CAS 60142-96-3|gabapentin|Gabapentin|1-(Aminomethyl)-cyclohexaneacetic acid|2-[1-(aminomethyl)cyclohexyl]acetic acid|Neurontin|Gabapentine [INN-French]|Gabapentinum [INN-Latin]|Aclonium|Neurontin|Ga...

General Information

Structure

Molecular Formula

C₉H₁₇NO₂

Molecular Mass

171.23678

Exact Mass

171.12592879

Charge

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

Canonic Smiles

NCC1(CCCCC1)CC(=O)O

Isomeric Smiles

OC(=O)CC1(CCCCC1)CN

Calculated Properties

JChem

LogD (pH = 7.4)

-1.27

LogD (pH = 5.5)

-1.32

Log P

-1.27

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

4.63

Polar Surface Area

63.32

Polarizability

18.92

Molar Refractivity

46.33

LOG S

-1.13

Data Source

Names and Identifiers

IUPAC Traditional name

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

Synonyms

Gabapentin1-(Aminomethyl)-cyclohexaneacetic acidNeurontinGabapentine [INN-French]Gabapentinum [INN-Latin]Gabapentino [Spanish]GabapentinGabapentino [INN-Spanish]gabapentinGabapentin GRGabapetinFanatrexGabarone2-(1-(aminomethyl)cyclohexyl)acetic acid2-[1-(aminomethyl)cyclohexyl]acetic acid1-(Aminomethyl)cyclohexaneacetic Acid, Neurontin, GOE-3450Aclonium(1-Aminomethyl-cyclohexyl)-acetic acidgabapentin1-(Aminomethyl)cyclohexaneacetic acid

IUPAC name

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

Brand Name

AcloniumNeurontinNovo-Gabapentin

API Name

Gabapentin

International Nonproprietary Name (INN)

gabapentingabapentinumgabapentinagabapentine

Names and Identifiers

Registration numbers

Beilstein Number

2359739

EC Number

262-076-3

PubChem SID

2427815946506529160964332160644672

MDL Number

CAS Number

PubChem CID

DrugBank ID

PubMed Citation Links

23018586222793472288880122422817222966502214403422865488229340772234540522556282224647462204828522467888222408392305364522240859

MetaboLights Database

MTBLS406MTBLS2878MTBLS1692MTBLS1918MTBLS2349MTBLS2406MTBLS591MTBLS407MTBLS804MTBLS136MTBLS1693MTBLS1455MTBLS2633MTBLS2145

BRENDA Database

2.7.1.12.6.1.42

Drug Central Database

1,264

BKMS React Database

9643

MassBank Database

EA256104EA256113EA256112EA256110EA256114EA256101EA256102EA256107EA256103EA256111EA256109EA256105EA256106EA256108

BRENDA Ligand Database

9643

Patent number

WO2010023694US2009043126US2012046272WO2005037784EP1140793US2008103334WO2008060572US2008269326US2009292138

Wikipedia Title

Gabapentin

SABIO-RK Database

6836130561352

LINCS Database

LSM-5716

UniProt Database

Q7Z3S7Q01650P54290Q8CFG5P13806Q9NY47Q8IZS8Q8CFG6O08532Q6PHS9P54289Q9Z1L5

CHEBI ID

CHEBI:42797CHEBI:5237

CHEMBL

HMDB Database

Protein Data Bank

VSDB Database

CompTox Database

SureChEMBL Database

PDBeChem Database

KEGG DRUG Database

Reaxys Registry

ACToR Database

BindingDB Database

Registration numbers

Properties

Pharmacology Properties

human ... ADORA1(134), CACNA2D1(781)rat ... Cacna1a(25398)

regulator

GABA-like amino acid which penetrates the blood-brain barrier

Voltage-gated N-type calcium ion channels

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule 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.

TRC

G117250

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

ChEBI

CHEBI:42797

A gamma-amino acid that is cyclohexane substituted at position 1 by aminomethyl and carboxymethyl groups. Used for treatment of neuropathic pain and restless legs syndrome.

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• 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

• Backonja MM, Serra J: Pharmacologic management part 1: better-studied neuropathic pain diseases. Pain Med. 2004 Mar;5 Suppl 1:S28-47. 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)

• Bartoszyk, G.D. et al., Curr. Probl. Epilepsy, 1986, 4, 147, (rev, pharmacol)

• Ger. Pat., 1976, Goedecke, 2 460 891; CA, 85, 94679h, (synth)

• Hengy, H. et al., J. Chromatogr., 1985, 341; 473, (hplc)

• Pellock, J.M., Drugs of Today (Barcelona), 1998, 34, 31-35, (rev, pharmacol)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 346

• Antiepileptic Drugs, 4th edn., (eds., Levy, R.H. et al), Raven Press, 1995

• Vollmer, K.O. et al., Arzneim.-Forsch., 1986, 36, 830, (metab)

• Griffiths, G. et al., Helv. Chim. Acta, 1991, 74, 309, (synth, bibl)

• Goa, K.L. et al., Drugs, 1993, 46, 409, (rev)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

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

Synonyms

IUPAC name

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

Brand Name

AcloniumNeurontinNovo-Gabapentin

API Name

Gabapentin

International Nonproprietary Name (INN)

gabapentingabapentinumgabapentinagabapentine

Molecule Details

DrugBank

DB00996

Drug Groups

approved; investigational

Description

Indication

Pharmacology

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

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]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Selleck Chemicals

S2133

Sigma Aldrich

G154

TRC

G117250

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

ChEBI

CHEBI:42797

A gamma-amino acid that is cyclohexane substituted at position 1 by aminomethyl and carboxymethyl groups. Used for treatment of neuropathic pain and restless legs syndrome.

References

PubChem Literature

From Data Sources

• 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

• 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

• Backonja MM, Serra J: Pharmacologic management part 1: better-studied neuropathic pain diseases. Pain Med. 2004 Mar;5 Suppl 1:S28-47. 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)

• Bartoszyk, G.D. et al., Curr. Probl. Epilepsy, 1986, 4, 147, (rev, pharmacol)

• Ger. Pat., 1976, Goedecke, 2 460 891; CA, 85, 94679h, (synth)

• Hengy, H. et al., J. Chromatogr., 1985, 341; 473, (hplc)

• Pellock, J.M., Drugs of Today (Barcelona), 1998, 34, 31-35, (rev, pharmacol)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 346

• Antiepileptic Drugs, 4th edn., (eds., Levy, R.H. et al), Raven Press, 1995

• Vollmer, K.O. et al., Arzneim.-Forsch., 1986, 36, 830, (metab)

• Griffiths, G. et al., Helv. Chim. Acta, 1991, 74, 309, (synth, bibl)