IRAMPANEL

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 Search

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

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12137411 | https://www.ncbi.nlm.nih.gov/pubmed/15857300 | https://www.ncbi.nlm.nih.gov/pubmed/11454651

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

Title	Date	PubMed
BIIR 561 CL: a novel combined antagonist of alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptors and voltage-dependent sodium channels with anticonvulsive and neuroprotective properties.	1999 Jun	10336525
In vivo pharmacology of BIIR 561 CL, a novel combined antagonist of AMPA receptors and voltage-dependent Na(+) channels.	2001 Jul	11454651
The AMPA receptor/Na(+) channel blocker BIIR 561 CL is protective in a model of global cerebral ischaemia.	2001 Jun 15	11516432
Irampanel Boehringer Ingelheim.	2002 Jun	12137411
AMPA receptor antagonists for the treatment of stroke.	2005 Apr	15857300

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 Created by `admin` on `Fri Dec 15 16:25:37 UTC 2023` Edited by `admin` on `Fri Dec 15 16:25:37 UTC 2023`
Record UNII	R2GZD7LMYX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IRAMPANEL

Official Name

English

BIIR 561

Code

English

BIIR-561

Code

English

BIIR-561 CL

Code

English

Irampanel [WHO-DD]

Common Name

English

5-(O-(2-(DIMETHYLAMINO)ETHOXY)PHENYL)-3-PHENYL-1,2,4-OXADIAZOLE

Common Name

English

irampanel [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47795