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Identification
NameVigabatrin
Accession NumberDB01080  (APRD00282)
TypeSmall Molecule
GroupsApproved
DescriptionAn analogue of gamma-aminobutyric acid, vigabatrin is an irreversible inhibitor of 4-aminobutyrate transaminase, the enzyme responsible for the catabolism of gamma-aminobutyric acid. (From Martindale The Extra Pharmacopoeia, 31st ed). Off-label uses include treatment of cocaine dependence.
Structure
Thumb
Synonyms
4-Amino-5-hexenoic acid
Gamma vinyl GABA
gamma-Vinyl GABA
gamma-Vinyl-gamma-aminobutyric acid
GVG
Vigabatrin
Vigabatrina
Vigabatrine
Vigabatrinum
Vinyl gamma-aminobutyric acid
External Identifiers
  • CPP-109
  • MDL 71,754
  • MDL-71754
  • RMI-71754
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
SabrilTablet500 mgOralLundbeck LLC1994-12-31Not applicableCanada
SabrilPowder500 mgOralLundbeck LLC1997-08-20Not applicableCanada
SabrilTablet, film coated500 mg/1OralLundbeck LLC2009-08-21Not applicableUs
SabrilPowder, for solution50 mg/mLOralLundbeck LLC2009-08-21Not applicableUs
Sabril Pwr 1g/sachetPowder1 gOralAventis Pharma IncNot applicableNot applicableCanada
Sabril Pwr 2g/sachetPowder2 gOralAventis Pharma IncNot applicableNot applicableCanada
Sabril Pwr 3g/sachetPowder3 gOralAventis Pharma IncNot applicableNot applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Sabrilan Lundbeck Inc.
Sabrilex Lundbeck Inc.
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIGR120KRT6K
CAS number68506-86-5
WeightAverage: 129.157
Monoisotopic: 129.078978601
Chemical FormulaC6H11NO2
InChI KeyPJDFLNIOAUIZSL-UHFFFAOYSA-N
InChI
InChI=1S/C6H11NO2/c1-2-5(7)3-4-6(8)9/h2,5H,1,3-4,7H2,(H,8,9)
IUPAC Name
4-aminohex-5-enoic acid
SMILES
NC(CCC(O)=O)C=C
Pharmacology
IndicationFor use as an adjunct in treatment resistant epilepsy, refractory complex partial seizures, and secondary generalized seizures. It is also used as monotherapy in infantile spasms in West syndrome.
Structured Indications
PharmacodynamicsVigabatrin is an anticonvulsant chemically unrelated to other anticonvulsants. Vigabatrin prevents the catabolism of GABA by irreversibly inhibiting the enzyme GABA transaminase. It is an analog of GABA, but it is not a receptor agonist. However, vigabatrin is not a potent inhibitor of GABA-T with a Ki of 10 mM.
Mechanism of actionVigabatrin increases brain concentrations of gamma-aminobutyric acid (GABA), an inhibitory neurotransmitter in the CNS, by irreversibly inhibiting enzymes that catabolize GABA (gamma-aminobutyric acid transaminase, GABA-T). Duration of action is determined by rate of GABA-T re-synthesis. Vigabatrin may also work by suppressing repetitive neuronal firing through inhibition of voltage-sensitive sodium channels. Although administered as a racemic mixture, only the S(+) enantiomer is pharmacologically active.
TargetKindPharmacological actionActionsOrganismUniProt ID
Gamma-aminobutyric acid type B receptor subunit 1Proteinyes
agonist
HumanQ9UBS5 details
4-aminobutyrate aminotransferase, mitochondrialProteinyes
inhibitor
HumanP80404 details
Related Articles
AbsorptionRapidly absorbed following oral administration, absorption is comparable between neonates, infants, and children. Cmax, 50 mg/kg dose, neonates= 14 mg/L; Tmax, 50 mg/kg dose, neonates = 2.1 hours; However, extent of absorption is higher and elimination half life is longer in neonates compared to children and infants. This is because neonates have reduced renal function compared to the aforementioned population groups. AUC, 50 mg/kg dose, neonates = 142.6 ± 44.0 mg/L/hr; Food may slightly decrease the rate (Cmax decreased by 33%, Tmax increased to 2 hours), but not the extent of absorption. Furthermore, vigabatrin does not cross the blood-brain-barrier well, thus high doses are needed.
Volume of distribution

1.1 L/kg

Protein bindingNot protein bound
Metabolism

Almost no metabolic transformation. Does not induce the hepatic cytochrome P450 system.

Route of eliminationEliminated primarily through renal excretion as unchanged drugs (80%).
