Gabapentin Enacarbil

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (2)Transporters (2)

Targets (2)Transporters (2)Biointeractions (1)

Identification

Name

Gabapentin Enacarbil

Accession Number

DB08872 (DB04922)

Type

Small Molecule

Groups

Approved

Description

Gabapentin enacarbil is marketed under the name Horizant. 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 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Gabapentina enacarbilo

Gabapentine enacarbil

Gabapentinum enacarbilum

External IDs

ASP-8825 / ASP8825 / GSK-1838262 / GSK1838262 / XP 13512 / XP-13512 / XP13512

Product Ingredients

Not Available

Product Images

Approved Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Horizant	Tablet, extended release	300 mg/1	Oral	Remedy Repack	2016-09-02	Not applicable	US
Horizant	Tablet, extended release	600 mg/1	Oral	Arbor Pharmaceuticals	2013-05-01	Not applicable	US
Horizant	Tablet, extended release	300 mg/1	Oral	Arbor Pharmaceuticals	2013-05-01	Not applicable	US

Approved Generic Prescription Products

Not Available

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Not Available

Brand mixtures

Not Available

Categories

UNII

75OCL1SPBQ

CAS number

478296-72-9

Weight

Average: 329.393
Monoisotopic: 329.183837593

Chemical Formula

C₁₆H₂₇NO₆

InChI Key

TZDUHAJSIBHXDL-UHFFFAOYSA-N

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)

IUPAC Name

SMILES

CC(C)C(=O)OC(C)OC(=O)NCC1(CC(O)=O)CCCCC1

Pharmacology

Indication

For the treatment of adult Restless Legs Syndrome (RLS) and postherpetic neuralgia (PHN).

Structured Indications

Pharmacodynamics

Since gabapentin enacarbil is a prodrug of gabapentin, it's physiological effects are the same as gabapentin. Concerning PHN, gabapentin prevents allodynia and hyperalgesia.

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.

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
Voltage-dependent calcium channel subunit alpha-2/delta-1	Protein	unknown	Not Available	Human	P54289	details
Voltage-dependent calcium channel subunit alpha-2/delta-2	Protein	unknown	Not Available	Human	Q9NY47	details

Absorption

Gabapentin enacarbil is absorbed in the intestines by active transport through the proton-linked monocarboxylate transporter, MCT-1.

Volume of distribution

The volume of distribution is 76L.

Protein binding

Gabapentin plasma protein binding is less than 3%.

Metabolism

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%).

Half life

The elimination half-life of gabapentin is 5.1 to 6.0 hours.

Clearance

Renal clearance of gabapentin is 5 to 7 L/hr.

Toxicity

Most common adverse reactions are headache, dizziness, and somnolence.

