Identification

Name
Gabapentin
Accession Number
DB00996
Description

Gabapentin is a structural analogue of the inhibitory neurotransmitter gamma-aminobutyric acid (GABA) that was first approved for use in the United States in 1993.16 It was originally developed as a novel anti-epileptic for the treatment of certain types of seizures14,5 - today it is also widely used to treat neuropathic pain.8,10 Gabapentin has some stark advantages as compared with other anti-epileptics, such as a relatively benign adverse effect profile, wide therapeutic index, and lack of appreciable metabolism making it unlikely to participate in pharmacokinetic drug interactions.5,3,16. It is structurally and functionally related to another GABA derivative, pregabalin.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 171.2368
Monoisotopic: 171.125928793
Chemical Formula
C9H17NO2
Synonyms
  • 1-(Aminomethyl)cyclohexaneacetic acid
  • Gabapentin
  • Gabapentina
  • Gabapentine
  • Gabapentino
  • Gabapentinum
External IDs
  • CI-945
  • DM-1796
  • GOE 3450
  • GOE-3450

Pharmacology

Indication

In the United States, gabapentin is officially indicated for the treatment of postherpetic neuralgia in adults and for the adjunctive treatment of partial-onset seizures, with or without secondary generalization, in patients 3 years of age and older.16 In Europe, gabapentin is indicated for adjunctive therapy in the treatment of partial-onset seizures, with or without secondary generalization, in patients 6 years of age and older and as monotherapy in patients 12 years of age and older. It is also used in adults for the treatment of various types of peripheral neuropathic pain, such as painful diabetic neuropathy.19

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Gabapentin is an anti-convulsant medication that inhibits the release of excitatory neurotransmitters, allowing for its use against pathologic neurotransmission such as that seen in neuropathic pain and seizure disorders.16,19 It has a wide therapeutic index, with doses in excess of 8000 mg/kg failing to cause a fatal reaction in rats.21

Gabapentin is ineffective in absence seizures and should be used in caution in patients with mixed seizure disorders involving absence seizures. Gabapentin has been associated with drug reaction with eosinophilia and systemic symptoms (DRESS), otherwise known as multi-organ hypersensitivity. This reaction can prove fatal and early symptoms such as fever, lymphadenopathy, and rash should be promptly investigated.16,17,19

Mechanism of action

The precise mechanism through which gabapentin exerts its therapeutic effects is unclear.16,17 The primary mode of action appears to be at the auxillary α2δ-1 subunit of voltage-gated calcium channels (though a low affinity for the α2δ-2 subunit has also been reported).10,8,14 The major function of these subunits is to facilitate the movement of pore-forming α1 subunits of calcium channels from the endoplasmic reticulum to the cell membrane of pre-synaptic neurons.10 There is evidence that chronic pain states can cause an increase in the expression of α2δ subunits and that these changes correlate with hyperalgesia.8 Gabapentin appears to inhibit the action of α2δ-1 subunits, thus decreasing the density of pre-synaptic voltage-gated calcium channels and subsequent release of excitatory neurotransmitters.10 It is likely that this inhibition is also responsible for the anti-epileptic action of gabapentin.14

There is some evidence that gabapentin also acts on adenosine receptors15,12 and voltage-gated potassium channels,13 though the clinical relevance of its action at these sites is unclear.

TargetActionsOrganism
AVoltage-dependent calcium channel subunit alpha-2/delta-1
inhibitor
Humans
UVoltage-dependent calcium channel subunit alpha-2/delta-2
inhibitor
Humans
UVoltage-dependent N-type calcium channel
inhibitor
Humans
UAdenosine receptor A1
agonist
Humans
UPotassium voltage-gated channel subfamily KQT member 3
activator
Humans
UPotassium voltage-gated channel subfamily KQT member 5
activator
Humans
Absorption

Absorption of gabapentin is thought to occur solely via facilitated transport by the LAT1 transporter within the intestines.5 As this process is saturable, the oral bioavailability of gabapentin is inversely proportional to the administered dose - the oral bioavailability of a 900mg/day regimen is approximately 60%, whereas a 4800mg/day regimen results in only 27% bioavailability.16,18 The Tmax of gabapentin has been estimated to be 2-3 hours.17,5 Food has no appreciable effect on gabapentin absorption.16,18

Volume of distribution

The apparent volume of distribution of gabapentin after IV administration is 58±6 L.16,17 The drug is found in the CSF in concentrations approximately 9-20% of the corresponding plasma concentrations and is secreted into breast milk in concentrations similar to that seen in plasma.16,17,5

Protein binding

Less than 3% of an orally administered dose of gabapentin is bound to plasma proteins.16,17

Metabolism

Gabapentin is not appreciably metabolized in humans16,17 - in humans, metabolites account for less than 1% of an administered dose, with the remainder being excreted as unchanged parent drug in the urine.5

