Identification

Name
Gabapentin
Accession Number
DB00996  (APRD00015)
Type
Small Molecule
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.

Structure
Thumb
Synonyms
  • 1-(Aminomethyl)cyclohexaneacetic acid
  • Gabapentin
  • Gabapentin GR
  • Gabapentina
  • Gabapentine
  • Gabapentino
  • Gabapentinum
  • Gabapetin
External IDs
CI-945 / DM-1796 / GOE 3450 / GOE-3450
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act GabapentinCapsule300 mgOralActavis Pharma Company2005-02-16Not applicableCanada
Act GabapentinCapsule100 mgOralActavis Pharma Company2005-02-16Not applicableCanada
Act GabapentinCapsule400 mgOralActavis Pharma Company2005-02-16Not applicableCanada
Bci GabapentinCapsule300 mgOralBaker Cummins IncNot applicableNot applicableCanada
GabapentinTablet300 mg/1OralIVAX Pharmaceuticals, Inc.2007-08-082007-08-08Us
GabapentinCapsule400 mgOralCobalt LaboratoriesNot applicableNot applicableCanada
GabapentinCapsule300 mgOralSanis Health Inc2010-07-30Not applicableCanada
GabapentinCapsule300 mgOralGenpharm Ulc2006-01-172009-02-17Canada
GabapentinCapsule300 mgOralOmni Laboratories Division, Warner Lambert Canada Inc.Not applicableNot applicableCanada
GabapentinCapsule100 mg/1OralTEVA PHARMACEUTICALS USA2007-07-132007-07-13Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-gabapentinTablet600 mgOralApotex Corporation2008-06-04Not applicableCanada
Apo-gabapentinTablet800 mgOralApotex Corporation2008-06-04Not applicableCanada
Apo-gabapentin CapsulesCapsule100 mgOralApotex Corporation2001-08-27Not applicableCanada
Apo-gabapentin CapsulesCapsule300 mgOralApotex Corporation2001-08-27Not applicableCanada
Apo-gabapentin CapsulesCapsule400 mgOralApotex Corporation2001-08-27Not applicableCanada
Auro-gabapentinCapsule100 mgOralAuro Pharma Inc2011-06-15Not applicableCanada
Auro-gabapentinCapsule300 mgOralAuro Pharma Inc2011-06-15Not applicableCanada
Auro-gabapentinCapsule400 mgOralAuro Pharma Inc2011-06-15Not applicableCanada
Auro-gabapentin TabletsTablet600 mgOralAuro Pharma IncNot applicableNot applicableCanada
Auro-gabapentin TabletsTablet800 mgOralAuro Pharma IncNot applicableNot applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
ACTIVE-PAC with GabapentinGabapentin (300 mg/1) + Levomenthol (1 g/100g) + Lidocaine hydrochloride (4 g/100g)KitN.O.R.T.H., Inc.2014-06-18Not applicableUs
Cyclo/Gaba 10/300 PackGabapentin (300 mg/1) + Cyclobenzaprine Hydrochloride (10 mg/1)KitOralTmig, Inc.2011-01-29Not applicableUs
Gralise Starter PackGabapentin (300 mg/1) + Gabapentin (600 mg/1)KitDepomed2011-01-28Not applicableUs
Gralise Starter PackGabapentin (300 mg/1) + Gabapentin (600 mg/1)KitDepomed2011-01-28Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Dipentocaine Topical Cream Compounding KitGabapentin (5.7 g/5.7g) + Diclofenac sodium (5.7 g/5.7g)KitTopicalAlvix Laboratories2014-11-062018-03-08Us
FanatrexGabapentin (10.8 g/10.8g)KitOralCalifornia Pharmaceuticals, Llc2016-01-01Not applicableUs
FanatrexGabapentin (10.5 g/10.5g)KitOralCalifornia Pharmaceuticals, Llc2010-05-15Not applicableUs
Gapeam BudibacGabapentin (1 g/1g) + Amantadine hydrochloride (1 g/1g) + Baclofen (1 g/1g) + Bupivacaine hydrochloride (1 g/1g) + Cyclobenzaprine Hydrochloride (1 g/1g) + Diclofenac sodium (1 g/1g) + Pentoxifylline (1 g/1g)KitTopicalAlvix Laboratories2014-12-052018-03-08Us
Innoprax-5Gabapentin (6 g/6g) + Amantadine hydrochloride (8 g/8g) + Baclofen (3 g/3g) + Diclofenac sodium (3 g/3g) + Lidocaine hydrochloride (5 g/5g)KitAccumix Pharmaceuticals2014-12-152015-07-17Us
SmartRx Gaba KitGabapentin (300 mg/1) + Levomenthol (1 g/100g) + Lidocaine hydrochloride (4 g/100g)KitOral; TopicalMas Management Group Inc.2016-04-012018-01-01Us
SmartRx Gaba-V KitGabapentin (300 mg/1) + Capsaicin (0.0375 g/100g) + Levomenthol (5 g/100g) + Methyl salicylate (20 g/100g)KitMas Management Group Inc2009-03-162018-01-01Us
Therapentin-60Gabapentin (300 mg/1) + gamma-Aminobutyric acid (100 mg/1)KitPhysician Therapeutics Llc2011-05-17Not applicableUs
Therapentin-90Gabapentin (100 mg/1) + gamma-Aminobutyric acid (100 mg/1)KitPhysician Therapeutics Llc2011-02-08Not applicableUs
Topical Nerve PainGabapentin (0.1 g/100mL) + Diazepam (0.1 g/100mL) + Diclofenac sodium (0.1 g/100mL) + Ketamine (0.1 g/100mL)CreamTopicalDr Marc's Manufacturing And Sales2016-02-232018-04-18Us
International/Other Brands
Aclonium / Neurontin / Novo-Gabapentin
Categories
UNII
6CW7F3G59X
CAS number
60142-96-3
Weight
Average: 171.2368
Monoisotopic: 171.125928793
Chemical Formula
C9H17NO2
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

