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Compound Detail

CHEMBL32503

GABAZINE
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COc1ccc(-c2ccc(=N)n(CCCC(=O)O)n2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL32503
Name GABAZINE
Phase Preclinical
Structure Type MOL
InChI Key ACVGNKYJVGNLIL-UHFFFAOYSA-N
6
Targets
17
Activities
2
Assay Types
0
PK Parameters
19
Publications
0
Known Names

Molecular Properties

287.3
MW (Da)
1.90
ALogP
5
HBA
2
HBD
88.2
PSA (Ų)
0.85
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C15H17N3O3
MW 287.32
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -0.91

Activity Summary

Ki 9 meas. best 7.13
IC50 8 meas. best 8.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
GABA-A receptor; anion channel
CHEMBL2093872
 IC50 8.1 7.475 8.0 2
GABA-A receptor; anion channel
CHEMBL1907607
 Ki 7.13 6.3533 74.0 3
GABA A receptor alpha-5/beta-3/gamma-2
CHEMBL2111374
 Ki 7.13 7.13 74.0 1
Unchecked
CHEMBL612545
 Ki 7.13 6.5475 74.0 4
GABA-A receptor; anion channel
CHEMBL1907607
 IC50 6.62 6.62 240.0 1
GABA-A receptor; alpha-1/beta-3/gamma-2
CHEMBL2094121
 Ki 6.62 6.62 240.0 1
GABA-A receptor; alpha-1/beta-2/gamma-2
CHEMBL2095172
 IC50 6.62 6.5667 240.0 3
Unchecked
CHEMBL612545
 IC50 5.34 5.235 4570.9 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
GABA-A receptor; anion channel IC50 = 8.0 nM 8.1 Affinity for gamma-aminobutyric-acid A receptor measured by its ability to displ... 1331456
GABA-A receptor; anion channel Ki = 74.0 nM 7.13 Displacement of [3H]muscimol from orthosteric binding site of GABA(A) receptor i... 30763084
Unchecked Ki = 74.0 nM 7.13 Displacement of [3H] muscimol from rat GABA A receptor 23855889
Unchecked Ki = 74.0 nM 7.13 Displacement of [3H]muscimol from GABAA receptor in Sprague-Dawley rat brain mem... -
Unchecked Ki = 74.13 nM 7.13 Displacement of [3H]muscimol from GABAA receptor in Sprague-Dawley rat brain mem... -
GABA A receptor alpha-5/beta-3/gamma-2 Ki = 74.0 nM 7.13 Displacement of [3H]muscimol from GABAA alpha-1-beta-3-gamma-2S in rat brain mem... 16480274
GABA-A receptor; anion channel Ki = 74.0 nM 7.13 In vitro inhibition of [3H]muscimol to rat brain synaptic membranes 11150163
GABA-A receptor; anion channel IC50 = 140.0 nM 6.85 Binding affinity in vivo for gamma-aminobutyric-acid A receptor measured by its ... 1331456
GABA-A receptor; alpha-1/beta-2/gamma-2 IC50 = 240.0 nM 6.62 Antagonist activity at human alpha1beta2gamma2S GABA(A) receptor expressed in hu... 30763084
GABA-A receptor; alpha-1/beta-2/gamma-2 IC50 = 240.0 nM 6.62 Antagonist activity at human alpha1beta2gamma2S GABA-A receptor expressed in tsA... 23855889
GABA-A receptor; anion channel IC50 = 240.0 nM 6.62 Inhibition of Gamma-aminobutyric acid A (GABA-A) receptor in vitro by whole-cell... 11150163
GABA-A receptor; alpha-1/beta-3/gamma-2 Ki = 240.0 nM 6.62 Binding affinity at human GABAA alpha-1-beta-3-gamma-2S expressed in Xenopus ooc... 16480274
GABA-A receptor; alpha-1/beta-2/gamma-2 IC50 = 349.0 nM 6.46 Antagonist activity at human recombinant GABA A receptor alpha1beta2gamma2S expr... 21664131
Unchecked IC50 = 4570.88 nM 5.34 Antagonist activity against GABA type-A receptor in human IMR32 cells assessed a... -
Unchecked IC50 = 7380.0 nM 5.13 Antagonist activity against GABA type-A receptor in human IMR32 cells assessed a... -
GABA-A receptor; anion channel Ki = 16000.0 nM 4.8 Displacement of [3H]NCS-382 from high-affinity GHB binding site of GABA(A) recep... 30763084
Unchecked Ki = 16000.0 nM 4.8 Displacement of [3H]NCS382 from high-affinity GHB binding site of alpha4betadelt... 30763084

Literature References

PubMed DOI Target Context # Activities
- 10.1039/C5MD00442J Unchecked 6
1331456 10.1021/jm00100a015 GABA-A receptor; anion channel 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
30763084 10.1021/acs.jmedchem.9b00131 GABA-A receptor; anion channel 2
- 10.1007/s00044-013-0583-7 Unchecked 2
11150163 10.1021/jm000371q GABA-A receptor; anion channel 2
21664131 10.1016/j.bmcl.2011.05.067 Unchecked 1
23855889 10.1021/jm4006466 GABA-A receptor; alpha-1/beta-2/gamma-2 1
23855889 10.1021/jm4006466 Unchecked 1
24053696 10.1021/jm4011719 Unchecked 1
21664131 10.1016/j.bmcl.2011.05.067 GABA-A receptor; alpha-1/beta-2/gamma-2 1
16480274 10.1021/jm050987l GABA-A receptor; alpha-1/beta-3/gamma-2 1
30763084 10.1021/acs.jmedchem.9b00131 GABA-A receptor; alpha-1/beta-2/gamma-2 1
30763084 10.1021/acs.jmedchem.9b00131 Unchecked 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
16480274 10.1021/jm050987l GABA A receptor alpha-5/beta-3/gamma-2 1
10780899 10.1021/jm9904349 GABA-C receptor 1

Data from ChEMBL 36 via Core Engine