SIBOPIRDINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H18N4.H2O
Molecular Weight	368.4311
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.C(C1=CC=NC=C1)C3(CC2=CC=NC=C2)C4=C(N=CC=C4)C5=C3C=CC=N5

InChI

InChIKey=NFNHFSQIMHVLMF-UHFFFAOYSA-N

InChI=1S/C23H18N4.H2O/c1-3-19-21(26-9-1)22-20(4-2-10-27-22)23(19,15-17-5-11-24-12-6-17)16-18-7-13-25-14-8-18;/h1-14H,15-16H2;1H2

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

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

Molecular Formula	C23H18N4
Molecular Weight	350.4158
Charge	0
Count

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

Description
Sources: https://adisinsight.springer.com/drugs/800004137 | https://www.ncbi.nlm.nih.gov/pubmed/8742228 |

Sibopirdine (EXP921) is a cognition enhancing agent structurally related to linopirdine that was in preclinical development with Bristol-Myers Squibb in the USA as a treatment of Alzheimer's disease. EXP921 was a potential drug candidate for the improvement of cognitive performance in patients with Alzheimer's-type dementia. It has been shown to improve cognitive performance in rodent and primate models of learning and memory. EXP921 was observed to increase the depolarization induced release of acetylcholine, dopamine, and, to a lesser extent, serotonin using slices from the rat cerebral cortex, hippocampus, and caudate nucleus.

CNS Activity

Originator

Approval Year

PubMed

Title	Date	PubMed
An approach to the design of novel cognitive enhancers using molecular modeling and X-ray crystallography.	1995 Apr	9040989
Determination of a novel cognitive enhancer, X9121, and its mono N-oxide metabolite, XG696, in dog plasma by reversed-phase high-performance liquid chromatography with ultraviolet detection.	1995 Mar 10	7795797

Patents

Sample Use Guides

In Vivo Use Guide

Rats were given single intravenous bolus (3, 10, and 30 mg/kg) or oral (3, 10, 30 and 60 mg/kg) doses of EXP921 after an overnight fast.

Route of Administration: Other

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:18:53 GMT 2023` Edited by `admin` on `Fri Dec 15 16:18:53 GMT 2023`
Record UNII	RAG2185DR1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SIBOPIRDINE

Official Name

English

SIBOPIRDINE [USAN]

Common Name

English

SIBOPIRDINE MONOHYDRATE

Common Name

English

DUP 921

Code

English

DUP-921

Code

English

Sibopirdine monohydrate [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47795