Gabapentin

Gabapentin
Clinical data
Trade names	Neurontin, others
Other names	CI-945; GOE-3450; DM-1796 (Gralise)
AHFS/Drugs.com	Monograph
MedlinePlus	a694007
License data	US DailyMed: Gabapentin;
Pregnancy; category	AU: B1;
Dependence; liability	Low – Moderate
Addiction; liability	Low
Routes of; administration	By mouth
Drug class	Gabapentinoid
ATC code	N02BF01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); CA: ℞-only; UK: Class C; 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 metabolized
Elimination half-life	5 to 7 hours
Excretion	Kidney
Identifiers
	IUPAC name 2-[1-(Aminomethyl)cyclohexyl]acetic acid;
CAS Number	60142-96-3 ;
PubChem CID	3446;
IUPHAR/BPS	5483;
DrugBank	DB00996 ;
ChemSpider	3328 ;
UNII	6CW7F3G59X;
KEGG	D00332 ;
ChEBI	CHEBI:42797 ;
ChEMBL	ChEMBL940 ;
PDB ligand	GBN (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID0020074 ;
ECHA InfoCard	100.056.415
Chemical and physical data
Formula	C9H17NO2
Molar mass	171.240 g·mol−1
3D model (JSmol)	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) ; Key:UGJMXCAKCUNAIE-UHFFFAOYSA-N ;
	(verify)

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

Sleepiness and dizziness are the most common side effects. Serious side effects include an increased risk of suicide, respiratory depression, and allergic reactions. Lower doses are recommended in those with kidney disease. Gabapentin acts by decreasing activity of a subset of calcium channels.

Gabapentin was first approved for use in 1993. It has been available as a generic medication in the United States since 2004. In 2021, it was the tenth most commonly prescribed medication in the United States, with more than 47 million prescriptions. 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. They have paid out millions of dollars to settle lawsuits regarding these activities.

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