Route of elimination

Gabapentin is eliminated solely in the urine as unchanged drug.16,17 Cimetidine, an inhibitor of renal tubular secretion, reduces clearance by approximately 12%, suggesting that some degree of tubular secretion is involved in the renal elimination of gabapentin.5

Half-life

The elimination t1/2 of gabapentin in patients with normal renal function is 5-7 hours.16,17,5 In patients with reduced renal function, the elimination t1/2 may be prolonged - in patients with a creatinine clearance of <30 mL/min, the reported half-life of gabapentin was approximately 52 hours.16,17

Clearance

Both the plasma clearance and renal clearance of gabapentin are directly proportional to the patient's creatinine clearance due to its primarily renal elimination.16,17,5

Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

The oral TDLo of gabapentin in humans is 2.86 mg/kg and the LD50 in rats has been found to be >8000 mg/kg.21 Symptoms of overdose are consistent with the drug's adverse effect profile and involve CNS depression (e.g. dizziness, drowsiness, slurred speech, lethargy, loss of consciousness) and gastrointestinal symptoms such as diarrhea.18,17 Management of overdose should involve symptomatic and supportive treatment. Gabapentin can be removed by hemodialysis - this may be of benefit in some patients, such as those with impaired renal function.20

Multi-drug overdoses involving gabapentin, particularly in combination with other CNS depressants such as opioids, can result in coma and death - this possibility should be considered when managing overdosage.17

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Gabapentin.
AcetophenazineThe risk or severity of adverse effects can be increased when Gabapentin is combined with Acetophenazine.
AclidiniumGabapentin may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Gabapentin is combined with Agomelatine.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Gabapentin.
AlimemazineThe risk or severity of adverse effects can be increased when Gabapentin is combined with Alimemazine.
AlmasilateThe bioavailability of Gabapentin can be decreased when combined with Almasilate.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Gabapentin.
AlosetronThe risk or severity of adverse effects can be increased when Alosetron is combined with Gabapentin.
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Gabapentin.
Additional Data Available
  • Extended Description
    Extended Description
    Available for Purchase

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity
    Available for Purchase

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level
    Available for Purchase

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action
    Available for Purchase

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid alcohol. Gabapentin possesses CNS depressant activity that may be potentiated by co-administration with alcohol.
  • Take with or without food. Co-administration with food slightly alters pharmacokinetics, but not to a clinically significant extent.

