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Details

Stereochemistry ACHIRAL
Molecular Formula C9H17NO2
Molecular Weight 171.2371
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GABAPENTIN

SMILES

C1CCC(CC1)(CC(=O)O)CN

InChI

InChIKey=UGJMXCAKCUNAIE-UHFFFAOYSA-N
InChI=1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12)

HIDE SMILES / InChI

Molecular Formula C9H17NO2
Molecular Weight 171.2371
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: description was created based on several sources, including http://www.xenoport.com/products/regnite/; http://files.shareholder.com/downloads/XNPT/0x0x827504/50A91A4D-7EBD-49B1-9D92-D6D9E100D46A/XNPT_News_2015_5_7_General.pdf; https://www.ncbi.nlm.nih.gov/pubmed/?term=23789956

Gabapentin enacarbil (Horizant in USA, Regnite in Japan), is a prodrug of gabapentin, an antiepileptic drug (AED). It was designed for increased oral bioavailability over gabapentin and to be transported through two high capacity transporters in the intestine, sodium-dependent multivitamin transporter (SMVT) and MCT1. It was shown that the prodrug is a substrate for both MCT1 and SMVT. The oral bioavailability of gabapentin following the administration of its prodrug was found to be 84.2% compared with 25.4% after a similar oral dose of gabapentin. Discovered and developed by XenoPort, gabapentin enacarbil was approved in the United States in 2011 for the treatment of moderate-to-severe primary restless legs syndrome (RLS) in adults and in June 2012 for the management of postherpetic neuralgia (PHN) in adults. Therapeutic effects of gabapentin enacarbil in RLS and PHN are attributable to gabapentin. The precise mechanism by which gabapentin is efficacious in RLS and PHN is unknown. In vitro studies have shown that gabapentin binds with high affinity to certain parts of voltage-activated calcium channels in the central nervous system. However, the relationship of this binding to the therapeutic effects of gabapentin enacarbil in RLS and PHN is unknown. The most common adverse reactions for adult patients with moderate-to-severe primary RLS and PHN receiving Horizant were somnolence/sedation, dizziness, headache, nausea and fatigue.

CNS Activity

Curator's Comment:: Gabapentin penetrates into the CNS

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.05 µM [Ki]
Target ID: Q8CFG6
Gene ID: 300992.0
Gene Symbol: Cacna2d2
Target Organism: Rattus norvegicus (Rat)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
HORIZANT

Approved Use

Indicated for the treatment of moderate-to-severe primary Restless Legs Syndrome (RLS) in adults, management of postherpetic neuralgia (PHN) in adults.

Launch Date

1.30204801E12
Secondary
HORIZANT

Approved Use

Indicated for the treatment of moderate-to-severe primary Restless Legs Syndrome (RLS) in adults, management of postherpetic neuralgia (PHN) in adults.

Launch Date

1.30204801E12
PubMed

PubMed

TitleDatePubMed
Pharmacokinetics and tolerability of single escalating doses of gabapentin enacarbil: a randomized-sequence, double-blind, placebo-controlled crossover study in healthy volunteers.
2009 Aug
A randomized, double-blind, placebo-controlled, crossover study of XP13512/GSK1838262 in the treatment of patients with primary restless legs syndrome.
2009 Feb
Randomized, double-blind, placebo-controlled study of XP13512/GSK1838262 in patients with RLS.
2009 Feb 3
Gabapentin enacarbil, a gabapentin prodrug for the treatment of the neurological symptoms associated with disorders such as restless legs syndrome.
2009 Jan
Gabapentin enacarbil in restless legs syndrome: a phase 2b, 2-week, randomized, double-blind, placebo-controlled trial.
2009 Nov-Dec
Gabapentin enacarbil (XP13512/GSK1838262) as an alternative treatment to dopaminergic agents for restless legs syndrome.
2010 Aug
The effect of food with varying fat content on the clinical pharmacokinetics of gabapentin after oral administration of gabapentin enacarbil.
2010 Feb
Gabapentin enacarbil in restless legs syndrome.
2010 Jan
Long-term maintenance treatment of restless legs syndrome with gabapentin enacarbil: a randomized controlled study.
2010 Jun
Clinical pharmacokinetic drug interaction studies of gabapentin enacarbil, a novel transported prodrug of gabapentin, with naproxen and cimetidine.
2010 May
Patents