Pharmacology

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.

Associated Conditions
Pharmacodynamics

Gabapentin, an analog of GABA, is used as an anticonvulsant to treat partial seizures, amyotrophic lateral sclerosis (ALS), and painful neuropathies. Potential uses include monotherapy of refractory partial seizure disorders, and treatment of spasticity in multiple sclerosis, tremor. mood disorders, and attenuation of disruptive behaviors in dementia. Gabapentin has high lipid solubility, is not metabolized by the liver, has no protein binding, and doesn't possess the usual drug interactions.

Mechanism of action

Gabapentin interacts with cortical neurons at auxillary subunits of voltage-sensitive calcium channels. Gabapentin increases the synaptic concentration of GABA, enhances GABA responses at non-synaptic sites in neuronal tissues, and reduces the release of mono-amine neurotransmitters. One of the mechanisms implicated in this effect of gabapentin is the reduction of the axon excitability measured as an amplitude change of the presynaptic fibre volley (FV) in the CA1 area of the hippocampus. This is mediated through its binding to presynaptic NMDA receptors. Other studies have shown that the antihyperalgesic and antiallodynic effects of gabapentin are mediated by the descending noradrenergic system, resulting in the activation of spinal alpha2-adrenergic receptors. Gabapentin has also been shown to bind and activate the adenosine A1 receptor.

TargetActionsOrganism
AVoltage-dependent calcium channel subunit alpha-2/delta-1
inhibitor
Human
AVoltage-dependent calcium channel subunit alpha-2/delta-2
inhibitor
Human
AVoltage-dependent N-type calcium channel subunit alpha-1B
inhibitor
Human
UAdenosine receptor A1
agonist
Human
UNMDA receptor
inhibitor
Human
UGamma-aminobutyric acid type B receptor subunit 1Not AvailableHuman
UGamma-aminobutyric acid type B receptor subunit 2Not AvailableHuman
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).

Volume of distribution
  • 58±6 L
Protein binding

Less than 3% of gabapentin circulates bound to plasma protein.

Metabolism

All pharmacological actions following gabapentin administration are due to the activity of the parent compound; gabapentin is not appreciably metabolized in humans.

Route of elimination

Gabapentin is eliminated from the systemic circulation by renal excretion as unchanged drug. Gabapentin is not appreciably metabolized in humans.

Half life

5-7 hours

Clearance
  • 190 mL/min
Toxicity

Symptoms of overdose include ataxia, labored breathing, ptosis, sedation, hypoactivity, and excitation.

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

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Gabapentin.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Gabapentin.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Gabapentin is combined with 2,4-thiazolidinedione.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Gabapentin is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineGabapentin may increase the excretion rate of 3-isobutyl-1-methyl-7H-xanthine which could result in a lower serum level and potentially a reduction in efficacy.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when Gabapentin is combined with 3,4-Methylenedioxyamphetamine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Gabapentin.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Gabapentin is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Gabapentin.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Gabapentin is combined with 4-Methoxyamphetamine.
Food Interactions
  • Avoid alcohol.
  • Take without regard to meals.