Products

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Product Images
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act GabapentinCapsuleOralActavis Pharma Company2005-02-162018-06-12Canada flag
Act GabapentinCapsuleOralActavis Pharma Company2005-02-162018-06-12Canada flag
Act GabapentinCapsuleOralActavis Pharma Company2005-02-162018-06-12Canada flag
Bci GabapentinCapsuleOralBaker Cummins IncNot applicableNot applicableCanada flag
FanatrexKit10.5 g/10.5gOralCalifornia Pharmaceuticals, Llc2010-05-15Not applicableUS flag
FanatrexKit10.8 g/10.8gOralCalifornia Pharmaceuticals, Llc2016-01-01Not applicableUS flag
Gaba 300-EZSKit300 mg/1OralPureTek Corporation2018-10-22Not applicableUS flag
GabapentinCapsule400 mgOralSivem Pharmaceuticals Ulc2003-01-07Not applicableCanada flag
GabapentinCapsule300 mgOralSorres Pharma Inc2009-02-262014-06-20Canada flag
GabapentinCapsule400 mg/1OralTEVA PHARMACEUTICALS USA2007-07-132007-07-13US flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ag-gabapentinCapsuleOralAngita Pharma Inc.2018-09-28Not applicableCanada flag
Ag-gabapentinCapsuleOralAngita Pharma Inc.2018-09-28Not applicableCanada flag
Ag-gabapentinCapsuleOralAngita Pharma Inc.2018-09-28Not applicableCanada flag
Apo-gabapentinCapsuleOralApotex Corporation2001-08-27Not applicableCanada flag
Apo-gabapentinCapsuleOralApotex Corporation2001-08-27Not applicableCanada flag
Apo-gabapentinCapsuleOralApotex Corporation2001-08-27Not applicableCanada flag
Apo-gabapentinTabletOralApotex Corporation2008-06-04Not applicableCanada flag
Apo-gabapentinTabletOralApotex Corporation2008-06-04Not applicableCanada flag
Auro-gabapentinCapsuleOralAuro Pharma Inc2011-06-15Not applicableCanada flag
Auro-gabapentinCapsuleOralAuro Pharma Inc2011-06-15Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ACTIVE-PAC with GabapentinGabapentin (300 mg/1) + Levomenthol (1 g/100g) + Lidocaine hydrochloride (4 g/100g)Oral; TopicalPharmaceutica North America, Inc.2014-06-182018-01-01US flag
Cyclo/Gaba 10/300 PackGabapentin (300 mg/1) + Cyclobenzaprine hydrochloride (10 mg/1)KitOralTmig, Inc.2011-01-29Not applicableUS flag
GraliseGabapentin (300 mg/1) + Gabapentin (600 mg/1)OralAlmatica Pharma LLC2020-10-01Not applicableUS flag
GraliseGabapentin (300 mg/1) + Gabapentin (600 mg/1)OralAlmatica Pharma LLC2020-10-01Not applicableUS flag
Gralise Starter PackGabapentin (300 mg/1) + Gabapentin (600 mg/1)OralAssertio Therapeutics, Inc.2011-01-282022-12-31US flag
Gralise Starter PackGabapentin (300 mg/1) + Gabapentin (600 mg/1)OralAssertio Therapeutics, Inc.2011-01-282022-12-31US flag
LipritinGabapentin (100 mg/1) + Lidocaine (25 mg/1g) + Prilocaine (25 mg/1g)Oral; TopicalPureTek Corporation2020-02-29Not applicableUS flag
Lipritin IIGabapentin (100 mg/1) + Lidocaine (25 mg/1g) + Prilocaine (25 mg/1g)Oral; TopicalPureTek Corporation2020-06-05Not applicableUS flag
PrilopentinGabapentin (300 mg/1) + Lidocaine (25 mg/1g) + Prilocaine (25 mg/1g)Oral; TopicalPureTek Corporation2019-08-19Not applicableUS flag
Prilopentin -IIGabapentin (300 mg/1) + Lidocaine (25 mg/1g) + Prilocaine (25 mg/1g)Oral; TopicalPureTek Corporation2020-07-02Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Dipentocaine Topical Cream Compounding KitGabapentin (5.7 g/5.7g) + Diclofenac sodium (5.7 g/5.7g)KitTopicalAlvix Laboratories2014-11-062018-03-08US flag
FanatrexGabapentin (10.8 g/10.8g)KitOralCalifornia Pharmaceuticals, Llc2016-01-01Not applicableUS flag
FanatrexGabapentin (10.5 g/10.5g)KitOralCalifornia Pharmaceuticals, Llc2010-05-15Not applicableUS flag
Gaba 300-EZSGabapentin (300 mg/1)KitOralPureTek Corporation2018-10-22Not applicableUS flag
GabacaineGabapentin (300 mg/1) + Lidocaine (50 mg/1g)KitCutaneous; OralPureTek Corporation2019-05-03Not applicableUS flag
GabapalGabapentin (100 mg/1) + Lidocaine hydrochloride (38.8 mg/1g)KitOral; TopicalPureTek Corporation2020-01-25Not applicableUS flag
Gapeam BudibacGabapentin (1 g/1g) + Amantadine hydrochloride (1 g/1g) + Baclofen (1 g/1g) + Bupivacaine hydrochloride anhydrous (1 g/1g) + Cyclobenzaprine hydrochloride (1 g/1g) + Diclofenac sodium (1 g/1g) + Pentoxifylline (1 g/1g)KitTopicalAlvix Laboratories2014-12-052018-03-08US flag
GPL PakGabapentin (300 mg/1) + Lidocaine hydrochloride (41.2 mg/1g)KitOral; TopicalPureTek Corporation2019-04-26Not applicableUS flag
Innoprax-5Gabapentin (6 g/6g) + Amantadine hydrochloride (8 g/8g) + Baclofen (3 g/3g) + Diclofenac sodium (3 g/3g) + Lidocaine hydrochloride (5 g/5g)KitTopicalAccumix Pharmaceuticals2014-12-152015-07-17US flag
Lido GB-300Gabapentin (300 mg/1) + Lidocaine hydrochloride (41.2 mg/1g)KitOral; TopicalPureTek Corporation2019-05-08Not applicableUS flag

Categories

ATC Codes
N03AX12 — Gabapentin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Gamma amino acids and derivatives
Alternative Parents
Amino fatty acids / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic homomonocyclic compound / Amine / Amino acid / Amino fatty acid / Carbonyl group / Carboxylic acid / Fatty acyl / Gamma amino acid or derivatives / Hydrocarbon derivative / Monocarboxylic acid or derivatives
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
gamma-amino acid (CHEBI:42797)

Chemical Identifiers

UNII
6CW7F3G59X
CAS number
60142-96-3
InChI Key
UGJMXCAKCUNAIE-UHFFFAOYSA-N
InChI
InChI=1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12)
IUPAC Name
2-[1-(aminomethyl)cyclohexyl]acetic acid
SMILES
NCC1(CC(O)=O)CCCCC1

References

Synthesis Reference

Donald E. Butler, Barbara J. Greenman, "Gabapentin mohohydrate and a process for producing the same." U.S. Patent US4960931, issued May, 1978.