Half lifeNeonates, 50 mg/kg = 7.5 ± 2.1 hours (due to reduced renal function); Infants = 5.7 hours; Adults = 7.5 hours; Elderly = 12 - 13 hours
Clearance

Infants = 2.4 ± 0.8 L/h;
Children = 5.7 ± 2.5 L/h

ToxicityLD50, oral, rat: 3000 mg/kg; Visual field defects may occur following cumulative doses in excess of 2 kg.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
1,1,1,2 TetrafluoroethaneThe risk or severity of adverse effects can be increased when Vigabatrin is combined with 1,1,1,2 Tetrafluoroethane.Investigational
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Vigabatrin.Experimental
AcepromazineThe risk or severity of adverse effects can be increased when Acepromazine is combined with Vigabatrin.Approved, Vet Approved
AceprometazineThe risk or severity of adverse effects can be increased when Aceprometazine is combined with Vigabatrin.Approved
adipiplonThe risk or severity of adverse effects can be increased when adipiplon is combined with Vigabatrin.Investigational
AgomelatineThe risk or severity of adverse effects can be increased when Agomelatine is combined with Vigabatrin.Approved, Investigational
AlfaxaloneThe risk or severity of adverse effects can be increased when Alfaxalone is combined with Vigabatrin.Vet Approved
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Vigabatrin.Approved, Illicit
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Alphacetylmethadol is combined with Vigabatrin.Experimental, Illicit
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Vigabatrin.Approved, Illicit, Investigational
AmisulprideThe risk or severity of adverse effects can be increased when Amisulpride is combined with Vigabatrin.Approved, Investigational
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Vigabatrin.Approved
AmobarbitalThe risk or severity of adverse effects can be increased when Amobarbital is combined with Vigabatrin.Approved, Illicit
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Vigabatrin.Approved
AmperozideThe risk or severity of adverse effects can be increased when Amperozide is combined with Vigabatrin.Experimental
AripiprazoleThe risk or severity of adverse effects can be increased when Aripiprazole is combined with Vigabatrin.Approved, Investigational
ArticaineThe risk or severity of adverse effects can be increased when Articaine is combined with Vigabatrin.Approved
AsenapineThe risk or severity of adverse effects can be increased when Asenapine is combined with Vigabatrin.Approved
AzaperoneThe risk or severity of adverse effects can be increased when Azaperone is combined with Vigabatrin.Vet Approved
AzelastineVigabatrin may increase the central nervous system depressant (CNS depressant) activities of Azelastine.Approved
AzelastineThe risk or severity of adverse effects can be increased when Azelastine is combined with Vigabatrin.Approved
BaclofenThe risk or severity of adverse effects can be increased when Baclofen is combined with Vigabatrin.Approved
BarbitalThe risk or severity of adverse effects can be increased when Barbital is combined with Vigabatrin.Illicit
BenperidolThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Benperidol.Investigational
BenzocaineThe risk or severity of adverse effects can be increased when Benzocaine is combined with Vigabatrin.Approved
Benzyl alcoholThe risk or severity of adverse effects can be increased when Benzyl alcohol is combined with Vigabatrin.Approved
BrexpiprazoleThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Brexpiprazole.Approved
BrimonidineThe risk or severity of adverse effects can be increased when Brimonidine is combined with Vigabatrin.Approved
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Vigabatrin.Approved
BromazepamThe risk or severity of adverse effects can be increased when Bromazepam is combined with Vigabatrin.Approved, Illicit
BrompheniramineThe risk or severity of adverse effects can be increased when Brompheniramine is combined with Vigabatrin.Approved
BrotizolamThe risk or severity of adverse effects can be increased when Brotizolam is combined with Vigabatrin.Approved, Withdrawn
BupivacaineThe risk or severity of adverse effects can be increased when Bupivacaine is combined with Vigabatrin.Approved, Investigational
BuprenorphineVigabatrin may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.Approved, Illicit, Investigational, Vet Approved
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Vigabatrin.Approved, Investigational
ButabarbitalThe risk or severity of adverse effects can be increased when Butabarbital is combined with Vigabatrin.Approved, Illicit
ButacaineThe risk or severity of adverse effects can be increased when Butacaine is combined with Vigabatrin.Vet Approved
ButalbitalThe risk or severity of adverse effects can be increased when Butalbital is combined with Vigabatrin.Approved, Illicit
ButambenThe risk or severity of adverse effects can be increased when Butamben is combined with Vigabatrin.Approved
ButethalThe risk or severity of adverse effects can be increased when Butethal is combined with Vigabatrin.Approved, Illicit
ButorphanolThe risk or severity of adverse effects can be increased when Butorphanol is combined with Vigabatrin.Approved, Illicit, Vet Approved
CarbamazepineThe risk or severity of adverse effects can be increased when Carbamazepine is combined with Vigabatrin.Approved, Investigational
CarbinoxamineThe risk or severity of adverse effects can be increased when Carbinoxamine is combined with Vigabatrin.Approved
CarfentanilThe risk or severity of adverse effects can be increased when Carfentanil is combined with Vigabatrin.Illicit, Vet Approved
CarisoprodolThe risk or severity of adverse effects can be increased when Carisoprodol is combined with Vigabatrin.Approved
CetirizineThe risk or severity of adverse effects can be increased when Cetirizine is combined with Vigabatrin.Approved
Chloral hydrateThe risk or severity of adverse effects can be increased when Chloral hydrate is combined with Vigabatrin.Approved, Illicit, Vet Approved
ChlordiazepoxideThe risk or severity of adverse effects can be increased when Chlordiazepoxide is combined with Vigabatrin.Approved, Illicit
ChlormezanoneThe risk or severity of adverse effects can be increased when Chlormezanone is combined with Vigabatrin.Approved, Withdrawn
ChloroprocaineThe risk or severity of adverse effects can be increased when Chloroprocaine is combined with Vigabatrin.Approved
ChlorphenamineThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Chlorphenamine.Approved
