RIMCAZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H27N3
Molecular Weight	321.4592
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H]1CN(CCCN2C3=C(C=CC=C3)C4=C2C=CC=C4)C[C@@H](C)N1

InChI

InChIKey=GUDVQJXODNJRIJ-CALCHBBNSA-N

InChI=1S/C21H27N3/c1-16-14-23(15-17(2)22-16)12-7-13-24-20-10-5-3-8-18(20)19-9-4-6-11-21(19)24/h3-6,8-11,16-17,22H,7,12-15H2,1-2H3/t16-,17+

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14978511 | https://www.ncbi.nlm.nih.gov/pubmed/12210554 | https://www.ncbi.nlm.nih.gov/pubmed/9826105 | https://www.ncbi.nlm.nih.gov/pubmed/1681560

Rimcazole is a carbazole derivative that acts as a sigma receptor antagonist and studied as potential antipsychotic agent for the treatment of acute schizophrenic patients. In open-clinical trials Rimcazole (BW 234U) appears to be effective in acute schizophrenic patients. However, subsequent clinical trials demonstrated that rimcazole lacked efficacy in schizophrenic patients and it is now primarily used as an experimental tool. In addition to its actions as  receptor antagonist, rimcazole also has high affinity for dopamine transporters, and inrecent years it has served as a lead compound for the development of novel dopamine transporter ligands.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sigma opioid receptor 63 Target ID: CHEMBL287 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2873494	Antagonist 2778
Dopamine transporter 180 Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9435903	Binding Agent 1064

PubMed

Title	Date	PubMed
Neuropharmacological profile of EMD 57445, a sigma receptor ligand with potential antipsychotic activity.	1996 Nov 21	8982660
Isothiocyanate derivatives of 9-[3-(cis-3,5-dimethyl-1-piperazinyl)propyl]carbazole (rimcazole): irreversible ligands for the dopamine transporter.	1997 Dec 19	9435903
Effect of sigma ligands on the cocaine-induced convulsions in mice.	1999 Nov-Dec	10817525
Rimcazole analogs attenuate the convulsive effects of cocaine: correlation with binding to sigma receptors rather than dopamine transporters.	2001 Dec	11684152
Dual probes for the dopamine transporter and sigma1 receptors: novel piperazinyl alkyl-bis(4'-fluorophenyl)amine analogues as potential cocaine-abuse therapeutic agents.	2003 Jun 19	12801223
Review of the pharmacological and clinical profile of rimcazole.	2004 Spring	14978511
Discovery of highly potent small molecule Hepatitis C Virus entry inhibitors.	2011 Nov 15	21978675
The role of RelA (p65) threonine 505 phosphorylation in the regulation of cell growth, survival, and migration.	2011 Sep	21737676

Patents

Sample Use Guides

In Vivo Use Guide

5 mg/kg

Route of Administration: Oral

Name

Type

Language

RIMCAZOLE

Official Name

English

BW 234U

Code

English

9H-CARBAZOLE, 9-(3-((3R,5S)-3,5-DIMETHYL-1-PIPERAZINYL)PROPYL)-, REL-

Common Name

English

9-(3-(CIS-3,5-DIMETHYL-1-PIPERAZINYL)PROPYL)CARBAZOLE

Systematic Name

English

BW-234U

Code

English

rimcazole [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29710