aniracetam   Click here for help

GtoPdb Ligand ID: 4133

Approved drug PDB Ligand
aniracetam is an approved drug
Compound class: Synthetic organic
Comment: Based on this compound's allosteric action on AMPA receptor activity [1] it was used as the structural basis for the development of novel potential ampakines. These compounds are being investigated as nootropics and neuroprotective drugs for the treatment of Alzheimer's disease (AD) and other neurodegenerative conditions (see patent US6730677).

aniracetam is commercially available from our sponsors

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 0
Rotatable bonds 3
Topological polar surface area 46.61
Molecular weight 219.09
XLogP 1.33
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 COc1ccc(cc1)C(=O)N1CCCC1=O
Isomeric SMILES COc1ccc(cc1)C(=O)N1CCCC1=O
InChI InChI=1S/C12H13NO3/c1-16-10-6-4-9(5-7-10)12(15)13-8-2-3-11(13)14/h4-7H,2-3,8H2,1H3
InChI Key ZXNRTKGTQJPIJK-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes
IUPAC Name Click here for help
1-[(4-methoxyphenyl)carbonyl]pyrrolidin-2-one
International Nonproprietary Names Click here for help
INN number INN
4902 aniracetam
Database Links Click here for help
CAS Registry No. 72432-10-1 (source: Scifinder)
ChEMBL Ligand CHEMBL36994
DrugBank Ligand DB04599
DrugCentral Ligand 221
GtoPdb PubChem SID 178100955
PubChem CID 2196
RCSB PDB Ligand 4MP
Search Google for chemical match using the InChIKey ZXNRTKGTQJPIJK-UHFFFAOYSA-N
Search Google for chemicals with the same backbone ZXNRTKGTQJPIJK
Search PubMed clinical trials aniracetam
Search PubMed titles aniracetam
Search PubMed titles/abstracts aniracetam
UniChem Compound Search for chemical match using the InChIKey ZXNRTKGTQJPIJK-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZXNRTKGTQJPIJK-UHFFFAOYSA-N
Wikipedia Aniracetam

Product suppliers

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Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

Links are provided in return for sponsorship, used to fund improvements to this database. The sponsorship account is managed and audited by the University of Edinburgh, a charitable body registered in Scotland, SC005336. If you are interested in sponsoring the database, please contact us.

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Tocris
Aniracetam (links to external site)
Cat. No. 0867