ChlorpromazineThe risk or severity of adverse effects can be increased when Chlorpromazine is combined with Vigabatrin.Approved, Vet Approved
ChlorprothixeneThe risk or severity of adverse effects can be increased when Chlorprothixene is combined with Vigabatrin.Approved, Withdrawn
ChlorzoxazoneThe risk or severity of adverse effects can be increased when Chlorzoxazone is combined with Vigabatrin.Approved
CinchocaineThe risk or severity of adverse effects can be increased when Cinchocaine is combined with Vigabatrin.Approved, Vet Approved
CitalopramThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Citalopram.Approved
ClemastineThe risk or severity of adverse effects can be increased when Clemastine is combined with Vigabatrin.Approved
ClidiniumThe risk or severity of adverse effects can be increased when Clidinium is combined with Vigabatrin.Approved
ClobazamThe risk or severity of adverse effects can be increased when Clobazam is combined with Vigabatrin.Approved, Illicit
clomethiazoleThe risk or severity of adverse effects can be increased when clomethiazole is combined with Vigabatrin.Investigational
ClomipramineThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Clomipramine.Approved, Vet Approved
ClonazepamVigabatrin may increase the central nervous system depressant (CNS depressant) activities of Clonazepam.Approved, Illicit
ClonidineThe risk or severity of adverse effects can be increased when Clonidine is combined with Vigabatrin.Approved
ClorazepateThe risk or severity of adverse effects can be increased when Clorazepate is combined with Vigabatrin.Approved, Illicit
ClozapineThe risk or severity of adverse effects can be increased when Clozapine is combined with Vigabatrin.Approved
CocaineThe risk or severity of adverse effects can be increased when Cocaine is combined with Vigabatrin.Approved, Illicit
CodeineThe risk or severity of adverse effects can be increased when Codeine is combined with Vigabatrin.Approved, Illicit
CyclizineThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Cyclizine.Approved
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Vigabatrin.Approved
CyproheptadineThe risk or severity of adverse effects can be increased when Cyproheptadine is combined with Vigabatrin.Approved
DantroleneThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Dantrolene.Approved
DapiprazoleThe risk or severity of adverse effects can be increased when Dapiprazole is combined with Vigabatrin.Approved
DapoxetineThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Dapoxetine.Investigational
deramciclaneThe risk or severity of adverse effects can be increased when deramciclane is combined with Vigabatrin.Investigational
DesfluraneThe risk or severity of adverse effects can be increased when Desflurane is combined with Vigabatrin.Approved
DesipramineThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Desipramine.Approved
DesloratadineThe risk or severity of adverse effects can be increased when Desloratadine is combined with Vigabatrin.Approved, Investigational
DesvenlafaxineThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Desvenlafaxine.Approved
DetomidineThe risk or severity of adverse effects can be increased when Detomidine is combined with Vigabatrin.Vet Approved
DexbrompheniramineThe risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with Vigabatrin.Approved
DexmedetomidineThe risk or severity of adverse effects can be increased when Dexmedetomidine is combined with Vigabatrin.Approved, Vet Approved
DextromoramideThe risk or severity of adverse effects can be increased when Dextromoramide is combined with Vigabatrin.Experimental, Illicit
DextropropoxypheneThe risk or severity of adverse effects can be increased when Dextropropoxyphene is combined with Vigabatrin.Approved, Illicit, Withdrawn
DezocineThe risk or severity of adverse effects can be increased when Dezocine is combined with Vigabatrin.Approved
DiazepamThe risk or severity of adverse effects can be increased when Diazepam is combined with Vigabatrin.Approved, Illicit, Vet Approved
DifenoxinThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Difenoxin.Approved, Illicit
DihydrocodeineThe risk or severity of adverse effects can be increased when Dihydrocodeine is combined with Vigabatrin.Approved, Illicit
DihydroetorphineThe risk or severity of adverse effects can be increased when Dihydroetorphine is combined with Vigabatrin.Experimental, Illicit
DihydromorphineThe risk or severity of adverse effects can be increased when Dihydromorphine is combined with Vigabatrin.Experimental, Illicit
DimenhydrinateThe risk or severity of adverse effects can be increased when Dimenhydrinate is combined with Vigabatrin.Approved
DiphenhydramineThe risk or severity of adverse effects can be increased when Diphenhydramine is combined with Vigabatrin.Approved
DiphenoxylateThe risk or severity of adverse effects can be increased when Diphenoxylate is combined with Vigabatrin.Approved, Illicit
DoramectinThe risk or severity of adverse effects can be increased when Doramectin is combined with Vigabatrin.Vet Approved
DoxepinThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Doxepin.Approved
DoxylamineDoxylamine may increase the central nervous system depressant (CNS depressant) activities of Vigabatrin.Approved, Vet Approved
DPDPEThe risk or severity of adverse effects can be increased when DPDPE is combined with Vigabatrin.Investigational
DronabinolDronabinol may increase the central nervous system depressant (CNS depressant) activities of Vigabatrin.Approved, Illicit
DroperidolDroperidol may increase the central nervous system depressant (CNS depressant) activities of Vigabatrin.Approved, Vet Approved
DrotebanolThe risk or severity of adverse effects can be increased when Drotebanol is combined with Vigabatrin.Experimental, Illicit
DuloxetineThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Duloxetine.Approved
DyclonineThe risk or severity of adverse effects can be increased when Dyclonine is combined with Vigabatrin.Approved
EcgonineThe risk or severity of adverse effects can be increased when Ecgonine is combined with Vigabatrin.Experimental, Illicit
ECGONINE METHYL ESTERThe risk or severity of adverse effects can be increased when ECGONINE METHYL ESTER is combined with Vigabatrin.Experimental
EcopipamThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Ecopipam.Investigational
EfavirenzThe risk or severity of adverse effects can be increased when Efavirenz is combined with Vigabatrin.Approved, Investigational
EnfluraneThe risk or severity of adverse effects can be increased when Enflurane is combined with Vigabatrin.Approved, Vet Approved