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. 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:11251695]
  2. Backonja MM, Serra J: Pharmacologic management part 1: better-studied neuropathic pain diseases. Pain Med. 2004 Mar;5 Suppl 1:S28-47. [PubMed:14996228]
  3. Choudhuri I, Sarvananthan N, Gottlob I: Survey of management of acquired nystagmus in the United Kingdom. Eye (Lond). 2007 Sep;21(9):1194-7. Epub 2006 May 26. [PubMed:16732211]
  4. 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:11249802]
  5. Su TZ, Feng MR, Weber ML: Mediation of highly concentrative uptake of pregabalin by L-type amino acid transport in Chinese hamster ovary and Caco-2 cells. J Pharmacol Exp Ther. 2005 Jun;313(3):1406-15. Epub 2005 Mar 15. [PubMed:15769862]
External Links
Human Metabolome Database
HMDB0005015
KEGG Drug
D00332
PubChem Compound
3446
PubChem Substance
46506529
ChemSpider
3328
BindingDB
50080153
ChEBI
42797
ChEMBL
CHEMBL940
Therapeutic Targets Database
DNC000670
PharmGKB
PA449720
HET
GBN
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Gabapentin
ATC Codes
N03AX12 — Gabapentin
AHFS Codes
  • 28:12.92 — Miscellaneous Anticonvulsants
PDB Entries
2a1h / 2coi / 2coj / 2ej3
FDA label
Download (1.5 MB)
MSDS
Download (73.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentLumbar Spinal Instability / Lumbar Spine Degeneration / Spinal Stenosis of Lumbar Region1
0CompletedTreatmentPain, Acute1
0RecruitingOtherAutism Spectrum Conditions/Disorders1
0RecruitingTreatmentCentral Centrifugal Cicatricial Alopecia / Central Centrifugal Scarring Alopecia / Frontal Fibrosing Alopecia / Lichen Planopilaris / Scarring Alopecia1
0WithdrawnTreatmentTourniquet-induced Hypertension / Tourniquet-induced Pain1
1Active Not RecruitingPreventionOpioids Use / Postoperative pain1
1CompletedNot AvailableHealthy Volunteers7
1CompletedNot AvailableImpaired Renal Function1
1CompletedNot AvailableSubstance, Addiction1
1CompletedOtherEpilepsies1
1CompletedPreventionPreterm Labor, Premature Birth1
1CompletedTreatmentDrug Usage1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentSleeplessness1
1WithdrawnTreatmentPruritus1
1, 2CompletedPreventionFeeling Anxious / Pain NOS1
1, 2Not Yet RecruitingTreatmentPostoperative pain1
1, 2RecruitingNot AvailableClinical High Risk for Psychosis1
2Active Not RecruitingTreatmentAlcohol Use Disorder (AUD) / Alcohol Withdrawal Syndrome(AWS)1
2Active Not RecruitingTreatmentIrritability / Neurologically Impaired / Pain, Chronic / Signs and Symptoms, Digestive / Sleeplessness1
2Active Not RecruitingTreatmentMenopausal Hot Flushes1
2CompletedSupportive CareAcute Lymphoblastic Leukaemias (ALL) / Neuropathy / Pain, Neuropathic1
2CompletedSupportive CareMucositis1
2CompletedTreatmentAlcohol Dependence2
2CompletedTreatmentAlcohol Withdrawal Syndrome(AWS)1
2CompletedTreatmentBack Pain Lower Back Chronic1
2CompletedTreatmentBenzodiazepine Dependence / Opioid Dependence1
2CompletedTreatmentCannabis Dependence1
2CompletedTreatmentCannabis Dependence / Cannabis Withdrawal / Cognitive Deficits1
2CompletedTreatmentDependence, Cocaine / Depressive Symptoms1
2CompletedTreatmentDiabetic Peripheral Neuropathy (DPN)1
2CompletedTreatmentMenopausal Hot Flushes1
2CompletedTreatmentNerve Pain / Neuropathy / Post-Herpetic Neuralgia (PHN)1
2CompletedTreatmentOpiate withdrawal symptoms / Opioid Dependence / Opioid Detoxification1
2CompletedTreatmentOpioid-Induced Hyperalgesia1
2CompletedTreatmentOther Abortion / Spontaneous Abortions1
2CompletedTreatmentPendular Nystagmus Patients With Multiple Sclerosis1
2CompletedTreatmentPost-traumatic Neuropathic Pain1
2CompletedTreatmentPostoperative Complications1
2CompletedTreatmentSickle Cell Disorders1
2CompletedTreatmentSleep Initiation and Maintenance Disorders1
2CompletedTreatmentSmoking, Cigarette / Tobacco Use1
2CompletedTreatmentTinnitus1
2Not Yet RecruitingBasic ScienceAlcohol Use Disorder (AUD) / Opioid-use Disorder1
2Not Yet RecruitingTreatmentEnd Stage Renal Disease (ESRD) / Restless Legs Syndrome (RLS)1
2Not Yet RecruitingTreatmentPain, Chronic1
2Not Yet RecruitingTreatmentPainful Diabetic Neuropathy (PDN)1
