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6/16/2014 Gabapentin - Wikipedia, the free encyclopedia

http://en.wikipedia.org/wiki/Neurotin

Gabapentin

Systematic (IUPAC) name

2-[1-(aminomethyl)cyclohexyl]acetic acid

Clinical data

Trade names Fanatrex, Gabarone, Gralise,

Neurontin, Nupentin, Neogab

AHFS/Drugs.com 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(

Routes Oral

Pharmacokinetic data

Bioavailability 27-60% (inversely proportion

to dose; a high fat meal also

increases bioavailability)[1][2]

Protein binding Less than 3%[1][2]

Metabolism Not significantly

metabolised[1][2]

GabapentinFrom Wikipedia, thefree encyclopedia

(Redirected from Neurotin)

Gabapentin(Neurontin) is a pharmaceutical drug,specifically a GABA analog. It was originally developed totreat epilepsy, and currently isalso used to relieve

neuropathic pain. It is recommended as a first line agent forthe treatment of neuropathicpain arising from diabeticneuropathy, post-herpetic neuralgia, and central neuropathic

pain.[3]

It is also commonly prescribed by doctors for many off-labeltreatments,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.[4]

Contents

1 Medical uses

1.1 Pain

1.2 Seizures

1.3 Other

2 Adverse effects2.1 Suicide

2.2 Overdosage

3 Pharmacology

4 Mechanism of action

5 Society andculture

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
http://en.wikipedia.org/wiki/File:Gabapentin3Dan.gifhttp://en.wikipedia.org/wiki/File:Gabapentin3Dan.gifhttp://en.wikipedia.org/wiki/File:Gabapentin3Dan.gifhttp://en.wikipedia.org/wiki/File:Gabapentin2DACS.svghttp://en.wikipedia.org/wiki/File:Gabapentin2DACS.svghttp://en.wikipedia.org/wiki/File:Gabapentin2DACS.svghttp://en.wikipedia.org/wiki/File:Gabapentin2DACS.svghttp://en.wikipedia.org/wiki/File:Gabapentin2DACS.svghttp://en.wikipedia.org/wiki/File:Gabapentin2DACS.svghttp://en.wikipedia.org/wiki/File:Gabapentin2DACS.svghttp://en.wikipedia.org/wiki/File:Gabapentin2DACS.svghttp://en.wikipedia.org/wiki/File:Gabapentin2DACS.svghttp://en.wikipedia.org/wiki/American_Society_of_Health-System_Pharmacistshttp://en.wikipedia.org/wiki/Off-label_usehttp://en.wikipedia.org/wiki/Restless_leg_syndromehttp://en.wikipedia.org/wiki/Off-label_usehttp://en.wikipedia.org/wiki/Neuropathic_painhttp://en.wikipedia.org/wiki/Gamma-Aminobutyric_acidhttp://en.wikipedia.org/wiki/Analogue_(chemistry)http://en.wikipedia.org/w/index.php?title=Neurotin&redirect=nohttp://en.wikipedia.org/wiki/Bipolar_disorderhttp://en.wikipedia.org/wiki/Insomniahttp://en.wikipedia.org/wiki/Restless_leg_syndromehttp://en.wikipedia.org/wiki/Off-label_usehttp://en.wikipedia.org/wiki/Neuropathic_painhttp://en.wikipedia.org/wiki/Epilepsyhttp://en.wikipedia.org/wiki/Analogue_(chemistry)http://en.wikipedia.org/wiki/Gamma-Aminobutyric_acidhttp://en.wikipedia.org/w/index.php?title=Neurotin&redirect=nohttp://en.wikipedia.org/wiki/Drug_metabolismhttp://en.wikipedia.org/wiki/Plasma_protein_bindinghttp://en.wikipedia.org/wiki/Bioavailabilityhttp://en.wikipedia.org/wiki/Route_of_administrationhttp://en.wikipedia.org/wiki/Prescription_drughttp://en.wikipedia.org/wiki/United_Kingdomhttp://en.wikipedia.org/wiki/Prescription_drughttp://en.wikipedia.org/wiki/Canadahttp://en.wikipedia.org/wiki/Prescription_drughttp://en.wikipedia.org/wiki/Australiahttp://en.wikipedia.org/wiki/Standard_for_the_Uniform_Scheduling_of_Drugs_and_Poisons#Schedule_4_Prescription_Only_Medicinehttp://en.wikipedia.org/wiki/Regulation_of_therapeutic_goodshttp://en.wikipedia.org/wiki/United_Stateshttp://en.wikipedia.org/wiki/Australiahttp://en.wikipedia.org/wiki/Pregnancy_categoryhttp://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=52049http://en.wikipedia.org/wiki/Daily_Medhttp://en.wikipedia.org/wiki/Regulation_of_therapeutic_goodshttp://www.nlm.nih.gov/medlineplus/druginfo/meds/a694007.htmlhttp://en.wikipedia.org/wiki/MedlinePlushttp://www.drugs.com/monograph/gabapentin.htmlhttp://en.wikipedia.org/wiki/Drugs.comhttp://en.wikipedia.org/wiki/American_Society_of_Health-System_Pharmacistshttp://en.wikipedia.org/wiki/Trade_namehttp://en.wikipedia.org/wiki/International_Union_of_Pure_and_Applied_Chemistry_nomenclaturehttp://en.wikipedia.org/wiki/File:Gabapentin3Dan.gifhttp://en.wikipedia.org/wiki/File:Gabapentin2DACS.svg