EntacaponeThe risk or severity of adverse effects can be increased when Entacapone is combined with Vigabatrin.Approved, Investigational
EscitalopramThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Escitalopram.Approved, Investigational
EstazolamThe risk or severity of adverse effects can be increased when Estazolam is combined with Vigabatrin.Approved, Illicit
EszopicloneThe risk or severity of adverse effects can be increased when Eszopiclone is combined with Vigabatrin.Approved
EthanolVigabatrin may increase the central nervous system depressant (CNS depressant) activities of Ethanol.Approved
EthchlorvynolThe risk or severity of adverse effects can be increased when Ethchlorvynol is combined with Vigabatrin.Approved, Illicit, Withdrawn
EthosuximideThe risk or severity of adverse effects can be increased when Ethosuximide is combined with Vigabatrin.Approved
EthotoinThe risk or severity of adverse effects can be increased when Ethotoin is combined with Vigabatrin.Approved
Ethyl carbamateThe risk or severity of adverse effects can be increased when Ethyl carbamate is combined with Vigabatrin.Withdrawn
Ethyl loflazepateThe risk or severity of adverse effects can be increased when Ethyl loflazepate is combined with Vigabatrin.Approved, Illicit
EthylmorphineThe risk or severity of adverse effects can be increased when Ethylmorphine is combined with Vigabatrin.Approved, Illicit
EtidocaineThe risk or severity of adverse effects can be increased when Etidocaine is combined with Vigabatrin.Approved
EtifoxineThe risk or severity of adverse effects can be increased when Etifoxine is combined with Vigabatrin.Withdrawn
EtizolamThe risk or severity of adverse effects can be increased when Etizolam is combined with Vigabatrin.Approved
EtomidateThe risk or severity of adverse effects can be increased when Etomidate is combined with Vigabatrin.Approved
EtoperidoneThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Etoperidone.Approved
EtorphineThe risk or severity of adverse effects can be increased when Etorphine is combined with Vigabatrin.Illicit, Vet Approved
EzogabineThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Ezogabine.Approved
FelbamateThe risk or severity of adverse effects can be increased when Felbamate is combined with Vigabatrin.Approved
FencamfamineThe risk or severity of adverse effects can be increased when Fencamfamine is combined with Vigabatrin.Approved, Illicit, Withdrawn
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Vigabatrin.Approved, Illicit, Investigational, Vet Approved
FexofenadineThe risk or severity of adverse effects can be increased when Fexofenadine is combined with Vigabatrin.Approved
FlibanserinThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Flibanserin.Approved
FludiazepamThe risk or severity of adverse effects can be increased when Fludiazepam is combined with Vigabatrin.Approved, Illicit
FlunarizineThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Flunarizine.Approved
FlunitrazepamThe risk or severity of adverse effects can be increased when Flunitrazepam is combined with Vigabatrin.Approved, Illicit
FluoxetineThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Fluoxetine.Approved, Vet Approved
FlupentixolThe risk or severity of adverse effects can be increased when Flupentixol is combined with Vigabatrin.Approved, Withdrawn
FluphenazineThe risk or severity of adverse effects can be increased when Fluphenazine is combined with Vigabatrin.Approved
FlurazepamThe risk or severity of adverse effects can be increased when Flurazepam is combined with Vigabatrin.Approved, Illicit
FluspirileneThe risk or severity of adverse effects can be increased when Fluspirilene is combined with Vigabatrin.Approved
Fluticasone PropionateThe risk or severity of adverse effects can be increased when Fluticasone Propionate is combined with Vigabatrin.Approved
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Vigabatrin.Approved, Investigational
FosphenytoinThe serum concentration of Fosphenytoin can be decreased when it is combined with Vigabatrin.Approved
FospropofolThe risk or severity of adverse effects can be increased when Fospropofol is combined with Vigabatrin.Approved, Illicit
GabapentinThe risk or severity of adverse effects can be increased when Gabapentin is combined with Vigabatrin.Approved, Investigational
gabapentin enacarbilThe risk or severity of adverse effects can be increased when Vigabatrin is combined with gabapentin enacarbil.Approved
Gamma Hydroxybutyric AcidThe risk or severity of adverse effects can be increased when Gamma Hydroxybutyric Acid is combined with Vigabatrin.Approved, Illicit
GepironeThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Gepirone.Investigational
GlutethimideThe risk or severity of adverse effects can be increased when Glutethimide is combined with Vigabatrin.Approved, Illicit
GuanfacineThe risk or severity of adverse effects can be increased when Guanfacine is combined with Vigabatrin.Approved, Investigational
HalazepamThe risk or severity of adverse effects can be increased when Halazepam is combined with Vigabatrin.Approved, Illicit, Withdrawn
HaloperidolThe risk or severity of adverse effects can be increased when Haloperidol is combined with Vigabatrin.Approved
HalothaneThe risk or severity of adverse effects can be increased when Halothane is combined with Vigabatrin.Approved, Vet Approved
HeroinThe risk or severity of adverse effects can be increased when Heroin is combined with Vigabatrin.Approved, Illicit
HexobarbitalThe risk or severity of adverse effects can be increased when Hexobarbital is combined with Vigabatrin.Approved
HydrocodoneVigabatrin may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.Approved, Illicit
HydromorphoneThe risk or severity of adverse effects can be increased when Hydromorphone is combined with Vigabatrin.Approved, Illicit
HydroxyzineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Vigabatrin.Approved
IloperidoneThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Iloperidone.Approved
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Vigabatrin.Approved
IndalpineThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Indalpine.Investigational, Withdrawn
IsofluraneThe risk or severity of adverse effects can be increased when Isoflurane is combined with Vigabatrin.Approved, Vet Approved
KetamineThe risk or severity of adverse effects can be increased when Ketamine is combined with Vigabatrin.Approved, Vet Approved
KetazolamThe risk or severity of adverse effects can be increased when Ketazolam is combined with Vigabatrin.Approved