2RecruitingBasic ScienceAlcohol Use Disorder (AUD) / Bipolar Disorder (BD)1
2RecruitingBasic ScienceBipolar I Disorder / Bipolar II Disorder / Cannabis Use Disorders / Substance Use Disorder (SUD)1
2RecruitingSupportive CareCancer of the Breast / Cancer, Breast / Malignant Neoplasm of Female Breast1
2RecruitingSupportive CareHPV-Related Squamous Cell Carcinoma / Oropharyngeal Cancers1
2TerminatedTreatmentBenzodiazepine Dependence1
2TerminatedTreatmentProstate Cancer1
2Unknown StatusTreatmentIntervertebral Disc Displacement / Intervertebral Disc Herniation1
2Unknown StatusTreatmentTinnitus, Subjective1
2WithdrawnTreatmentFabry's Disease / Pain, Neuropathic1
2, 3CompletedPreventionEffect of Laryngoscopy and Tracheal Intubation1
2, 3CompletedPreventionPost-Operative Nausea and Vomiting (PONV)1
2, 3CompletedTreatmentAlcohol Dependence2
2, 3CompletedTreatmentDetrusor Uninhibited Activity / Incontinence / Nocturia / Quality of Life / Urinary Frequency / Urination urgency of1
2, 3CompletedTreatmentFemale Genital Diseases1
2, 3CompletedTreatmentFibromyalgia1
2, 3Not Yet RecruitingTreatmentAnterior Cruciate Ligament Rupture / Muscle Weakness1
2, 3Not Yet RecruitingTreatmentArthralgia/joint pain / Breast Cancer Invasive Nos / Chemotherapeutic Toxicity / Muscle Soreness1
2, 3RecruitingSupportive CareBladder Carcinoma1
2, 3RecruitingTreatmentSubstance, Addiction1
2, 3TerminatedTreatmentAnalgesia / Inguinal Hernias / Pain NOS1
2, 3TerminatedTreatmentTinnitus1
3Active Not RecruitingTreatmentPain NOS1
3Active Not RecruitingTreatmentPain NOS / Quality of Life1
3CompletedNot AvailableSeizures1
3CompletedPreventionPostoperative pain1
3CompletedSupportive CareCancer, Breast / Menopausal Hot Flushes2
3CompletedSupportive CareIntervertebral Disc Herniation1
3CompletedSupportive CareMenopausal Hot Flushes / Prostate Cancer1
3CompletedSupportive CareNausea and vomiting / Unspecified Adult Solid Tumor, Protocol Specific1
3CompletedSupportive CareNeurologic toxicity / Pain NOS1
3CompletedTreatmentCarpal Tunnel Syndrome (CTS)2
3CompletedTreatmentCholestasis / Itching / Liver Cirrhosis / Liver Diseases / Pruritus1
3CompletedTreatmentCisplatin Adverse Reaction / Vomiting1
3CompletedTreatmentDiabetic Neuropathies / Polyneuropathies1
3CompletedTreatmentEpilepsy, Localization Related2
3CompletedTreatmentFibromyalgia1
3CompletedTreatmentHealthy Volunteers1
3CompletedTreatmentMenopausal Hot Flushes3
3CompletedTreatmentMenopausal Hot Flushes / Menopause1
3CompletedTreatmentPost-Operative Pain1
3CompletedTreatmentPostherpetic Neuralgia1
3CompletedTreatmentPostoperative pain1
3CompletedTreatmentScoliosis1
3CompletedTreatmentTransient Insomnia7
3Not Yet RecruitingPreventionHerpetic Neuralgia1
3Not Yet RecruitingSupportive CareCancer of Head and Neck / Narcotic Use1
3Not Yet RecruitingTreatmentAnaesthesia therapy / Shock, Septic1
3Not Yet RecruitingTreatmentBladder Pain Syndrome / Interstitial Cystitis1
3Not Yet RecruitingTreatmentHead Neck Cancer / Pain, Neuropathic / Radiation neuropathy1
3Not Yet RecruitingTreatmentLiver Cirrhosis1
3Not Yet RecruitingTreatmentPediatric Chronic Neuropathic Pain1
3Not Yet RecruitingTreatmentSleeplessness1
3RecruitingPreventionAdjunct to general anesthesia therapy / Anaesthesia therapy / Analgesics / Analgesics, Opioid / Dexmedetomidine / Gabapentin / Ketamine / Lidocaine / Narcotics / Obstructive Sleep Apnea of Child / Oximetry, Pulse / Pathologic Processes / Physiologic Effects of Drugs / Postoperative Complications / Respiratory Depression / Sleep Disordered Breathing (SDB) / Tonsillectomy1
3RecruitingSupportive CareMalignant Head and Neck Neoplasm / Mucositis / Radiation-Induced Disorder1
3RecruitingSupportive CareOropharynx Cancers1
3RecruitingTreatmentHyperemesis Gravidarum1
3RecruitingTreatmentPain, Chronic1
3RecruitingTreatmentPain, Chronic / Postoperative pain1
3RecruitingTreatmentPelvic Organ Prolapse (POP)1
3RecruitingTreatmentPelvic Pain1
3TerminatedNot AvailableNeuroleptic-Induced Tremor1
3TerminatedSupportive CareCancer, Breast / Lung Cancers / Pain NOS1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3Unknown StatusTreatmentFunctional Dyspepsia1
3WithdrawnPreventionPost-thoracotomy Pain1