US4960931
General References
  1. Yagi T, Naito T, Mino Y, Umemura K, Kawakami J: Impact of concomitant antacid administration on gabapentin plasma exposure and oral bioavailability in healthy adult subjects. Drug Metab Pharmacokinet. 2012;27(2):248-54. Epub 2012 Jan 13. [PubMed:22240839]
  2. Czapinski P, Blaszczyk B, Czuczwar SJ: Mechanisms of action of antiepileptic drugs. Curr Top Med Chem. 2005;5(1):3-14. doi: 10.2174/1568026053386962. [PubMed:15638774]
  3. Patsalos PN, Berry DJ, Bourgeois BF, Cloyd JC, Glauser TA, Johannessen SI, Leppik IE, Tomson T, Perucca E: Antiepileptic drugs--best practice guidelines for therapeutic drug monitoring: a position paper by the subcommission on therapeutic drug monitoring, ILAE Commission on Therapeutic Strategies. Epilepsia. 2008 Jul;49(7):1239-76. doi: 10.1111/j.1528-1167.2008.01561.x. [PubMed:18397299]
  4. Abou-Khalil BW: Antiepileptic Drugs. Continuum (Minneap Minn). 2016 Feb;22(1 Epilepsy):132-56. doi: 10.1212/CON.0000000000000289. [PubMed:26844734]
  5. Bockbrader HN, Wesche D, Miller R, Chapel S, Janiczek N, Burger P: A comparison of the pharmacokinetics and pharmacodynamics of pregabalin and gabapentin. Clin Pharmacokinet. 2010 Oct;49(10):661-9. doi: 10.2165/11536200-000000000-00000. [PubMed:20818832]
  6. Goto M, Miyahara I, Hirotsu K, Conway M, Yennawar N, Islam MM, Hutson SM: Structural determinants for branched-chain aminotransferase isozyme-specific inhibition by the anticonvulsant drug gabapentin. J Biol Chem. 2005 Nov 4;280(44):37246-56. Epub 2005 Sep 1. [PubMed:16141215]
  7. Dickens D, Webb SD, Antonyuk S, Giannoudis A, Owen A, Radisch S, Hasnain SS, Pirmohamed M: Transport of gabapentin by LAT1 (SLC7A5). Biochem Pharmacol. 2013 Jun 1;85(11):1672-83. doi: 10.1016/j.bcp.2013.03.022. Epub 2013 Apr 6. [PubMed:23567998]
  8. Maneuf YP, Luo ZD, Lee K: alpha2delta and the mechanism of action of gabapentin in the treatment of pain. Semin Cell Dev Biol. 2006 Oct;17(5):565-70. Epub 2006 Sep 24. [PubMed:17067834]
  9. Hendrich J, Van Minh AT, Heblich F, Nieto-Rostro M, Watschinger K, Striessnig J, Wratten J, Davies A, Dolphin AC: Pharmacological disruption of calcium channel trafficking by the alpha2delta ligand gabapentin. Proc Natl Acad Sci U S A. 2008 Mar 4;105(9):3628-33. doi: 10.1073/pnas.0708930105. Epub 2008 Feb 25. [PubMed:18299583]
  10. Kukkar A, Bali A, Singh N, Jaggi AS: Implications and mechanism of action of gabapentin in neuropathic pain. Arch Pharm Res. 2013 Mar;36(3):237-51. doi: 10.1007/s12272-013-0057-y. Epub 2013 Feb 24. [PubMed:23435945]
  11. Cheng JK, Chen CC, Yang JR, Chiou LC: The antiallodynic action target of intrathecal gabapentin: Ca2+ channels, KATP channels or N-methyl-d-aspartic acid receptors? Anesth Analg. 2006 Jan;102(1):182-7. [PubMed:16368827]
  12. Martins DF, Prado MR, Daruge-Neto E, Batisti AP, Emer AA, Mazzardo-Martins L, Santos AR, Piovezan AP: Caffeine prevents antihyperalgesic effect of gabapentin in an animal model of CRPS-I: evidence for the involvement of spinal adenosine A1 receptor. J Peripher Nerv Syst. 2015 Dec;20(4):403-9. doi: 10.1111/jns.12149. [PubMed:26456872]
  13. Manville RW, Abbott GW: Gabapentin Is a Potent Activator of KCNQ3 and KCNQ5 Potassium Channels. Mol Pharmacol. 2018 Oct;94(4):1155-1163. doi: 10.1124/mol.118.112953. Epub 2018 Jul 18. [PubMed:30021858]
  14. Sills GJ: The mechanisms of action of gabapentin and pregabalin. Curr Opin Pharmacol. 2006 Feb;6(1):108-13. doi: 10.1016/j.coph.2005.11.003. Epub 2005 Dec 22. [PubMed:16376147]
  15. Zuchora B, Wielosz M, Urbanska EM: Adenosine A1 receptors and the anticonvulsant potential of drugs effective in the model of 3-nitropropionic acid-induced seizures in mice. Eur Neuropsychopharmacol. 2005 Jan;15(1):85-93. [PubMed:15572277]
  16. FDA Approved Drug Products: Neurontin (gabapentin) for oral use [Link]
  17. DPD Approved Drugs: Gabapentin [Link]
  18. MedSafe NZ: Gabapentin [Link]
  19. EMA Approved Drugs: Gabapentin [Link]
  20. FDA Approved Drugs: Gabapentin XR [Link]
  21. CaymenChem: Gabapentin MSDS [Link]
Human Metabolome Database
HMDB0005015
KEGG Drug
D00332
PubChem Compound
3446
PubChem Substance
46506529
ChemSpider
3328
BindingDB
50080153
RxNav
25480
ChEBI
42797
ChEMBL
CHEMBL940
ZINC
ZINC000000004949
Therapeutic Targets Database
DNC000670
PharmGKB
PA449720
PDBe Ligand
GBN
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Gabapentin
AHFS Codes
  • 28:12.92 — Miscellaneous Anticonvulsants
PDB Entries
2a1h / 2coi / 2coj / 2ej3