Sample Use Guides

For restless legs syndrome: 600 mg once daily taken at about 5 PM. A dose of 1,200 mg once daily provided no additional benefit compared with the 600-mg dose, but caused an increase in adverse reactions. If the dose is not taken at the recommended time, the next dose should be taken the following day as prescribed. For postherpetic neuralgia: The starting dose is 600 mg in the morning for 3 days, then increase to 600 mg twice daily beginning on day 4. A daily dose greater than 1,200 mg provided no additional benefit. If the dose is not taken at the recommended time, skip this dose, and the next dose should be taken at the time of next scheduled dose.
Route of Administration: Oral
MCT-1-mediated transport of XP13512 (gabapentin enacarbil) was evaluated by direct measurement of uptake into X. laevis oocytes expressing human MCT-1. MCT-1-expressing oocytes were incubated with 0.25–1.0 mM XP13512 at room temperature for 5 min. Concentrations of prodrug and gabapentin in cell lysates were determined by LC/MS/MS. XP13512 was taken up by X. laevis oocytes expressing human MCT-1 to a significantly greater extent than uninjected oocytes.
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:35:32 UTC 2021
Edited
by admin
on Fri Jun 25 20:35:32 UTC 2021
Record UNII
6CW7F3G59X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GABAPENTIN
EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
GABAPENTIN [EP]
Common Name English
CYCLOHEXANEACETIC ACID, 1-(AMINOMETHYL)-
Common Name English
GABAPENTIN [INN]
Common Name English
GABAPENTIN [ORANGE BOOK]
Common Name English
GRALISE
Brand Name English
GABAPENTIN [USP-RS]
Common Name English
1-(AMINOMETHYL)CYCLOHEXANEACETIC ACID
Systematic Name English
GABAPENTIN [WHO-DD]
Common Name English
GABAPENTIN [MART.]
Common Name English
GABAPENTIN [MI]
Common Name English
GABAPENTIN [JAN]
Common Name English
NSC-742194
Code English
NSC-759254
Code English
GABAPENTIN [USAN]
Common Name English
GABAPENTIN [HSDB]
Common Name English
GABAPENTIN [USP MONOGRAPH]
Common Name English
GABAPENTIN [VANDF]
Common Name English
GABAPENTIN [EP MONOGRAPH]
Common Name English
GOE 3450
Code English
DM-1796
Code English
CARBATIN
Systematic Name English
GOE-3450
Code English
GABAPENTINE
Common Name English
CI-945
Code English
Classification Tree Code System Code
WHO-VATC QN03AX12
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
WHO-ATC N03AX12
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
FDA ORPHAN DRUG 236506
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
NDF-RT N0000008486
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
NDF-RT N0000175753
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
FDA ORPHAN DRUG 88695
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
NCI_THESAURUS C29756
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
LIVERTOX 446
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
Code System Code Type Description
FDA UNII
6CW7F3G59X
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
PRIMARY
MESH
C040029
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
PRIMARY
MERCK INDEX
M5618
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
PRIMARY Merck Index
IUPHAR
5483
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
PRIMARY
NCI_THESAURUS
C1108
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
PRIMARY
CAS
60142-96-3
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
PRIMARY
HSDB
7364
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
PRIMARY
ECHA (EC/EINECS)
262-076-3
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
PRIMARY
DRUG BANK
DB00996
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
PRIMARY
INN
5094
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
PRIMARY
EVMPD
SUB07857MIG
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
PRIMARY
PUBCHEM
3446
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
PRIMARY
USP_CATALOG
1287303
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
PRIMARY USP-RS
RXCUI
25480
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL940
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
PRIMARY
LACTMED
Gabapentin
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
PRIMARY
DRUG CENTRAL
1264
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
PRIMARY
EPA CompTox
60142-96-3
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
PRIMARY
WIKIPEDIA
GABAPENTIN
Created by admin on Fri Jun 25 20:35:33 UTC 2021 , Edited by admin on Fri Jun 25 20:35:33 UTC 2021
PRIMARY
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SALT/SOLVATE -> PARENT
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BASIS OF STRENGTH->SUBSTANCE
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CLINICALLY SIGNIFICANT
BINDER->LIGAND
BINDING
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CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC RENAL IMPAIRMENT
PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC IMMEDIATE-RELEASE
PHARMACOKINETIC
ORAL BIOAVAILABILITY PHARMACOKINETIC
MAXIMUM TOLERATED DOSE TOXICITY