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction	Drug group
7-Nitroindazole	The risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with gabapentin enacarbil.	Experimental
Acepromazine	The risk or severity of adverse effects can be increased when Acepromazine is combined with gabapentin enacarbil.	Approved, Vet Approved
Aceprometazine	The risk or severity of adverse effects can be increased when Aceprometazine is combined with gabapentin enacarbil.	Approved
Adipiplon	The risk or severity of adverse effects can be increased when adipiplon is combined with gabapentin enacarbil.	Investigational
Agomelatine	The risk or severity of adverse effects can be increased when Agomelatine is combined with gabapentin enacarbil.	Approved, Investigational
Alfaxalone	The risk or severity of adverse effects can be increased when Alfaxalone is combined with gabapentin enacarbil.	Vet Approved
Alfentanil	The risk or severity of adverse effects can be increased when Alfentanil is combined with gabapentin enacarbil.	Approved, Illicit
Allopregnanolone	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Sage 547.	Investigational
Alphacetylmethadol	The risk or severity of adverse effects can be increased when Alphacetylmethadol is combined with gabapentin enacarbil.	Experimental, Illicit
Alprazolam	The risk or severity of adverse effects can be increased when Alprazolam is combined with gabapentin enacarbil.	Approved, Illicit, Investigational
Amisulpride	The risk or severity of adverse effects can be increased when Amisulpride is combined with gabapentin enacarbil.	Approved, Investigational
Amitriptyline	The risk or severity of adverse effects can be increased when Amitriptyline is combined with gabapentin enacarbil.	Approved
Amobarbital	The risk or severity of adverse effects can be increased when Amobarbital is combined with gabapentin enacarbil.	Approved, Illicit
Amoxapine	The risk or severity of adverse effects can be increased when Amoxapine is combined with gabapentin enacarbil.	Approved
Amperozide	The risk or severity of adverse effects can be increased when Amperozide is combined with gabapentin enacarbil.	Experimental
Aripiprazole	The risk or severity of adverse effects can be increased when Aripiprazole is combined with gabapentin enacarbil.	Approved, Investigational
Articaine	The risk or severity of adverse effects can be increased when Articaine is combined with gabapentin enacarbil.	Approved
Asenapine	The risk or severity of adverse effects can be increased when Asenapine is combined with gabapentin enacarbil.	Approved
Azelastine	gabapentin enacarbil may increase the central nervous system depressant (CNS depressant) activities of Azelastine.	Approved
Azelastine	The risk or severity of adverse effects can be increased when Azelastine is combined with gabapentin enacarbil.	Approved
Baclofen	The risk or severity of adverse effects can be increased when Baclofen is combined with gabapentin enacarbil.	Approved
Barbital	The risk or severity of adverse effects can be increased when Barbital is combined with gabapentin enacarbil.	Illicit
Benperidol	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Benperidol.	Investigational
Benzocaine	The risk or severity of adverse effects can be increased when Benzocaine is combined with gabapentin enacarbil.	Approved
Benzyl alcohol	The risk or severity of adverse effects can be increased when Benzyl alcohol is combined with gabapentin enacarbil.	Approved
Brexpiprazole	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Brexpiprazole.	Approved
Brimonidine	The risk or severity of adverse effects can be increased when Brimonidine is combined with gabapentin enacarbil.	Approved
Brimonidine	Brimonidine may increase the central nervous system depressant (CNS depressant) activities of gabapentin enacarbil.	Approved
Bromazepam	The risk or severity of adverse effects can be increased when Bromazepam is combined with gabapentin enacarbil.	Approved, Illicit
Brompheniramine	The risk or severity of adverse effects can be increased when Brompheniramine is combined with gabapentin enacarbil.	Approved
Brotizolam	The risk or severity of adverse effects can be increased when Brotizolam is combined with gabapentin enacarbil.	Approved, Withdrawn
Bupivacaine	The risk or severity of adverse effects can be increased when Bupivacaine is combined with gabapentin enacarbil.	Approved, Investigational
Buprenorphine	gabapentin enacarbil may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.	Approved, Illicit, Investigational, Vet Approved
Buspirone	The risk or severity of adverse effects can be increased when Buspirone is combined with gabapentin enacarbil.	Approved, Investigational
Butabarbital	The risk or severity of adverse effects can be increased when Butabarbital is combined with gabapentin enacarbil.	Approved, Illicit
Butalbital	The risk or severity of adverse effects can be increased when Butalbital is combined with gabapentin enacarbil.	Approved, Illicit
Butethal	The risk or severity of adverse effects can be increased when Butethal is combined with gabapentin enacarbil.	Approved, Illicit
Butorphanol	The risk or severity of adverse effects can be increased when Butorphanol is combined with gabapentin enacarbil.	Approved, Illicit, Vet Approved
Carbamazepine	The risk or severity of adverse effects can be increased when Carbamazepine is combined with gabapentin enacarbil.	Approved, Investigational
Carbinoxamine	The risk or severity of adverse effects can be increased when Carbinoxamine is combined with gabapentin enacarbil.	Approved
Carfentanil	The risk or severity of adverse effects can be increased when Carfentanil is combined with gabapentin enacarbil.	Illicit, Vet Approved
Carisoprodol	The risk or severity of adverse effects can be increased when Carisoprodol is combined with gabapentin enacarbil.	Approved
Cetirizine	The risk or severity of adverse effects can be increased when Cetirizine is combined with gabapentin enacarbil.	Approved
Chloral hydrate	The risk or severity of adverse effects can be increased when Chloral hydrate is combined with gabapentin enacarbil.	Approved, Illicit, Vet Approved
Chlordiazepoxide	The risk or severity of adverse effects can be increased when Chlordiazepoxide is combined with gabapentin enacarbil.	Approved, Illicit
Chlormezanone	The risk or severity of adverse effects can be increased when Chlormezanone is combined with gabapentin enacarbil.	Approved, Withdrawn
Chloroprocaine	The risk or severity of adverse effects can be increased when Chloroprocaine is combined with gabapentin enacarbil.	Approved
Chlorphenamine	The risk or severity of adverse effects can be increased when Chlorphenamine is combined with gabapentin enacarbil.	Approved
Chlorpromazine	The risk or severity of adverse effects can be increased when Chlorpromazine is combined with gabapentin enacarbil.	Approved, Vet Approved
Chlorprothixene	The risk or severity of adverse effects can be increased when Chlorprothixene is combined with gabapentin enacarbil.	Approved, Withdrawn
Chlorzoxazone	The risk or severity of adverse effects can be increased when Chlorzoxazone is combined with gabapentin enacarbil.	Approved
Cinchocaine	The risk or severity of adverse effects can be increased when Cinchocaine is combined with gabapentin enacarbil.	Approved, Vet Approved
Citalopram	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Citalopram.	Approved
Clemastine	The risk or severity of adverse effects can be increased when Clemastine is combined with gabapentin enacarbil.	Approved
Clidinium	The risk or severity of adverse effects can be increased when Clidinium is combined with gabapentin enacarbil.	Approved
Clobazam	The risk or severity of adverse effects can be increased when Clobazam is combined with gabapentin enacarbil.	Approved, Illicit
Clomipramine	The risk or severity of adverse effects can be increased when Clomipramine is combined with gabapentin enacarbil.	Approved, Vet Approved
Clonazepam	The risk or severity of adverse effects can be increased when Clonazepam is combined with gabapentin enacarbil.	Approved, Illicit
Clonidine	The risk or severity of adverse effects can be increased when Clonidine is combined with gabapentin enacarbil.	Approved
Clorazepate	The risk or severity of adverse effects can be increased when Clorazepate is combined with gabapentin enacarbil.	Approved, Illicit
