APTIGANEL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H21N3
Molecular Weight	303.4008
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC1=CC(=CC=C1)N(C)C(=N)NC2=C3C=CC=CC3=CC=C2

InChI

InChIKey=BFNCJMURTMZBTE-UHFFFAOYSA-N

InChI=1S/C20H21N3/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)

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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Ischemic stroke 41 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11730442	Preventing		Withdrawn	Unknown Approved Use Unknown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
Ensuring patient safety in clinical trials for treatment of acute stroke.	2001 Dec 5	11730448
Effects of cerestat and NBQX on functional and morphological outcomes in rat focal cerebral ischemia.	2001 Mar	11325397
Glutamate AMPA receptor antagonist treatment for ischaemic stroke.	2002	12365832
Patient safety in trials of therapy for acute ischemic stroke.	2002 Feb 27	11866641
Future of neuroprotective drugs in doubt.	2002 Jan	11786882
Why did NMDA receptor antagonists fail clinical trials for stroke and traumatic brain injury?	2002 Oct	12849400
Excitatory amino acid antagonists for acute stroke.	2003	12917902
Inhibition of human alpha 7 nicotinic acetylcholine receptors by open channel blockers of N-methyl-D-aspartate receptors.	2003 Dec	14645141
The rise and fall of NMDA antagonists for ischemic stroke.	2004 Mar	15032709
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

Official Name

English

Aptiganel [WHO-DD]

Common Name

English

APTIGANEL [MI]

Common Name

English

aptiganel [INN]

Common Name

English

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

Systematic Name

English

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

Common Name

English

APTIGANEL [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1509