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Half-life 5 to 7 hours[1][2]

Excretion Renal[1][2]

Identifiers

CAS number 60142-96-3

ATC code N03AX12

PubChem CID 3446

DrugBank DB00996

ChemSpider 3328

UNII 6CW7F3G59X

KEGG D00332

ChEBI CHEBI:42797

ChEMBL

CHEMBL940

PDB ligand ID GBN (PDBe, RCSB PDB)

Chemical data

Formula C9H17NO2

Mol. mass 171.237 g/mol

(what is this?) (verify)

8 References

9 External links

Medical uses

Gabapentin is used primarily to treat seizures, neuropathicpain, including concussions, and hot flashes.[5]There are,however, concerns regarding the quality of the research on its

use to treat migraines, bipolar disorders, and pain.[4]

Pain

Gabapentin provides significant pain relief in about a third ofpeople who take it for fibromyalgia or chronic neuropathicpain; however, there are side effects in two thirds of

people.[6]It is effective in reducing narcotic usage post

operatively[7]and is helpful in neuropathic pain due to

cancer.[8]It has not been shown useful for HIV-associated

sensory neuropathy.[9]When used for neuropathic pain it

does not appear superior to carbamazepine.[10]It appears as

effective as pregabalin and costs less.[11]It does not appear

to provide benefit for complex regional pain syndrome[12]or

to be useful for migraine prevention.[13]

Seizures

Gabapentin is approved for treatment of focal seizures in a number of countries[14]and evidence supports its usfor treating partial and mixed seizure disorders however there is insufficient evidence for its use in generalized

epilepsy.[15]

Other

There is some evidence of benefit in acquired pendular nystagmus and infantile nystagmus but not in periodicalternating nystagmus.[16][17]Gabapentin may help with menopausal symptoms.[18][19]It may be effective in

reducing pain and spasticity in multiple sclerosis.[20]Gabapentin is not supported for alcohol withdrawal,[21]an

treatment of smoking cessation has had mixed results.[22][23]Gabapentin helps with itching (pruritus) associated

with renal failure (uremic pruritus)[24]and other conditions.[25]

Other off-label uses include treatment for mental health disorders. Numerous trials show that it is not effective aas a mood-stabilizing treatment for bipolar disorder and so has no therapeutic advantage in having fewer sideeffects over better established bipolar drugs such as lithium and valproic acid. Gabapentin is useful in the treatm

SMILES

InChI
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of anxiety associated with bipolar disorder and restless leg syndrome and for insomnia, but has limited usefulnesdisorders such as social anxiety disorder and obsessive-compulsive disorder, and in treatment-resistant

depression.[26]

Gabapentin does not appear effective for the treatment of tinnitus.[27]

Adverse effects

Gabapentin's most common side effects in adult patients include dizziness, fatigue, weight gain, drowsiness, and

peripheral edema (swelling of extremities);[28]these mainly occur at higher doses in the elderly. Also, in childrento 12 years of age, researchers observed susceptibility to mild-to-moderate mood swings, hostility, concentrati

problems, and hyperactivity. Though rare, the literature reports several cases of hepatotoxicity.[29][30]Gabapen

should be used carefully in patients with renal impairment due to possible accumulation and toxicity.[31][32]

An increase in formation of adenocarcinomas was observed in rats during preclinical trials; however, the clinicasignificance 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 didaffect the lifespan of the rats and did not metastasize.[33]

May cause adverse effects to patient decision making ability.