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceInsomnia1
4CompletedBasic ScienceOsteoarthritis (OA)1
4CompletedOtherHealthy Volunteers1
4CompletedPreventionPain, Neuropathic / Spinal Cord Injuries (SCI)1
4CompletedPreventionPelvic Organ Prolapse (POP)1
4CompletedPreventionPost Operative Nausea and Vomiting (PONV)1
4CompletedPreventionPostoperative pain1
4CompletedSupportive CareCerebral Palsy (CP) / Crying1
4CompletedSupportive CareInjuries, Hand1
4CompletedSupportive CarePain1

Pharmacoeconomics

Manufacturers
  • Actavis elizabeth llc
  • Amneal pharmaceuticals ny llc
  • Apotex inc etobicoke site
  • Aurobindo pharma usa inc
  • Hikma pharmaceuticals
  • Invagen pharmaceuticals inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mutual pharmaceutical co inc
  • Ranbaxy laboratories ltd
  • Sandoz inc
  • Sun pharmaceutical industries ltd
  • Teva pharmaceuticals usa
  • Watson laboratories inc
  • Pfizer pharmaceuticals ltd
  • Parke davis div warner lambert co
  • Glenmark generics ltd
  • Matrix laboratories ltd
  • Teva pharmaceuticals usa inc
Packagers
  • 4uOrtho LLC
  • Actavis Group
  • Aidarex Pharmacuticals LLC
  • Amerisource Health Services Corp.
  • Amneal Pharmaceuticals
  • Apotex Inc.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Aurobindo Pharma Ltd.
  • Blenheim Pharmacal
  • Blu Pharmaceuticals LLC
  • Bryant Ranch Prepack
  • Camber Pharmaceuticals Inc.
  • Cardinal Health
  • Comprehensive Consultant Services Inc.
  • Corepharma LLC
  • Coupler Enterprises Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Eon Labs
  • Fusion Pharmaceuticals LLC
  • Glenmark Generics Ltd.
  • Golden State Medical Supply Inc.
  • Greenstone LLC
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Hikma Pharmaceuticals
  • Innoviant Pharmacy Inc.
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Keltman Pharmaceuticals Inc.
  • Lake Erie Medical and Surgical Supply
  • Living Well Pharmacy Inc.
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Medvantx Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Neuman Distributors Inc.
  • Northstar Rx LLC
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pfizer Inc.
  • Pharmaceutical Packaging Center
  • Pharmacy Service Center
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepak Systems Inc.
  • Professional Co.
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Sandhills Packaging Inc.
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • Sun Pharmaceutical Industries Ltd.
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • United Research Laboratories Inc.
  • Vangard Labs Inc.
  • Warner Lambert Company LLC
  • West-Ward Pharmaceuticals
Dosage Forms
FormRouteStrength
Tablet, film coatedOral100 mg
Tablet, film coatedOral300 mg
Tablet, film coatedOral400 mg
KitOral10.5 g/10.5g
KitOral10.8 g/10.8g
KitOral300 mg/1
KitCutaneous; Oral
CapsuleOral100 MG
CapsuleOral300 MG
CapsuleOral400 MG
Tablet, film coatedOral600 MG
Tablet, film coatedOral800 MG
CapsuleOral100 mg/1
CapsuleOral300 mg/300mg
CapsuleOral300 mg/1
CapsuleOral400 mg/1
CapsuleOral600 mg/1
PowderNot applicable1 g/1g
SolutionOral250 mg/5mL
SuspensionOral250 mg/5mL
TabletOral100 mg/1
TabletOral300 mg/1
TabletOral400 mg/1
TabletOral600 1/1
TabletOral600 mg/1
TabletOral800 mg/1
TabletOral800 mg/800mg
Tablet, coatedOral600 mg/1
Tablet, coatedOral800 mg/1
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral400 mg/1
Tablet, film coatedOral600 mg/1
Tablet, film coatedOral600 mg/1001
Tablet, film coatedOral800 mg/1
Tablet, film coatedOral
Capsule, coatedOral300 mg
Tablet, coatedOral800 MG
Capsule, coatedOral400 mg
Tablet, multilayer, extended releaseOral
Tablet, film coatedOral300 mg/1
CapsuleOral
KitTopical
Tablet, coatedOral100 mg
Tablet, coatedOral300 mg
Tablet, coatedOral400 mg
TabletOral800 mg
Tablet, coatedOral600 mg
TabletOral600 mg
KitOral; Topical
TabletOral
KitOral
CreamTopical
Prices
Unit descriptionCostUnit
Gabapentin powder30.0USD g
Neurontin 800 mg tablet4.73USD tablet
Neurontin 600 mg tablet3.94USD tablet
Gabapentin 800 mg tablet3.09USD tablet
Gabapentin 600 mg tablet2.58USD tablet
Neurontin 400 mg Capsule1.97USD capsule
Neurontin 300 mg Capsule1.67USD capsule
