Editing Gabapentin (section)

{{Short description|Anticonvulsant medication}}
{{Use American English|date=September 2017}}
{{Use dmy dates|date=August 2024}}
{{Cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| verifiedrevid      = 461115603
| image              = Gabapentin2DACS.svg
| image_class        = skin-invert-image
| width              = 
| alt                = Gabapentin.acid
| image2             = Gabapentin3Dan.gif
| width2             = 
| alt2               = 
| caption            = 

<!-- Clinical data -->
| pronounce          = 
| tradename          = Neurontin, others<ref name="Drugs.com"/>
| Drugs.com          = {{drugs.com|monograph|gabapentin}}
| MedlinePlus        = a694007
| DailyMedID         = Gabapentin
| pregnancy_AU       = B1
| pregnancy_AU_comment = <ref name="Drugs.com Pregnancy">{{cite web | title=Gabapentin Use During Pregnancy | website=Drugs.com | date=2 December 2019 | url=https://www.drugs.com/pregnancy/gabapentin.html | access-date=21 December 2019}}</ref>
| pregnancy_category = 
| dependency_liability = [[Physical dependence|Physical]]: High<ref>{{cite journal | vauthors = Tran KT, Hranicky D, Lark T, Jacob NJ | title = Gabapentin withdrawal syndrome in the presence of a taper | journal = Bipolar Disorders | volume = 7 | issue = 3 | pages = 302–4 | date = June 2005 | pmid = 15898970 | doi = 10.1111/j.1399-5618.2005.00200.x }}</ref><br/>[[Psychological dependence|Psychological]]: Moderate
| addiction_liability = Low<ref name="Sch2014">{{cite journal | vauthors = Schifano F | title = Misuse and abuse of pregabalin and gabapentin: cause for concern? | journal = CNS Drugs | volume = 28 | issue = 6 | pages = 491–496 | date = June 2014 | pmid = 24760436 | doi = 10.1007/s40263-014-0164-4 | doi-access = free }}</ref>
| routes_of_administration = [[Oral administration|By mouth]]
| class              = [[Gabapentinoid]]
| ATC_prefix         = N02
| ATC_suffix         = BF01
| ATC_supplemental   = 

<!-- Legal status -->
| legal_AU           = S4
| legal_AU_comment   = <ref>{{cite web | title=Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017 | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 | url=https://www.tga.gov.au/resources/publication/publications/prescription-medicines-registration-new-generic-medicines-and-biosimilar-medicines-2017 | access-date=30 March 2024}}</ref>
| legal_BR           = C1
| legal_BR_comment   = <ref>{{cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=31 March 2023 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=3 August 2023 |access-date=16 August 2023 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=4 April 2023}}</ref>
| legal_CA           = Rx-only
| legal_CA_comment   = 
| legal_DE           = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment   = 
| legal_NZ           = <!-- Class A, B, C -->
| legal_NZ_comment   = 
| legal_UK           = Class C
| legal_UK_comment   = 
| legal_US           = Rx-only, schedule 5 in select states
| legal_US_comment   = <ref name="Neurontin label" />
| legal_UN           = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment   = 
| legal_status       = <!-- For countries not listed above -->

<!-- Pharmacokinetic data -->
| bioavailability    = 27–60% (inversely proportional to dose; a high-fat meal also increases bioavailability)<ref name=MSR>{{cite web |title = Neurontin, Gralise (gabapentin) dosing, indications, interactions, adverse effects, and more |work = Medscape Reference |publisher = WebMD |access-date = 6 April 2014 |url = http://reference.medscape.com/drug/neurontin-gralise-gabapentin-343011#showall |url-status=live |archive-url = https://web.archive.org/web/20141216215811/http://reference.medscape.com/drug/neurontin-gralise-gabapentin-343011#showall |archive-date = 16 December 2014 }}</ref><ref name = drugs93>{{cite journal | vauthors = Goa KL, Sorkin EM | title = Gabapentin. A review of its pharmacological properties and clinical potential in epilepsy | journal = Drugs | volume = 46 | issue = 3 | pages = 409–427 | date = September 1993 | pmid = 7693432 | doi = 10.2165/00003495-199346030-00007 | s2cid = 265753780 }}</ref>
| protein_bound      = Less than 3%<ref name = MSR /><ref name = drugs93 />
| metabolism         = Not significantly metabolized<ref name = MSR /><ref name = drugs93 />
| metabolites        = 
| onset              = 
| elimination_half-life = 5 to 7 hours<ref name = MSR /><ref name = drugs93 />
| duration_of_action = 
| excretion          = [[Kidney]]<ref name = MSR /><ref name = drugs93 />

<!-- Identifiers -->
| CAS_number_Ref     = {{cascite|correct|CAS}}
| CAS_number         = 60142-96-3
| PubChem            = 3446
| IUPHAR_ligand      = 5483
| DrugBank_Ref       = {{drugbankcite|correct|drugbank}}
| DrugBank           = DB00996
| ChemSpiderID_Ref   = {{chemspidercite|correct|chemspider}}
| ChemSpiderID       = 3328
| UNII_Ref           = {{fdacite|correct|FDA}}
| UNII               = 6CW7F3G59X
| KEGG_Ref           = {{keggcite|correct|kegg}}
| KEGG               = D00332
| ChEBI_Ref          = {{ebicite|correct|EBI}}
| ChEBI              = 42797
| ChEMBL_Ref         = {{ebicite|correct|EBI}}
| ChEMBL             = 940
| NIAID_ChemDB       = 
| PDB_ligand         = GBN
| synonyms           = CI-945; GOE-3450; DM-1796 (Gralise)