Clozapine	The risk or severity of adverse effects can be increased when Clozapine is combined with gabapentin enacarbil.	Approved
Cocaine	The risk or severity of adverse effects can be increased when Cocaine is combined with gabapentin enacarbil.	Approved, Illicit
Codeine	The risk or severity of adverse effects can be increased when Codeine is combined with gabapentin enacarbil.	Approved, Illicit
Cyclizine	The risk or severity of adverse effects can be increased when Cyclizine is combined with gabapentin enacarbil.	Approved
Cyclobenzaprine	The risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with gabapentin enacarbil.	Approved
Cyproheptadine	The risk or severity of adverse effects can be increased when Cyproheptadine is combined with gabapentin enacarbil.	Approved
Dantrolene	The risk or severity of adverse effects can be increased when Dantrolene is combined with gabapentin enacarbil.	Approved
Dapiprazole	The risk or severity of adverse effects can be increased when Dapiprazole is combined with gabapentin enacarbil.	Approved
Dapoxetine	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Dapoxetine.	Investigational
Deramciclane	The risk or severity of adverse effects can be increased when deramciclane is combined with gabapentin enacarbil.	Investigational
Desflurane	The risk or severity of adverse effects can be increased when Desflurane is combined with gabapentin enacarbil.	Approved
Desipramine	The risk or severity of adverse effects can be increased when Desipramine is combined with gabapentin enacarbil.	Approved
Desloratadine	The risk or severity of adverse effects can be increased when Desloratadine is combined with gabapentin enacarbil.	Approved, Investigational
Desvenlafaxine	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Desvenlafaxine.	Approved
Dexbrompheniramine	The risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with gabapentin enacarbil.	Approved
Dexmedetomidine	The risk or severity of adverse effects can be increased when Dexmedetomidine is combined with gabapentin enacarbil.	Approved, Vet Approved
Dextromoramide	The risk or severity of adverse effects can be increased when Dextromoramide is combined with gabapentin enacarbil.	Experimental, Illicit
Dextropropoxyphene	The risk or severity of adverse effects can be increased when Dextropropoxyphene is combined with gabapentin enacarbil.	Approved, Illicit, Withdrawn
Dezocine	The risk or severity of adverse effects can be increased when Dezocine is combined with gabapentin enacarbil.	Approved
Diazepam	The risk or severity of adverse effects can be increased when Diazepam is combined with gabapentin enacarbil.	Approved, Illicit, Vet Approved
Difenoxin	The risk or severity of adverse effects can be increased when Difenoxin is combined with gabapentin enacarbil.	Approved, Illicit
Dihydrocodeine	The risk or severity of adverse effects can be increased when Dihydrocodeine is combined with gabapentin enacarbil.	Approved, Illicit
Dihydroetorphine	The risk or severity of adverse effects can be increased when Dihydroetorphine is combined with gabapentin enacarbil.	Experimental, Illicit
Dihydromorphine	The risk or severity of adverse effects can be increased when Dihydromorphine is combined with gabapentin enacarbil.	Experimental, Illicit
Dimenhydrinate	The risk or severity of adverse effects can be increased when Dimenhydrinate is combined with gabapentin enacarbil.	Approved
Diphenhydramine	The risk or severity of adverse effects can be increased when Diphenhydramine is combined with gabapentin enacarbil.	Approved
Diphenoxylate	The risk or severity of adverse effects can be increased when Diphenoxylate is combined with gabapentin enacarbil.	Approved, Illicit
Doxepin	The risk or severity of adverse effects can be increased when Doxepin is combined with gabapentin enacarbil.	Approved
Doxylamine	Doxylamine may increase the central nervous system depressant (CNS depressant) activities of gabapentin enacarbil.	Approved, Vet Approved
Dronabinol	Dronabinol may increase the central nervous system depressant (CNS depressant) activities of gabapentin enacarbil.	Approved, Illicit
Droperidol	Droperidol may increase the central nervous system depressant (CNS depressant) activities of gabapentin enacarbil.	Approved, Vet Approved
Drotebanol	The risk or severity of adverse effects can be increased when Drotebanol is combined with gabapentin enacarbil.	Experimental, Illicit
Duloxetine	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Duloxetine.	Approved
Dyclonine	The risk or severity of adverse effects can be increased when Dyclonine is combined with gabapentin enacarbil.	Approved
Ecgonine	The risk or severity of adverse effects can be increased when Ecgonine is combined with gabapentin enacarbil.	Experimental, Illicit
Ecopipam	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Ecopipam.	Investigational
Efavirenz	The risk or severity of adverse effects can be increased when Efavirenz is combined with gabapentin enacarbil.	Approved, Investigational
Eltanolone	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Pregnanolone.	Investigational
Enflurane	The risk or severity of adverse effects can be increased when Enflurane is combined with gabapentin enacarbil.	Approved, Vet Approved
Entacapone	The risk or severity of adverse effects can be increased when Entacapone is combined with gabapentin enacarbil.	Approved, Investigational
Escitalopram	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Escitalopram.	Approved, Investigational
Estazolam	The risk or severity of adverse effects can be increased when Estazolam is combined with gabapentin enacarbil.	Approved, Illicit
Eszopiclone	The risk or severity of adverse effects can be increased when Eszopiclone is combined with gabapentin enacarbil.	Approved
Ethanol	Ethanol may increase the central nervous system depressant (CNS depressant) activities of gabapentin enacarbil.	Approved
Ethchlorvynol	The risk or severity of adverse effects can be increased when Ethchlorvynol is combined with gabapentin enacarbil.	Approved, Illicit, Withdrawn
Ethosuximide	The risk or severity of adverse effects can be increased when Ethosuximide is combined with gabapentin enacarbil.	Approved
Ethotoin	The risk or severity of adverse effects can be increased when Ethotoin is combined with gabapentin enacarbil.	Approved
Ethyl carbamate	The risk or severity of adverse effects can be increased when Ethyl carbamate is combined with gabapentin enacarbil.	Withdrawn
Ethyl loflazepate	The risk or severity of adverse effects can be increased when Ethyl loflazepate is combined with gabapentin enacarbil.	Approved, Illicit
Ethylmorphine	The risk or severity of adverse effects can be increased when Ethylmorphine is combined with gabapentin enacarbil.	Approved, Illicit
Etidocaine	The risk or severity of adverse effects can be increased when Etidocaine is combined with gabapentin enacarbil.	Approved
Etifoxine	The risk or severity of adverse effects can be increased when Etifoxine is combined with gabapentin enacarbil.	Withdrawn
Etizolam	The risk or severity of adverse effects can be increased when Etizolam is combined with gabapentin enacarbil.	Approved
Etomidate	The risk or severity of adverse effects can be increased when Etomidate is combined with gabapentin enacarbil.	Approved
Etoperidone	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Etoperidone.	Approved
Etorphine	The risk or severity of adverse effects can be increased when Etorphine is combined with gabapentin enacarbil.	Illicit, Vet Approved
Ezogabine	The risk or severity of adverse effects can be increased when Ezogabine is combined with gabapentin enacarbil.	Approved
Felbamate	The risk or severity of adverse effects can be increased when Felbamate is combined with gabapentin enacarbil.	Approved
Fencamfamine	The risk or severity of adverse effects can be increased when Fencamfamine is combined with gabapentin enacarbil.	Approved, Illicit, Withdrawn
Fentanyl	The risk or severity of adverse effects can be increased when Fentanyl is combined with gabapentin enacarbil.	Approved, Illicit, Investigational, Vet Approved
Fexofenadine	The risk or severity of adverse effects can be increased when Fexofenadine is combined with gabapentin enacarbil.	Approved
Flibanserin	The risk or severity of adverse effects can be increased when Flibanserin is combined with gabapentin enacarbil.	Approved
Fludiazepam	The risk or severity of adverse effects can be increased when Fludiazepam is combined with gabapentin enacarbil.	Approved, Illicit
