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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 of APTIGANEL HYDROCHLORIDE

SMILES

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

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

HIDE SMILES / InChI
Molecular Formula C20H21N3
Molecular Weight 303.4008
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Withdrawn
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Catalpol increases brain angiogenesis and up-regulates VEGF and EPO in the rat after permanent middle cerebral artery occlusion.
2010-08-20
Caffeinol at the receptor level: anti-ischemic effect of N-methyl-D-aspartate receptor blockade is potentiated by caffeine.
2010-02
The rise and fall of NMDA antagonists for ischemic stroke.
2004-03
Inhibition of human alpha 7 nicotinic acetylcholine receptors by open channel blockers of N-methyl-D-aspartate receptors.
2003-12
Excitatory amino acid antagonists for acute stroke.
2003
Why did NMDA receptor antagonists fail clinical trials for stroke and traumatic brain injury?
2002-10
Patient safety in trials of therapy for acute ischemic stroke.
2002-02-27
Future of neuroprotective drugs in doubt.
2002-01
Glutamate AMPA receptor antagonist treatment for ischaemic stroke.
2002
Ensuring patient safety in clinical trials for treatment of acute stroke.
2001-12-05
Aptiganel hydrochloride in acute ischemic stroke: a randomized controlled trial.
2001-12-05
Effects of cerestat and NBQX on functional and morphological outcomes in rat focal cerebral ischemia.
2001-03

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)
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:05:43 GMT 2025
Edited
by admin
on Mon Mar 31 18:05:43 GMT 2025
Record UNII
40PWH14OXW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CERESTAT
Preferred Name English
APTIGANEL HYDROCHLORIDE
MART.   MI   USAN  
USAN  
Official Name English
CNS-1102
Code 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
Created by admin on Mon Mar 31 18:05:43 GMT 2025 , Edited by admin on Mon Mar 31 18:05:43 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID9045762
Created by admin on Mon Mar 31 18:05:43 GMT 2025 , Edited by admin on Mon Mar 31 18:05:43 GMT 2025
PRIMARY
USAN
GG-9
Created by admin on Mon Mar 31 18:05:43 GMT 2025 , Edited by admin on Mon Mar 31 18:05:43 GMT 2025
PRIMARY
ChEMBL
CHEMBL92484
Created by admin on Mon Mar 31 18:05:43 GMT 2025 , Edited by admin on Mon Mar 31 18:05:43 GMT 2025
PRIMARY
CAS
137160-11-3
Created by admin on Mon Mar 31 18:05:43 GMT 2025 , Edited by admin on Mon Mar 31 18:05:43 GMT 2025
PRIMARY
FDA UNII
40PWH14OXW
Created by admin on Mon Mar 31 18:05:43 GMT 2025 , Edited by admin on Mon Mar 31 18:05:43 GMT 2025
PRIMARY
SMS_ID
300000055067
Created by admin on Mon Mar 31 18:05:43 GMT 2025 , Edited by admin on Mon Mar 31 18:05:43 GMT 2025
PRIMARY
MERCK INDEX
m2017
Created by admin on Mon Mar 31 18:05:43 GMT 2025 , Edited by admin on Mon Mar 31 18:05:43 GMT 2025
PRIMARY Merck Index
PUBCHEM
60839
Created by admin on Mon Mar 31 18:05:43 GMT 2025 , Edited by admin on Mon Mar 31 18:05:43 GMT 2025
PRIMARY
NCI_THESAURUS
C142929
Created by admin on Mon Mar 31 18:05:43 GMT 2025 , Edited by admin on Mon Mar 31 18:05:43 GMT 2025
PRIMARY
Related Record Type Details
Structure of APTIGANEL
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of APTIGANEL
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