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 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 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

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 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

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. FDA (2011)
Is prodrug? Yes
Active form gabapentin
IUPAC Name Click here for help
2-[1-[[1-(2-methylpropanoyloxy)ethoxycarbonylamino]methyl]cyclohexyl]acetic acid
International Nonproprietary Names Click here for help
INN number INN
8611 gabapentin enacarbil
Synonyms Click here for help
Horizant® | Regnite® | XP-13512
Database Links Click here for help
CAS Registry No. 478296-72-9
ChEBI CHEBI:68840
ChEMBL Ligand CHEMBL1628502
DrugCentral Ligand 4177
GtoPdb PubChem SID 223365896
PubChem CID 9883933
Search Google for chemical match using the InChIKey TZDUHAJSIBHXDL-UHFFFAOYSA-N
Search Google for chemicals with the same backbone TZDUHAJSIBHXDL
Search PubMed clinical trials gabapentin enacarbil
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UniChem Compound Search for chemical match using the InChIKey TZDUHAJSIBHXDL-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey TZDUHAJSIBHXDL-UHFFFAOYSA-N
Wikipedia Gabapentin enacarbil

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MedChemExpress
Gabapentin enacarbil (links to external site)
Cat. No. HY-16216