4Active Not RecruitingTreatmentPeripheral Nerve Disorder Associated With Repair of Hernia1
4CompletedNot AvailableEpilepsy, Localization Related1
4CompletedBasic ScienceOsteoarthritis (OA)1
4CompletedBasic ScienceSleeplessness1
4CompletedOtherHealthy Volunteers1
4CompletedPreventionPost-Operative Nausea and Vomiting (PONV)1
4CompletedPreventionPostoperative pain1
4CompletedSupportive CarePain After Photorefractive Keratectomy1
4CompletedSupportive CarePain NOS1
4CompletedTreatmentAlcohol Withdrawal Syndrome(AWS)1
4CompletedTreatmentAmputation of Lower Limb1
4CompletedTreatmentAnalgesia / Postoperative pain1
4CompletedTreatmentAneurysmal Subarachnoid Hemorrhage1
4CompletedTreatmentBronchial Asthma1
4CompletedTreatmentCardiopulmonary Bypass1
4CompletedTreatmentCarpal Tunnel Syndrome (CTS) / Complex Regional Pain Syndrome (CRPS) / Diabetic Neuropathies / HIV Neuropathy / Idiopathic Sensory Neuropathy / Peripheral Neuropathy / Postherpetic Neuralgia1
4CompletedTreatmentColorectal Disorders1
4CompletedTreatmentComplex Partial Seizure Disorder / Epilepsies / Epilepsy, Localization Related / Seizure Disorder, Partial1
4CompletedTreatmentDiabetic Neuropathies2
4CompletedTreatmentDiabetic Neuropathy, Painful1
4CompletedTreatmentDiabetic Peripheral Neuropathic Pain (DPN)1
4CompletedTreatmentEpilepsies / Pain, Chronic1
4CompletedTreatmentEpilepsy, Localization Related1
4CompletedTreatmentHead and Neck Carcinoma / Pain, Acute / Postoperative pain1
4CompletedTreatmentHerpes Zoster / Pain NOS / Postherpetic Neuralgia1
4CompletedTreatmentLaparoscopic Cholecystectomy / Postoperative pain1
4CompletedTreatmentMenopausal Hot Flushes1
4CompletedTreatmentNarcotic Use / Nausea / Occasional Constipation / Pain NOS1
4CompletedTreatmentNeuropathy / Pain NOS1
4CompletedTreatmentOculopalatal Tremor / Pendular Nystagmus1
4CompletedTreatmentOrthopedic Disorders / Postoperative pain1
4CompletedTreatmentPain NOS1
4CompletedTreatmentParesthesia / Thoracic Pain1
4CompletedTreatmentPostoperative pain / Postoperative Sedation1
4CompletedTreatmentPostoperative pain2
4CompletedTreatmentProstate Cancer1
4Enrolling by InvitationPreventionPostoperative pain1
4Enrolling by InvitationTreatmentDiabetic Neuropathy, Painful / Pain, Neuropathic / Type 2 Diabetes Mellitus1
4Enrolling by InvitationTreatmentNonspecific Pain Post Traumatic Injury1
4Not Yet RecruitingTreatmentEpilepsy, Localization Related1
4Not Yet RecruitingTreatmentFacial Pain / Pain, Acute / Postoperative pain1
4Not Yet RecruitingTreatmentKnee Osteoarthritis (Knee OA) / Knee Pain Chronic / Opioid Dependence / Opioids Use1
4Not Yet RecruitingTreatmentPostoperative pain3
4Not Yet RecruitingTreatmentPostoperative pain / Renal Stones1
4RecruitingHealth Services ResearchTonsillectomy / Tonsillitis1
4RecruitingPreventionAnaesthesia therapy / Urethral Obstruction1
4RecruitingPreventionPelvic Organ Prolapse (POP)1
4RecruitingSupportive CareColon Diverticulosis / Colonic Neoplasms / Constipation Drug Induced / Diverticulitis, Colonic / Ileus / Ileus paralytic / Ileus; Mechanical / Malignant Neoplasm of Colon / Occasional Constipation / Postoperative pain / Rectum Cancer / Rectum Neoplasm1
4RecruitingTreatmentAlcohol Dependence1
4RecruitingTreatmentAlcohol Withdrawal Syndrome(AWS)1
4RecruitingTreatmentCervical Preparation / Pain NOS / Pregnancy Termination1
4RecruitingTreatmentCesarean Delivery / Pain Management1
4RecruitingTreatmentChronic Pain Syndrome / Opioids Use / Postpartum disorder1
4RecruitingTreatmentKnee Replacement Surgery / Pain NOS1
4RecruitingTreatmentMyofacial Pain1
4RecruitingTreatmentPain Management1
4RecruitingTreatmentPain NOS2
4RecruitingTreatmentPost-laminectomy Pain Syndrome1
4RecruitingTreatmentPostoperative pain1
4RecruitingTreatmentPostoperative pain / Surgery, Thoracic1
4RecruitingTreatmentRib Fracture Multiple / Rib Fractures1
4TerminatedTreatmentAbdominal Pain (AP) / Surgical Adhesions1
4TerminatedTreatmentBack Pain Lower Back Chronic / Diabetic Neuropathic Pain1
4TerminatedTreatmentDegenerative Joint Disease of Hip and Knee1
4TerminatedTreatmentImpaired Renal Function1
4TerminatedTreatmentInterstitial Cystitis / Irritable Bowel Syndrome (IBS) / Pelvic Pain / Prostatitis / Ulcerative Colitis (UC)1
