Identification
- Summary
Gabapentin is an anticonvulsant medication used in the management of peripheral neuropathic pains, postherpetic neuralgia, and partial-onset seizures.
- Brand Names
- Gralise, Neurontin
- Generic Name
- Gabapentin
- DrugBank Accession Number
- DB00996
- Background
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
Structure for Gabapentin (DB00996)
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Partial-onset seizures •••••••••••• Adjunct therapy in treatment of Partial-onset seizures •••••••••••• Adjunct therapy in treatment of Partial-onset seizures •••••••••••• Treatment of Peripheral neuropathic pain •••••••••••• ••••• Treatment of Postherpetic neuralgia •••••••••••• ••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism AVoltage-dependent calcium channel subunit alpha-2/delta-1 inhibitorHumans UVoltage-dependent calcium channel subunit alpha-2/delta-2 inhibitorHumans UVoltage-dependent N-type calcium channel inhibitorHumans UAdenosine receptor A1 agonistHumans UPotassium voltage-gated channel subfamily KQT member 3 activatorHumans UPotassium voltage-gated channel subfamily KQT member 5 activatorHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Gabapentin is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Gabapentin. Acetophenazine The risk or severity of CNS depression can be increased when Gabapentin is combined with Acetophenazine. Agomelatine The risk or severity of CNS depression can be increased when Gabapentin is combined with Agomelatine. Alfentanil The risk or severity of CNS depression can be increased when Alfentanil is combined with Gabapentin. - 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
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Images
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Act Gabapentin Capsule 300 mg Oral Actavis Pharma Company 2005-02-16 2018-06-12 Canada 
Act Gabapentin Capsule 100 mg Oral Actavis Pharma Company 2005-02-16 2018-06-12 Canada Act Gabapentin Capsule 400 mg Oral Actavis Pharma Company 2005-02-16 2018-06-12 Canada Bci Gabapentin Capsule 300 mg Oral Baker Cummins Inc Not applicable Not applicable Canada Fanatrex Kit 10.5 g/10.5g Oral California Pharmaceuticals, Llc 2010-05-15 Not applicable US 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ag-gabapentin Capsule 100 mg Oral Angita Pharma Inc. 2018-09-28 Not applicable Canada Ag-gabapentin Capsule 300 mg Oral Angita Pharma Inc. 2018-09-28 Not applicable Canada Ag-gabapentin Capsule 400 mg Oral Angita Pharma Inc. 2018-09-28 Not applicable Canada Apo-gabapentin Capsule 100 mg Oral Apotex Corporation 2001-08-27 Not applicable Canada Apo-gabapentin Capsule 300 mg Oral Apotex Corporation 2001-08-27 Not applicable Canada - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image กาบาเพนติน จีพีโอ (300 มก.) Capsule 300 mg Oral องค์การเภสัชกรรม 2015-09-10 Not applicable Thailand 
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ACTIVE-PAC with Gabapentin Gabapentin (300 mg/1) + Lidocaine hydrochloride (4 g/100g) + Menthol (1 g/100g) Kit Oral; Topical Pharmaceutica North America, Inc. 2014-06-18 2018-01-01 US Cyclo/Gaba 10/300 Pack Gabapentin (300 mg/1) + Cyclobenzaprine hydrochloride (10 mg/1) Kit Oral Tmig, Inc. 2011-01-29 Not applicable US Gralise Gabapentin (300 mg/1) + Gabapentin (600 mg/1) Kit; Tablet, film coated Oral Almatica Pharma LLC 2020-10-01 2024-08-01 US Gralise Gabapentin (300 mg/1) + Gabapentin (600 mg/1) Kit; Tablet, film coated Oral Almatica Pharma LLC 2020-10-01 2024-08-01 US Gralise Starter Pack Gabapentin (300 mg/1) + Gabapentin (600 mg/1) Kit; Tablet, film coated Oral Assertio Therapeutics, Inc. 2011-01-28 2020-12-31 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Dipentocaine Topical Cream Compounding Kit Gabapentin (5.7 g/5.7g) + Diclofenac sodium (5.7 g/5.7g) Kit Topical Alvix Laboratories 2014-11-06 2018-03-08 US Fanatrex Gabapentin (10.8 g/10.8g) Kit Oral California Pharmaceuticals, Llc 2016-01-01 Not applicable US Fanatrex Gabapentin (10.5 g/10.5g) Kit Oral California Pharmaceuticals, Llc 2010-05-15 Not applicable US Gaba 300-EZS Gabapentin (300 mg/1) Kit Oral PureTek Corporation 2018-10-22 Not applicable US Gabacaine Gabapentin (300 mg/1) + Lidocaine (50 mg/1g) Kit Cutaneous; Oral PureTek Corporation 2019-05-03 2021-03-27 US
Categories
- ATC Codes
- N02BF01 — Gabapentin
- Drug Categories
- Acids, Acyclic
- Acids, Carbocyclic
- Amines
- Amino Acids
- Amino Acids, Peptides, and Proteins
- Aminobutyrates
- Analgesics
- Anti-epileptic Agent
- Anticonvulsants
- Butyrates
- Central Nervous System Agents
- Central Nervous System Depressants
- Cyclohexanecarboxylic Acids
- Cyclohexanes
- Cycloparaffins
- Decreased Central Nervous System Disorganized Electrical Activity
- Drugs causing inadvertant photosensitivity
- Gabapentin and Prodrugs
- Gabapentinoids
- Miscellaneous Anticonvulsants
- Nervous System
- Neurotransmitter Agents
- Peripheral Nervous System Agents
- Photosensitizing Agents
- Psychotropic Drugs
- Sensory System Agents
- Tranquilizing Agents
- 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)
- Affected organisms
- Humans and other mammals
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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Abou-Khalil BW: Antiepileptic Drugs. Continuum (Minneap Minn). 2016 Feb;22(1 Epilepsy):132-56. doi: 10.1212/CON.0000000000000289. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- FDA Approved Drug Products: Neurontin (gabapentin) for oral use [Link]
- DPD Approved Drugs: Gabapentin [Link]
- MedSafe NZ: Gabapentin [Link]
- EMA Approved Drugs: Gabapentin [Link]
- FDA Approved Drugs: Gabapentin XR [Link]
- CaymenChem: Gabapentin MSDS [Link]
- External Links
- Human Metabolome Database
- HMDB0005015
- KEGG Drug
- D00332
- PubChem Compound
- 3446
- PubChem Substance
- 46506529
- ChemSpider
- 3328
- BindingDB
- 50080153
- 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
- PDB Entries
- 2a1h / 2coi / 2coj / 2ej3 / 8fd7
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Postoperative pain 1 4 Completed Basic Science Insomnia 1 4 Completed Basic Science Osteoarthritis (OA) 1 4 Completed Other Abuse Potential 2 4 Completed Other Healthy Subjects (HS) 1
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
Form Route Strength Tablet Oral Capsule Oral 300.00 mg Tablet, film coated Oral 100 mg Tablet, film coated Oral 300 mg Tablet, film coated Oral 400 mg Kit Oral 10.5 g/10.5g Kit Oral 10.8 g/10.8g Kit Oral 300 mg/1 Kit Cutaneous; Oral Capsule Oral Tablet, film coated Oral Capsule Oral 300.000 mg Capsule Oral 100 mg/1 Capsule Oral 100 mg / cap Capsule Oral 300 mg/300mg Capsule Oral 300 mg/1 Capsule Oral 300 mg / cap Capsule Oral 400 mg / cap Capsule Oral 400 mg/1 Capsule Oral 600 mg/1 Powder Not applicable 1 g/1g Solution Oral 250 mg/5mL Suspension