Suicide

In 2009 the U.S. Food and Drug Administration issued a warning of an increased risk of depression and suicid

thoughts and behaviors in patients taking gabapentin, along with other anticonvulsant drugs[34]modifying the

packaging insert to reflect this.[28]

In July 2009 the manufacturer of gabapentin (Pfizer) went to trial regarding thassociation between gabapentin and the increased risk of suicide.[35]

Overdosage

Persons who accidentally or intentionally ingested overdoses have manifested drowsiness, sedation, blurred visislurred speech and somnolence or coma. Serum gabapentin concentrations may be measured to confirm

diagnosis.[36]

PharmacologyGabapentin was initially synthesized to mimic the chemical structure of the neurotransmitter gamma-aminobutyriacid (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 2subunit (1 and 2) and has been found to reduce calcium currents after chronic but not acute application via an e

on trafficking[37]of voltage-dependent calcium channels in the central nervous system.[38]Another possiblemechanism of action, reported by Ben Barres and colleagues in Cellin 2009, is that gabapentin halts the forma

of new synapses.[39]
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Mechanism of action

Gabapentin interacts with voltage-sensitive calcium channels in cortical neurons. Gabapentin increases the synapconcentration of GABA, enhances GABA responses at non-synaptic sites in neuronal tissues, and reduces therelease of mono-amine neurotransmitters. One of the mechanisms implicated in this effect of gabapentin is thereduction of the axon excitability measured as an amplitude change of the presynaptic fibre volley (FV) in the Carea of the hippocampus. This is mediated through its binding to presynaptic NMDA receptors. Other studies h

shown that the antihyperalgesic and antiallodynic effects of gabapentin are mediated by the descendingnoradrenergic system, resulting in the activation of spinal alpha-2 adrenergic receptors. Gabapentin has also beshown to bind and activate the adenosine A1 receptor.

Society and culture

Sales

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 firmTeva.

Neurontin began as one of Pfizer's best selling drugs; however, Pfizer has come under heavy criticism and seriolitigation for its marketing of the drug. They face allegations that, behind the scenes, Parke-Davis marketed the

for at least a dozen supposed uses that the FDA had not approved. [40][41]Today it is a mainstay drug for

migraines, even though it was not approved for such use in 2004. [42]

FDA approval

Gabapentin was originally approved by the U.S. Food and Drug Administration (FDA) in 1994, for use as anadjuvant 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).[43]

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,[20]the preponderance of evidence

suggests that it is not effective.[44]Subsequent to the corporate acquisition of the original patent holder, thepharmaceutical company Pfizer admitted that there had been violations of FDA guidelines regarding the promotof 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 promotinthe epilepsy drug Neurontin ... Under federal RICO law the penalty is automatically tripled, so the finding will c

Pfizer $141 million."[45]The case stems from a claim from Kaiser Foundation Health Plan Inc. that "it was misle
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A capsule of

gabapentin

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."[46]

Bloomberg News(3/26/10, Van Voris, Lawrence) added that "during the trial, Pfizer argued that Kaiser doctocontinued to prescribe the drug even after the health insurer sued Pfizer in 2005. The insurer's website also still

Neurontin as a drug for neuropathic pain, Pfizer lawyers said in closing argument."[47]

The Wall Street Journal(3/26/10, Kamp) noted that Pfizer spokesman Christopher Loder said, "We aredisappointed with the verdict and will pursue post-trial motions and an appeal."[48]He would later add that "the

verdict and the judge's rulings are not consistent with the facts and the law."[45]

Franklin v. Pfizercase

By some estimates, off-labelprescriptions account for roughly 90 percent of Neurontin sales.[49]While off-lab

prescriptions are common for a number of drugs and are legal, marketing of off-label uses of a drug is illegal.[40

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 2004settlement was one of the largest in U.S. history, and the first off-label promotion case brought successfully undthe False Claims Act. The courts of New York State, for example, have refused to certify a class of injured par

who took Neurontin for off-label use, finding that they had failed to state that they had any injury.[50]

The University of California, San Francisco (UCSF) has archived[51]and studied[52]the documents made publthis case, which opens a window into the illegal promotion and marketing of pharmaceuticals. However, Pfizermaintains that the illegal activity originated in 1996, well before it acquired Parke-Davis (through its acquisition Warner-Lambert) in 2000. Several lawsuits are underway after people who had been prescribed gabapentin fooff-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, Fana

Gabarone, Gralise, Nupentin, Gabrion,[53]Penral, Gabapin.