Gabapentin 400 mg tablet1.59USD tablet
Gabapentin 300 mg tablet1.32USD tablet
Gabapentin 400 mg Capsule1.21USD capsule
Gabapentin 300 mg Capsule1.02USD capsule
Apo-Gabapentin 400 mg Capsule0.76USD capsule
Co Gabapentin 400 mg Capsule0.76USD capsule
Mylan-Gabapentin 400 mg Capsule0.76USD capsule
Novo-Gabapentin 400 mg Capsule0.76USD capsule
Phl-Gabapentin 400 mg Capsule0.76USD capsule
Pms-Gabapentin 400 mg Capsule0.76USD capsule
Ran-Gabapentin 400 mg Capsule0.76USD capsule
Ratio-Gabapentin 400 mg Capsule0.76USD capsule
Neurontin 100 mg Capsule0.65USD capsule
Apo-Gabapentin 300 mg Capsule0.64USD capsule
Co Gabapentin 300 mg Capsule0.64USD capsule
Mylan-Gabapentin 300 mg Capsule0.64USD capsule
Novo-Gabapentin 300 mg Capsule0.64USD capsule
Phl-Gabapentin 300 mg Capsule0.64USD capsule
Pms-Gabapentin 300 mg Capsule0.64USD capsule
Ran-Gabapentin 300 mg Capsule0.64USD capsule
Ratio-Gabapentin 300 mg Capsule0.64USD capsule
Gabapentin 100 mg tablet0.53USD tablet
Gabapentin 100 mg Capsule0.41USD capsule
Neurontin 250 mg/5ml Solution0.32USD ml
Apo-Gabapentin 100 mg Capsule0.26USD capsule
Co Gabapentin 100 mg Capsule0.26USD capsule
Mylan-Gabapentin 100 mg Capsule0.26USD capsule
Novo-Gabapentin 100 mg Capsule0.26USD capsule
Phl-Gabapentin 100 mg Capsule0.26USD capsule
Pms-Gabapentin 100 mg Capsule0.26USD capsule
Ran-Gabapentin 100 mg Capsule0.26USD capsule
Ratio-Gabapentin 100 mg Capsule0.26USD capsule
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Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2327285No2005-06-142019-05-10Canada flag
CA2215923No2001-10-092016-04-26Canada flag
US6054482Yes2000-04-252017-10-25US flag
US7256216Yes2007-08-142022-11-28US flag
US6340475No2002-01-222016-09-19US flag
US6635280No2003-10-212016-09-19US flag
US6488962No2002-12-032020-06-20US flag
US6723340No2004-04-202021-10-25US flag
US7438927No2008-10-212024-02-26US flag
US8192756No2012-06-052022-10-25US flag
US8252332No2012-08-282022-10-25US flag
US8333992No2012-12-182022-10-25US flag
US7731989No2010-06-082022-10-25US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility>100mg/mLBockbrader, H. et. al. 2010
logP1.25Bockbrader, H. et. al. 2010; DPD Label
pKa3.7Bockbrader, H. et. al. 2010
Predicted Properties
PropertyValueSource
Water Solubility4.34 mg/mLALOGPS
logP-1.9ALOGPS
logP-1.3ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)4.63ChemAxon
pKa (Strongest Basic)9.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.33 m3·mol-1ChemAxon
Polarizability18.92 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.941
Blood Brain Barrier+0.9382
Caco-2 permeable-0.7271
P-glycoprotein substrateNon-substrate0.6557
P-glycoprotein inhibitor INon-inhibitor0.9789
P-glycoprotein inhibitor IINon-inhibitor0.8866
Renal organic cation transporterNon-inhibitor0.7982
CYP450 2C9 substrateNon-substrate0.893
CYP450 2D6 substrateNon-substrate0.8124
CYP450 3A4 substrateNon-substrate0.7612
CYP450 1A2 substrateNon-inhibitor0.9409
CYP450 2C9 inhibitorNon-inhibitor0.9273
CYP450 2D6 inhibitorNon-inhibitor0.9418
CYP450 2C19 inhibitorNon-inhibitor0.9547
CYP450 3A4 inhibitorNon-inhibitor0.8438
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9706
Ames testNon AMES toxic0.9162
CarcinogenicityNon-carcinogens0.8536
BiodegradationNot ready biodegradable0.7046
Rat acute toxicity1.6472 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9406
hERG inhibition (predictor II)Non-inhibitor0.8659
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-00di-0900000000-bccc9bd5f1637db7b6c7
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-00di-0900000000-67139ca9559173bf9859
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0006-9000000000-bfe6527f738e4c67eb2b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-bb175ef297a289e1936b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udr-0900000000-258d4493623d0ab7b415
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0f79-0900000000-bc24764f394c6fee34fd
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0900000000-006ecd4a58af763b087f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-012c52738f11970adb8d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-8f0d390195aa406adb5d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0uk9-0900000000-72f8d5cb88eda76dab56
