ChemicalBook > CAS DataBase List > Gabapentin enacarbil

Gabapentin enacarbil

Product Name: Gabapentin enacarbil
CAS No.: 478296-72-9
Chemical Name: Gabapentin enacarbil
Synonyms: XP 13512;GABAPENTIN ENACARBIL;Gabapentin Enarcarbil;Gabapentin Impurity 11;Gabapentin enacarbil (XP-13512);TIANFUCHEM-478296-72-9---Gabapentin enacarbil;1-[[[[1-(2-Methyl-1-oxopropoxy)ethoxy]carbonyl]amino]methyl]...;2-(1-((((1-(Isobutyryloxy)ethoxy)carbonyl)amino)methyl)cyclohexyl)acetic acid;1-[[[[1-(2-Methyl-1-oxopropoxy)ethoxy]carbonyl]amino]methyl]cyclohexaneacetic acid;Cyclohexaneacetic acid,1-[[[[1-(2-Methyl-1-oxopropoxy)ethoxy]carbonyl]aMino]Methyl]-
CBNumber: CB01011737
Molecular Formula: C16H27NO6
Formula Weight: 329.39
MOL File: 478296-72-9.mol

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Gabapentin enacarbil Property

Melting point:: 65 °C
Boiling point:: 482.0±20.0 °C(Predicted)
Density: 1.134
storage temp.: Store at -20°C
solubility: DMSO:100.0(Max Conc. mg/mL);303.59(Max Conc. mM)
Ethanol:100.0(Max Conc. mg/mL);303.59(Max Conc. mM)
Water:0.67(Max Conc. mg/mL);2.03(Max Conc. mM)
form: Powder
pka: 4.72±0.10(Predicted)
color: Light yellow to brown
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)
InChIKey: TZDUHAJSIBHXDL-UHFFFAOYSA-N
SMILES: C1(CNC(OC(OC(=O)C(C)C)C)=O)(CC(O)=O)CCCCC1
CAS DataBase Reference: 478296-72-9(CAS DataBase Reference)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML3803
Product name: Gabapentin Enacarbil
Purity: ≥95% (HPLC)
Packaging: 5mg
Price: $96.9
Updated: 2025/07/31

Sigma-Aldrich

Product number: SML3803
Product name: Gabapentin Enacarbil
Purity: ≥95% (HPLC)
Packaging: 25mg
Price: $410
Updated: 2025/07/31

ChemScene

Product number: CS-1698
Product name: Gabapentinenacarbil
Packaging: 10mg
Price: $300
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FG31551
Product name: Gabapentin enacarbil
Packaging: 25mg
Price: $300
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FG31551
Product name: Gabapentin enacarbil
Packaging: 50mg
Price: $350
Updated: 2021/12/16

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Gabapentin enacarbil Chemical Properties,Usage,Production

Description

Gabapentin enacarbil (GEn) is an actively transported prodrug of gabapentin that provides sustained doseproportional exposure to gabapentin and predictable bioavailability. In April 2011, Gabapentin enacarbil is approved by the US Food and Drug Administration for the treatment of moderate-to-severe primary restless legssyndrome (RLS) in adults.
Gabapentin enacarbil was designed to be recognized as a substrate for two high-capacity nutrient transports, monocarboxylate transporter type 1 and sodium-dependent multivitamin transporter, and to be efficiently cleaved after absorption to give gabapentin. The separated enantiomers of gabapentin enacarbil have similar cleavage rates in human tissues. Preclinical studies showed that gabapentin enacarbil provides good systemic exposure of gabapentin in rats and monkeys.

Originator

Xenoport (United States)

Uses

Gabapentin enacarbil (HORIZANT GlaxoSmithKline/XenoPort) is a prodrug of gabapentin used as an anticonvulsant as well as a treatment for neurogenic pain, with the same mechanism of action as pregabalin.

Preparation

Gabapentin enacarbil is prepared as a racemic mixture from gabapentin either by sequential coupling with 1-chloroethyl chloroformate in the presence of trimethylsilyl chloride and triethylamine followed by addition of isobutyric acid or by direct coupling with an activated 1-(isobutyryloxy) ethyl carbonate.

Definition

ChEBI: A carbamate ester that is the N-[1-(isobutyryloxy)ethoxy]carbonyl derivative of [1-(aminomethyl)cyclohexyl]acetic acid. The prodrug for gabapentin, used for treatment of neuropathic pain and restless legs syndrome.

brand name

Horizant

Pharmacokinetics

Gabapentin enacarbil is an acyloxyalkylcarbamate prodrug of analgesic and anticonvulsant drug gabapentin which has problematic pharmacokinetic properties, including short half-life, saturable absorption, high inter-patient variability, and lack of linear dose–response relationship. Gabapentin enacarbil was designed to be absorbed throughout the entire length of the gastrointestinal tract, and its absorption is mediated by high-capacity nutrient transporters, including monocarboxylate transporter 1 (MCT-1) and sodium-dependent multivitamin transporter (SMVT). Prodrug modification produced an extended release of gabapentin with twofold improved, more predictable, and dose-proportional oral bioavailability in humans. During and after its absorption, gabapentin enacarbil is efficiently hydrolyzed by nonspecific esterases to yield gabapentin. Currently, gabapentin enacarbil is commercially available for the treatment of restless legs syndrome and post-herpetic neuralgia of adults.

