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Compound Detail

CHEMBL559456

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Clc1cccc(OC(c2cccnc2)C2CCNCC2)c1Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL559456
Phase Preclinical
Structure Type MOL
InChI Key NTBRVAZZXJHBGJ-UHFFFAOYSA-N
6
Targets
14
Activities
1
Assay Types
5
PK Parameters
13
Publications
0
Known Names

Molecular Properties

337.2
MW (Da)
4.51
ALogP
3
HBA
1
HBD
34.1
PSA (Ų)
0.89
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C17H18Cl2N2O
MW 337.25
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -0.84

Activity Summary

IC50 14 meas. best 8.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 8.52 8.21 3.0 3
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 8.22 7.7533 6.0 3
Sodium-dependent dopamine transporter
CHEMBL238
 IC50 7.15 6.8 71.0 3
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.71 5.5 1970.0 2
Cytochrome P450 2D6
CHEMBL289
 IC50 5.7 5.2 2000.0 2
Unchecked
CHEMBL612545
 IC50 5.6 5.6 2530.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 180.0 mL.min-1.kg-1 Rattus norvegicus
T1/2 2.0 hr Homo sapiens
T1/2 2.0 hr Homo sapiens
T1/2 2.0 hr Rattus norvegicus
Vd 33.0 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent serotonin transporter IC50 = 3.0 nM 8.52 Inhibition of [3H]5-HT uptake at human 5HTT expressed in HEK293 cells 19359175
Sodium-dependent noradrenaline transporter IC50 = 6.0 nM 8.22 Inhibition of [3H]NA uptake at human NET expressed in HEK293 cells 19359175
Sodium-dependent serotonin transporter IC50 = 7.0 nM 8.15 Inhibition of [3H]5-HT uptake at human 5HTT expressed in HEK293 cells 19359175
Sodium-dependent noradrenaline transporter IC50 = 7.0 nM 8.15 Inhibition of [3H]NA uptake at human NET expressed in HEK293 cells 19359175
Sodium-dependent serotonin transporter IC50 = 11.0 nM 7.96 Inhibition of [3H]5-HT uptake at human 5HTT expressed in HEK293 cells 19359175
Sodium-dependent dopamine transporter IC50 = 71.0 nM 7.15 Inhibition of [3H]DA uptake at human DAT expressed in HEK293 cells 19359175
Sodium-dependent noradrenaline transporter IC50 = 128.0 nM 6.89 Inhibition of [3H]NA uptake at human NET expressed in HEK293 cells 19359175
Sodium-dependent dopamine transporter IC50 = 150.0 nM 6.82 Inhibition of [3H]DA uptake at human DAT expressed in HEK293 cells 19359175
Sodium-dependent dopamine transporter IC50 = 375.0 nM 6.43 Inhibition of [3H]DA uptake at human DAT expressed in HEK293 cells 19359175
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 1970.0 nM 5.71 Inhibition of human ERG channel 19359175
Cytochrome P450 2D6 IC50 = 2000.0 nM 5.7 Inhibition of CYP2D6 19359175
Unchecked IC50 = 2530.0 nM 5.6 Inhibition of tetrodotoxin-sensitive sodium channel 19359175
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 5180.0 nM 5.29 Inhibition of human ERG channel 19359175
Cytochrome P450 2D6 IC50 = 20000.0 nM 4.7 Inhibition of CYP2D6 19359175

Literature References

PubMed DOI Target Context # Activities
19359175 10.1016/j.bmcl.2009.03.090 Sodium-dependent serotonin transporter 3
19359175 10.1016/j.bmcl.2009.03.090 Sodium-dependent noradrenaline transporter 3
19359175 10.1016/j.bmcl.2009.03.090 Sodium-dependent dopamine transporter 3
19359175 10.1016/j.bmcl.2009.03.090 Rattus norvegicus 3
19359175 10.1016/j.bmcl.2009.03.090 Unchecked 3
19359175 10.1016/j.bmcl.2009.03.090 Liver microsomes 2
19359175 10.1016/j.bmcl.2009.03.090 Voltage-gated inwardly rectifying potassium channel KCNH2 2
19359175 10.1016/j.bmcl.2009.03.090 Cytochrome P450 2D6 2
19359175 10.1016/j.bmcl.2009.03.090 5-hydroxytryptamine receptor 1A 1
19359175 10.1016/j.bmcl.2009.03.090 5-hydroxytryptamine receptor 3A 1
19359175 10.1016/j.bmcl.2009.03.090 Histamine H3 receptor 1
19359175 10.1016/j.bmcl.2009.03.090 5-hydroxytryptamine receptor 2A 1
19359175 10.1016/j.bmcl.2009.03.090 No relevant target 1

Data from ChEMBL 36 via Core Engine