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6/16/2014 Gabapentin - Wikipedia, the free encyclopedia 1/12
Systematic (IUPAC) name
2-[1-(aminomet hyl)cyclohexyl]acet ic acid
Clinical data
Trade names Fanatrex, Gabarone, Gralise,
Neurontin, Nupentin, Neogab
AHFS/ monograph
MedlinePlus a694007
Licence data US Daily Med:link
Pregnancy cat. B1 (AU) C (US)
Legal status Prescription Only (S4) (AU) -
only (CA) POM (UK) -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability 27-60% (inversely proportional
to dose; a high fat meal also
increases bioavailability)[1][2]
Protein binding Less than 3%[1][2]
Metabolism Not significantly
From Wikipedia, the free encyclopedia
(Redirected from Neurotin)
Gabapentin (Neurontin) is a pharmaceutical drug,
specifically a GABA analog. It was originally developed to
treat epilepsy, and currently is also used to relieve
neuropathic pain. It is recommended as a first line agent for
the treatment of neuropathic pain arising from diabetic
neuropathy, post-herpetic neuralgia, and central neuropathic
It is also commonly prescribed by doctors for many off-label
treatments, such as restless leg syndrome, insomnia, and
bipolar disorder. There are, however, concerns regarding the
quality of the trials conducted for a number of conditions.
1 Medical uses
1.1 Pain
1.2 Seizures
1.3 Other
2 Adverse effects
2.1 Suicide
2.2 Overdosage
3 Pharmacology
4 Mechanism of action
5 Society and culture
5.1 Sales
5.2 FDA approval
5.3 Legal action
5.4 Off label promotion
5.5 Brand names
5.6 Forms
5.7 Related drugs
6 Veterinary use
7 See also
6/16/2014 Gabapentin - Wikipedia, the free encyclopedia 2/12
Half-life 5 to 7 hours[1][2]
CAS number

ATC code N03AX12
PubChem CID 3446
DrugBank DB00996





Chemical data

Mol. mass 171.237 g/mol
(what is this?) (verify)
8 References
9 External links
Medical uses
Gabapentin is used primarily to treat seizures, neuropathic
pain, including concussions, and hot flashes.
There are,
however, concerns regarding the quality of the research on its
use to treat migraines, bipolar disorders, and pain.
Gabapentin provides significant pain relief in about a third of
people who take it for fibromyalgia or chronic neuropathic
pain; however, there are side effects in two thirds of
It is effective in reducing narcotic usage post
and is helpful in neuropathic pain due to
It has not been shown useful for HIV-associated
sensory neuropathy.
When used for neuropathic pain it
does not appear superior to carbamazepine.
It appears as
effective as pregabalin and costs less.
It does not appear
to provide benefit for complex regional pain syndrome
to be useful for migraine prevention.
Gabapentin is approved for treatment of focal seizures in a number of countries
and evidence supports its use
for treating partial and mixed seizure disorders however there is insufficient evidence for its use in generalized
There is some evidence of benefit in acquired pendular nystagmus and infantile nystagmus but not in periodic
alternating nystagmus.
Gabapentin may help with menopausal symptoms.
It may be effective in
reducing pain and spasticity in multiple sclerosis.
Gabapentin is not supported for alcohol withdrawal,
treatment of smoking cessation has had mixed results.
Gabapentin helps with itching (pruritus) associated
with renal failure (uremic pruritus)
and other conditions.
Other off-label uses include treatment for mental health disorders. Numerous trials show that it is not effective alone
as a mood-stabilizing treatment for bipolar disorder and so has no therapeutic advantage in having fewer side
effects over better established bipolar drugs such as lithium and valproic acid. Gabapentin is useful in the treatment
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of anxiety associated with bipolar disorder and restless leg syndrome and for insomnia, but has limited usefulness in
disorders such as social anxiety disorder and obsessive-compulsive disorder, and in treatment-resistant
Gabapentin does not appear effective for the treatment of tinnitus.
Adverse effects
Gabapentin's most common side effects in adult patients include dizziness, fatigue, weight gain, drowsiness, and
peripheral edema (swelling of extremities);
these mainly occur at higher doses in the elderly. Also, in children 3
to 12 years of age, researchers observed susceptibility to mild-to-moderate mood swings, hostility, concentration
problems, and hyperactivity. Though rare, the literature reports several cases of hepatotoxicity.
should be used carefully in patients with renal impairment due to possible accumulation and toxicity.