Flunarizine	The risk or severity of adverse effects can be increased when Flunarizine is combined with gabapentin enacarbil.	Approved
Flunitrazepam	The risk or severity of adverse effects can be increased when Flunitrazepam is combined with gabapentin enacarbil.	Approved, Illicit
Fluoxetine	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Fluoxetine.	Approved, Vet Approved
Flupentixol	The risk or severity of adverse effects can be increased when Flupentixol is combined with gabapentin enacarbil.	Approved, Withdrawn
Fluphenazine	The risk or severity of adverse effects can be increased when Fluphenazine is combined with gabapentin enacarbil.	Approved
Flurazepam	The risk or severity of adverse effects can be increased when Flurazepam is combined with gabapentin enacarbil.	Approved, Illicit
Fluspirilene	The risk or severity of adverse effects can be increased when Fluspirilene is combined with gabapentin enacarbil.	Approved
Fluticasone propionate	The risk or severity of adverse effects can be increased when Fluticasone Propionate is combined with gabapentin enacarbil.	Approved
Fluvoxamine	The risk or severity of adverse effects can be increased when Fluvoxamine is combined with gabapentin enacarbil.	Approved, Investigational
Fosphenytoin	The risk or severity of adverse effects can be increased when Fosphenytoin is combined with gabapentin enacarbil.	Approved
Fospropofol	The risk or severity of adverse effects can be increased when Fospropofol is combined with gabapentin enacarbil.	Approved, Illicit
Gabapentin	The risk or severity of adverse effects can be increased when Gabapentin is combined with gabapentin enacarbil.	Approved, Investigational
Gamma Hydroxybutyric Acid	The risk or severity of adverse effects can be increased when Gamma Hydroxybutyric Acid is combined with gabapentin enacarbil.	Approved, Illicit
Gepirone	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Gepirone.	Investigational
Glutethimide	The risk or severity of adverse effects can be increased when Glutethimide is combined with gabapentin enacarbil.	Approved, Illicit
Guanfacine	The risk or severity of adverse effects can be increased when Guanfacine is combined with gabapentin enacarbil.	Approved, Investigational
Halazepam	The risk or severity of adverse effects can be increased when Halazepam is combined with gabapentin enacarbil.	Approved, Illicit, Withdrawn
Haloperidol	The risk or severity of adverse effects can be increased when Haloperidol is combined with gabapentin enacarbil.	Approved
Halothane	The risk or severity of adverse effects can be increased when Halothane is combined with gabapentin enacarbil.	Approved, Vet Approved
Heroin	The risk or severity of adverse effects can be increased when Heroin is combined with gabapentin enacarbil.	Approved, Illicit
Hexobarbital	The risk or severity of adverse effects can be increased when Hexobarbital is combined with gabapentin enacarbil.	Approved
Hydrocodone	gabapentin enacarbil may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.	Approved, Illicit
Hydromorphone	The risk or severity of adverse effects can be increased when Hydromorphone is combined with gabapentin enacarbil.	Approved, Illicit
Hydroxyzine	Hydroxyzine may increase the central nervous system depressant (CNS depressant) activities of gabapentin enacarbil.	Approved
Iloperidone	The risk or severity of adverse effects can be increased when Iloperidone is combined with gabapentin enacarbil.	Approved
Imipramine	The risk or severity of adverse effects can be increased when Imipramine is combined with gabapentin enacarbil.	Approved
Indalpine	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Indalpine.	Investigational, Withdrawn
Isoflurane	The risk or severity of adverse effects can be increased when Isoflurane is combined with gabapentin enacarbil.	Approved, Vet Approved
Ketamine	The risk or severity of adverse effects can be increased when Ketamine is combined with gabapentin enacarbil.	Approved, Vet Approved
Ketazolam	The risk or severity of adverse effects can be increased when Ketazolam is combined with gabapentin enacarbil.	Approved
Ketobemidone	The risk or severity of adverse effects can be increased when Ketobemidone is combined with gabapentin enacarbil.	Approved
Lamotrigine	The risk or severity of adverse effects can be increased when Lamotrigine is combined with gabapentin enacarbil.	Approved, Investigational
Levetiracetam	The risk or severity of adverse effects can be increased when Levetiracetam is combined with gabapentin enacarbil.	Approved, Investigational
Levobupivacaine	The risk or severity of adverse effects can be increased when Levobupivacaine is combined with gabapentin enacarbil.	Approved
Levocabastine	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Levocabastine.	Approved
Levocetirizine	The risk or severity of adverse effects can be increased when Levocetirizine is combined with gabapentin enacarbil.	Approved
Levodopa	The risk or severity of adverse effects can be increased when Levodopa is combined with gabapentin enacarbil.	Approved
Levomethadyl Acetate	The risk or severity of adverse effects can be increased when Levomethadyl Acetate is combined with gabapentin enacarbil.	Approved
Levomilnacipran	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Levomilnacipran.	Approved
Levorphanol	The risk or severity of adverse effects can be increased when Levorphanol is combined with gabapentin enacarbil.	Approved
Lidocaine	The risk or severity of adverse effects can be increased when Lidocaine is combined with gabapentin enacarbil.	Approved, Vet Approved
Lithium	The risk or severity of adverse effects can be increased when Lithium is combined with gabapentin enacarbil.	Approved
Lofentanil	The risk or severity of adverse effects can be increased when Lofentanil is combined with gabapentin enacarbil.	Illicit
Loratadine	The risk or severity of adverse effects can be increased when Loratadine is combined with gabapentin enacarbil.	Approved
Lorazepam	The risk or severity of adverse effects can be increased when Lorazepam is combined with gabapentin enacarbil.	Approved
Loxapine	The risk or severity of adverse effects can be increased when Loxapine is combined with gabapentin enacarbil.	Approved
Lurasidone	The risk or severity of adverse effects can be increased when Lurasidone is combined with gabapentin enacarbil.	Approved
Magnesium Sulfate	Magnesium Sulfate may increase the central nervous system depressant (CNS depressant) activities of gabapentin enacarbil.	Approved, Vet Approved
Maprotiline	The risk or severity of adverse effects can be increased when Maprotiline is combined with gabapentin enacarbil.	Approved
Meclizine	The risk or severity of adverse effects can be increased when Meclizine is combined with gabapentin enacarbil.	Approved
Melatonin	The risk or severity of adverse effects can be increased when Melatonin is combined with gabapentin enacarbil.	Approved, Nutraceutical, Vet Approved
Melperone	The risk or severity of adverse effects can be increased when Melperone is combined with gabapentin enacarbil.	Approved
Mepivacaine	The risk or severity of adverse effects can be increased when Mepivacaine is combined with gabapentin enacarbil.	Approved, Vet Approved
Meprobamate	The risk or severity of adverse effects can be increased when Meprobamate is combined with gabapentin enacarbil.	Approved, Illicit
Mesoridazine	The risk or severity of adverse effects can be increased when Mesoridazine is combined with gabapentin enacarbil.	Approved
Metaxalone	The risk or severity of adverse effects can be increased when Metaxalone is combined with gabapentin enacarbil.	Approved
Methadone	The risk or severity of adverse effects can be increased when Methadone is combined with gabapentin enacarbil.	Approved
Methadyl Acetate	The risk or severity of adverse effects can be increased when Methadyl Acetate is combined with gabapentin enacarbil.	Approved, Illicit
Methapyrilene	The risk or severity of adverse effects can be increased when Methapyrilene is combined with gabapentin enacarbil.	Withdrawn
Methaqualone	The risk or severity of adverse effects can be increased when Methaqualone is combined with gabapentin enacarbil.	Illicit, Withdrawn
Methocarbamol	The risk or severity of adverse effects can be increased when Methocarbamol is combined with gabapentin enacarbil.	Approved, Vet Approved
