Gabapentin

Gabapentin

Clinical data
Trade names	Neurontin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a694007
License data	US DailyMed: 52049
Pregnancy category	AU: B1 US: C (Risk not ruled out)
Routes of administration	By mouth
ATC code	N03AX12 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	27–60% (inversely proportional to dose; a high fat meal also increases bioavailability)
Protein binding	Less than 3%
Metabolism	Not significantly metabolised
Biological half-life	5 to 7 hours
Excretion	Renal
Identifiers
IUPAC name 1-(aminomethyl)cyclohexaneacetic acid
CAS Number	60142-96-3 Y
PubChem (CID)	3446
IUPHAR/BPS	5483
DrugBank	DB00996 Y
ChemSpider	3328 Y
UNII	6CW7F3G59X Y
KEGG	D00332 Y
ChEBI	CHEBI:42797 Y
ChEMBL	CHEMBL940 Y
PDB ligand ID	GBN (PDBe, RCSB PDB)
ECHA InfoCard	100.056.415
Chemical and physical data
Formula	C9H17NO2
Molar mass	171.237 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(O)CC1(CN)CCCCC1
InChI InChI=1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12) Y Key:UGJMXCAKCUNAIE-UHFFFAOYSA-N Y

Gabapentin (GPN) marketed under the brand name Neurontin among others, is a medication used to treat epilepsy, neuropathic pain, hot flashes, and restless leg syndrome. In epilepsy it may be used for those with partial seizures. It is recommended as one of a number of first line medications for the treatment of neuropathic pain in diabetic neuropathy, post-herpetic neuralgia, and central neuropathic pain. A 2014 review of its use for diabetic neuropathy and postherpetic neuralgia found about 14% of people have a meaningful benefit.

Common side effects include sleepiness and dizziness. Serious side effects may include an increased risk of suicide, aggressive behaviour, and drug reaction with eosinophilia and systemic symptoms. It is unclear if it is safe during pregnancy or breastfeeding. Lower doses should be used in people with kidney problems. Gabapentin affects the inhibitory neurotransmitter γ-aminobutyric acid (GABA) but how it works is otherwise unclear.

Gabapentin was first approved for use in 1993. The wholesale price in the developing world is about US$40.50 per month. In the United States it has been available as a generic medication since 2004. As of 2015 the cost for a typical month of medication in the United States is US$100 to US$200. During the 1990s Parke-Davis, a sub-company of Pfizer, used a number of techniques to encourage physicians in the United States to use gabapentin for unapproved uses.