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Compound Detail

CHEMBL89598

VIGABATRIN
💊 Approved Drug
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💊 Approved Drug
C=CC(N)CCC(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL89598
Name VIGABATRIN
Phase Approved
Structure Type MOL
InChI Key PJDFLNIOAUIZSL-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

5-hexenoic acid, 4-amino- CPP-109 Gamma vinyl gaba Gamma-vinyl gaba Kigabeq MDL 71,754 MDL-71754 RMI-71754 Sabril Vigabatrin Vigabatrina Vigabatrine +2 more
2
Targets
9
Activities
2
Assay Types
1
PK Parameters
20
Publications
14
Known Names
12
Indications
1
Mechanisms

Molecular Properties

129.2
MW (Da)
0.36
ALogP
2
HBA
2
HBD
63.3
PSA (Ų)
0.54
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2009
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -gab-
USAN Year 1985

Extended Properties

Molecular Formula C6H11NO2
MW 129.16
Aromatic Rings 0
Heavy Atoms 9
NP-Likeness 1.30

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Gamma-amino-N-butyrate transaminase inhibitor INHIBITOR 4-aminobutyrate aminotransferase, mitochondrial ✓ ✓

Indications

Epilepsies, Partial Epilepsy Epilepsy, Complex Partial Spasms, Infantile Spasms, Infantile Spasms, Infantile Alcoholism Amphetamine-Related Disorders Cocaine-Related Disorders Obesity Tuberous Sclerosis Tourette Syndrome

ATC Classification

N03AG04
vigabatrin
Level 1: NERVOUS SYSTEM
Level 2: ANTIEPILEPTICS

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

Ki 7 meas.
IC50 2 meas. best 4.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
4-aminobutyrate aminotransferase, mitochondrial
CHEMBL4523258
 IC50 4.4 4.4 39720.0 1
4-aminobutyrate aminotransferase, mitochondrial
CHEMBL3148
 IC50 4.38 4.38 41210.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.005 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
4-aminobutyrate aminotransferase, mitochondrial IC50 = 39720.0 nM 4.4 Inhibition of GABA aminotransferase in mouse brain homogenates using GABA and al... 31084949
4-aminobutyrate aminotransferase, mitochondrial IC50 = 41210.0 nM 4.38 Inhibition of Rattus norvegicus (rat) brain gamma-amino butyrate aminotransferas... -

Literature References

PubMed DOI Target Context # Activities
22128851 10.1021/jm201231w Rattus norvegicus 27
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
10762036 10.1016/s0960-894x(00)00064-0 Mus musculus 8
33062178 10.1021/acsmedchemlett.9b00672 4-aminobutyrate aminotransferase, mitochondrial 4
14640537 10.1021/jm034162s 4-aminobutyrate aminotransferase, mitochondrial 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
22128851 10.1021/jm201231w 4-aminobutyrate aminotransferase, mitochondrial 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
12238932 10.1021/jm020134i 4-aminobutyrate aminotransferase, mitochondrial 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
3806611 10.1021/jm00385a007 Mus musculus 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2

Data from ChEMBL 36 via Core Engine