03-01)
Felbamate and meprobamate are structurally related propanediol dicarbamates that possess distinct pharmacological profiles. Felbamate is a minimally sedative, broad-spectrum anticonvulsant, whereas meprobamate is a strong sedative-anxiolytic agent. Previously, we reported that felbamate potentiates gamma-aminobutyric acid(A) (GABA(A)) receptor Cl- currents and
W M Brown et al.
Critical reviews in neurobiology, 12(3), 205-222 (1998-12-10)
Felbamate was launched in 1993 in the U.S. as a "new generation" antiepileptic drug (AED) with a unique mechanism of action. It proved efficacious in patients refractory to other AEDs and was particularly beneficial in children suffering from Lennox-Gastaut syndrome
Huai-Ren Chang et al.
Journal of medicinal chemistry, 51(6), 1534-1545 (2008-03-04)
The antiepileptic effect of felbamate (FBM) is ascribable to gating modification of NMDA receptors. Using site-directed mutagenesis and electrophysiological studies, we found that single-point mutations of four pairs of homologous residues in the external vestibule of the receptor pore, namely
Huai-Ren Chang et al.
Biophysical journal, 93(6), 1981-1992 (2007-05-22)
Felbamate (FBM) is a potent nonsedative anticonvulsant whose clinical effect is chiefly related to gating modification (and thus use-dependent inhibition) rather than pore block of N-methyl-D-aspartate (NMDA) channels at pH 7.4. Using whole-cell recording in rat hippocampal neurons, we examined
K D Laxer
The Western journal of medicine, 161(3), 309-314 (1994-09-01)
For the first time in 15 years, new antiepileptic medications are available for the treatment of patients with seizure disorders. These drugs have demonstrated efficacy in animal models of epilepsy and in controlled clinical trials. Felbamate was licensed in 1993
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