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-3900000000-b634b4e7144ec6ffdc83
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0ktn-9800000000-20c4131179b228ab3440
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00ke-9300000000-dd9d44ed4f16961ed075
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-f9a7deaa778e9d893ee8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-4f85e6ac9fd91a3e3b81
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0uk9-0900000000-d3a4c5658e343cf3cf8d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-3900000000-712133d5b9eae1b27ffb
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0ktn-9800000000-c652847259e0851b428e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00ke-9200000000-77e258cf26b045a7e46e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0900000000-bb0075e8b8166387ff3a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0uk9-0900000000-9e92acbd730e00943058
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0pvs-9800000000-ba043efa192e3c526cab
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0aou-9000000000-f44876af37d1698389cd
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-1900000000-8304d09827a02dd8f392
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0005-9800000000-aa9f205e389c72aead8d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0900000000-eb3bc990b07a9471ea6e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0900000000-6514211d36ec828dafb5
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0fk9-0900000000-fb527245013f4d56589f
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Voltage-gated calcium channel activity
Specific Function
The alpha-2/delta subunit of voltage-dependent calcium channels regulates calcium current density and activation/inactivation kinetics of the calcium channel. Plays an important role in excitation-...
Gene Name
CACNA2D1
Uniprot ID
P54289
Uniprot Name
Voltage-dependent calcium channel subunit alpha-2/delta-1
Molecular Weight
124566.93 Da
References
  1. Maneuf YP, Luo ZD, Lee K: alpha2delta and the mechanism of action of gabapentin in the treatment of pain. Semin Cell Dev Biol. 2006 Oct;17(5):565-70. Epub 2006 Sep 24. [PubMed:17067834]
  2. Hendrich J, Van Minh AT, Heblich F, Nieto-Rostro M, Watschinger K, Striessnig J, Wratten J, Davies A, Dolphin AC: Pharmacological disruption of calcium channel trafficking by the alpha2delta ligand gabapentin. Proc Natl Acad Sci U S A. 2008 Mar 4;105(9):3628-33. doi: 10.1073/pnas.0708930105. Epub 2008 Feb 25. [PubMed:18299583]
  3. Kukkar A, Bali A, Singh N, Jaggi AS: Implications and mechanism of action of gabapentin in neuropathic pain. Arch Pharm Res. 2013 Mar;36(3):237-51. doi: 10.1007/s12272-013-0057-y. Epub 2013 Feb 24. [PubMed:23435945]
  4. FDA Approved Drug Products: Neurontin (gabapentin) for oral use [Link]
  5. DPD Approved Drugs: Gabapentin [Link]
  6. EMA Approved Drugs: Gabapentin [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated calcium channel activity
Specific Function
The alpha-2/delta subunit of voltage-dependent calcium channels regulates calcium current density and activation/inactivation kinetics of the calcium channel. Acts as a regulatory subunit for P/Q-t...
Gene Name
CACNA2D2
Uniprot ID
Q9NY47
Uniprot Name
Voltage-dependent calcium channel subunit alpha-2/delta-2
Molecular Weight
129816.095 Da
References
  1. Hendrich J, Van Minh AT, Heblich F, Nieto-Rostro M, Watschinger K, Striessnig J, Wratten J, Davies A, Dolphin AC: Pharmacological disruption of calcium channel trafficking by the alpha2delta ligand gabapentin. Proc Natl Acad Sci U S A. 2008 Mar 4;105(9):3628-33. doi: 10.1073/pnas.0708930105. Epub 2008 Feb 25. [PubMed:18299583]
  2. Kukkar A, Bali A, Singh N, Jaggi AS: Implications and mechanism of action of gabapentin in neuropathic pain. Arch Pharm Res. 2013 Mar;36(3):237-51. doi: 10.1007/s12272-013-0057-y. Epub 2013 Feb 24. [PubMed:23435945]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1B gives rise to N-type calcium currents.
Specific Function
Voltage-gated calcium channel activity

