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Compound Detail

CHEMBL1027

TIAGABINE
💊 Approved Drug
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💊 Approved Drug
Cc1ccsc1C(=CCCN1CCC[C@@H](C(=O)O)C1)c1sccc1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1027
Name TIAGABINE
Phase Approved
Structure Type MOL
InChI Key PBJUNZJWGZTSKL-MRXNPFEDSA-N
Therapeutic ✓ Yes

Known Names

A-70569-1 ABBOTT-70569 FREE BASE Abbott-70569-1 ABBOTT-705691 FREE BASE ABT-569 FREE BASE Gabitril NNC-050328 FREE BASE NO-050328 FREE BASE Tiagabina Tiagabine
5
Targets
63
Activities
3
Assay Types
9
PK Parameters
20
Publications
10
Known Names
6
Indications

Molecular Properties

375.6
MW (Da)
5.04
ALogP
4
HBA
1
HBD
40.5
PSA (Ų)
0.77
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1997
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -gab-
USAN Year 1996

Extended Properties

Molecular Formula C20H25NO2S2
MW 375.56
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.62

Indications

Epilepsy Anxiety Schizophrenia Cocaine-Related Disorders Sleep Apnea, Obstructive Alcoholism

ATC Classification

N03AG06
tiagabine
Level 1: NERVOUS SYSTEM
Level 2: ANTIEPILEPTICS

Activity Summary

IC50 50 meas. best 7.43
Ki 11 meas. best 7.77
Kd 2 meas. best 7.39

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium- and chloride-dependent GABA transporter 1
CHEMBL1903
 Ki 7.77 7.545 17.0 2
Sodium- and chloride-dependent GABA transporter 1
CHEMBL5445
 Ki 7.56 7.4233 27.5 9
Sodium- and chloride-dependent GABA transporter 1
CHEMBL5445
 IC50 7.43 6.8483 37.1 18
Sodium- and chloride-dependent GABA transporter 1
CHEMBL1903
 Kd 7.39 7.11 40.5 2
Sodium- and chloride-dependent GABA transporter 1
CHEMBL1903
 IC50 7.16 6.735 70.0 4
Sodium- and chloride-dependent GABA transporter 1
CHEMBL4054
 IC50 7.16 5.8529 70.0 17
Unchecked
CHEMBL612545
 IC50 6.8 6.8 159.0 1
GABA transporter 2
CHEMBL4228
 IC50 6.75 6.595 180.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 1.6 mL.min-1.kg-1 Homo sapiens
CL 1.6 mL.min-1.kg-1 Homo sapiens
CL 1.6 mL.min-1.kg-1 Homo sapiens
CL 1.6 mL.min-1.kg-1 Homo sapiens
F 90.0 % Homo sapiens
Fu 0.04 - Homo sapiens
Fu 0.04 - Homo sapiens
MRT 12.0 hr Homo sapiens
T1/2 10.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium- and chloride-dependent GABA transporter 1 Ki = 16.98 nM 7.77 Displacement of [3H]Tiagabine from human recombinant GAT1 expressed in HEK293 ce... 21134748
Sodium- and chloride-dependent GABA transporter 1 Ki = 27.54 nM 7.56 Inhibition of NO711 binding to mouse GAT1 expressed in HEK293 cell membranes ass... 30376325
Sodium- and chloride-dependent GABA transporter 1 IC50 = 37.15 nM 7.43 Inhibition of [3H]NO711 binding to mouse GAT1 expressed in human HEK293 cell lin... 34015586
Sodium- and chloride-dependent GABA transporter 1 Ki = 37.15 nM 7.43 Binding affinity to mouse GAT1 expressed in HEK293 cells using NO71156 as unlabe... 25698617
Sodium- and chloride-dependent GABA transporter 1 Ki = 37.15 nM 7.43 Displacement of NO 711 from mouse GAT1 expressed in HEK293 cell membranes after ... 27039250
Sodium- and chloride-dependent GABA transporter 1 Ki = 37.15 nM 7.43 Inhibition of [2H10]NO 711 binding to mouse GAT1 expressed in HEK293 cell membra... 29886082
Sodium- and chloride-dependent GABA transporter 1 Ki = 37.15 nM 7.43 Inhibition of NO711 binding to mouse GAT1 expressed in HEK293 cell membranes ass... 31097402
Sodium- and chloride-dependent GABA transporter 1 Ki = 37.15 nM 7.43 Displacement of NO711 from mouse GAT1 expressed in stable HEK293 cell membranes ... 30718063
Sodium- and chloride-dependent GABA transporter 1 Ki = 37.15 nM 7.43 Binding affinity to mouse GAT-1 expressed in human HEK293 cells assessed as inhi... 35306287
Sodium- and chloride-dependent GABA transporter 1 Ki = 38.9 nM 7.41 Binding affinity to mouse GAT1 stably transfected in HEK293 cells by NO-711 bind... 23859778
Sodium- and chloride-dependent GABA transporter 1 Kd = 40.5 nM 7.39 Competitive inhibition of human GAT1 expressed in COS cells assessed as reductio... 30376325
Sodium- and chloride-dependent GABA transporter 1 Ki = 47.86 nM 7.32 Binding affinity to human GAT1 expressed in HEK293 cells using NO71156 as unlabe... 25698617
Sodium- and chloride-dependent GABA transporter 1 Ki = 54.95 nM 7.26 Binding affinity to mouse GAT-1 expressed in HEK293 cells after 4 hrs in presenc... 30777661
Sodium- and chloride-dependent GABA transporter 1 IC50 = 63.1 nM 7.2 Inhibition of [3H]GABA uptake at mouse GAT1 expressed in HEK293 cells after 25 m... 23336362
Sodium- and chloride-dependent GABA transporter 1 IC50 = 70.0 nM 7.16 Inhibitory activity against human GABA transporter-1 (hGAT1) 8057281
Sodium- and chloride-dependent GABA transporter 1 IC50 = 70.0 nM 7.16 Inhibition of GAT-1 in rat brain homogenate assessed as decrease in [3H]GABA upt... 30777661
Sodium- and chloride-dependent GABA transporter 1 IC50 = 70.0 nM 7.16 Inhibition of rat brain synaptosomes GAT1 assessed as inhibition of [3H]GABA upt... 25679268
Sodium- and chloride-dependent GABA transporter 1 IC50 = 70.0 nM 7.16 Inhibition of [3H]GABA uptake at mouse GAT1 expressed in HEK293 cells after 25 m... 23336362
Sodium- and chloride-dependent GABA transporter 1 IC50 = 131.83 nM 6.88 Inhibition of mouse GAT1 expressed in HEK293 cells assessed as decrease in [3H]G... 29886082
Sodium- and chloride-dependent GABA transporter 1 IC50 = 131.83 nM 6.88 Inhibition of mouse GAT1 assessed as reduction in GABA uptake 29924931