Methohexital	The risk or severity of adverse effects can be increased when Methohexital is combined with gabapentin enacarbil.	Approved
Methotrimeprazine	gabapentin enacarbil may increase the central nervous system depressant (CNS depressant) activities of Methotrimeprazine.	Approved
Methoxyflurane	The risk or severity of adverse effects can be increased when Methoxyflurane is combined with gabapentin enacarbil.	Approved, Vet Approved
Methsuximide	The risk or severity of adverse effects can be increased when Methsuximide is combined with gabapentin enacarbil.	Approved
Methylecgonine	The risk or severity of adverse effects can be increased when ECGONINE METHYL ESTER is combined with gabapentin enacarbil.	Experimental
Methylphenobarbital	The risk or severity of adverse effects can be increased when Methylphenobarbital is combined with gabapentin enacarbil.	Approved
Metyrosine	gabapentin enacarbil may increase the sedative activities of Metyrosine.	Approved
Midazolam	The risk or severity of adverse effects can be increased when Midazolam is combined with gabapentin enacarbil.	Approved, Illicit
Milnacipran	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Milnacipran.	Approved
Minocycline	Minocycline may increase the central nervous system depressant (CNS depressant) activities of gabapentin enacarbil.	Approved, Investigational
Mirtazapine	gabapentin enacarbil may increase the central nervous system depressant (CNS depressant) activities of Mirtazapine.	Approved
Molindone	The risk or severity of adverse effects can be increased when Molindone is combined with gabapentin enacarbil.	Approved
Morphine	The risk or severity of adverse effects can be increased when Morphine is combined with gabapentin enacarbil.	Approved, Investigational
Nabilone	Nabilone may increase the central nervous system depressant (CNS depressant) activities of gabapentin enacarbil.	Approved, Investigational
Nalbuphine	The risk or severity of adverse effects can be increased when Nalbuphine is combined with gabapentin enacarbil.	Approved
Nefazodone	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Nefazodone.	Approved, Withdrawn
Nitrazepam	The risk or severity of adverse effects can be increased when Nitrazepam is combined with gabapentin enacarbil.	Approved
Nitrous oxide	The risk or severity of adverse effects can be increased when Nitrous oxide is combined with gabapentin enacarbil.	Approved, Vet Approved
Norflurane	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with 1,1,1,2 Tetrafluoroethane.	Investigational
Normethadone	The risk or severity of adverse effects can be increased when Normethadone is combined with gabapentin enacarbil.	Approved, Illicit
Nortriptyline	The risk or severity of adverse effects can be increased when Nortriptyline is combined with gabapentin enacarbil.	Approved
Olanzapine	The risk or severity of adverse effects can be increased when Olanzapine is combined with gabapentin enacarbil.	Approved, Investigational
Olopatadine	The risk or severity of adverse effects can be increased when Olopatadine is combined with gabapentin enacarbil.	Approved
Ondansetron	The risk or severity of adverse effects can be increased when Ondansetron is combined with gabapentin enacarbil.	Approved
Opium	The risk or severity of adverse effects can be increased when Opium is combined with gabapentin enacarbil.	Approved, Illicit
Orphenadrine	gabapentin enacarbil may increase the central nervous system depressant (CNS depressant) activities of Orphenadrine.	Approved
Osanetant	The risk or severity of adverse effects can be increased when Osanetant is combined with gabapentin enacarbil.	Investigational
Oxazepam	The risk or severity of adverse effects can be increased when Oxazepam is combined with gabapentin enacarbil.	Approved
Oxethazaine	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Oxetacaine.	Investigational
Oxprenolol	The risk or severity of adverse effects can be increased when Oxprenolol is combined with gabapentin enacarbil.	Approved
Oxybuprocaine	The risk or severity of adverse effects can be increased when Oxybuprocaine is combined with gabapentin enacarbil.	Approved
Oxycodone	The risk or severity of adverse effects can be increased when Oxycodone is combined with gabapentin enacarbil.	Approved, Illicit, Investigational
Oxymorphone	The risk or severity of adverse effects can be increased when Oxymorphone is combined with gabapentin enacarbil.	Approved, Investigational, Vet Approved
Paliperidone	The risk or severity of adverse effects can be increased when Paliperidone is combined with gabapentin enacarbil.	Approved
Paraldehyde	gabapentin enacarbil may increase the central nervous system depressant (CNS depressant) activities of Paraldehyde.	Approved
Paroxetine	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Paroxetine.	Approved, Investigational
Pentazocine	The risk or severity of adverse effects can be increased when Pentazocine is combined with gabapentin enacarbil.	Approved, Vet Approved
Pentobarbital	The risk or severity of adverse effects can be increased when Pentobarbital is combined with gabapentin enacarbil.	Approved, Vet Approved
Perampanel	Perampanel may increase the central nervous system depressant (CNS depressant) activities of gabapentin enacarbil.	Approved
Perazine	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Perazine.	Investigational
Perospirone	The risk or severity of adverse effects can be increased when Perospirone is combined with gabapentin enacarbil.	Approved
Perphenazine	The risk or severity of adverse effects can be increased when Perphenazine is combined with gabapentin enacarbil.	Approved
Pethidine	The risk or severity of adverse effects can be increased when Pethidine is combined with gabapentin enacarbil.	Approved
Phenobarbital	The risk or severity of adverse effects can be increased when Phenobarbital is combined with gabapentin enacarbil.	Approved
Phenytoin	The risk or severity of adverse effects can be increased when Phenytoin is combined with gabapentin enacarbil.	Approved, Vet Approved
Pimozide	The risk or severity of adverse effects can be increased when Pimozide is combined with gabapentin enacarbil.	Approved
Pipamperone	The risk or severity of adverse effects can be increased when Pipamperone is combined with gabapentin enacarbil.	Approved
Pipotiazine	The risk or severity of adverse effects can be increased when Pipotiazine is combined with gabapentin enacarbil.	Approved
Piritramide	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Piritramide.	Investigational
Pomalidomide	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Pomalidomide.	Approved
Pramipexole	gabapentin enacarbil may increase the sedative activities of Pramipexole.	Approved, Investigational
Pramocaine	The risk or severity of adverse effects can be increased when Pramocaine is combined with gabapentin enacarbil.	Approved
Prazepam	The risk or severity of adverse effects can be increased when Prazepam is combined with gabapentin enacarbil.	Approved, Illicit
Pregabalin	The risk or severity of adverse effects can be increased when Pregabalin is combined with gabapentin enacarbil.	Approved, Illicit, Investigational
Prilocaine	The risk or severity of adverse effects can be increased when Prilocaine is combined with gabapentin enacarbil.	Approved
Primidone	The risk or severity of adverse effects can be increased when Primidone is combined with gabapentin enacarbil.	Approved, Vet Approved
Procaine	The risk or severity of adverse effects can be increased when Procaine is combined with gabapentin enacarbil.	Approved, Investigational, Vet Approved
Prochlorperazine	The risk or severity of adverse effects can be increased when Prochlorperazine is combined with gabapentin enacarbil.	Approved, Vet Approved
Promazine	The risk or severity of adverse effects can be increased when Promazine is combined with gabapentin enacarbil.	Approved, Vet Approved
Promethazine	The risk or severity of adverse effects can be increased when Promethazine is combined with gabapentin enacarbil.	Approved
Proparacaine	The risk or severity of adverse effects can be increased when Proparacaine is combined with gabapentin enacarbil.	Approved, Vet Approved
Propofol	The risk or severity of adverse effects can be increased when Propofol is combined with gabapentin enacarbil.	Approved, Investigational, Vet Approved
Propoxycaine	The risk or severity of adverse effects can be increased when Propoxycaine is combined with gabapentin enacarbil.	Approved
