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Gabapentin enacarbil

Gabapentin enacarbil structure

CAS No:
478296-72-9
Formula:
C16H27NO6
Chemical Name:
Gabapentin enacarbil
Synonyms:
Cyclohexaneacetic acid,1-[[[[1-(2-methyl-1-oxopropoxy)ethoxy]carbonyl]amino]methyl]-;1-[[[[1-(2-Methyl-1-oxopropoxy)ethoxy]carbonyl]amino]methyl]cyclohexaneacetic acid;XP 13512;Gabapentin enacarbil;Horizant;Regnite;1-[[(1-(Isobutanoyloxy)ethoxy)carbonyl]aminomethyl]cyclohex-1-ylacetic acid;791632-57-0
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Gabapentin enacarbil is 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. It has a role as a prodrug, an anticonvulsant and a calcium channel blocker. It is a monocarboxylic acid, a carbamate ester, a carboxylic ester and an acetal. It derives from a gamma-aminobutyric acid and a gabapentin.|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).|Gabapentin enacarbil is a long acting form of gabapentin that is used for restless leg syndrome and for painful postherpetic neuropathy. Gabapentin enacarbil and gabapentin are associated with a low rate of transient serum enzyme elevations during treatment and with rare instances of clinically apparent liver injury.

Gabapentin enacarbil Basic Attributes

Molecular Weight：

329.38900

Exact Mass：

329.39

Characteristics

PSA：

101.93000

XLogP3：

3.07390

Density：

1.134

Melting Point：

65 °C

Boiling Point：

482.021ºC at 760 mmHg

Water Solubility：

Solubility of 0.5 mg/mL in water

Dissociation Constants：

pKa 5.0

Toxicity

Toxicity Summary：

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

Hepatotoxicity：

In prelicensure clinical trials, gabapentin enacarbil was not linked to an increased rate of serum enzyme elevations during treatment or to episodes of clinically apparent acute liver injury. Gabapentin has been implicated in isolated cases of acute liver injury, but in most instances the association was weakened by the coadministration with other potentially hepatotoxic agents. Too few cases have been reported in sufficient detail to characterize the clinical features of the associated injury. No published case has specifically implicated gabapentin enacarbil. Thus, gabapentin enacarbil may be associated with isolated instances of clinically apparent liver injury, but they must be rare, if they occur at all.

Protein Binding：

Gabapentin plasma protein binding is less than 3%.

Drug Information

Drug Indication：

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

LiverTox Summary：

Gabapentin enacarbil is a long acting form of gabapentin that is used for restless leg syndrome and for painful postherpetic neuropathy. Gabapentin enacarbil and gabapentin are associated with a low rate of transient serum enzyme elevations during treatment and with rare instances of clinically apparent liver injury.

Drug Classes：

Anticonvulsants

Pharmacology：

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

Absorption：

Gabapentin enacarbil is absorbed in the intestines by active transport through the proton-linked monocarboxylate transporter, MCT-1.|Gabapentin enacarbil is eliminated primarily in the urine (94%) and to a lesser extent in the feces (5%).|The volume of distribution is 76L.|Renal clearance of gabapentin is 5 to 7 L/hr.

Metabolism/Metabolites：

Gabapentin enacarbil does not interact with any of the major cytochrome P450 enzymes.

Biological Half-Life：

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

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.

MeSH Entry Terms：

1-(((alpha-isobutanoyloxyethoxy)carbonyl)aminomethyl)-1-cyclohexaneacetic acid

Gabapentin enacarbil Use and Manufacturing

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:329.39
XLogP3:3.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:9
Exact Mass:329.18383758
Monoisotopic Mass:329.18383758
Topological Polar Surface Area:102
Heavy Atom Count:23
Complexity:428
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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