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pregabalin   Click here for help

GtoPdb Ligand ID: 5484

Synonyms: (S)-pregabalin | CI 1008 | Lyrica® | Nervalin® | PD 144723
Approved drug
pregabalin is an approved drug (FDA and EMA (2004))
Compound class: Synthetic organic
Comment: Pregabalin is a gabapentinoid class anti-seizure medication. Chemically, it is a 3-isobutyl derivative of the inhibitory neurotransmitter γ-aminobutyric acid (GABA), but it appears to function as a modulator of voltage-gated calcium channels, rather than a GABA receptor agonist.
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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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Click here for structure editor
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 2
Rotatable bonds 5
Topological polar surface area 63.32
Molecular weight 159.13
XLogP 1.27
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES NCC(CC(=O)O)CC(C)C
Isomeric SMILES NC[C@H](CC(=O)O)CC(C)C
InChI InChI=1S/C8H17NO2/c1-6(2)3-7(5-9)4-8(10)11/h6-7H,3-5,9H2,1-2H3,(H,10,11)/t7-/m0/s1
InChI Key AYXYPKUFHZROOJ-ZETCQYMHSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. US FDA (2004)  |  EU EMA (2004)
IUPAC Name Click here for help
(3S)-3-(aminomethyl)-5-methylhexanoic acid
International Nonproprietary Names Click here for help
INN number INN
7643 pregabalin
Synonyms Click here for help
(S)-pregabalin | CI 1008 | Lyrica® | Nervalin® | PD 144723
Database Links Click here for help
CAS Registry No. 148553-50-8
ChEBI CHEBI:64356
ChEMBL Ligand CHEMBL1059
DrugBank Ligand DB00230
DrugCentral Ligand 2255
GtoPdb PubChem SID 178102131
PubChem CID 5486971
Search Google for chemical match using the InChIKey AYXYPKUFHZROOJ-ZETCQYMHSA-N
Search Google for chemicals with the same backbone AYXYPKUFHZROOJ
Search PubMed clinical trials pregabalin
Search PubMed titles pregabalin
Search PubMed titles/abstracts pregabalin
UniChem Compound Search for chemical match using the InChIKey AYXYPKUFHZROOJ-ZETCQYMHSA-N
UniChem Connectivity Search for chemical match using the InChIKey AYXYPKUFHZROOJ-ZETCQYMHSA-N
Wikipedia Pregabalin