Protriptyline	The risk or severity of adverse effects can be increased when Protriptyline is combined with gabapentin enacarbil.	Approved
Quazepam	The risk or severity of adverse effects can be increased when Quazepam is combined with gabapentin enacarbil.	Approved, Illicit
Quetiapine	The risk or severity of adverse effects can be increased when Quetiapine is combined with gabapentin enacarbil.	Approved
Raclopride	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Raclopride.	Investigational
Ramelteon	The risk or severity of adverse effects can be increased when Ramelteon is combined with gabapentin enacarbil.	Approved, Investigational
Remifentanil	The risk or severity of adverse effects can be increased when Remifentanil is combined with gabapentin enacarbil.	Approved
Remoxipride	The risk or severity of adverse effects can be increased when Remoxipride is combined with gabapentin enacarbil.	Approved, Withdrawn
Reserpine	The risk or severity of adverse effects can be increased when Reserpine is combined with gabapentin enacarbil.	Approved
Risperidone	The risk or severity of adverse effects can be increased when Risperidone is combined with gabapentin enacarbil.	Approved, Investigational
Ritanserin	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Ritanserin.	Investigational
Ropinirole	gabapentin enacarbil may increase the sedative activities of Ropinirole.	Approved, Investigational
Ropivacaine	The risk or severity of adverse effects can be increased when Ropivacaine is combined with gabapentin enacarbil.	Approved
Rotigotine	gabapentin enacarbil may increase the sedative activities of Rotigotine.	Approved
Rufinamide	The risk or severity of adverse effects can be increased when Rufinamide is combined with gabapentin enacarbil.	Approved
Scopolamine	The risk or severity of adverse effects can be increased when Scopolamine is combined with gabapentin enacarbil.	Approved
Secobarbital	The risk or severity of adverse effects can be increased when Secobarbital is combined with gabapentin enacarbil.	Approved, Vet Approved
Sepranolone	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Uc1010.	Investigational
Sertindole	The risk or severity of adverse effects can be increased when Sertindole is combined with gabapentin enacarbil.	Approved, Withdrawn
Sertraline	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Sertraline.	Approved
Sevoflurane	The risk or severity of adverse effects can be increased when Sevoflurane is combined with gabapentin enacarbil.	Approved, Vet Approved
Sodium oxybate	Sodium oxybate may increase the central nervous system depressant (CNS depressant) activities of gabapentin enacarbil.	Approved
Stiripentol	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Stiripentol.	Approved
Sufentanil	The risk or severity of adverse effects can be increased when Sufentanil is combined with gabapentin enacarbil.	Approved, Investigational
Sulpiride	The risk or severity of adverse effects can be increased when Sulpiride is combined with gabapentin enacarbil.	Approved
Suvorexant	gabapentin enacarbil may increase the central nervous system depressant (CNS depressant) activities of Suvorexant.	Approved
Tandospirone	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Tandospirone.	Investigational
Tapentadol	Tapentadol may increase the central nervous system depressant (CNS depressant) activities of gabapentin enacarbil.	Approved
Tasimelteon	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Tasimelteon.	Approved
Temazepam	The risk or severity of adverse effects can be increased when Temazepam is combined with gabapentin enacarbil.	Approved
Tetrabenazine	The risk or severity of adverse effects can be increased when Tetrabenazine is combined with gabapentin enacarbil.	Approved
Tetracaine	The risk or severity of adverse effects can be increased when Tetracaine is combined with gabapentin enacarbil.	Approved, Vet Approved
Tetrodotoxin	The risk or severity of adverse effects can be increased when Tetrodotoxin is combined with gabapentin enacarbil.	Investigational
Thalidomide	gabapentin enacarbil may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.	Approved, Investigational, Withdrawn
Thiamylal	The risk or severity of adverse effects can be increased when Thiamylal is combined with gabapentin enacarbil.	Approved, Vet Approved
Thiopental	The risk or severity of adverse effects can be increased when Thiopental is combined with gabapentin enacarbil.	Approved, Vet Approved
Thioridazine	The risk or severity of adverse effects can be increased when Thioridazine is combined with gabapentin enacarbil.	Withdrawn
Thiothixene	The risk or severity of adverse effects can be increased when Thiothixene is combined with gabapentin enacarbil.	Approved
Tiagabine	The risk or severity of adverse effects can be increased when Tiagabine is combined with gabapentin enacarbil.	Approved
Tiapride	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Tiapride.	Approved, Investigational
Tizanidine	The risk or severity of adverse effects can be increased when Tizanidine is combined with gabapentin enacarbil.	Approved
Tolcapone	The risk or severity of adverse effects can be increased when Tolcapone is combined with gabapentin enacarbil.	Approved, Withdrawn
Topiramate	The risk or severity of adverse effects can be increased when Topiramate is combined with gabapentin enacarbil.	Approved
Tramadol	The risk or severity of adverse effects can be increased when Tramadol is combined with gabapentin enacarbil.	Approved, Investigational
Trans-2-Phenylcyclopropylamine	The risk or severity of adverse effects can be increased when Trans-2-Phenylcyclopropylamine is combined with gabapentin enacarbil.	Experimental
Tranylcypromine	The risk or severity of adverse effects can be increased when Tranylcypromine is combined with gabapentin enacarbil.	Approved
Trazodone	The risk or severity of adverse effects can be increased when Trazodone is combined with gabapentin enacarbil.	Approved, Investigational
Triazolam	The risk or severity of adverse effects can be increased when Triazolam is combined with gabapentin enacarbil.	Approved
Trifluoperazine	The risk or severity of adverse effects can be increased when Trifluoperazine is combined with gabapentin enacarbil.	Approved
Triflupromazine	The risk or severity of adverse effects can be increased when Triflupromazine is combined with gabapentin enacarbil.	Approved, Vet Approved
Trimipramine	The risk or severity of adverse effects can be increased when Trimipramine is combined with gabapentin enacarbil.	Approved
Triprolidine	The risk or severity of adverse effects can be increased when Triprolidine is combined with gabapentin enacarbil.	Approved
Valproic Acid	The risk or severity of adverse effects can be increased when Valproic Acid is combined with gabapentin enacarbil.	Approved, Investigational
Venlafaxine	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Venlafaxine.	Approved
Vigabatrin	The risk or severity of adverse effects can be increased when Vigabatrin is combined with gabapentin enacarbil.	Approved
Vortioxetine	The risk or severity of adverse effects can be increased when Vortioxetine is combined with gabapentin enacarbil.	Approved
Zaleplon	The risk or severity of adverse effects can be increased when Zaleplon is combined with gabapentin enacarbil.	Approved, Illicit, Investigational
Ziconotide	The risk or severity of adverse effects can be increased when Ziconotide is combined with gabapentin enacarbil.	Approved
Zimelidine	The risk or severity of adverse effects can be increased when gabapentin enacarbil is combined with Zimelidine.	Withdrawn
Ziprasidone	The risk or severity of adverse effects can be increased when Ziprasidone is combined with gabapentin enacarbil.	Approved
Zolpidem	gabapentin enacarbil may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.	Approved
Zonisamide	The risk or severity of adverse effects can be increased when Zonisamide is combined with gabapentin enacarbil.	Approved, Investigational
Zopiclone	The risk or severity of adverse effects can be increased when Zopiclone is combined with gabapentin enacarbil.	Approved
Zotepine	The risk or severity of adverse effects can be increased when Zotepine is combined with gabapentin enacarbil.	Approved
Zuclopenthixol	The risk or severity of adverse effects can be increased when Zuclopenthixol is combined with gabapentin enacarbil.	Approved, Investigational

