APTIGANEL HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H21N3.ClH
Molecular Weight	339.862
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CCC1=CC=CC(=C1)N(C)C(=N)NC2=CC=CC3=CC=CC=C23

InChI

InChIKey=CKAKVKWRMCAYJD-UHFFFAOYSA-N

InChI=1S/C20H21N3.ClH/c1-3-15-8-6-11-17(14-15)23(2)20(21)22-19-13-7-10-16-9-4-5-12-18(16)19;/h4-14H,3H2,1-2H3,(H2,21,22);1H

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15032709 | https://www.ncbi.nlm.nih.gov/pubmed/11730442

Aptiganel (CNS 1102, Cerestat), a selective ligand with antagonized properties for the ion-channel site of the N-methyl-D-aspartate receptor-channel complex, was developed as a neuroprotective agent for focal brain ischemia. However, in the clinical trials in patients with acute ischemic stroke aptiganel was not efficacious at either of the tested doses and may be harmful. That is why its further study was discontinued.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glutamate [NMDA] receptor 125 Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9260729 \| https://www.ncbi.nlm.nih.gov/pubmed/15032709	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ischemic stroke 41 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11730442	Preventing		Withdrawn	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Catalpol increases brain angiogenesis and up-regulates VEGF and EPO in the rat after permanent middle cerebral artery occlusion.	2010 Aug 20	20827397
Caffeinol at the receptor level: anti-ischemic effect of N-methyl-D-aspartate receptor blockade is potentiated by caffeine.	2010 Feb	20044532

Sample Use Guides

In Vivo Use Guide

Short intravenous infusions of up to 30 microg/kg have been well tolerated by healthy male volunteers. There were undertook a randomized, double-blind, placebo-controlled study in 20 male volunteers to examine the safety, tolerability, and cardiovascular and psychomotor effects of a dosing paradigm similar to that envisaged for therapeutic use. Aptiganel HCl was infused over 4 h in total doses of 15, 32, 50, or 73 microg kg.

Route of Administration: Intravenous

In Vitro Use Guide

N-1-naphthyl-N'-(3-ethylphenyl)-N'-methylguanidine (aptiganel) showed high affinity for the NMDA receptor ion channel site (IC50 = 36 nM vs [3H]-3) and low affinity for sigma receptors (IC50 = 2540 nM vs [3H]-5)

Name

Type

Language

APTIGANEL HYDROCHLORIDE

Official Name

English

CNS-1102

Code

English

CERESTAT

Brand Name

English

APTIGANEL HYDROCHLORIDE [MI]

Common Name

English

1-(M-ETHYLPHENYL)-1-METHYL-3-(1-NAPHTHYL)GUANIDINE MONOHYDROCHLORIDE

Systematic Name

English

APTIGANEL HYDROCHLORIDE [MART.]

Common Name

English

APTIGANEL HCL

Common Name

English

CNS1102

Code

English

GUANIDINE, N-(3-ETHYLPHENYL)-N-METHYL-N'-1-NAPHTHALENYL, MONOHYDROCHLORIDE

Common Name

English

APTIGANEL HYDROCHLORIDE [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1509