reboxetine   Click here for help

GtoPdb Ligand ID: 4808

Synonyms: Edronax® | PNU-165442G
Approved drug PDB Ligand
reboxetine is an approved drug
Compound class: Synthetic organic
Comment: Reboxetine is a norepinephrine reuptake inhibitor (NRI) antidepressant. It is ~20-fold selective for the norepinephrine transporter over the serotonin transporter, so at therapeutic doses some inhibition of serotonin uptake is observed.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: reboxetine

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 39.72
Molecular weight 313.17
XLogP 3.07
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCOc1ccccc1OC(c1ccccc1)C1OCCNC1
Isomeric SMILES CCOc1ccccc1O[C@@H](c1ccccc1)[C@H]1OCCNC1
InChI InChI=1S/C19H23NO3/c1-2-21-16-10-6-7-11-17(16)23-19(15-8-4-3-5-9-15)18-14-20-12-13-22-18/h3-11,18-20H,2,12-14H2,1H3/t18-,19-/m0/s1
InChI Key CBQGYUDMJHNJBX-OALUTQOASA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes
IUPAC Name Click here for help
(2S)-2-[(S)-2-ethoxyphenoxy(phenyl)methyl]morpholine
International Nonproprietary Names Click here for help
INN number INN
5858 reboxetine
Synonyms Click here for help
Edronax® | PNU-165442G
Database Links Click here for help
CAS Registry No. 71620-89-8 (source: Scifinder)
ChEBI CHEBI:114263
ChEMBL Ligand CHEMBL180101
DrugBank Ligand DB00234
GtoPdb PubChem SID 178101510
PubChem CID 65856
RCSB PDB Ligand A1D9Y
Search Google for chemical match using the InChIKey CBQGYUDMJHNJBX-OALUTQOASA-N
Search Google for chemicals with the same backbone CBQGYUDMJHNJBX
Search PubMed clinical trials reboxetine
Search PubMed titles reboxetine
Search PubMed titles/abstracts reboxetine
UniChem Compound Search for chemical match using the InChIKey CBQGYUDMJHNJBX-OALUTQOASA-N
UniChem Connectivity Search for chemical match using the InChIKey CBQGYUDMJHNJBX-OALUTQOASA-N
Wikipedia Reboxetine