ContaminantDB: Aptiganel hydrochloride

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 05:18:50 UTC

Update Date

2016-11-09 01:15:49 UTC

Accession Number

CHEM018531

Identification

Common Name

Aptiganel hydrochloride

Class

Small Molecule

Description

Aptiganel (Cerestat; CNS-1102) is an unsuccessful drug candidate which acts as a noncompetitive NMDA antagonist, and that was under development by Cambridge Neuroscience, Inc as a treatment for stroke. It has neuroprotective effects and was researched for potential use in the treatment of stroke, but despite positive results in animal studies, human trials showed limited efficacy, as well as undesirable side effects such as sedation and hallucinations, and clinical development was ultimately not continued.The drug's failure led to the collapse of Cambridge Neuroscience in 1998 and its eventual sale to CeNeS Pharmaceuticals in 2000.

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-(1-Naphthyl)-n'-(3-ethylphenyl)-n'-methylguanidine HCL	MeSH
Aptiganel hydrochloride	MeSH
Aptiganel	MeSH
Aptiganel HCL	ChEMBL
CNS-1102Cerestat	ChEMBL
CERESTAT	MeSH

Chemical Formula

C₂₀H₂₂ClN₃

Average Molecular Mass

339.870 g/mol

Monoisotopic Mass

339.150 g/mol

CAS Registry Number

137160-11-3

IUPAC Name

N-(3-ethylphenyl)-N-methyl-N'-(naphthalen-1-yl)guanidine hydrochloride

Traditional Name

N-(3-ethylphenyl)-N-methyl-N'-(naphthalen-1-yl)guanidine hydrochloride

SMILES

Cl.CCC1=CC(=CC=C1)N(C)C(=N)NC1=CC=CC2=CC=CC=C12

InChI Identifier

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

InChI Key

CKAKVKWRMCAYJD-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Monocyclic benzene moiety
Guanidine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Hydrochloride
Organonitrogen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.005 g/L	ALOGPS
logP	4.64	ALOGPS
logP	5.25	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	8.84	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	39.12 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	108.85 m³·mol⁻¹	ChemAxon
Polarizability	35.09 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0009000000-5c03b7b95fd900b9e1b0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0009000000-5c03b7b95fd900b9e1b0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-0009000000-5c03b7b95fd900b9e1b0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-da5c992e3c14111ff058	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0009000000-da5c992e3c14111ff058	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0009000000-da5c992e3c14111ff058	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Aptiganel

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

60839

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Aptiganel hydrochloride (CHEM018531)

Structure for CHEM018531: Aptiganel hydrochloride