2-[1-(aminomethyl)cyclohexyl]acetic acid

• ChemBase ID: 869
• Molecular Formular: C9H17NO2
• Molecular Mass: 171.23678
• Monoisotopic Mass: 171.12592879
• SMILES: OC(=O)CC1(CCCCC1)CN
• Canonical SMILES: NCC1(CCCCC1)CC(=O)O
• InChI: InChI=1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12)
• InChIKey: UGJMXCAKCUNAIE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[1-(aminomethyl)cyclohexyl]acetic acid
• IUPAC Traditional name: gabapentin; 2-[1-(aminomethyl)cyclohexyl]acetic acid
• Brand Name: Aclonium; Neurontin; Novo-Gabapentin
• Synonyms: 1-(Aminomethyl)cyclohexaneacetic Acid, Neurontin, GOE-3450; Fanatrex; Gabarone; Neurontin; 1-(Aminomethyl)-cyclohexaneacetic acid; Gabapentin; Gabapentine [INN-French]; Gabapentino [INN-Spanish]; Gabapentino [Spanish]; Gabapentinum [INN-Latin]; Gabapetin; Gabapentin GR; gabapentin; Gabapentin; 2-(1-(aminomethyl)cyclohexyl)acetic acid; (1-Aminomethyl-cyclohexyl)-acetic acid; Aclonium; 2-[1-(aminomethyl)cyclohexyl]acetic acid

Database IDs

• CAS Number: 60142-96-3
• EC Number: 262-076-3
• MDL Number: MFCD00865286
• Beilstein Number: 2359739
• PubChem SID: 160964332; 46506529; 24278159
• PubChem CID: 3446

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.6313047
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.3162769
• LogD (pH = 7.4): -1.2728618
• Log P: -1.273033
• Molar Refractivity: 46.3283 cm^3
• Polarizability: 18.621471 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.88
• LOG S: -1.6
• Solubility (Water): 4.34e+00 g/l

PROPERTIES

Physical Property

• Solubility: 4490 mg/L; H2O: soluble10 mg/mL; Methanol; Water
• Apperance: off-white solid; White to Off-White Solid
• Melting Point: 162-166°C; 169 - 171°C
• Hydrophobicity(logP): -0.66; 1.4

Safety Information

• Storage Condition: -20°C; Refrigerator
• Storage Warning: IRRITANT
• RTECS: GU6496000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 61-36/37/38
• Safety Statements: 26-36/37/39-45
• TSCA Listed: false
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H319-H335-H360
• GHS Precautionary statements: P201-P261-P305 + P351 + P338-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Pharmacology Properties

• Gene Information: human ... ADORA1(134), CACNA2D1(781)rat ... Cacna1a(25398)
• Mechanism of Action: GABA-like amino acid which penetrates the blood-brain barrier; regulator; Voltage-gated N-type calcium ion channels

Product Information

• Purity: >98.; 95%; 97%; 98%
• Salt Data: Free Base
• Application(s): Anticonvulsant; CNS depressant
• Pharmacopeia Traceability: traceable to USP 1287303
• Empirical Formula (Hill Notation): C9H17NO2

DETAILS

DrugBank - DB00996

• Drug Groups: approved; investigational
• Description: Gabapentin (brand name Neurontin) is a medication originally developed for the treatment of epilepsy. Presently, gabapentin is widely used to relieve pain, especially neuropathic pain. Gabapentin is well tolerated in most patients, has a relatively mild side-effect profile, and passes through the body unmetabolized.
• 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.
• Pharmacology: 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.
• Toxicity: Symptoms of overdose include ataxia, labored breathing, ptosis, sedation, hypoactivity, and excitation.
• Affected Organisms: Humans and other mammals
• Biotransformation: All pharmacological actions following gabapentin administration are due to the activity of the parent compound; gabapentin is not appreciably metabolized in humans.
• Absorption: Rapid. Absorbed in part by the L-amino acid transport system, which is a carrier-mediated, saturable transport system; as the dose increases, bioavailability decreases. Bioavailability ranges from approximately 60% for a 900 mg dose per day to approximately 27% for a 4800 milligram dose per day. Food has a slight effect on the rate and extent of absorption of gabapentin (14% increase in AUC).
• Half Life: 5-7 hours
• Protein Binding: Less than 3% of gabapentin circulates bound to plasma protein.
• Elimination: Gabapentin is eliminated from the systemic circulation by renal excretion as unchanged drug.; Gabapentin is not appreciably metabolized in humans.
• Distribution: * 58±6 L
• Clearance: * 190 mL/min
• References: 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]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S2133

Research Area: Neurological Disease
Biological Activity:
Gabapentin (Neurontin) is a pharmaceutical agent, specifically a GABA analogue. Gabapentin (Neurontin) was originally developed for the treatment of epilepsy, and currently, gabapentin is widely used to relieve pain, especially neuropathic pain. Its therapeutic action on neuropathic pain is thought to involve voltage-gated N-type calcium ion channels. It is thought to bind to the α2δ subunit (1 and 2) of the voltage-dependent calcium channel in the central nervous system. [1][2]

Sigma Aldrich - G154

Biochem/physiol Actions
Anticonvulsant with unknown mechanism of action; crosses the blood brain barrier; increases GABA concentrations in the brain and reduces excitatory amino acid neurotransmission, perhaps through its effects on voltage-gated calcium channels; exhibits antinociceptive, anxiolytic, neuroprotective and anti-epileptic effects.

Toronto Research Chemicals - G117250

Amino acid structurally related to γ-Aminobutyric Acid (GABA), designed to cross the blood brain barrier. Used as an anticonvulsant.

REFERENCES

• 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
• http://en.wikipedia.org/wiki/Gabapentin
• Vollmer, K.-O. et al.: Arzneimittel-Forshc., 36, 830 (1986)
• Saletu, B., et al.: Int. J. Clin. Pharmacol. Ther. Toxicol., 24, 362 (1986)
• Ger. Pat., 1976, Goedecke, 2 460 891; CA, 85, 94679h, (synth)
• Hengy, H. et al., J. Chromatogr., 1985, 341; 473, (hplc)
• Vollmer, K.O. et al., Arzneim.-Forsch., 1986, 36, 830, (metab)
• Bartoszyk, G.D. et al., Curr. Probl. Epilepsy, 1986, 4, 147, (rev, pharmacol)
• Griffiths, G. et al., Helv. Chim. Acta, 1991, 74, 309, (synth, bibl)
• Goa, K.L. et al., Drugs, 1993, 46, 409, (rev)
• Antiepileptic Drugs, 4th edn., (eds., Levy, R.H. et al), Raven Press, 1995
• Pellock, J.M., Drugs of Today (Barcelona), 1998, 34, 31-35, (rev, pharmacol)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 346