NAV

NS-2359

Identification

Generic Name
NS-2359
DrugBank Accession Number
DB05805
Background

NS2359 is a triple monoamine re-uptake inhibitor with a new, unique drug profile expected to yield important benefits compared to existing treatments of depression. Enhancing the function of the three neurotransmitters serotonin, noradrenalin and dopamine, NS2359 has a desired "triple-mode-of-action". This mode of action is expected to produce an optimal reduction in all disease symptoms and the possibility of an earlier onset of action compared to antidepressants already on the market.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 314.25
Monoisotopic: 313.1000197
Chemical Formula
C16H21Cl2NO
Synonyms
Not Available
External IDs
  • GSK-372,475
  • GSK-372475
  • GSK372475
  • NS-2359
  • NS2359
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Pharmacology

Indication

Investigated for use/treatment in addictions, attention deficit/hyperactivity disorder (ADHD), and depression.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

NS2359 has a triple mode of action, inhibiting neuronal reuptake of the three neurotransmitters serotonin, noradrenaline and dopamine, all of which play an important role in the development of depression. NS2359 also increases release of the neurotransmitter acetylcholine. This mode of action is expected to produce a better and faster reduction of the symptoms associated with depression. This rationale has been confirmed in independent studies in which existing anti-depressants affecting serotonin have been combined with drugs that affect noradrenaline/dopamine. Drugs with this triple mode of action are expected to become the future standard in the treatment of depression.

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
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenyltropanes. These are compounds containing a phenyl group linked to a tropane moiety. Tropane is an organonitrogenous [3.2.1] bicyclic organic compound.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Tropane alkaloids
Sub Class
Phenyltropanes
Direct Parent
Phenyltropanes
Alternative Parents
Phenylpiperidines / Dichlorobenzenes / Aralkylamines / N-alkylpyrrolidines / Aryl chlorides / Trialkylamines / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Organochlorides
show 1 more
Substituents
1,2-dichlorobenzene / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Chlorobenzene / Dialkyl ether
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
76H76554PA
CAS number
195875-68-4
InChI Key
PGYDXVBZYKQYCS-VPWBDBDCSA-N
InChI
InChI=1S/C16H21Cl2NO/c1-19-11-4-6-16(19)13(9-20-2)12(8-11)10-3-5-14(17)15(18)7-10/h3,5,7,11-13,16H,4,6,8-9H2,1-2H3/t11-,12+,13+,16+/m0/s1
IUPAC Name
(1R,2R,3S,5S)-3-(3,4-dichlorophenyl)-2-(methoxymethyl)-8-methyl-8-azabicyclo[3.2.1]octane
SMILES
COC[C@H]1[C@H]2CC[C@@H](C[C@@H]1C1=CC(Cl)=C(Cl)C=C1)N2C

References

General References
Not Available
PubChem Compound
68470595
PubChem Substance
347827744
ChemSpider
32698248
Wikipedia
NS-2359

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentAttention Deficit Hyperactivity Disorder (ADHD)1
2CompletedTreatmentCocaine Use Disorders1
2CompletedTreatmentDepressive Disorder2
1CompletedTreatmentDepressive Disorder1
1CompletedTreatmentDepressive Disorder / Healthy Volunteers (HV)1

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 Solubility0.00223 mg/mLALOGPS
logP4.35ALOGPS
logP3.81Chemaxon
logS-5.2ALOGPS
pKa (Strongest Basic)9.76Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area12.47 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity84.32 m3·mol-1Chemaxon
Polarizability33.66 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0002-8690000000-3714255d2c6b1f9cd3cf
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0009000000-8b4ccaa4a5ab01b85426
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-b26558da51bcdb3f0983
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0009000000-61aac4a21283c4790c88
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001j-1591000000-768b182b5a3959f8510d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03yi-2097000000-1e626f67151daa0de9b5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9431000000-191cfecc09bc825b3c94
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]-171.33748
predicted
DeepCCS 1.0 (2019)
[M+H]+173.73305
predicted
DeepCCS 1.0 (2019)
[M+Na]+180.18611
predicted
DeepCCS 1.0 (2019)

Drug created at November 18, 2007 18:27 / Updated at June 12, 2020 16:52