KetobemidoneThe risk or severity of adverse effects can be increased when Ketobemidone is combined with Vigabatrin.Approved
LamotrigineThe risk or severity of adverse effects can be increased when Lamotrigine is combined with Vigabatrin.Approved, Investigational
LevetiracetamThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Levetiracetam.Approved, Investigational
LevobupivacaineThe risk or severity of adverse effects can be increased when Levobupivacaine is combined with Vigabatrin.Approved
LevocabastineThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Levocabastine.Approved
LevocetirizineThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Levocetirizine.Approved
LevodopaThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Levodopa.Approved
Levomethadyl AcetateThe risk or severity of adverse effects can be increased when Levomethadyl Acetate is combined with Vigabatrin.Approved
LevomilnacipranThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Levomilnacipran.Approved
LevorphanolThe risk or severity of adverse effects can be increased when Levorphanol is combined with Vigabatrin.Approved
LidocaineThe risk or severity of adverse effects can be increased when Lidocaine is combined with Vigabatrin.Approved, Vet Approved
LithiumThe risk or severity of adverse effects can be increased when Lithium is combined with Vigabatrin.Approved
LofentanilThe risk or severity of adverse effects can be increased when Lofentanil is combined with Vigabatrin.Illicit
LoratadineThe risk or severity of adverse effects can be increased when Loratadine is combined with Vigabatrin.Approved
LorazepamThe risk or severity of adverse effects can be increased when Lorazepam is combined with Vigabatrin.Approved
LoxapineThe risk or severity of adverse effects can be increased when Loxapine is combined with Vigabatrin.Approved
Lu AA21004The risk or severity of adverse effects can be increased when Lu AA21004 is combined with Vigabatrin.Investigational
LurasidoneThe risk or severity of adverse effects can be increased when Lurasidone is combined with Vigabatrin.Approved
Magnesium SulfateMagnesium Sulfate may increase the central nervous system depressant (CNS depressant) activities of Vigabatrin.Approved, Vet Approved
MaprotilineThe risk or severity of adverse effects can be increased when Maprotiline is combined with Vigabatrin.Approved
MeclizineThe risk or severity of adverse effects can be increased when Meclizine is combined with Vigabatrin.Approved
MedetomidineThe risk or severity of adverse effects can be increased when Medetomidine is combined with Vigabatrin.Vet Approved
MefloquineThe therapeutic efficacy of Vigabatrin can be decreased when used in combination with Mefloquine.Approved
MelatoninThe risk or severity of adverse effects can be increased when Melatonin is combined with Vigabatrin.Approved, Nutraceutical, Vet Approved
MelperoneThe risk or severity of adverse effects can be increased when Melperone is combined with Vigabatrin.Approved
MepivacaineThe risk or severity of adverse effects can be increased when Mepivacaine is combined with Vigabatrin.Approved, Vet Approved
MeprobamateThe risk or severity of adverse effects can be increased when Meprobamate is combined with Vigabatrin.Approved, Illicit
MesoridazineThe risk or severity of adverse effects can be increased when Mesoridazine is combined with Vigabatrin.Approved
MetaxaloneThe risk or severity of adverse effects can be increased when Metaxalone is combined with Vigabatrin.Approved
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Vigabatrin.Approved
Methadyl AcetateThe risk or severity of adverse effects can be increased when Methadyl Acetate is combined with Vigabatrin.Approved, Illicit
MethapyrileneThe risk or severity of adverse effects can be increased when Methapyrilene is combined with Vigabatrin.Withdrawn
MethaqualoneThe risk or severity of adverse effects can be increased when Methaqualone is combined with Vigabatrin.Illicit, Withdrawn
MethocarbamolThe risk or severity of adverse effects can be increased when Methocarbamol is combined with Vigabatrin.Approved, Vet Approved
MethohexitalThe risk or severity of adverse effects can be increased when Methohexital is combined with Vigabatrin.Approved
MethotrimeprazineVigabatrin may increase the central nervous system depressant (CNS depressant) activities of Methotrimeprazine.Approved
MethoxyfluraneThe risk or severity of adverse effects can be increased when Methoxyflurane is combined with Vigabatrin.Approved, Vet Approved
MethsuximideThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Methsuximide.Approved
MethylphenobarbitalThe risk or severity of adverse effects can be increased when Methylphenobarbital is combined with Vigabatrin.Approved
MetyrosineVigabatrin may increase the sedative activities of Metyrosine.Approved
MianserinThe therapeutic efficacy of Vigabatrin can be decreased when used in combination with Mianserin.Approved
MidazolamThe risk or severity of adverse effects can be increased when Midazolam is combined with Vigabatrin.Approved, Illicit
MilnacipranThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Milnacipran.Approved
MinocyclineMinocycline may increase the central nervous system depressant (CNS depressant) activities of Vigabatrin.Approved, Investigational
MirtazapineVigabatrin may increase the central nervous system depressant (CNS depressant) activities of Mirtazapine.Approved
MolindoneThe risk or severity of adverse effects can be increased when Molindone is combined with Vigabatrin.Approved
MorphineThe risk or severity of adverse effects can be increased when Morphine is combined with Vigabatrin.Approved, Investigational
NabiloneNabilone may increase the central nervous system depressant (CNS depressant) activities of Vigabatrin.Approved, Investigational
NalbuphineThe risk or severity of adverse effects can be increased when Nalbuphine is combined with Vigabatrin.Approved
NefazodoneThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Nefazodone.Approved, Withdrawn
NitrazepamThe risk or severity of adverse effects can be increased when Nitrazepam is combined with Vigabatrin.Approved
Nitrous oxideThe risk or severity of adverse effects can be increased when Nitrous oxide is combined with Vigabatrin.Approved, Vet Approved
NormethadoneThe risk or severity of adverse effects can be increased when Normethadone is combined with Vigabatrin.Approved, Illicit
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Vigabatrin.Approved
OlanzapineThe risk or severity of adverse effects can be increased when Olanzapine is combined with Vigabatrin.Approved, Investigational