<!-- Chemical and physical data -->
| IUPAC_name         = 2-[1-(Aminomethyl)cyclohexyl]acetic acid
| C                  = 9
| H                  = 17
| N                  = 1
| O                  = 2
| SMILES             = O=C(O)CC1(CN)CCCCC1
| StdInChI_Ref       = {{stdinchicite|correct|chemspider}}
| StdInChI           = 1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12)
| StdInChI_comment   = 
| StdInChIKey_Ref    = {{stdinchicite|correct|chemspider}}
| StdInChIKey        = UGJMXCAKCUNAIE-UHFFFAOYSA-N
| density            = 
| density_notes      = 
| melting_point      = 
| melting_high       = 
| melting_notes      = 
| boiling_point      = 
| boiling_notes      = 
| solubility         = 
| sol_units          = 
| specific_rotation  = 
}}

<!-- Definition and medical uses -->
'''Gabapentin''', sold under the brand name '''Neurontin''' among others, is an [[anticonvulsant]] medication primarily used to treat [[neuropathic pain]] and also for [[partial seizures]]<ref name="NICE"/><ref name="Neurontin label" /> of [[epilepsy]]. It is a commonly used medication for the treatment of neuropathic pain caused by [[diabetic neuropathy]], [[postherpetic neuralgia]], and [[central neuropathic pain|central pain]].<ref name=Attal2010>{{cite journal | vauthors = Attal N, Cruccu G, Baron R, Haanpää M, Hansson P, Jensen TS, Nurmikko T | title = EFNS guidelines on the pharmacological treatment of neuropathic pain: 2010 revision | journal = European Journal of Neurology | volume = 17 | issue = 9 | pages = 1113–1e88 | date = September 2010 | pmid = 20402746 | doi = 10.1111/j.1468-1331.2010.02999.x | s2cid = 14236933 | title-link = doi | doi-access = free }}</ref> It is moderately effective: about 30–40% of those given gabapentin for diabetic neuropathy or postherpetic neuralgia have a meaningful benefit.<ref name=Wiffen2017 />

<!-- Side effects and mechanism -->
Gabapentin, like other [[gabapentinoid]] drugs, acts by decreasing activity of the [[CACNA2D1|α<sub>2</sub>δ-1 protein, coded by the CACNA2D1 gene]], first known as an auxiliary subunit of [[Voltage-gated calcium channel#α2δ Subunit|voltage gated calcium channels]].<ref name="pmid32521436" /><ref name="pmid23642658" /><ref name="pmid32321743" /> However, see Pharmacodynamics, below. By binding to α<sub>2</sub>δ-1, gabapentin reduces the release of excitatory [[Neurotransmitter|neurotransmitters]] (primarily [[Glutamic acid|glutamate]]) and as a result, reduces excess excitation of neuronal networks in the [[spinal cord]] and brain. Sleepiness and [[dizziness]] are the most common [[side effect]]s. Serious side effects include [[respiratory depression]], and [[allergy|allergic reactions]].<ref name="Neurontin label" /> As with all other antiepileptic drugs approved by the [[Food and Drug Administration|FDA]], gabapentin is labeled for an increased risk of [[suicide]]. Lower doses are recommended in those with [[kidney disease]].<ref name="Neurontin label" /> 

<!-- History, society and culture -->
Gabapentin was first approved for use in the United Kingdom in 1993.<ref>{{cite book | vauthors = Pitkänen A, Schwartzkroin PA, Moshé SL |title = Models of Seizures and Epilepsy |date = 2005 |publisher = Elsevier |location = Burlington |isbn = 978-0-08-045702-4 |page = 539 |url = https://books.google.com/books?id=Qw6KqLjwtZQC&pg=PA539 |url-status=live |archive-url = https://web.archive.org/web/20170908192246/https://books.google.com/books?id=Qw6KqLjwtZQC&pg=PA539 |archive-date = 8 September 2017 }}</ref> It has been available as a [[generic medication]] in the United States since 2004.<ref name="Reed2012"/> It is the first of several other drugs that are similar in structure and mechanism, called [[Gabapentinoid|gabapentinoids]]. In 2022, it was the tenth most commonly prescribed medication in the United States, with more than 40{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Gabapentin Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Gabapentin | access-date = 30 August 2024 }}</ref> During the 1990s, [[Parke-Davis]], a subsidiary of [[Pfizer]], used a number of illegal techniques to encourage [[physician]]s in the United States to prescribe gabapentin for [[off-label|unapproved]] uses.<ref name=Hen2006>{{cite journal | vauthors = Henney JE | title = Safeguarding patient welfare: who's in charge? | journal = Annals of Internal Medicine | volume = 145 | issue = 4 | pages = 305–307 | date = August 2006 | pmid = 16908923 | doi = 10.7326/0003-4819-145-4-200608150-00013 | s2cid = 39262014 }}</ref> They have paid out millions of dollars to settle lawsuits regarding these activities.<ref>{{cite news | vauthors = Stempel J |title=Pfizer to pay $325 million in Neurontin settlement |url=https://www.reuters.com/article/us-pfizer-neurontin-settlement/pfizer-to-pay-325-million-in-neurontin-settlement-idUSKBN0ED1IS20140602 |access-date=11 June 2018 |work=Reuters |date=2 June 2014}}</ref>

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