NAV

CNS-5161

Identification

Generic Name
CNS-5161
DrugBank Accession Number
DB05824
Background

CNS 5161 is a blocker of the NMDA ion channel and has completed Phase IIa proof of concept clinical trials as a novel compound for the treatment of neuropathic pain.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 351.917
Monoisotopic: 351.063066678
Chemical Formula
C16H18ClN3S2
Synonyms
Not Available
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Pharmacology

Indication

Investigated for use/treatment in migraine and cluster headaches, neuropathy (diabetic), and pain (acute or chronic).

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

CNS 5161 is a selective and high affinity N-methyl-D-aspartate (NMDA) receptor antagonist with preferential binding to the activated form of the receptor. CNS 5161 also penetrates the brain well and can be used to label selectively brain NMDA receptors in vivo. A radioactive form of CNS 5161 may be used as an agent to monitor NMDA receptors in the human brain using Positron Emission Tomography ("PET") and "the significance of a selective, validated radiopharmaceutical agent suitable for detecting widespread as well as highly localized changes in the NMDA receptor in the living brain cannot be exaggerated".

TargetActionsOrganism
UGlutamate receptor ionotropic, NMDA 1Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aryl thioethers. These are organosulfur compounds containing a thioether group that is substituted by an aryl group.
Kingdom
Organic compounds
Super Class
Organosulfur compounds
Class
Thioethers
Sub Class
Aryl thioethers
Direct Parent
Aryl thioethers
Alternative Parents
Thiophenol ethers / Chlorobenzenes / Alkylarylthioethers / Aryl chlorides / Guanidines / Sulfenyl compounds / Propargyl-type 1,3-dipolar organic compounds / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives
Substituents
Alkylarylthioether / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Aryl thioether / Benzenoid / Chlorobenzene / Guanidine / Halobenzene / Hydrocarbon derivative
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
58S83M36V6
CAS number
Not Available
InChI Key
JHVHEDNLONERHY-UHFFFAOYSA-N
InChI
InChI=1S/C16H18ClN3S2/c1-20(11-5-4-6-12(9-11)21-2)16(18)19-15-10-13(22-3)7-8-14(15)17/h4-10H,1-3H3,(H2,18,19)
IUPAC Name
(E)-N''-[2-chloro-5-(methylsulfanyl)phenyl]-N-methyl-N-[3-(methylsulfanyl)phenyl]guanidine
SMILES
CSC1=CC(\N=C(/N)N(C)C2=CC(SC)=CC=C2)=C(Cl)C=C1

References

General References
  1. Biegon A, Gibbs A, Alvarado M, Ono M, Taylor S: In vitro and in vivo characterization of [3H]CNS-5161--a use-dependent ligand for the N-methyl-D-aspartate receptor in rat brain. Synapse. 2007 Aug;61(8):577-86. [Article]
  2. Walters MR, Bradford AP, Fischer J, Lees KR: Early clinical experience with the novel NMDA receptor antagonist CNS 5161. Br J Clin Pharmacol. 2002 Mar;53(3):305-11. [Article]
PubChem Compound
192711
PubChem Substance
175427040
ChemSpider
167230
BindingDB
50096974
ChEMBL
CHEMBL41306
ZINC
ZINC000005423063

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00076 mg/mLALOGPS
logP4.05ALOGPS
logP4.79Chemaxon
logS-5.7ALOGPS
pKa (Strongest Acidic)18.79Chemaxon
pKa (Strongest Basic)8.51Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area41.62 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity103.02 m3·mol-1Chemaxon
Polarizability37.49 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9392
Blood Brain Barrier+0.9006
Caco-2 permeable+0.6029
P-glycoprotein substrateNon-substrate0.7981
P-glycoprotein inhibitor INon-inhibitor0.8364
P-glycoprotein inhibitor IINon-inhibitor0.6471
Renal organic cation transporterNon-inhibitor0.6024
CYP450 2C9 substrateNon-substrate0.7183
CYP450 2D6 substrateNon-substrate0.764
CYP450 3A4 substrateNon-substrate0.5388
CYP450 1A2 substrateInhibitor0.5256
CYP450 2C9 inhibitorNon-inhibitor0.6176
CYP450 2D6 inhibitorInhibitor0.5506
CYP450 2C19 inhibitorInhibitor0.6297
CYP450 3A4 inhibitorNon-inhibitor0.5255
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8978
Ames testNon AMES toxic0.6453
CarcinogenicityNon-carcinogens0.5538
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6133 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9654
hERG inhibition (predictor II)Non-inhibitor0.6559
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0f79-0916000000-f56b515cd16eeedb22c3
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0109000000-83ed714d5f60f5298d31
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-2309000000-d42eb31c0f44bc521fb4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zfr-0903000000-b345e821675da60ba313
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9401000000-785336918e0a3c62f633
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9000000000-482903056c61f37e6231
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pb9-0900000000-5ad8192ce515c22f4cdd
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-185.78255
predicted
DeepCCS 1.0 (2019)
[M+H]+188.49196
predicted
DeepCCS 1.0 (2019)
[M+Na]+196.70222
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Glutamate receptor ionotropic, NMDA 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Voltage-gated cation channel activity
Specific Function
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. This protein plays a key role in synaptic p...
Gene Name
GRIN1
Uniprot ID
Q05586
Uniprot Name
Glutamate receptor ionotropic, NMDA 1
Molecular Weight
105371.945 Da

Drug created at November 18, 2007 18:28 / Updated at June 12, 2020 16:52