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Details

Stereochemistry ACHIRAL
Molecular Formula C18H19N3O2
Molecular Weight 309.3624
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IRAMPANEL

SMILES

CN(C)CCOC1=CC=CC=C1C2=NC(=NO2)C3=CC=CC=C3

InChI

InChIKey=QZULPCPLWGCGSL-UHFFFAOYSA-N
InChI=1S/C18H19N3O2/c1-21(2)12-13-22-16-11-7-6-10-15(16)18-19-17(20-23-18)14-8-4-3-5-9-14/h3-11H,12-13H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C18H19N3O2
Molecular Weight 309.3624
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

IRAMPANEL, an oxazole derivative, is a dual non-competitive antagonist of the AMPA receptor and neuronal voltage-gated sodium channel blocker. It was under development for the potential treatment of stroke and other neurological disorders, including epilepsy and pain.

Originator

Approval Year

PubMed

Patents

Sample Use Guides

In Vitro Use Guide
Irampanel (BIIR 561 CL) inhibited AMPA receptor-mediated membrane currents in cultured cortical neurons with an IC50 value of 8.5 microM. The inhibition was noncompetitive. In a cortical wedge preparation, BIIR 561 CL reduced AMPA-induced depolarizations with an IC50 value of 10.8 microM. In addition to the effects on the glutamatergic system, BIIR 561 CL inhibited binding of radiolabeled batrachotoxin to rat brain synaptosomal membranes with a Ki value of 1.2 microM. The compound reduced sodium currents in voltage-clamped cortical neurons with an IC50 value of 5.2 microM and inhibited the veratridine-induced release of glutamate from rat brain slices with an IC50 value of 2.3 microM.
Substance Class Chemical
Record UNII
R2GZD7LMYX
Record Status Validated (UNII)
Record Version