4TerminatedTreatmentNeuropathic Chronic Pain1
4TerminatedTreatmentPK Properties Of Gabapentin In Subjects With Impaired Renal Function1
4TerminatedTreatmentPain NOS1
4TerminatedTreatmentPostoperative pain1
4TerminatedTreatmentRestless Legs Syndrome (RLS)1
4TerminatedTreatmentSleep1
4Unknown StatusTreatmentCholecystolithiasis1
4Unknown StatusTreatmentConscious Sedation Failure During Procedure1
4Unknown StatusTreatmentHyperalgesia1
4Unknown StatusTreatmentPlanned Abdominal Hysterectomy1
4WithdrawnPreventionKnee Arthroscopy / Shoulder Arthroscopy1
4WithdrawnTreatmentPost Operative Pain Control1
Not AvailableActive Not RecruitingNot AvailableCancer, Breast / Depression / Menopausal Hot Flushes / Psychosocial Effects of Cancer and Its Treatment1
Not AvailableActive Not RecruitingOtherPain NOS1
Not AvailableCompletedNot AvailableAcute Gouty Arthritis / Arthritis / Headaches / Migraines / Muscle Spasms / Radicular syndrome / Synovitis / Tendonitis1
Not AvailableCompletedNot AvailableEpilepsy, Localization Related1
Not AvailableCompletedNot AvailableHealthy Volunteers4
Not AvailableCompletedBasic ScienceHealthy Volunteers1
Not AvailableCompletedOtherAlcohol Dependence / Sleeplessness1
Not AvailableCompletedPreventionPruritus1
Not AvailableCompletedSupportive CareAnxiety Disorders / Cancer, Breast / Depression / Menopausal Hot Flushes1
Not AvailableCompletedSupportive CareHead and Neck Squamous Cell Carcinoma (HNSCC) / Pain NOS / Vesicular Stomatitis1
Not AvailableCompletedSupportive CareTotal Knee Arthroplasty (TKA)1
Not AvailableCompletedTreatmentAlzheimer's Disease (AD) / Dementias1
Not AvailableCompletedTreatmentAnal Condyloma / Fissure in Ano / Hemorrhoids / Rectal Fistulas1
Not AvailableCompletedTreatmentBurn Injuries / Pain NOS1
Not AvailableCompletedTreatmentCerebral Tumors1
Not AvailableCompletedTreatmentChronic Pelvic Pain1
Not AvailableCompletedTreatmentFibromyalgia1
Not AvailableCompletedTreatmentHerpes Zoster / Post-Herpetic Neuralgia (PHN)1
Not AvailableCompletedTreatmentHyperalgesia / Opioid-Related Disorders1
Not AvailableCompletedTreatmentKnee Replacement Surgery / Post Operative Pain1
Not AvailableCompletedTreatmentMenopausal Hot Flushes / Menopause / Vasomotor Disturbance1
Not AvailableCompletedTreatmentNystagmus / Nystagmus, Pathological1
Not AvailableCompletedTreatmentObesity, Morbid / Post-Operative Nausea and Vomiting (PONV) / Postoperative pain1
Not AvailableCompletedTreatmentPain NOS4
Not AvailableCompletedTreatmentPost Operative Pain Management in Children With Tonsillectomy/Adenoidectomy1
Not AvailableCompletedTreatmentPostoperative pain3
Not AvailableCompletedTreatmentPostoperative pain / Total Hip Replacement1
Not AvailableCompletedTreatmentRadicular syndrome / Sciatica1
Not AvailableCompletedTreatmentSedation, Conscious1
Not AvailableCompletedTreatmentSleep Bruxism1
Not AvailableCompletedTreatmentSpinal Stenosis of Lumbar Region1
Not AvailableCompletedTreatmentVulvodynia1
Not AvailableNot Yet RecruitingPreventionPost-Operative Nausea and Vomiting (PONV)1
Not AvailableNot Yet RecruitingTreatmentHerpes Zoster / Post-Herpetic Neuralgia (PHN)1
Not AvailableNot Yet RecruitingTreatmentSurgery, Cardiac1
Not AvailableRecruitingSupportive CareStage III Cutaneous Squamous Cell Carcinoma of the Head and Neck AJCC v8 / Stage IV Cutaneous Squamous Cell Carcinoma of the Head and Neck AJCC v81
Not AvailableRecruitingTreatmentAmputations / Phantom Pain Following Amputation of Lower Limb1
Not AvailableRecruitingTreatmentEmergence Agitation After Desflurane Anesthesia1
Not AvailableRecruitingTreatmentHip Pain Chronic1
Not AvailableTerminatedTreatmentComplex Regional Pain Syndrome I (CRPS I)1
Not AvailableTerminatedTreatmentPain NOS1
Not AvailableTerminatedTreatmentPostoperative pain1
Not AvailableTerminatedTreatmentVulvar Pain Symptoms / Vulvar Vestibulitis Syndrome (Chronic Vulvar Pain Localized to the Vaginal Opening) / Vulvodynia (Chronic Vulvar Pain)1
Not AvailableUnknown StatusTreatmentPruritus / Uremia1
Not AvailableWithdrawnNot AvailablePain NOS1
Not AvailableWithdrawnTreatmentCardiovascular Health / Vasomotor Symptoms1