Food Interactions

No food effects.

References

Synthesis Reference

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.

General 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:15146028 ]
Bialer M: New antiepileptic drugs that are second generation to existing antiepileptic drugs. Expert Opin Investig Drugs. 2006 Jun;15(6):637-47. [PubMed:16732716 ]
Cundy KC, Annamalai T, Bu L, De Vera J, Estrela J, Luo W, Shirsat P, Torneros A, Yao F, Zou J, Barrett RW, Gallop MA: XP13512 [(+/-)-1-([(alpha-isobutanoyloxyethoxy)carbonyl] aminomethyl)-1-cyclohexane acetic acid], a novel gabapentin prodrug: II. Improved oral bioavailability, dose proportionality, and colonic absorption compared with gabapentin in rats and monkeys. J Pharmacol Exp Ther. 2004 Oct;311(1):324-33. Epub 2004 May 14. [PubMed:15146029 ]

External Links

Resource	Link
KEGG Drug	D09539
ChemSpider	8059607
ChEBI	68840
ChEMBL	CHEMBL1628502
RxList	http://www.rxlist.com/horizant-drug.htm
Drugs.com	http://www.drugs.com/sfx/gabapentin-enacarbil-side-effects.html
Wikipedia	Gabapentin_enacarbil

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Download (347 KB)

MSDS

Download (30.7 KB)