Oral 250 mg/5mL Tablet Oral 100 mg/1 Tablet Oral 300 mg/1 Tablet Oral 400 mg/1 Tablet Oral 600 1/1 Tablet Oral 600 mg/1 Tablet Oral 800 mg/1 Tablet Oral 800 mg/800mg Tablet, coated Oral 600 mg/1 Tablet, coated Oral 800 mg/1 Tablet, film coated Oral 100 mg/1 Tablet, film coated Oral 400 mg/1 Tablet, film coated Oral 600 mg/1001 Tablet, film coated Oral 600 mg/1 Tablet, film coated Oral 800 mg/1 Capsule, coated Oral 30000000 mg Tablet, film coated Oral 800 MG Capsule, coated Oral 400 mg Capsule, gelatin coated Oral 100 mg Capsule, gelatin coated Oral 300 mg Capsule, gelatin coated Oral Capsule Oral 400.000 mg Tablet, multilayer, extended release Oral 600 mg Tablet, multilayer, extended release Oral 800 mg Kit Oral; Topical Tablet, film coated Oral 300 mg/1 Tablet, film coated Oral 450 mg/1 Tablet, film coated Oral 750 mg/1 Tablet, film coated Oral 900 mg/1 Kit; tablet, film coated Oral Kit Topical Capsule, coated Oral 300 mg Tablet Oral 600 mg Tablet Oral 600.000 mg Tablet Oral 800 mg Tablet, coated Oral 800 mg Capsule; cream; kit Oral; Topical Kit Oral Capsule Oral 400.00 mg Cream Topical Tablet Oral Capsule Oral Tablet, coated Oral 300 mg Tablet, coated Oral 400 mg Tablet, coated Oral 600 mg Capsule Oral 100 mg Capsule Oral 300 mg Capsule Oral 400 mg Tablet, film coated Oral 600 mg - Prices
Unit description Cost Unit Gabapentin powder 30.0USD g Neurontin 800 mg tablet 4.73USD tablet Neurontin 600 mg tablet 3.94USD tablet Gabapentin 800 mg tablet 3.09USD tablet Gabapentin 600 mg tablet 2.58USD tablet Neurontin 400 mg Capsule 1.97USD capsule Neurontin 300 mg Capsule 1.67USD capsule Gabapentin 400 mg tablet 1.59USD tablet Gabapentin 300 mg tablet 1.32USD tablet Gabapentin 400 mg Capsule 1.21USD capsule Gabapentin 300 mg Capsule 1.02USD capsule Apo-Gabapentin 400 mg Capsule 0.76USD capsule Co Gabapentin 400 mg Capsule 0.76USD capsule Mylan-Gabapentin 400 mg Capsule 0.76USD capsule Novo-Gabapentin 400 mg Capsule 0.76USD capsule Phl-Gabapentin 400 mg Capsule 0.76USD capsule Pms-Gabapentin 400 mg Capsule 0.76USD capsule Ran-Gabapentin 400 mg Capsule 0.76USD capsule Ratio-Gabapentin 400 mg Capsule 0.76USD capsule Neurontin 100 mg Capsule 0.65USD capsule Apo-Gabapentin 300 mg Capsule 0.64USD capsule Co Gabapentin 300 mg Capsule 0.64USD capsule Mylan-Gabapentin 300 mg Capsule 0.64USD capsule Novo-Gabapentin 300 mg Capsule 0.64USD capsule Phl-Gabapentin 300 mg Capsule 0.64USD capsule Pms-Gabapentin 300 mg Capsule 0.64USD capsule Ran-Gabapentin 300 mg Capsule 0.64USD capsule Ratio-Gabapentin 300 mg Capsule 0.64USD capsule Gabapentin 100 mg tablet 0.53USD tablet Gabapentin 100 mg Capsule 0.41USD capsule Neurontin 250 mg/5ml Solution 0.32USD ml Apo-Gabapentin 100 mg Capsule 0.26USD capsule Co Gabapentin 100 mg Capsule 0.26USD capsule Mylan-Gabapentin 100 mg Capsule 0.26USD capsule Novo-Gabapentin 100 mg Capsule 0.26USD capsule Phl-Gabapentin 100 mg Capsule 0.26USD capsule Pms-Gabapentin 100 mg Capsule 0.26USD capsule Ran-Gabapentin 100 mg Capsule 0.26USD capsule Ratio-Gabapentin 100 mg Capsule 0.26USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region CA2327285 No 2005-06-14 2019-05-10 Canada CA2215923 No 2001-10-09 2016-04-26 Canada US6054482 Yes 2000-04-25 2017-10-25 US US7256216 Yes 2007-08-14 2022-11-28 US US6340475 No 2002-01-22 2016-09-19 US US6635280 No 2003-10-21 2016-09-19 US US6488962 No 2002-12-03 2020-06-20 US US6723340 No 2004-04-20 2021-10-25 US US7438927 No 2008-10-21 2024-02-26 US US8192756 No 2012-06-05 2022-10-25 US US8252332 No 2012-08-28 2022-10-25 US US8333992 No 2012-12-18 2022-10-25 US US7731989 No 2010-06-08 2022-10-25 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility >100mg/mL Bockbrader, H. et. al. 2010 logP 1.25 Bockbrader, H. et. al. 2010; DPD Label pKa 3.7 Bockbrader, H. et. al. 2010 - Predicted Properties