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15509161 10.1021/jm040809c Sodium- and chloride-dependent GABA transporter 1 14
30376325 10.1021/acs.jmedchem.8b01602 Sodium- and chloride-dependent GABA transporter 1 12
20070106 10.1021/jm901371v Homo sapiens 8
18426954 10.1124/dmd.108.020479 ADMET 4
25698617 10.1016/j.bmc.2015.01.035 Sodium- and chloride-dependent GABA transporter 1 4
23398473 10.1021/jm301872x GABA transporter 2 3
30718063 10.1016/j.bmc.2019.01.024 GABA transporter 4 2
23336362 10.1021/jm301800j Sodium- and chloride-dependent GABA transporter 1 2
20219271 10.1016/j.ejmech.2010.02.029 Unchecked 2
29886082 10.1016/j.bmc.2018.05.049 Sodium- and chloride-dependent GABA transporter 1 2
25679268 10.1021/jm5015428 Sodium- and chloride-dependent GABA transporter 1 2
19445515 10.1021/jm900403j Homo sapiens 2
30777661 10.1016/j.bmc.2019.02.015 Sodium- and chloride-dependent GABA transporter 1 2
- 10.6019/CHEMBL3301361 ADMET 2
23859778 10.1016/j.bmc.2013.06.038 Sodium- and chloride-dependent GABA transporter 1 2
29886082 10.1016/j.bmc.2018.05.049 GABA transporter 4 2
30718063 10.1016/j.bmc.2019.01.024 Sodium- and chloride-dependent GABA transporter 1 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
31097402 10.1016/j.bmc.2019.05.001 Sodium- and chloride-dependent GABA transporter 1 2

Data from ChEMBL 36 via Core Engine