Structure and hydrolysis of gabapentin enacarbil to the active gabapentin

Clinical Use

Gabapentin enacarbil is a prodrug of gabapentin (Neurontin, Pfizer) which binds to the a2-d subunit of L-type voltage-regulated calcium channels, reducing the release of several neurotransmitters. 122,123 Gabapentin enacarbil was discovered at XenoPort, codeveloped with GlaxoSmithKline, is marketed under the brand name Horizant, and is approved for the treatment of moderate to severe restless leg syndrome. Gabapentin enacarbil was designed to increase the absorption of gabapentin through the interaction with sodium-dependent multivitamin transporter (SMVT) and monocarboxylate transporter type 1 (MCT-1). As a result, the drug demonstrated much better oral bioavailability and more consistent exposure compared to the parent.

Synthesis

Gabapentin 155 was treated with chlorotrimethylsilane and triethylamine followed by acylation with 1-chloroethyl chloroformate 156 to give acid 157 after hydrolysis of the intermediate silyl ester. This acid was then used without purification and reacted with isobutyric acid (158) and triethylamine to afford gabapentin enacarbil (XIII) in 9.1% overall yield after crystallization. Alternatively, gabapentin 155 was reacted directly with the fully elaborated p-nitrophenyl activated side chain 161 in the presence of potassium carbonate. The resulting mixture of products and p-nitrophenol was treated with 10% Pd/C and potassium formate followed by acidic workup to remove the resulting aniline, providing gabaentin enacarbil (XIII) in 36% overall yield from p-nitrophenol 159 after crystallization. The required activated side chain 161 was prepared from p-nitrophenol 159 via a two-step, one-pot process involving acylation of the phenol with 1-chloroethyl chloroformate 156 in triethylamine. This provided intermediate 160 which was alkylated with isobutyric acid (158) in the presence of zinc oxide and potassium iodide, ultimately furnishing the mixed carbonate 161.

Mode of action

Gabapentin enacarbil is a prodrug of gabapentin and, accordingly, its therapeutic effects in RLS and PHN are attributable to gabapentin.
The mechanism of action by which gabapentin is efficacious in PHN is unknown but in animal models of analgesia, gabapentin prevents allodynia (pain-related behavior in response to a normally innocuous stimulus) and hyperalgesia (exaggerated response to painful stimuli). Gabapentin prevents pain-related responses in several models of neuropathic pain in rats and mice (e.g., spinal nerve ligation models, spinal cord injury model, acute herpes zoster infection model). Gabapentin also decreases pain-related responses after peripheral inflammation (carrageenan footpad test, late phase of formalin test), but does not alter immediate pain-related behaviors (rat tail flick test, formalin footpad acute phase). The relevance of these models to human pain is not known.

Gabapentin enacarbil Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Gabapentin enacarbil manufacturers

Shaanxi Dideu New Materials Co. Ltd

Product: Gabapentin enacarbil 478296-72-9
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 10000KGS
Release date: 2025-03-17

Zhuozhou Wenxi import and Export Co., Ltd

Product: Gabapentin enacarbil 478296-72-9
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-08-10

Career Henan Chemical Co

Product: Gabapentin enacarbil 478296-72-9
Price: US $2.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: ask
Release date: 2018-12-23

478296-72-9, Gabapentin enacarbilRelated Search:

Phenetidine PYRAZOPHOS Ethoxyethyne CARBONYL SULFIDE Gabapentin Bensulfuron methyl Methylparaben acetic acid, triethoxy-, ethyl ester Ethoxyquin DIETHOXYMETHANE Kresoxim-methyl 2-Ethoxyphenol Thiophanate-methyl Methyl Methyl bromide Methylcyclohexane Gabapentin enacarbil Ethoxy

GABAPENTIN ENACARBIL

Gabapentin Enarcarbil

Gabapentin Impurity 11

1-[[[[1-(2-Methyl-1-oxopropoxy)ethoxy]carbonyl]amino]methyl]cyclohexaneacetic acid

Cyclohexaneacetic acid,1-[[[[1-(2-Methyl-1-oxopropoxy)ethoxy]carbonyl]aMino]Methyl]-

XP 13512

1-[[[[1-(2-Methyl-1-oxopropoxy)ethoxy]carbonyl]amino]methyl]...

TIANFUCHEM-478296-72-9---Gabapentin enacarbil

2-(1-((((1-(Isobutyryloxy)ethoxy)carbonyl)amino)methyl)cyclohexyl)acetic acid

inhibit,Calcium Channel,XP 13512,Inhibitor,XP13512,Ca channels,Gabapentin enacarbil,Ca2+ channels

Gabapentin enacarbil (XP-13512)

478296-72-9