Back غابابنتين Arabic گاباپنتین AZB Gabapentina Catalan Gabapentin Welsh Gabapentin German Γκαμπαπεντίνη Greek Gabapentina Spanish Gabapentina Basque گاباپنتین Persian Gabapentiini Finnish

Gabapentin

Gabapentin
Gabapentin.acid
Clinical data
Trade namesNeurontin, others[1]
Other namesCI-945; GOE-3450; DM-1796 (Gralise)
AHFS/Drugs.comMonograph
MedlinePlusa694007
License data
Pregnancy
category
Dependence
liability		Physical: High[3]
Psychological: Moderate
Addiction
liability		Low[4]
Routes of
administration		By mouth
Drug classGabapentinoid
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability27–60% (inversely proportional to dose; a high-fat meal also increases bioavailability)[8][9]
Protein bindingLess than 3%[8][9]
MetabolismNot significantly metabolized[8][9]
Elimination half-life5 to 7 hours[8][9]
ExcretionKidney[8][9]
Identifiers
  • 2-[1-(Aminomethyl)cyclohexyl]acetic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.056.415 Edit this at Wikidata
Chemical and physical data
FormulaC9H17NO2
Molar mass171.240 g·mol−1
3D model (JSmol)
  • O=C(O)CC1(CN)CCCCC1
  • InChI=1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12) checkY
  • Key:UGJMXCAKCUNAIE-UHFFFAOYSA-N checkY
  (verify)

Gabapentin, sold under the brand name Neurontin among others, is an anticonvulsant medication primarily used to treat neuropathic pain and also for partial seizures[10][7] of epilepsy. It is a commonly used medication for the treatment of neuropathic pain caused by diabetic neuropathy, postherpetic neuralgia, and central pain.[11] It is moderately effective: about 30–40% of those given gabapentin for diabetic neuropathy or postherpetic neuralgia have a meaningful benefit.[12]

Gabapentin, like other gabapentinoid drugs, acts by decreasing activity of the α2δ-1 protein, coded by the CACNA2D1 gene, first known as an auxiliary subunit of voltage gated calcium channels.[13][14][15] However, see Pharmacodynamics, below. By binding to α2δ-1, gabapentin reduces the release of excitatory neurotransmitters (primarily 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 effects. Serious side effects include respiratory depression, and allergic reactions.[7] As with all other antiepileptic drugs approved by the FDA, gabapentin is labeled for an increased risk of suicide. Lower doses are recommended in those with kidney disease.[7]

Gabapentin was first approved for use in the United Kingdom in 1993.[16] It has been available as a generic medication in the United States since 2004.[17] It is the first of several other drugs that are similar in structure and mechanism, called gabapentinoids. In 2022, it was the tenth most commonly prescribed medication in the United States, with more than 40 million prescriptions.[18][19] During the 1990s, Parke-Davis, a subsidiary of Pfizer, used a number of illegal techniques to encourage physicians in the United States to prescribe gabapentin for unapproved uses.[20] They have paid out millions of dollars to settle lawsuits regarding these activities.[21]

  1. ^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  2. ^ "Gabapentin Use During Pregnancy". Drugs.com. 2 December 2019. Retrieved 21 December 2019.
  3. ^ Tran KT, Hranicky D, Lark T, Jacob NJ (June 2005). "Gabapentin withdrawal syndrome in the presence of a taper". Bipolar Disorders. 7 (3): 302–4. doi:10.1111/j.1399-5618.2005.00200.x. PMID 15898970.
  4. ^ Schifano F (June 2014). "Misuse and abuse of pregabalin and gabapentin: cause for concern?". CNS Drugs. 28 (6): 491–496. doi:10.1007/s40263-014-0164-4. PMID 24760436.
  5. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  6. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
  7. ^ a b c d Cite error: The named reference Neurontin label was invoked but never defined (see the help page).
  8. ^ a b c d e "Neurontin, Gralise (gabapentin) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Archived from the original on 16 December 2014. Retrieved 6 April 2014.
  9. ^ a b c d e Goa KL, Sorkin EM (September 1993). "Gabapentin. A review of its pharmacological properties and clinical potential in epilepsy". Drugs. 46 (3): 409–427. doi:10.2165/00003495-199346030-00007. PMID 7693432. S2CID 265753780.
  10. ^ Cite error: The named reference NICE was invoked but never defined (see the help page).
  11. ^ Attal N, Cruccu G, Baron R, Haanpää M, Hansson P, Jensen TS, et al. (September 2010). "EFNS guidelines on the pharmacological treatment of neuropathic pain: 2010 revision". European Journal of Neurology. 17 (9): 1113–1e88. doi:10.1111/j.1468-1331.2010.02999.x. PMID 20402746. S2CID 14236933.
  12. ^ Cite error: The named reference Wiffen2017 was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference pmid32521436 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference pmid23642658 was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference pmid32321743 was invoked but never defined (see the help page).
  16. ^ Pitkänen A, Schwartzkroin PA, Moshé SL (2005). Models of Seizures and Epilepsy. Burlington: Elsevier. p. 539. ISBN 978-0-08-045702-4. Archived from the original on 8 September 2017.
  17. ^ Cite error: The named reference Reed2012 was invoked but never defined (see the help page).
  18. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  19. ^ "Gabapentin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  20. ^ Henney JE (August 2006). "Safeguarding patient welfare: who's in charge?". Annals of Internal Medicine. 145 (4): 305–307. doi:10.7326/0003-4819-145-4-200608150-00013. PMID 16908923. S2CID 39262014.
  21. ^ Stempel J (2 June 2014). "Pfizer to pay $325 million in Neurontin settlement". Reuters. Retrieved 11 June 2018.
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