Property Value Source Water Solubility 4.34 mg/mL ALOGPS logP -1.9 ALOGPS logP -1.3 Chemaxon logS -1.6 ALOGPS pKa (Strongest Acidic) 4.63 Chemaxon pKa (Strongest Basic) 9.91 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 63.32 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 46.33 m3·mol-1 Chemaxon Polarizability 18.92 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.941 Blood Brain Barrier + 0.9382 Caco-2 permeable - 0.7271 P-glycoprotein substrate Non-substrate 0.6557 P-glycoprotein inhibitor I Non-inhibitor 0.9789 P-glycoprotein inhibitor II Non-inhibitor 0.8866 Renal organic cation transporter Non-inhibitor 0.7982 CYP450 2C9 substrate Non-substrate 0.893 CYP450 2D6 substrate Non-substrate 0.8124 CYP450 3A4 substrate Non-substrate 0.7612 CYP450 1A2 substrate Non-inhibitor 0.9409 CYP450 2C9 inhibitor Non-inhibitor 0.9273 CYP450 2D6 inhibitor Non-inhibitor 0.9418 CYP450 2C19 inhibitor Non-inhibitor 0.9547 CYP450 3A4 inhibitor Non-inhibitor 0.8438 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9706 Ames test Non AMES toxic 0.9162 Carcinogenicity Non-carcinogens 0.8536 Biodegradation Not ready biodegradable 0.7046 Rat acute toxicity 1.6472 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9406 hERG inhibition (predictor II) Non-inhibitor 0.8659
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 140.427516 predictedDarkChem Lite v0.1.0 [M-H]- 140.209216 predictedDarkChem Lite v0.1.0 [M-H]- 140.190516 predictedDarkChem Lite v0.1.0 [M-H]- 143.01044 predictedDeepCCS 1.0 (2019) [M+H]+ 140.460816 predictedDarkChem Lite v0.1.0 [M+H]+ 140.685516 predictedDarkChem Lite v0.1.0 [M+H]+ 140.346716 predictedDarkChem Lite v0.1.0 [M+H]+ 145.70842 predictedDeepCCS 1.0 (2019) [M+Na]+ 140.458616 predictedDarkChem Lite v0.1.0 [M+Na]+ 140.415616 predictedDarkChem Lite v0.1.0 [M+Na]+ 140.251816 predictedDarkChem Lite v0.1.0 [M+Na]+ 154.48927 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- FDA Approved Drug Products: Neurontin (gabapentin) for oral use [Link]
- DPD Approved Drugs: Gabapentin [Link]
- 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
- 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. [Article]
- 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. [Article]
- 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:
| Name | UniProt ID |
|---|---|
| Voltage-dependent N-type calcium channel subunit alpha | A0A024R8I1 |
| Voltage-dependent N-type calcium channel subunit alpha-1B | Q00975 |
References
- 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. [Article]
- 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
- 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. [Article]
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
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
- 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. [Article]
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
- 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. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55