An increase in formation of adenocarcinomas was observed in rats during preclinical trials; however, the clinical
significance of these results remains undetermined. Gabapentin is also known to induce pancreatic acinar cell
carcinomas in rats through an unknown mechanism, perhaps by stimulation of DNA synthesis; these tumors did not
affect the lifespan of the rats and did not metastasize.
May cause adverse effects to patient decision making ability.
In 2009 the U.S. Food and Drug Administration issued a warning of an increased risk of depression and suicidal
thoughts and behaviors in patients taking gabapentin, along with other anticonvulsant drugs
modifying the
packaging insert to reflect this.
In July 2009 the manufacturer of gabapentin (Pfizer) went to trial regarding the
association between gabapentin and the increased risk of suicide.
Persons who accidentally or intentionally ingested overdoses have manifested drowsiness, sedation, blurred vision,
slurred speech and somnolence or coma. Serum gabapentin concentrations may be measured to confirm
Gabapentin was initially synthesized to mimic the chemical structure of the neurotransmitter gamma-aminobutyric
acid (GABA), but is not believed to act on the same brain receptors.
Some of its activity may involve interaction with voltage-gated calcium channels. Gabapentin binds to the 2
subunit (1 and 2) and has been found to reduce calcium currents after chronic but not acute application via an effect
on trafficking
of voltage-dependent calcium channels in the central nervous system.
Another possible
mechanism of action, reported by Ben Barres and colleagues in Cell in 2009, is that gabapentin halts the formation
of new synapses.
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Mechanism of action
Gabapentin interacts with voltage-sensitive calcium channels in cortical neurons. Gabapentin increases the synaptic
concentration of GABA, enhances GABA responses at non-synaptic sites in neuronal tissues, and reduces the
release of mono-amine neurotransmitters. One of the mechanisms implicated in this effect of gabapentin is the
reduction of the axon excitability measured as an amplitude change of the presynaptic fibre volley (FV) in the CA1
area of the hippocampus. This is mediated through its binding to presynaptic NMDA receptors. Other studies have
shown that the antihyperalgesic and antiallodynic effects of gabapentin are mediated by the descending
noradrenergic system, resulting in the activation of spinal alpha-2 adrenergic receptors. Gabapentin has also been
shown to bind and activate the adenosine A1 receptor.
Society and culture
Gabapentin is best known under the brand name Neurontin manufactured by Pfizer subsidiary Parke-Davis. A
Pfizer subsidiary named Greenstone markets generic gabapentin.
In December 2004 the FDA granted final approval to a generic equivalent to Neurontin made by the Israeli firm
Neurontin began as one of Pfizer's best selling drugs; however, Pfizer has come under heavy criticism and serious
litigation for its marketing of the drug. They face allegations that, behind the scenes, Parke-Davis marketed the drug
for at least a dozen supposed uses that the FDA had not approved.
Today it is a mainstay drug for
migraines, even though it was not approved for such use in 2004.
FDA approval
Gabapentin was originally approved by the U.S. Food and Drug Administration (FDA) in 1994, for use as an
adjuvant medication to control partial seizures (effective when added to other antiseizure drugs). In 2002, an
indication was added for treating postherpetic neuralgia (neuropathic pain following shingles).
Legal action
Off label promotion
Although some small, non-controlled studies in the 1990smostly sponsored by gabapentin's manufacturer
suggested that gabapentin treatment for bipolar disorder may be promising,
the preponderance of evidence
suggests that it is not effective.
Subsequent to the corporate acquisition of the original patent holder, the
pharmaceutical company Pfizer admitted that there had been violations of FDA guidelines regarding the promotion
of unproven off-label uses for gabapentin in the Franklin v. Pfizer case.
Reuters reported on March 25, 2010, that "Pfizer Inc violated federal racketeering law by improperly promoting
the epilepsy drug Neurontin ... Under federal RICO law the penalty is automatically tripled, so the finding will cost
Pfizer $141 million."