Forms

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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The400-mg capsule shell also contains: gelatin, red iron oxide, titanium dioxide, and yellow iron oxide. T

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.[54]

Relateddrugs

Parke-Davisdeveloped a drug called pregabalin as a successor to gabapentin.[55]Pregabalin was brought tomarket byPfizer as Lyrica after the company acquired Warner-Lambert. Pregabalin is related in structure to

gabapentin.[56]Another new drug atagabalin has been trialled by Pfizer as a treatment for insomnia.[57]

Veterinary use

Gabapentin is also used for some animal treatments, but formulations (especially liquid forms) for human use macontain the sweetener Xylitol, which is toxic to dogsso veterinary use of the human version requires caution.[

See also

Gabapentin enacarbil

Pregabalin

Atagabalin

PhenibutBaclofen

References

1. ^ abcde"Neurontin, Gralise (gabapentin) dosing, indications, interactions, adverse effects, and more"

(http://reference.medscape.com/drug/neurontin-gralise-gabapentin-343011#showall). Medscape Reference.

WebMD. Retrieved 6 April 2014.

2. ^ abcdeGoa, KL; Sorkin, EM (September 1993). "Gabapentin. A review of its pharmacological properties anclinical potential in epilepsy.".Drugs46(3): 40927. doi:10.2165/00003495-199346030-00007

(http://dx.doi.org/10.2165%2F00003495-199346030-00007). PMID 7693432

(https://www.ncbi.nlm.nih.gov/pubmed/7693432).

3. ^Attal N, Cruccu G, Baron R, et al. (September 2010). "EFNS guidelines on the pharmacological treatment of

neuropathic pain: 2010 revision".Eur. J. Neurol.17(9): 1113e88. doi:10.1111/j.1468-1331.2010.02999.x

(http://dx.doi.org/10.1111%2Fj.1468-1331.2010.02999.x). PMID 20402746


4. ^ abVedula, SS; Bero L; Scherer RW; Dickersin K (November 2009). "Outcome reporting in industry-sponso
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doi:10.1056/NEJMsa0906126 (http://dx.doi.org/10.1056%2FNEJMsa0906126). PMID 19907043


5. ^"Gabapentin" (http://www.drugs.com/monograph/gabapentin.html). The American Society of Health-System

Pharmacists. Retrieved 3 April 2011.

6. ^Moore, RA; Wiffen PJ; Derry S; McQuay HJ (2011-03-16). "Gabapentin for chronic neuropathic pain and

fibromyalgia in adults". In Moore, R Andrew. Cochrane database of systematic reviews (Online)(3): CD00793

doi:10.1002/14651858.CD007938.pub2 (http://dx.doi.org/10.1002%2F14651858.CD007938.pub2).

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7. ^Ho, KY; Gan TJ; Habib AS (2006-12-15). "Gabapentin and postoperative pain--a systematic review of

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(http://dx.doi.org/10.1016%2Fj.pain.2006.06.018). PMID 16846695


8. ^Bar Ad, V (September 2010). "Gabapentin for the treatment of cancer-related pain syndromes". Reviews on

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(https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3010990). In Pai, Nitika Pant.Plos One5(12): e14433.

Bibcode:2010PLoSO...514433P (http://adsabs.harvard.edu/abs/2010PLoSO...514433P).

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(http://www.nlm.nih.gov/medlineplus/druginfo/meds/a694007.html)

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"Suicidal Behavior and Ideation and Antiepileptic Drugs"

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90.htm) U.S. Food and Drug Administration (FDA)

Neurontin (http://topics.nytimes.com/topics/news/health/diseasesconditionsandhealthtopics/neurontin_dru

collected news and commentary at The New York Times

"Gabapentin" (http://druginfo.nlm.nih.gov/drugportal/dpdirect.jsp?name=Gabapentin) Drug Information

Portal. U.S. National Library of Medicine.

Retrieved from "http://en.wikipedia.org/w/index.php?title=Gabapentin&oldid=611623921"

Categories: Amino acids Analgesics Anticonvulsants Anxiolytics GABA analogues Mood stabilizers

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center/professional-monographs/gabapentin-for-veterinary-use.html).
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