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
- Weight
- Average: 351.917
Monoisotopic: 351.063066678 - Chemical Formula
- C16H18ClN3S2
- Synonyms
- Not Available
Pharmacology
- Indication
Investigated for use/treatment in migraine and cluster headaches, neuropathy (diabetic), and pain (acute or chronic).
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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".
Target Actions Organism UGlutamate receptor ionotropic, NMDA 1 Not Available Humans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- 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]
- 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]
- External Links
- PubChem Compound
- 192711
- PubChem Substance
- 175427040
- ChemSpider
- 167230
- BindingDB
- 50096974
- ChEMBL
- CHEMBL41306
- ZINC
- ZINC000005423063
Clinical Trials
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
Property Value Source Water Solubility 0.00076 mg/mL ALOGPS logP 4.05 ALOGPS logP 4.79 Chemaxon logS -5.7 ALOGPS pKa (Strongest Acidic) 18.79 Chemaxon pKa (Strongest Basic) 8.51 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 41.62 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 103.02 m3·mol-1 Chemaxon Polarizability 37.49 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9392 Blood Brain Barrier + 0.9006 Caco-2 permeable + 0.6029 P-glycoprotein substrate Non-substrate 0.7981 P-glycoprotein inhibitor I Non-inhibitor 0.8364 P-glycoprotein inhibitor II Non-inhibitor 0.6471 Renal organic cation transporter Non-inhibitor 0.6024 CYP450 2C9 substrate Non-substrate 0.7183 CYP450 2D6 substrate Non-substrate 0.764 CYP450 3A4 substrate Non-substrate 0.5388 CYP450 1A2 substrate Inhibitor 0.5256 CYP450 2C9 inhibitor Non-inhibitor 0.6176 CYP450 2D6 inhibitor Inhibitor 0.5506 CYP450 2C19 inhibitor Inhibitor 0.6297 CYP450 3A4 inhibitor Non-inhibitor 0.5255 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8978 Ames test Non AMES toxic 0.6453 Carcinogenicity Non-carcinogens 0.5538 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.6133 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9654 hERG inhibition (predictor II) Non-inhibitor 0.6559
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets

- 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