gabapentin enacarbil   Click here for help

GtoPdb Ligand ID: 7560

Synonyms: Horizant® | Regnite® | XP-13512
Approved drug
gabapentin enacarbil is an approved drug (FDA (2011))
Compound class: Synthetic organic
Comment: Gabapentin enacarbil is a prodrug of gabapentin. It exhibits increased bioavailability compared to gabapentin.
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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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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 7
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 101.93
Molecular weight 329.18
XLogP 3.01
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 CC(OC(=O)C(C)C)OC(=O)NCC1(CCCCC1)CC(=O)O
Isomeric SMILES CC(OC(=O)C(C)C)OC(=O)NCC1(CCCCC1)CC(=O)O
InChI InChI=1S/C16H27NO6/c1-11(2)14(20)22-12(3)23-15(21)17-10-16(9-13(18)19)7-5-4-6-8-16/h11-12H,4-10H2,1-3H3,(H,17,21)(H,18,19)
InChI Key TZDUHAJSIBHXDL-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Indicated for the treatment of restless leg syndrome. May also be used to treat post-herpetic neuralgia.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
This is the MMOA for the active drug, gabapentin: Gabapentin is a voltage-gated calcium channel modulator which acts via a cascade involving GABA receptors, to reduce the release of monoamine neurotransmitters, potentially in the CA1 area of the hippocampus.