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.
Click here for help

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.

✖

View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: pregabalin

pregabalin is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
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
SMILES / InChI / InChIKey
Click here for help

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.

✖
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
No information available.
Summary of Clinical Use Click here for help
Used to treat generalised anxiety disorder (GAD) and in the management of neuropathic pain associated with diabetic peripheral neuropathy or spinal chord injury, and post herpetic neuralgia. Also used in the management of fibromyalgia and as an adjunctive therapy for partial onset seizures.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Like gabapentin, pregabalin likely acts, at least in part, via inhibition of the α2δ subunit (CACNA2D1, P54289) of the VGCC. Some evidence exists to support the hypothesis that compounds such as pregabalin and gabapentin don't actually block presynaptic calcium channels, but rather exert an inhibitory effect on the re-cycling of the channels from endosomal pools back to the plasma membrane via interaction with intracellular δ subunits [1].
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)