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
KitOral
KitTopical
KitOral10.5 g/10.5g
KitOral10.8 g/10.8g
CapsuleOral100 mg/1
CapsuleOral300 mg/300mg
CapsuleOral300 mg/1
CapsuleOral400 mg/1
CapsuleOral600 mg/1
SolutionOral250 mg/5mL
SuspensionOral250 mg/5mL
TabletOral100 mg/1
TabletOral300 mg/1
TabletOral400 mg/1
TabletOral600 mg/1
TabletOral600 1/1
TabletOral800 mg/1
TabletOral800 mg/800mg
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral400 mg/1
Tablet, film coatedOral600 mg/1001
Tablet, film coatedOral600 mg/1
Tablet, film coatedOral800 mg/1
Kit300 mg/1
Tablet, multilayer, extended releaseOral600 mg
Tablet, multilayer, extended releaseOral800 mg
Tablet, film coatedOral300 mg/1
TabletOral600 mg
TabletOral800 mg
CapsuleOral100 mg
CapsuleOral300 mg
CapsuleOral400 mg
KitOral; Topical
Kit
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
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2327285No2005-06-142019-05-10Canada
CA2215923No2001-10-092016-04-26Canada
US6054482Yes2000-04-252017-10-25Us
US7256216Yes2007-08-142022-11-28Us
US6340475No2002-01-222016-09-19Us
US6635280No2003-10-212016-09-19Us
US6488962No2002-12-032020-06-20Us
US6723340No2004-04-202021-10-25Us
US7438927No2008-10-212024-02-26Us
US8192756No2012-06-052022-10-25Us
US8252332No2012-08-282022-10-25Us
US8333992No2012-12-182022-10-25Us
US7731989No2010-06-082022-10-25Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)162-166 °CNot Available
water solubility4490 mg/LNot Available
logP-1.10SANGSTER (1994)
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

