Gabapentin

Title: Gabapentin
CAS Registry Number: 60142-96-3
CAS Name: 1-(Aminomethyl)cyclohexaneacetic acid
Manufacturers' Codes: CI-945; Gö-3450; GOE-3450
Trademarks: Neurontin (Parke-Davis)
Molecular Formula: C9H17NO2
Molecular Weight: 171.24
Percent Composition: C 63.13%, H 10.01%, N 8.18%, O 18.69%
Literature References: Calcium channel ligand structurally related to g-aminobutyric acid (GABA), q.v., designed to cross the blood brain barrier. Prepn: G. Satzinger et al., DE 2460891 (1976 to Gödecke); eidem, US 4024175 (1977 to Warner-Lambert). Pharmacokinetics and metabolism: K.-O. Vollmer et al., Arzneim.-Forsch. 36, 830 (1986). Clinical pharmacology: B. Saletu et al., Int. J. Clin. Pharmacol. Ther. Toxicol. 24, 362 (1986). GC determn in biological fluids: W. D. Hooper et al., J. Chromatogr. 529, 167 (1990). Clinical trial in treatment of pain in diabetic neuropathy: M. Backonja et al., J. Am. Med. Assoc. 280, 1831 (1998); in treatment of postherpetic neuralgia: M. Rowbotham et al., ibid. 1837. Review of pharmacology and clinical trials in epilepsy: B. Schmidt in Antiepileptic Drugs, R. H. Levy et al., Eds. (Raven Press, New York, 3rd ed., 1989) pp 925-935; K. L. Goa, E. M. Sorkin, Drugs 46, 409-427 (1993); of pharmacology and use in pain management: M. A. Rose, P. C. A. Kam, Anaesthesia 57, 451-462 (2002); of interactions with voltage-gated calcium channels: K. G. Sutton, T. P. Snutch, Drug Dev. Res. 54, 167-172 (2002).
Properties: Crystals from ethanol/ether, mp 162-166° (Satzinger); also reported as mp 165-167° (Schmidt). pKa1 (25°) 3.68; pKa2 10.70. Isoelectric point 7.14. Partition coefficient (octanol/buffer): 0.075 (pH 7.4). Solubility in water at pH 7.4 exceeds 10%.
Melting point: mp 162-166° (Satzinger); mp 165-167° (Schmidt)
pKa: pKa1 (25°) 3.68; pKa2 10.70
Log P: Partition coefficient (octanol/buffer): 0.075 (pH 7.4)
Therap-Cat: Anticonvulsant; analgesic.
Keywords: Anticonvulsant; Analgesic (Non-Narcotic).
Gabexate Gaboxadol Gadobenate Dimeglumine Gadodiamide Gadofosveset

Gabapentin
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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 POM (UK) -only (US) Prescription only
Routes Oral
Pharmacokinetic data
Bioavailability Rapid, in part by saturable carrier-mediated L-amino acid transport system
Protein binding Less than 3%
Metabolism Not appreciably metabolized
Half-life 5 to 7 hours
Excretion Renal
Identifiers
CAS number 60142-96-3 YesY
ATC code N03AX12
PubChem CID 3446
DrugBank DB00996
ChemSpider 3328 YesY
UNII 6CW7F3G59X YesY
KEGG D00332 YesY
ChEMBL CHEMBL940 YesY
Chemical data
Formula C9H17NO2 
Mol. mass 171.237 g/mol
 YesY (what is this?)  (verify)

Gabapentin (Neurontin) is a pharmaceutical drug, specifically a GABA analog. It was originally developed to treat epilepsy, and currently is also used to relieve neuropathic pain. It is also commonly prescribed by doctors for many off-label treatments, 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.[1][2]