OlopatadineThe risk or severity of adverse effects can be increased when Olopatadine is combined with Vigabatrin.Approved
OndansetronThe risk or severity of adverse effects can be increased when Ondansetron is combined with Vigabatrin.Approved
OpiumThe risk or severity of adverse effects can be increased when Opium is combined with Vigabatrin.Approved, Illicit
OrlistatThe serum concentration of Vigabatrin can be decreased when it is combined with Orlistat.Approved, Investigational
OrphenadrineVigabatrin may increase the central nervous system depressant (CNS depressant) activities of Orphenadrine.Approved
OsanetantThe risk or severity of adverse effects can be increased when Osanetant is combined with Vigabatrin.Investigational
OxazepamThe risk or severity of adverse effects can be increased when Oxazepam is combined with Vigabatrin.Approved
OxetacaineThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Oxetacaine.Investigational
OxprenololThe risk or severity of adverse effects can be increased when Oxprenolol is combined with Vigabatrin.Approved
OxybuprocaineThe risk or severity of adverse effects can be increased when Oxybuprocaine is combined with Vigabatrin.Approved
OxycodoneThe risk or severity of adverse effects can be increased when Oxycodone is combined with Vigabatrin.Approved, Illicit, Investigational
OxymorphoneThe risk or severity of adverse effects can be increased when Oxymorphone is combined with Vigabatrin.Approved, Investigational, Vet Approved
PaliperidoneThe risk or severity of adverse effects can be increased when Paliperidone is combined with Vigabatrin.Approved
ParaldehydeVigabatrin may increase the central nervous system depressant (CNS depressant) activities of Paraldehyde.Approved
ParoxetineThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Paroxetine.Approved, Investigational
PentazocineThe risk or severity of adverse effects can be increased when Pentazocine is combined with Vigabatrin.Approved, Vet Approved
PentobarbitalThe risk or severity of adverse effects can be increased when Pentobarbital is combined with Vigabatrin.Approved, Vet Approved
PerampanelPerampanel may increase the central nervous system depressant (CNS depressant) activities of Vigabatrin.Approved
PerazineThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Perazine.Investigational
PerospironeThe risk or severity of adverse effects can be increased when Perospirone is combined with Vigabatrin.Approved
PerphenazineThe risk or severity of adverse effects can be increased when Perphenazine is combined with Vigabatrin.Approved
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Vigabatrin.Approved
PhenobarbitalThe risk or severity of adverse effects can be increased when Phenobarbital is combined with Vigabatrin.Approved
PhenoxyethanolThe risk or severity of adverse effects can be increased when Phenoxyethanol is combined with Vigabatrin.Approved
PhenytoinThe serum concentration of Phenytoin can be decreased when it is combined with Vigabatrin.Approved, Vet Approved
PimozideThe risk or severity of adverse effects can be increased when Pimozide is combined with Vigabatrin.Approved
PipamperoneThe risk or severity of adverse effects can be increased when Pipamperone is combined with Vigabatrin.Approved
PipotiazineThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Pipotiazine.Approved
PiritramideThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Piritramide.Investigational
PizotifenThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Pizotifen.Approved
PomalidomideThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Pomalidomide.Approved
PramipexoleVigabatrin may increase the sedative activities of Pramipexole.Approved, Investigational
PramocaineThe risk or severity of adverse effects can be increased when Pramocaine is combined with Vigabatrin.Approved
PrazepamThe risk or severity of adverse effects can be increased when Prazepam is combined with Vigabatrin.Approved, Illicit
PregabalinThe risk or severity of adverse effects can be increased when Pregabalin is combined with Vigabatrin.Approved, Illicit, Investigational
PregnanoloneThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Pregnanolone.Investigational
PrilocaineThe risk or severity of adverse effects can be increased when Prilocaine is combined with Vigabatrin.Approved
PrimidoneThe risk or severity of adverse effects can be increased when Primidone is combined with Vigabatrin.Approved, Vet Approved
ProcaineThe risk or severity of adverse effects can be increased when Procaine is combined with Vigabatrin.Approved, Investigational, Vet Approved
ProchlorperazineThe risk or severity of adverse effects can be increased when Prochlorperazine is combined with Vigabatrin.Approved, Vet Approved
PromazineThe risk or severity of adverse effects can be increased when Promazine is combined with Vigabatrin.Approved, Vet Approved
PromethazineThe risk or severity of adverse effects can be increased when Promethazine is combined with Vigabatrin.Approved
ProparacaineThe risk or severity of adverse effects can be increased when Proparacaine is combined with Vigabatrin.Approved, Vet Approved
PropofolThe risk or severity of adverse effects can be increased when Propofol is combined with Vigabatrin.Approved, Investigational, Vet Approved
PropoxycaineThe risk or severity of adverse effects can be increased when Propoxycaine is combined with Vigabatrin.Approved
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Vigabatrin.Approved
PSD502The risk or severity of adverse effects can be increased when PSD502 is combined with Vigabatrin.Investigational
QuazepamThe risk or severity of adverse effects can be increased when Quazepam is combined with Vigabatrin.Approved, Illicit
QuetiapineThe risk or severity of adverse effects can be increased when Quetiapine is combined with Vigabatrin.Approved
RacloprideThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Raclopride.Investigational
RamelteonThe risk or severity of adverse effects can be increased when Ramelteon is combined with Vigabatrin.Approved, Investigational
RemifentanilThe risk or severity of adverse effects can be increased when Remifentanil is combined with Vigabatrin.Approved
RemoxiprideThe risk or severity of adverse effects can be increased when Remoxipride is combined with Vigabatrin.Approved, Withdrawn
ReserpineThe risk or severity of adverse effects can be increased when Reserpine is combined with Vigabatrin.Approved
RisperidoneThe risk or severity of adverse effects can be increased when Risperidone is combined with Vigabatrin.Approved, Investigational
RitanserinThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Ritanserin.Investigational
RomifidineThe risk or severity of adverse effects can be increased when Romifidine is combined with Vigabatrin.Vet Approved
RopiniroleVigabatrin may increase the sedative activities of Ropinirole.Approved, Investigational
RopivacaineThe risk or severity of adverse effects can be increased when Ropivacaine is combined with Vigabatrin.Approved
RotigotineVigabatrin may increase the sedative activities of Rotigotine.Approved
RufinamideThe risk or severity of adverse effects can be increased when Rufinamide is combined with Vigabatrin.Approved
S-EthylisothioureaThe risk or severity of adverse effects can be increased when S-Ethylisothiourea is combined with Vigabatrin.Experimental
Sage 547The risk or severity of adverse effects can be increased when Vigabatrin is combined with Sage 547.Investigational
ScopolamineThe risk or severity of adverse effects can be increased when Scopolamine is combined with Vigabatrin.Approved
SecobarbitalThe risk or severity of adverse effects can be increased when Secobarbital is combined with Vigabatrin.Approved, Vet Approved
SertindoleThe risk or severity of adverse effects can be increased when Sertindole is combined with Vigabatrin.Approved, Withdrawn
SertralineThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Sertraline.Approved
SevofluraneThe risk or severity of adverse effects can be increased when Sevoflurane is combined with Vigabatrin.Approved, Vet Approved
Sodium oxybateSodium oxybate may increase the central nervous system depressant (CNS depressant) activities of Vigabatrin.Approved
StiripentolThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Stiripentol.Approved
SufentanilThe risk or severity of adverse effects can be increased when Sufentanil is combined with Vigabatrin.Approved, Investigational
SulpirideThe risk or severity of adverse effects can be increased when Sulpiride is combined with Vigabatrin.Approved
SuvorexantVigabatrin may increase the central nervous system depressant (CNS depressant) activities of Suvorexant.Approved
TandospironeThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Tandospirone.Investigational
TapentadolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Vigabatrin.Approved
TasimelteonThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Tasimelteon.Approved
TemazepamThe risk or severity of adverse effects can be increased when Temazepam is combined with Vigabatrin.Approved
TetrabenazineThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Tetrabenazine.Approved
TetracaineThe risk or severity of adverse effects can be increased when Tetracaine is combined with Vigabatrin.Approved, Vet Approved
TetrodotoxinThe risk or severity of adverse effects can be increased when Tetrodotoxin is combined with Vigabatrin.Investigational
ThalidomideVigabatrin may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.Approved, Investigational, Withdrawn
ThiamylalThe risk or severity of adverse effects can be increased when Thiamylal is combined with Vigabatrin.Approved, Vet Approved
ThiopentalThe risk or severity of adverse effects can be increased when Thiopental is combined with Vigabatrin.Approved, Vet Approved
ThioridazineThe risk or severity of adverse effects can be increased when Thioridazine is combined with Vigabatrin.Approved
ThiothixeneThe risk or severity of adverse effects can be increased when Thiothixene is combined with Vigabatrin.Approved
TiagabineThe risk or severity of adverse effects can be increased when Tiagabine is combined with Vigabatrin.Approved
TiaprideThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Tiapride.Investigational
TiletamineThe risk or severity of adverse effects can be increased when Tiletamine is combined with Vigabatrin.Vet Approved
TizanidineThe risk or severity of adverse effects can be increased when Tizanidine is combined with Vigabatrin.Approved
TolcaponeThe risk or severity of adverse effects can be increased when Tolcapone is combined with Vigabatrin.Approved, Withdrawn
TopiramateThe risk or severity of adverse effects can be increased when Topiramate is combined with Vigabatrin.Approved
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Vigabatrin.Approved, Investigational
Trans-2-PhenylcyclopropylamineThe risk or severity of adverse effects can be increased when Trans-2-Phenylcyclopropylamine is combined with Vigabatrin.Experimental
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Vigabatrin.Approved
TrazodoneThe risk or severity of adverse effects can be increased when Trazodone is combined with Vigabatrin.Approved, Investigational
TriazolamThe risk or severity of adverse effects can be increased when Triazolam is combined with Vigabatrin.Approved
TrifluoperazineThe risk or severity of adverse effects can be increased when Trifluoperazine is combined with Vigabatrin.Approved
TriflupromazineThe risk or severity of adverse effects can be increased when Triflupromazine is combined with Vigabatrin.Approved, Vet Approved
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Vigabatrin.Approved
TriprolidineThe risk or severity of adverse effects can be increased when Triprolidine is combined with Vigabatrin.Approved
Uc1010The risk or severity of adverse effects can be increased when Vigabatrin is combined with Uc1010.Investigational
Valproic AcidThe risk or severity of adverse effects can be increased when Valproic Acid is combined with Vigabatrin.Approved, Investigational
VenlafaxineThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Venlafaxine.Approved
VortioxetineThe risk or severity of adverse effects can be increased when Vortioxetine is combined with Vigabatrin.Approved
XylazineThe risk or severity of adverse effects can be increased when Xylazine is combined with Vigabatrin.Vet Approved
ZaleplonThe risk or severity of adverse effects can be increased when Zaleplon is combined with Vigabatrin.Approved, Illicit, Investigational
ZiconotideThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Ziconotide.Approved
ZimelidineThe risk or severity of adverse effects can be increased when Vigabatrin is combined with Zimelidine.Withdrawn
ZiprasidoneThe risk or severity of adverse effects can be increased when Ziprasidone is combined with Vigabatrin.Approved
ZolazepamThe risk or severity of adverse effects can be increased when Zolazepam is combined with Vigabatrin.Vet Approved
ZolpidemVigabatrin may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.Approved