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Treatment	Healthy Volunteers	1
1	Completed	Treatment	Patients With Impaired Renal Function and Haemodialysis	1
1	Completed	Treatment	Restless Legs Syndrome (RLS)	2
1	Recruiting	Treatment	RLS	1
2	Active Not Recruiting	Treatment	Irritability / Neurologically Impaired / Pain, Chronic / Signs and Symptoms, Digestive / Sleeplessness	1
2	Completed	Prevention	Migraine Disorders / Migraines	1
2	Completed	Treatment	Alcohol Use Disorder (AUD)	1
2	Completed	Treatment	Diabetic Neuropathies	1
2	Completed	Treatment	Postherpetic Neuralgia	2
2	Completed	Treatment	Restless Legs Syndrome (RLS)	3
2	Terminated	Treatment	Diabetic Neuropathies	1
2	Terminated	Treatment	Malignant Neoplasm of Prostate	1
3	Completed	Treatment	Restless Legs Syndrome (RLS)	6
4	Completed	Treatment	Postoperative pain	1
4	Completed	Treatment	Restless Legs Syndrome (RLS)	2
4	Not Yet Recruiting	Treatment	Facial Pain / Pain, Acute / Postoperative pain	1
4	Not Yet Recruiting	Treatment	Restless Legs Syndrome (RLS)	1
4	Recruiting	Treatment	Alzheimer's Disease (AD)	1
4	Recruiting	Treatment	RLS	2
4	Recruiting	Treatment	Restless Legs Syndrome (RLS)	1
4	Terminated	Treatment	Restless Legs Syndrome (RLS)	1
Not Available	Recruiting	Not Available	Restless Legs Syndrome (RLS)	1
Not Available	Recruiting	Treatment	Pain	1
Not Available	Recruiting	Treatment	Restless Legs Syndrome (RLS)	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Form	Route	Strength
Tablet, extended release	Oral	300 mg/1
Tablet, extended release	Oral	600 mg/1

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US6818787	No	2002-11-06	2022-11-06	US
US8026279	No	2006-11-10	2026-11-10	US
US8048917	No	2002-11-06	2022-11-06	US
US8114909	No	2006-04-11	2026-04-11	US
US8686034	No	2005-01-24	2025-01-24	US
US8795725	No	2009-06-10	2029-06-10	US

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	Melting onset of about 64°C.	From FDA label.
water solubility	Solubility of 0.5 mg/mL in water	From FDA label.
pKa	pKa 5.0	From The Merck Index.

Predicted Properties

Property	Value	Source

Predicted ADMET features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

Taxonomy

Description

This compound belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Gamma amino acids and derivatives

Alternative Parents

Dicarboxylic acids and derivatives / Carbamate esters / Organic carbonic acids and derivatives / Carboxylic acid esters / Carboxylic acids / Acetals / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives

Substituents

Gamma amino acid or derivatives / Dicarboxylic acid or derivatives / Carbamic acid ester / Carboxylic acid ester / Carbonic acid derivative / Acetal / Carboxylic acid / Organic nitrogen compound / Organonitrogen compound / Organooxygen compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

carbamate ester, monocarboxylic acid, carboxylic ester, acetal (CHEBI:68840 )

Targets

Details

1. Voltage-dependent calcium channel subunit alpha-2/delta-1

Kind: Protein
Organism: Human
Pharmacological action: unknown

General Function:: Voltage-gated calcium channel activity
Specific Function:: The alpha-2/delta subunit of voltage-dependent calcium channels regulates calcium current density and activation/inactivation kinetics of the calcium channel. Plays an important role in excitation-contraction coupling (By similarity).
Gene Name:: CACNA2D1
Uniprot ID:: P54289
Uniprot Name:: Voltage-dependent calcium channel subunit alpha-2/delta-1
Molecular Weight:: 124566.93 Da

Details

2. Voltage-dependent calcium channel subunit alpha-2/delta-2

Kind: Protein
Organism: Human
Pharmacological action: unknown

General Function:: Voltage-gated calcium channel activity
Specific Function:: The alpha-2/delta subunit of voltage-dependent calcium channels regulates calcium current density and activation/inactivation kinetics of the calcium channel. Acts as a regulatory subunit for P/Q-type calcium channel (CACNA1A), N-type (CACNA1B), L-type (CACNA1C OR CACNA1D) and possibly T-type (CACNA1G). Overexpression induces apoptosis.
Gene Name:: CACNA2D2
Uniprot ID:: Q9NY47
Uniprot Name:: Voltage-dependent calcium channel subunit alpha-2/delta-2
Molecular Weight:: 129816.095 Da

Transporters

Details

1. Sodium-coupled monocarboxylate transporter 1

Kind: Protein
Organism: Human
Pharmacological action: no
Actions: substrate

General Function:: Symporter activity
Specific Function:: Acts as an electrogenic sodium (Na(+)) and chloride (Cl-)-dependent sodium-coupled solute transporter, including transport of monocarboxylates (short-chain fatty acids including L-lactate, D-lactate, pyruvate, acetate, propionate, valerate and butyrate), lactate, mocarboxylate drugs (nicotinate, benzoate, salicylate and 5-aminosalicylate) and ketone bodies (beta-D-hydroxybutyrate, acetoacetate ...
Gene Name:: SLC5A8
Uniprot ID:: Q8N695
Uniprot Name:: Sodium-coupled monocarboxylate transporter 1
Molecular Weight:: 66577.005 Da

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:15146028 ]

Details

2. Sodium-dependent multivitamin transporter

Kind: Protein
Organism: Human
Pharmacological action: no
Actions: substrate

General Function:: Sodium-dependent multivitamin transmembrane transporter activity
Specific Function:: Transports pantothenate, biotin and lipoate in the presence of sodium.
Gene Name:: SLC5A6
Uniprot ID:: Q9Y289
Uniprot Name:: Sodium-dependent multivitamin transporter
Molecular Weight:: 68641.27 Da

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:15146028 ]

Drug created on May 02, 2013 15:20 / Updated on July 27, 2017 16:04

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Structure for DB08872 (Gabapentin Enacarbil)

Targets

Transporters

References

References