DT-Web

DB08872 - gabapentin enacarbil


Identification
Name gabapentin enacarbil
Accession Number DB08872
Type small molecule
Description Gabapentin enacarbil is marketed under the name Horizant(R). It is a prodrug of gabapentin, and indicated in adults for the treatment of Restless Legs Syndrome (RLS) and postherpetic neuralgia (PHN).
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight Not Available
Groups approved
Monoisotopic Weight Not Available
Pharmacology
Indication For the treatment of adult Restless Legs Syndrome (RLS) and postherpetic neuralgia (PHN).
Mechanism of action Although the exact mechanism of action of gabapentin in RLS and PHN is unknown, it is presumed to involve the descending noradrenergic system, resulting in the activation of spinal alpha2-adrenergic receptors.
Absorption Gabapentin enacarbil is absorbed in the intestines by active transport through the proton-linked monocarboxylate transporter, MCT-1.
Protein binding Gabapentin plasma protein binding is less than 3%.
Biotransformation Gabapentin enacarbil does not interact with any of the major cytochrome P450 enzymes.
Route of elimination Gabapentin enacarbil is eliminated primarily in the urine (94%) and to a lesser extent in the feces (5%).
Toxicity Most common adverse reactions are headache, dizziness, and somnolence.
Affected organisms
  • Humans and other mammals
Interactions
Drug Interactions
Drug Mechanism of interaction
Azelastine Avoid combination due to increased CNS depression.
Ethanol Avoid combination due to ethanol induced increased absorption of gabapentin enacarbil and increased CNS depression.
Food Interactions
  • No food effects.

Transporters


Sodium-coupled monocarboxylate transporter 1
Name Sodium-coupled monocarboxylate transporter 1
Gene Name Not Available
Actions substrate
References
  • Cundy KC, Branch R, Chernov-Rogan T, Dias T, Estrada T, Hold K, Koller K, Liu X, Mann A, Panuwat M, Raillard SP, Upadhyay S, Wu QQ, Xiang JN, Yan H, Zerangue N, Zhou CX, Barrett RW, Gallop MA: XP13512 [(+/-)-1-([(alpha-isobutanoyloxyethoxy)carbonyl] aminomethyl)-1-cyclohexane acetic acid], a novel gabapentin prodrug: I. Design, synthesis, enzymatic conversion to gabapentin, and transport by intestinal solute transporters. J Pharmacol Exp Ther. 2004 Oct;311(1):315-23. Epub 2004 May 14. - Pubmed
DTHybrid score Not Available
Sodium-dependent multivitamin transporter
Name Sodium-dependent multivitamin transporter
Gene Name SLC5A6
Actions substrate
References
  • Cundy KC, Branch R, Chernov-Rogan T, Dias T, Estrada T, Hold K, Koller K, Liu X, Mann A, Panuwat M, Raillard SP, Upadhyay S, Wu QQ, Xiang JN, Yan H, Zerangue N, Zhou CX, Barrett RW, Gallop MA: XP13512 [(+/-)-1-([(alpha-isobutanoyloxyethoxy)carbonyl] aminomethyl)-1-cyclohexane acetic acid], a novel gabapentin prodrug: I. Design, synthesis, enzymatic conversion to gabapentin, and transport by intestinal solute transporters. J Pharmacol Exp Ther. 2004 Oct;311(1):315-23. Epub 2004 May 14. - Pubmed
DTHybrid score 0.8652

Predictions


Id Partner name Gene Name Score
45 Lipoyltransferase 1, mitochondrial LIPT1 0.1647
4079 Lipoic acid synthetase, mitochondrial LIAS 0.1647
4120 NADPH--cytochrome P450 reductase POR 0.0829
81 Methylcrotonoyl-CoA carboxylase beta chain, mitochondrial MCCC2 0.0659
547 Propionyl-CoA carboxylase alpha chain, mitochondrial PCCA 0.0658
495 Methylcrotonoyl-CoA carboxylase subunit alpha, mitochondrial MCCC1 0.0658
177 Biotin--protein ligase HLCS 0.0658
690 Acetyl-CoA carboxylase 1 ACACA 0.0658
601 Propionyl-CoA carboxylase beta chain, mitochondrial PCCB 0.0534
771 Pyruvate carboxylase, mitochondrial PC 0.0484
775 Acetyl-CoA carboxylase 2 ACACB 0.04
1898 Cytochrome P450 1B1 CYP1B1 0.0268
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