ZonisamideThe risk or severity of adverse effects can be increased when Zonisamide is combined with Vigabatrin.Approved, Investigational
ZopicloneThe risk or severity of adverse effects can be increased when Zopiclone is combined with Vigabatrin.Approved
ZotepineThe risk or severity of adverse effects can be increased when Zotepine is combined with Vigabatrin.Approved
ZuclopenthixolThe risk or severity of adverse effects can be increased when Zuclopenthixol is combined with Vigabatrin.Approved, Investigational
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  1. Gram L, Larsson OM, Johnsen A, Schousboe A: Experimental studies of the influence of vigabatrin on the GABA system. Br J Clin Pharmacol. 1989;27 Suppl 1:13S-17S. [PubMed:2757904 ]
  2. Browne TR: Pharmacokinetics of antiepileptic drugs. Neurology. 1998 Nov;51(5 Suppl 4):S2-7. [PubMed:9818917 ]
  3. Lindberger M, Luhr O, Johannessen SI, Larsson S, Tomson T: Serum concentrations and effects of gabapentin and vigabatrin: observations from a dose titration study. Ther Drug Monit. 2003 Aug;25(4):457-62. [PubMed:12883229 ]
  4. Zwanzger P, Baghai TC, Schuele C, Strohle A, Padberg F, Kathmann N, Schwarz M, Moller HJ, Rupprecht R: Vigabatrin decreases cholecystokinin-tetrapeptide (CCK-4) induced panic in healthy volunteers. Neuropsychopharmacology. 2001 Nov;25(5):699-703. [PubMed:11682253 ]
  5. Tulloch JK, Carr RR, Ensom MH: A systematic review of the pharmacokinetics of antiepileptic drugs in neonates with refractory seizures. J Pediatr Pharmacol Ther. 2012 Jan;17(1):31-44. doi: 10.5863/1551-6776-17.1.31. [PubMed:23118657 ]
  6. Clayton LM, Stern WM, Newman WD, Sander JW, Acheson J, Sisodiya SM: Evolution of visual field loss over ten years in individuals taking vigabatrin. Epilepsy Res. 2013 Aug;105(3):262-71. doi: 10.1016/j.eplepsyres.2013.02.014. Epub 2013 Mar 28. [PubMed:23541931 ]
  7. Hawker DD, Silverman RB: Synthesis and evaluation of novel heteroaromatic substrates of GABA aminotransferase. Bioorg Med Chem. 2012 Oct 1;20(19):5763-73. doi: 10.1016/j.bmc.2012.08.009. Epub 2012 Aug 16. [PubMed:22944334 ]
External Links
ATC CodesN03AG04
AHFS Codes
  • 28:12.92
PDB Entries
FDA labelDownload (307 KB)
MSDSDownload (63.9 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9213
Blood Brain Barrier+0.9382
Caco-2 permeable-0.5191
P-glycoprotein substrateNon-substrate0.797
P-glycoprotein inhibitor INon-inhibitor0.949
P-glycoprotein inhibitor IINon-inhibitor0.9856
Renal organic cation transporterNon-inhibitor0.8944
CYP450 2C9 substrateNon-substrate0.8785
CYP450 2D6 substrateNon-substrate0.8115
CYP450 3A4 substrateNon-substrate0.7664
CYP450 1A2 substrateNon-inhibitor0.9149
CYP450 2C9 inhibitorNon-inhibitor0.9389
CYP450 2D6 inhibitorNon-inhibitor0.9654
CYP450 2C19 inhibitorNon-inhibitor0.963
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9824
Ames testNon AMES toxic0.8409
CarcinogenicityNon-carcinogens0.7678
BiodegradationReady biodegradable0.7494
Rat acute toxicity1.6656 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9617
hERG inhibition (predictor II)Non-inhibitor0.9772
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
PowderOral500 mg
Powder, for solutionOral50 mg/mL
TabletOral500 mg
Tablet, film coatedOral500 mg/1
PowderOral1 g
PowderOral2 g
PowderOral3 g
Prices
Unit descriptionCostUnit
Sabril 500 mg tablet16.66USD tablet
Sabril 500 mg Powder Packet0.95USD packet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubility55.1 mg/mLNot Available
logP-2.16HENCZI,M ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility96.6 mg/mLALOGPS
logP-2.6ALOGPS
logP-2.1ChemAxon
logS-0.13ALOGPS
pKa (Strongest Acidic)4.61ChemAxon
pKa (Strongest Basic)9.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.29 m3·mol-1ChemAxon
Polarizability13.64 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGamma amino acids and derivatives
Alternative Parents
Substituents
  • Gamma amino acid or derivatives
  • Medium-chain fatty acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
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 coupling to G proteins. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such a...
Gene Name:
GABBR1
Uniprot ID:
Q9UBS5
Molecular Weight:
108319.4 Da
References
  1. Tyacke RJ, Lingford-Hughes A, Reed LJ, Nutt DJ: GABAB receptors in addiction and its treatment. Adv Pharmacol. 2010;58:373-96. doi: 10.1016/S1054-3589(10)58014-1. [PubMed:20655489 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Succinate-semialdehyde dehydrogenase binding
Specific Function:
Catalyzes the conversion of gamma-aminobutyrate and L-beta-aminoisobutyrate to succinate semialdehyde and methylmalonate semialdehyde, respectively. Can also convert delta-aminovalerate and beta-alanine.
Gene Name:
ABAT
Uniprot ID:
P80404
Molecular Weight:
56438.405 Da
References
  1. Weber OM, Verhagen A, Duc CO, Meier D, Leenders KL, Boesiger P: Effects of vigabatrin intake on brain GABA activity as monitored by spectrally edited magnetic resonance spectroscopy and positron emission tomography. Magn Reson Imaging. 1999 Apr;17(3):417-25. [PubMed:10195585 ]
  2. Valdizan EM, Garcia AP, Armijo JA: Effects of increasing doses of vigabatrin on platelet gamma-aminobutyric acid-transaminase and brain gamma-aminobutyric acid in rats. Eur J Pharmacol. 1999 Mar 19;369(2):169-73. [PubMed:10206175 ]
  3. Arndt CF, Derambure P, Defoort-Dhellemmes S, Hache JC: Outer retinal dysfunction in patients treated with vigabatrin. Neurology. 1999 Apr 12;52(6):1201-5. [PubMed:10214744 ]
  4. Molina PE, Ahmed N, Ajmal M, Dewey S, Volkow N, Fowler J, Abumrad N: Co-administration of gamma-vinyl GABA and cocaine: preclinical assessment of safety. Life Sci. 1999;65(11):1175-82. [PubMed:10503933 ]
  5. French JA: Vigabatrin. Epilepsia. 1999;40 Suppl 5:S11-6. [PubMed:10530689 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
L-proline transmembrane transporter activity
Specific Function:
Neutral amino acid/proton symporter. Has a pH-dependent electrogenic transport activity for small amino acids such as glycine, alanine and proline. Besides small apolar L-amino acids, it also recognize their D-enantiomers and selected amino acid derivatives such as gamma-aminobutyric acid (By similarity).
Gene Name:
SLC36A1
Uniprot ID:
Q7Z2H8
Molecular Weight:
53075.045 Da
References
  1. Abbot EL, Grenade DS, Kennedy DJ, Gatfield KM, Thwaites DT: Vigabatrin transport across the human intestinal epithelial (Caco-2) brush-border membrane is via the H+ -coupled amino-acid transporter hPAT1. Br J Pharmacol. 2006 Feb;147(3):298-306. [PubMed:16331283 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23