NERISPIRDINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H18FN3
Molecular Weight	283.3433
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCN(N1C=C(C)C2=C1C=CC=C2)C3=C(F)C=NC=C3

InChI

InChIKey=BTDHTARYCBHHPJ-UHFFFAOYSA-N

InChI=1S/C17H18FN3/c1-3-10-20(17-8-9-19-11-15(17)18)21-12-13(2)14-6-4-5-7-16(14)21/h4-9,11-12H,3,10H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C17H18FN3
Molecular Weight	283.3433
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/800002157 | https://www.ncbi.nlm.nih.gov/pubmed/19413590

Nerispirdine, an acetylcholine release enhancer and a K+/Na+ use-dependent channel blocker, was in clinical development with sanofi-aventis for the treatment of multiple sclerosis. Nerispirdine is not proconvulsant. It can inhibit axonal K(+) channels and this mechanism may underlie the ability of the drug to enhance neuronal conduction. Nerispirdine can also inhibit neuronal Na(+) channels, a mechanism that may explain why nerispirdine lacks proconvulsant activity.

CNS Activity

Originator

Approval Year

PubMed

Title	Date	PubMed
In Vitro electrophysiological activity of nerispirdine, a novel 4-aminopyridine derivative.	2009 Nov	19413590
New approaches in the management of multiple sclerosis.	2010 Nov 24	21151622

Sample Use Guides

In Vivo Use Guide

Visual function in patients with multiple sclerosis: single oral doses of 50 mg and 400 mg Nerispirdine

Route of Administration: Oral

In Vitro Use Guide

Nerispirdine inhibited K(v)1.1 and K(v)1.2 with IC(50) values of 3.6 and 3.7 umol/L, respectively. Nerispirdine also inhibited voltage-dependent Na(+) channel currents recorded from human SH-SY5Y cells with an IC(50) of 11.9 umol/L when measured from a -70 mV holding potential.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:39:14 UTC 2023` Edited by `admin` on `Fri Dec 15 16:39:14 UTC 2023`
Record UNII	G7M7YWO6CG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NERISPIRDINE

Official Name

English

nerispirdine [INN]

Common Name

English

N-(3-FLUOROPYRIDIN-4-YL)-3-METHYL-N-PROPYL-1H-INDOL-1-AMINE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1509