Taxonomy

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
Gamma amino acid or derivatives / Amino fatty acid / Fatty acyl / Amino acid / Carboxylic acid / Monocarboxylic acid or derivatives / Organopnictogen compound / Primary amine / Organooxygen compound / Organonitrogen compound
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
gamma-amino acid (CHEBI:42797)

Targets

Kind
Protein
Organism
Human
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. Hota D, Bansal V, Pattanaik S: Evaluation of ketamine, nimodipine, gabapentin and imipramine in partial sciatic nerve transection model of neuropathic pain in rat: an experimental study. Methods Find Exp Clin Pharmacol. 2007 Sep;29(7):443-6. [PubMed:17982508]
  3. Gazulla J, Tintore MA: The P/Q-type voltage-dependent calcium channel as pharmacological target in spinocerebellar ataxia type 6: gabapentin and pregabalin may be of therapeutic benefit. Med Hypotheses. 2007;68(1):131-6. Epub 2006 Aug 8. [PubMed:16899342]
  4. 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]
  5. Hoffmann U, Dilekoz E, Kudo C, Ayata C: Gabapentin suppresses cortical spreading depression susceptibility. J Cereb Blood Flow Metab. 2010 Sep;30(9):1588-92. doi: 10.1038/jcbfm.2010.92. Epub 2010 Jun 30. [PubMed:20588320]
Kind
Protein
Organism
Human
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. 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. Hota D, Bansal V, Pattanaik S: Evaluation of ketamine, nimodipine, gabapentin and imipramine in partial sciatic nerve transection model of neuropathic pain in rat: an experimental study. Methods Find Exp Clin Pharmacol. 2007 Sep;29(7):443-6. [PubMed:17982508]
  2. Gazulla J, Tintore MA: The P/Q-type voltage-dependent calcium channel as pharmacological target in spinocerebellar ataxia type 6: gabapentin and pregabalin may be of therapeutic benefit. Med Hypotheses. 2007;68(1):131-6. Epub 2006 Aug 8. [PubMed:16899342]
  3. 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]
  4. Hoffmann U, Dilekoz E, Kudo C, Ayata C: Gabapentin suppresses cortical spreading depression susceptibility. J Cereb Blood Flow Metab. 2010 Sep;30(9):1588-92. doi: 10.1038/jcbfm.2010.92. Epub 2010 Jun 30. [PubMed:20588320]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Voltage-gated calcium channel activity
Specific 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, hor...
Gene Name
CACNA1B
Uniprot ID
Q00975
Uniprot Name
Voltage-dependent N-type calcium channel subunit alpha-1B
Molecular Weight
262493.84 Da
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]
  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. Hoffmann U, Dilekoz E, Kudo C, Ayata C: Gabapentin suppresses cortical spreading depression susceptibility. J Cereb Blood Flow Metab. 2010 Sep;30(9):1588-92. doi: 10.1038/jcbfm.2010.92. Epub 2010 Jun 30. [PubMed:20588320]
Kind
Protein
Organism
Human
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. De Vry J, Kuhl E, Franken-Kunkel P, Eckel G: Pharmacological characterization of the chronic constriction injury model of neuropathic pain. Eur J Pharmacol. 2004 May 3;491(2-3):137-48. [PubMed:15140630]
  2. 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]
  3. Kralic JE, Criswell HE, Osterman JL, O'Buckley TK, Wilkie ME, Matthews DB, Hamre K, Breese GR, Homanics GE, Morrow AL: Genetic essential tremor in gamma-aminobutyric acidA receptor alpha1 subunit knockout mice. J Clin Invest. 2005 Mar;115(3):774-9. [PubMed:15765150]
Kind
Protein group
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated cation channel activity
Specific Function
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. This protein plays a key role in synaptic p...

Components:
References
  1. Shimoyama M, Shimoyama N, Hori Y: Gabapentin affects glutamatergic excitatory neurotransmission in the rat dorsal horn. Pain. 2000 Apr;85(3):405-14. [PubMed:10781913]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
G-protein coupled gaba receptor activity
Specific Function
Component of a heterodimeric G-protein coupled receptor for GABA, formed by GABBR1 and GABBR2. Within the heterodimeric GABA receptor, only GABBR1 seems to bind agonists, while GABBR2 mediates coup...
Gene Name
GABBR1
Uniprot ID
Q9UBS5
Uniprot Name
Gamma-aminobutyric acid type B receptor subunit 1
Molecular Weight
108319.4 Da
References
  1. Ng GY, Bertrand S, Sullivan R, Ethier N, Wang J, Yergey J, Belley M, Trimble L, Bateman K, Alder L, Smith A, McKernan R, Metters K, O'Neill GP, Lacaille JC, Hebert TE: Gamma-aminobutyric acid type B receptors with specific heterodimer composition and postsynaptic actions in hippocampal neurons are targets of anticonvulsant gabapentin action. Mol Pharmacol. 2001 Jan;59(1):144-52. [PubMed:11125035]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
G-protein coupled gaba receptor activity
Specific Function
Component of a heterodimeric G-protein coupled receptor for GABA, formed by GABBR1 and GABBR2. Within the heterodimeric GABA receptor, only GABBR1 seems to bind agonists, while GABBR2 mediates coup...
Gene Name
GABBR2
Uniprot ID
O75899
Uniprot Name
Gamma-aminobutyric acid type B receptor subunit 2
Molecular Weight
105820.52 Da
References
  1. Ng GY, Bertrand S, Sullivan R, Ethier N, Wang J, Yergey J, Belley M, Trimble L, Bateman K, Alder L, Smith A, McKernan R, Metters K, O'Neill GP, Lacaille JC, Hebert TE: Gamma-aminobutyric acid type B receptors with specific heterodimer composition and postsynaptic actions in hippocampal neurons are targets of anticonvulsant gabapentin action. Mol Pharmacol. 2001 Jan;59(1):144-52. [PubMed:11125035]

Enzymes

Kind
Protein
Organism
Human
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]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Uesawa Y, Takeuchi T, Mohri K: Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17. [PubMed:22039822]

Drug created on June 13, 2005 07:24 / Updated on December 16, 2018 23:30