General
Preferred name
VIGABATRIN
Synonyms
(±)-gamma-Vinyl GABA ()
¦Ã-Vinyl-GABA hydrochloride ()
¦Ã-Vinyl-GABA ()
Sabril ()
Vigabatrine ()
??Vinyl-GABA hydrochloride ()
??Vinyl-GABA ()
Vigabatrin hydrochloride ()
Vigabatrin (Hydrochloride) ()
γ-Vinyl-GABA ()
γ-Vinyl-GABA (hydrochloride) ()
MDL 71,754 ()
Gamma vinyl gaba ()
CPP-109 ()
5-hexenoic acid, 4-amino- ()
Kigabeq ()
RMI-71754 ()
Vigabatrina ()
MDL-71754 ()
Vigafyde ()
Gamma-Vinyl Gaba ()
Vinyl Gamma-Aminobutyric Acid ()
¦Ã-Vinyl-GABA (hydrochloride) ()
Vigabatrin-13C-d2 (hydrochloride) ()
P&D ID
PD002625
CAS
68506-86-5
60643-86-9
74046-07-4
1391054-02-6
2749628-08-6
Tags
available
covalent binder
drug
Approved by
FDA
First approval
2009
Drug indication
cocaine dependence
Infantile spasm
Complex partial seizure
Epilepsy
Drug Status
approved
Max Phase
4.0
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
HALF-LIFE Neonates, 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; ; ;
TOXICITY LD50, oral, rat: 3000 mg/kg; ; Visual field defects may occur following cumulative doses in excess of 2 kg.
ABSORPTION Rapidly 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. ;
DESCRIPTION The approved drug vigabatrin is a mixture to two stereoisomers: an R(-)- form (see PubChem CID 157018) and an S(+)-form (see PubChem CID 10219440). Only the S(+)-form is pharmacologically active. The structure shown here does not specify stereochemistry and represents the mixture. (GtoPdb)
PRICE 36
DESCRIPTION Vigabatrin (Sabril), an analogue of gamma-aminobutyric acid, is an irreversible inhibitor of 4-aminobutyrate Transaminase responsible for the catabolism of ??-aminobutyric acid.
DESCRIPTION Vigabatrin hydrochloride (¦Ã-Vinyl-GABA hydrochloride), a inhibitory neurotransmitter GABA vinyl-derivative, is an orally active and irreversible GABA transaminase inhibitor. Vigabatrin hydrochloride is an antiepileptic agent, which acts by increasing GABA levels in the brain by inhibiting the catabolism of GABA by GABA transaminase[1][2][3].
DESCRIPTION Selective GABA transaminase (GABA-T) inhibitor; anticonvulsant (LOPAC library)
DESCRIPTION Inhibits desensitization; AMPA > kainate (Tocris Bioactive Compound Library)
DESCRIPTION Vigabatrin is an analog of gamma-aminobutyric acid, the main inhibitory neurotransmitter in the central nervous system. It used in the treatment of refractory seizures and infantile spasms. It irreversibly inhibits the enzyme responsible for GABA metabolism, thereby increasing levels of circulating GABA. Although administered as a racemic mixture, only the S(+) enantiomer is pharmacologically active. (Enamine Bioactive Compounds)
DESCRIPTION Vigabatrin (Sabril), an analogue of gamma-aminobutyric acid, is an irreversible inhibitor of 4-aminobutyrate Transaminase responsible for the catabolism of γ-aminobutyric acid. (TargetMol Bioactive Compound Library)
Compound Sets
30
AdooQ Bioactive Compound Library
A15277
Cayman Chemical Bioactives
9000976
26672
ChEMBL Approved Drugs
CHEMBL89598
ChEMBL Drugs
CHEMBL89598
Concise Guide to Pharmacology 2017/18
4821
Concise Guide to Pharmacology 2019/20
4821
Concise Guide to Pharmacology 2021/22
4821
Concise Guide to Pharmacology 2023/24
4821
CovalentInDB
CI002225
DrugBank
DB01080
DrugBank Approved Drugs
DB01080
DrugCentral
2819
DrugCentral Approved Drugs
2819
DrugMAP
DMYT0OG
DrugMAP Approved Drugs
DMYT0OG
DrugMatrix
Enamine Bioactive Compounds
EBC-06162
Enamine BioReference Compounds
Guide to Pharmacology
4821
LOPAC library
Mcule NIBR MoA Box Subset
MCULE-4435406748
MedChem Express Bioactive Compound Library
HY-15399
HY-B0033
Natural product-based probes and drugs
NCATS Inxight Approved Drugs
GR120KRT6K
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Prestwick Chemical Library
ReFrame library
TargetMol Bioactive Compound Library
T0128
Tocris Bioactive Compound Library
0808
External IDs
55
Properties
(calculated by RDKit )
Molecular Weight
129.08
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
2
Rotatable Bonds
4
Ring Count
0
Aromatic Ring Count
0
cLogP
0.36
TPSA
63.32
Fraction CSP3
0.5
Chiral centers
1.0
Largest ring
0.0
QED
0.54
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Selectivity
Transaminase
Target
ABAT
GABA
GABA Receptor
Primary Target
Miscellaneous GABA
MOA
ABC antagonist
GABA Receptor agonist
GABA Aminotransferase Inhibitors
Member status
member
Pathway
Membrane Transporter/Ion Channel
Neuroscience
Neuronal Signaling
Biosynthetic Origin
Alkaloid
Therapeutic Indication
Antiepileptic
Therapeutic Class
CNS & PNS
Anticonvulsants
Source data