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Product Details:

  • CAS No: 60142-96-3
  • AHFC code: 28:12.9
  • Synonyms: Gabapentin GR Gabapentine [INN-French] Gabapentino [INN-Spanish] Gabapentino [Spanish] Gabapentinum [INN-Latin] Gabapetin
  • ATC Code: N03AX12
  • Chemical Formula: C18H20FN5O4
  • Molecular Weight: 171.2368
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB00996 (APRD00015)
  • SMILES: NCC1(CC(O)=O)CCCCC1
  • InChl: UGJMXCAKCUNAIE-UHFFFAOYSA-N
  • PubChem: 3446
  • IUPAC: 2-[1-(aminomethyl)cyclohexyl]acetic acid

Additional Details

Indication:
For the management of postherpetic neuralgia in adults and as adjunctive therapy in the treatment of partial seizures with and without secondary generalization in patients over 12 years of age with epilepsy.
Pharmacodynamics:
Gabapentin, an analog of GABA, is used as an anticonvulsant to treat partial seizures, amyotrophic lateral sclerosis (ALS), and painful neuropathies. Potential uses include monotherapy of refractory partial seizure disorders, and treatment of spasticity in multiple sclerosis, tremor. mood disorders, and attenuation of disruptive behaviors in dementia. Gabapentin has high lipid solubility, is not metabolized by the liver, has no protein binding, and doesn’t possess the usual drug interactions.
Mode of Action:
Gabapentin interacts with cortical neurons at auxillary subunits of voltage-sensitive calcium channels. Gabapentin increases the synaptic concentration of GABA, enhances GABA responses at non-synaptic sites in neuronal tissues, and reduces the release of mono-amine neurotransmitters. One of the mechanisms implicated in this effect of gabapentin is the reduction of the axon excitability measured as an amplitude change of the presynaptic fibre volley (FV) in the CA1 area of the hippocampus. This is mediated through its binding to presynaptic NMDA receptors. Other studies have shown that the antihyperalgesic and antiallodynic effects of gabapentin are mediated by the descending noradrenergic system, resulting in the activation of spinal alpha2-adrenergic receptors. Gabapentin has also been shown to bind and activate the adenosine A1 receptor.
Metabolism:
All pharmacological actions following gabapentin administration are due to the activity of the parent compound; gabapentin is not appreciably metabolized in humans.
Toxicity:
Symptoms of overdose include ataxia, labored breathing, ptosis, sedation, hypoactivity, and excitation.
General Reference:
Mathew NT, Rapoport A, Saper J, Magnus L, Klapper J, Ramadan N, Stacey B, Tepper S: Efficacy of gabapentin in migraine prophylaxis. Headache. 2001 Feb;41(2):119-28. Pubmed Backonja MM, Serra J: Pharmacologic management part 1: better-studied neuropathic pain diseases. Pain Med. 2004 Mar;5 Suppl 1:S28-47. Pubmed Choudhuri I, Sarvananthan N, Gottlob I: Survey of management of acquired nystagmus in the United Kingdom. Eye. 2007 Sep;21(9):1194-7. Epub 2006 May 26. Pubmed Pande AC, Crockatt JG, Janney CA, Werth JL, Tsaroucha G: Gabapentin in bipolar disorder: a placebo-controlled trial of adjunctive therapy. Gabapentin Bipolar Disorder Study Group. Bipolar Disord. 2000 Sep;2(3 Pt 2):249-55. Pubmed
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