Components:
References
  1. Cheng JK, Chen CC, Yang JR, Chiou LC: The antiallodynic action target of intrathecal gabapentin: Ca2+ channels, KATP channels or N-methyl-d-aspartic acid receptors? Anesth Analg. 2006 Jan;102(1):182-7. [PubMed:16368827]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Purine nucleoside binding
Specific Function
Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
ADORA1
Uniprot ID
P30542
Uniprot Name
Adenosine receptor A1
Molecular Weight
36511.325 Da
References
  1. Zuchora B, Wielosz M, Urbanska EM: Adenosine A1 receptors and the anticonvulsant potential of drugs effective in the model of 3-nitropropionic acid-induced seizures in mice. Eur Neuropsychopharmacol. 2005 Jan;15(1):85-93. [PubMed:15572277]
  2. Martins DF, Prado MR, Daruge-Neto E, Batisti AP, Emer AA, Mazzardo-Martins L, Santos AR, Piovezan AP: Caffeine prevents antihyperalgesic effect of gabapentin in an animal model of CRPS-I: evidence for the involvement of spinal adenosine A1 receptor. J Peripher Nerv Syst. 2015 Dec;20(4):403-9. doi: 10.1111/jns.12149. [PubMed:26456872]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Voltage-gated potassium channel activity
Specific Function
Probably important in the regulation of neuronal excitability. Associates with KCNQ2 or KCNQ5 to form a potassium channel with essentially identical properties to the channel underlying the native ...
Gene Name
KCNQ3
Uniprot ID
O43525
Uniprot Name
Potassium voltage-gated channel subfamily KQT member 3
Molecular Weight
96741.515 Da
References
  1. Manville RW, Abbott GW: Gabapentin Is a Potent Activator of KCNQ3 and KCNQ5 Potassium Channels. Mol Pharmacol. 2018 Oct;94(4):1155-1163. doi: 10.1124/mol.118.112953. Epub 2018 Jul 18. [PubMed:30021858]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Voltage-gated potassium channel activity
Specific Function
Probably important in the regulation of neuronal excitability. Associates with KCNQ3 to form a potassium channel which contributes to M-type current, a slowly activating and deactivating potassium ...
Gene Name
KCNQ5
Uniprot ID
Q9NR82
Uniprot Name
Potassium voltage-gated channel subfamily KQT member 5
Molecular Weight
102178.015 Da
References
  1. Manville RW, Abbott GW: Gabapentin Is a Potent Activator of KCNQ3 and KCNQ5 Potassium Channels. Mol Pharmacol. 2018 Oct;94(4):1155-1163. doi: 10.1124/mol.118.112953. Epub 2018 Jul 18. [PubMed:30021858]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
L-valine transaminase activity
Specific Function
Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine.
Gene Name
BCAT1
Uniprot ID
P54687
Uniprot Name
Branched-chain-amino-acid aminotransferase, cytosolic
Molecular Weight
42965.815 Da
References
  1. Goto M, Miyahara I, Hirotsu K, Conway M, Yennawar N, Islam MM, Hutson SM: Structural determinants for branched-chain aminotransferase isozyme-specific inhibition by the anticonvulsant drug gabapentin. J Biol Chem. 2005 Nov 4;280(44):37246-56. Epub 2005 Sep 1. [PubMed:16141215]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Peptide antigen binding
Specific Function
Sodium-independent, high-affinity transport of large neutral amino acids such as phenylalanine, tyrosine, leucine, arginine and tryptophan, when associated with SLC3A2/4F2hc. Involved in cellular a...
Gene Name
SLC7A5
Uniprot ID
Q01650
Uniprot Name
Large neutral amino acids transporter small subunit 1
Molecular Weight
55009.62 Da
References
  1. Dickens D, Webb SD, Antonyuk S, Giannoudis A, Owen A, Radisch S, Hasnain SS, Pirmohamed M: Transport of gabapentin by LAT1 (SLC7A5). Biochem Pharmacol. 2013 Jun 1;85(11):1672-83. doi: 10.1016/j.bcp.2013.03.022. Epub 2013 Apr 6. [PubMed:23567998]
  2. Bockbrader HN, Wesche D, Miller R, Chapel S, Janiczek N, Burger P: A comparison of the pharmacokinetics and pharmacodynamics of pregabalin and gabapentin. Clin Pharmacokinet. 2010 Oct;49(10):661-9. doi: 10.2165/11536200-000000000-00000. [PubMed:20818832]

Drug created on June 13, 2005 07:24 / Updated on November 23, 2020 09:08

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