alosetron   Click here for help

GtoPdb Ligand ID: 2296

Synonyms: GR68755 | Lotronex®
Approved drug PDB Ligand
alosetron is an approved drug (FDA (2002))
Compound class: Synthetic organic
Comment: Having been withdrawn by the manufacturer in 2000 following reports of severe adverse effects, the FDA approved a supplemental new drug application (2002) which allows remarketing of the drug, but under conditions of restricted use.
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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
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 3
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 53.92
Molecular weight 294.15
XLogP 2.32
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 O=C1N(CCc2c1c1ccccc1n2C)Cc1nc[nH]c1C
Isomeric SMILES O=C1N(CCc2c1c1ccccc1n2C)Cc1nc[nH]c1C
InChI InChI=1S/C17H18N4O/c1-11-13(19-10-18-11)9-21-8-7-15-16(17(21)22)12-5-3-4-6-14(12)20(15)2/h3-6,10H,7-9H2,1-2H3,(H,18,19)
InChI Key JSWZEAMFRNKZNL-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2002))
IUPAC Name Click here for help
5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-3,4-dihydropyrido[4,3-b]indol-1-one
International Nonproprietary Names Click here for help
INN number INN
6906 alosetron
Synonyms Click here for help
GR68755 | Lotronex®
Database Links Click here for help
BindingDB Ligand 50131429
CAS Registry No. 122852-42-0
ChEBI CHEBI:253342
ChEMBL Ligand CHEMBL1110
DrugBank Ligand DB00969
DrugCentral Ligand 129
GtoPdb PubChem SID 135649921
PubChem CID 2099
RCSB PDB Ligand S7Y
Search Google for chemical match using the InChIKey JSWZEAMFRNKZNL-UHFFFAOYSA-N
Search Google for chemicals with the same backbone JSWZEAMFRNKZNL
Search PubMed clinical trials alosetron
Search PubMed titles alosetron
Search PubMed titles/abstracts alosetron
UniChem Compound Search for chemical match using the InChIKey JSWZEAMFRNKZNL-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey JSWZEAMFRNKZNL-UHFFFAOYSA-N
Wikipedia Alosetron