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Compound Detail

CHEMBL18116

TOLOXATONE
💊 Approved Drug
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💊 Approved Drug
Cc1cccc(N2CC(CO)OC2=O)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL18116
Name TOLOXATONE
Phase Approved
Structure Type MOL
InChI Key MXUNKHLAEDCYJL-UHFFFAOYSA-N

Known Names

Humoryl Toloxatona Toloxatone
5
Targets
33
Activities
2
Assay Types
5
PK Parameters
20
Publications
3
Known Names
1
Indications
1
Mechanisms

Molecular Properties

207.2
MW (Da)
1.31
ALogP
3
HBA
1
HBD
49.8
PSA (Ų)
0.80
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1984
Availability Unknown
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product

Extended Properties

Molecular Formula C11H13NO3
MW 207.23
Aromatic Rings 1
Heavy Atoms 15
NP-Likeness -0.90

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Monoamine oxidase A inhibitor INHIBITOR Amine oxidase [flavin-containing] A ✓ ✓

Indications

Depressive Disorder

ATC Classification

N06AG03
toloxatone
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 25 meas. best 6.42
Ki 8 meas. best 6.42

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Amine oxidase [flavin-containing] A
CHEMBL3254
 IC50 6.42 6.42 380.2 2
Amine oxidase [flavin-containing] A
CHEMBL3254
 Ki 6.42 6.1967 380.0 3
Amine oxidase [flavin-containing] A
CHEMBL3358
 Ki 6.42 6.42 380.0 1
Amine oxidase [flavin-containing] A
CHEMBL1951
 IC50 6.04 5.5995 920.0 20
Amine oxidase [flavin-containing] A
CHEMBL1951
 Ki 5.82 5.82 1500.0 1
Amine oxidase [flavin-containing] A
CHEMBL3358
 IC50 5.49 5.49 3260.0 1
Amine oxidase [flavin-containing] B
CHEMBL2039
 Ki 4.82 4.82 15000.0 1
Amine oxidase [flavin-containing] B
CHEMBL2756
 IC50 4.82 4.82 15135.6 2
Amine oxidase [flavin-containing] B
CHEMBL2756
 Ki 4.82 4.82 15000.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 11.0 mL.min-1.kg-1 Homo sapiens
CL 11.0 mL.min-1.kg-1 Homo sapiens
Fu 0.49 - Homo sapiens
MRT 2.3 hr Homo sapiens
T1/2 1.6 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Amine oxidase [flavin-containing] A IC50 = 380.19 nM 6.42 Inhibition of bovine mitochondrial MAOA 18281126
Amine oxidase [flavin-containing] A IC50 = 380.19 nM 6.42 Inhibition of MAO-A in bovine brain mitochondria by fluorimetric method 17266193
Amine oxidase [flavin-containing] A Ki = 380.0 nM 6.42 Inhibition of bovine brain MAOA using kynuramine as a substrate after 30 mins by... 22017497
Amine oxidase [flavin-containing] A Ki = 380.0 nM 6.42 Inhibitory concentration for rat Monoamine oxidase A 15974574
Amine oxidase [flavin-containing] A Ki = 380.0 nM 6.42 Inhibition of bovine brain mitochondrial Monoamine oxidase A (MAO-A) compared to... 11881986
Amine oxidase [flavin-containing] A IC50 = 920.0 nM 6.04 Inhibition of MAOA (unknown origin) using kynuramine as substrate preincubated f... 30568755
Amine oxidase [flavin-containing] A IC50 = 930.0 nM 6.03 Inhibition of human recombinant MAO-A expressed in baculovirus infected BTI inse... 30686752
Amine oxidase [flavin-containing] A IC50 = 980.0 nM 6.01 Inhibition of recombinant human MAO-A using kynuramine as substrate incubated fo... 29925480
Amine oxidase [flavin-containing] A IC50 = 1100.0 nM 5.96 Inhibition of human recombinant MAOA using kynuramine as substrate preincubated ... 29395970
Amine oxidase [flavin-containing] A Ki = 1500.0 nM 5.82 Inhibition of MAO-A (unknown origin) by luciferase reporter gene assay 23273607
Amine oxidase [flavin-containing] A IC50 = 1640.0 nM 5.79 Inhibition of recombinant human MAO-A using using kynuramine as substrate assess... 36307034
Amine oxidase [flavin-containing] A IC50 = 1640.0 nM 5.79 Inhibition of human recombinant MAO-A assessed as inhibition of 4-hydroxyquinoli... 36179486
Amine oxidase [flavin-containing] A IC50 = 1780.0 nM 5.75 Inhibition of recombinant human MAO-A using kynuramine as substrate incubated fo... 28188065
Amine oxidase [flavin-containing] A Ki = 1800.0 nM 5.75 Inhibition of bovine MAO-A by fluorimetric method 16792415
Amine oxidase [flavin-containing] A IC50 = 2000.0 nM 5.7 Reversible inhibition of recombinant human MAO-A assessed as residual activity u... 29925480
Amine oxidase [flavin-containing] A IC50 = 3260.0 nM 5.49 Inhibition of Sprague-Dawley rat brain MAO-A using [14C]5-HT as substrate preinc... 27855360
Amine oxidase [flavin-containing] A IC50 = 3920.0 nM 5.41 Inhibition of human recombinant MAO-A using kynuramine as substrate incubated fo... 27020523
Amine oxidase [flavin-containing] A IC50 = 3920.0 nM 5.41 Inhibition of human MAO-A 32942081
Amine oxidase [flavin-containing] A IC50 = 3920.0 nM 5.41 Inhibition of human recombinant MAOA using kynuramine substrate incubated for 20... 35447344
Amine oxidase [flavin-containing] A IC50 = 3920.0 nM 5.41 Inhibition of recombinant human MAOA expressed in insect cell microsomes using k... 30455149

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
29925480 10.1016/j.bmcl.2018.06.023 Amine oxidase [flavin-containing] A 4
18426954 10.1124/dmd.108.020479 ADMET 4
30686752 10.1016/j.bmcl.2019.01.016 Amine oxidase [flavin-containing] A 4
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
30568755 10.1039/C8MD00399H Amine oxidase [flavin-containing] A 3
29395970 10.1016/j.bmcl.2018.01.049 Amine oxidase [flavin-containing] A 3
37468498 10.1038/s41467-023-40064-9 Androgen receptor 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
19445515 10.1021/jm900403j Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2

Data from ChEMBL 36 via Core Engine