The case stems from a claim from Kaiser Foundation Health Plan Inc. that "it was misled
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A capsule of
into believing Neurontin was effective for off-label treatment of migraines, bipolar disorder and other conditions.
Pfizer argued that Kaiser physicians still recommend the drug for those uses."
Bloomberg News (3/26/10, Van Voris, Lawrence) added that "during the trial, Pfizer argued that Kaiser doctors
continued to prescribe the drug even after the health insurer sued Pfizer in 2005. The insurer's website also still lists
Neurontin as a drug for neuropathic pain, Pfizer lawyers said in closing argument."
The Wall Street Journal (3/26/10, Kamp) noted that Pfizer spokesman Christopher Loder said, "We are
disappointed with the verdict and will pursue post-trial motions and an appeal."
He would later add that "the
verdict and the judge's rulings are not consistent with the facts and the law."
Franklin v. Pfizer case
By some estimates, off-label prescriptions account for roughly 90 percent of Neurontin sales.
While off-label
prescriptions are common for a number of drugs and are legal, marketing of off-label uses of a drug is illegal.
2004, Warner-Lambert agreed to plead guilty and pay $430 million in fines to settle civil and criminal charges
regarding the illegal marketing of Neurontin for off-label purposes, and further legal action is pending. The 2004
settlement was one of the largest in U.S. history, and the first off-label promotion case brought successfully under
the False Claims Act. The courts of New York State, for example, have refused to certify a class of injured parties
who took Neurontin for off-label use, finding that they had failed to state that they had any injury.
The University of California, San Francisco (UCSF) has archived
and studied
the documents made public by
this case, which opens a window into the illegal promotion and marketing of pharmaceuticals. However, Pfizer
maintains that the illegal activity originated in 1996, well before it acquired Parke-Davis (through its acquisition of
Warner-Lambert) in 2000. Several lawsuits are underway after people who had been prescribed gabapentin for
off-label treatment of bipolar disorder later attempted or committed suicide.
Brand names
Various suppliers of gabapentin market it under a number of brand names, including Neurostil, Neurontin, Fanatrex,
Gabarone, Gralise, Nupentin, Gabrion,
Penral, Gabapin.
Gabapentin comes as:
100 mg, 300 mg, and 400 mg capsules
300 mg, 600 mg, and 800 mg tablets
a 250 mg/5 mL oral (by mouth) solution.
Inactive ingredients in the capsules include lactose, cornstarch, and talc.
The 100-mg capsule shell also contains: gelatin and titanium dioxide.
The 300-mg capsule shell also contains: gelatin, titanium dioxide, and yellow iron oxide.
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The 400-mg capsule shell also contains: gelatin, red iron oxide, titanium dioxide, and yellow iron oxide. The
imprinting ink contains FD&C Blue No. 2 and titanium dioxide.
Inactive ingredients in the tablets include poloxamer 407, copolyvidonum, cornstarch, magnesium stearate,
hydroxypropyl cellulose, talc, candelilla wax, and purified water.
Inactive ingredients in the oral solution include glycerin, xylitol, purified water, and artificial flavor.
Related drugs
Parke-Davis developed a drug called pregabalin as a successor to gabapentin.
Pregabalin was brought to
market by Pfizer as Lyrica after the company acquired Warner-Lambert. Pregabalin is related in structure to
Another new drug atagabalin has been trialled by Pfizer as a treatment for insomnia.
Veterinary use
Gabapentin is also used for some animal treatments, but formulations (especially liquid forms) for human use may
contain the sweetener Xylitol, which is toxic to dogsso veterinary use of the human version requires caution.
See also
Gabapentin enacarbil
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External links
DrugBank: gabapentin (
Gabapentin information from MedlinePlus
"Gabapentin" ( PubMed Health. National Center
for Biotechnology Information (NCBI)
"Suicidal Behavior and Ideation and Antiepileptic Drugs"
90.htm) U.S. Food and Drug Administration (FDA)
Neurontin (
collected news and commentary at The New York Times
"Gabapentin" ( Drug Information
Portal. U.S. National Library of Medicine.
Retrieved from ""
Categories: Amino acids Analgesics Anticonvulsants Anxiolytics GABA analogues Mood stabilizers
( The Wall Street Journal.
Retrieved 13 January 2012.
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