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Compound Detail

CHEMBL298406

ECOPIPAM
🧪 Phase III
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🧪 Phase III
CN1CCc2cc(Cl)c(O)cc2[C@H]2c3ccccc3CC[C@@H]21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL298406
Name ECOPIPAM
Phase Phase III
Structure Type MOL
InChI Key DMJWENQHWZZWDF-PKOBYXMFSA-N

Known Names

Ecopipam
7
Targets
22
Activities
2
Assay Types
9
PK Parameters
20
Publications
1
Known Names
5
Indications
1
Mechanisms

Molecular Properties

313.8
MW (Da)
3.98
ALogP
2
HBA
1
HBD
23.5
PSA (Ų)
0.79
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Year 1998

Extended Properties

Molecular Formula C19H20ClNO
MW 313.83
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness 0.52

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Dopamine D1 receptor antagonist ANTAGONIST D(1A) dopamine receptor ✓ ✓

Indications

Tourette Syndrome Gambling Stuttering Lesch-Nyhan Syndrome Restless Legs Syndrome

Activity Summary

Ki 21 meas. best 9.05
IC50 1 meas. best 4.81

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(1A) dopamine receptor
CHEMBL2056
 Ki 9.05 8.875 0.9 6
Unchecked
CHEMBL612545
 Ki 8.92 7.0217 1.2 6
D(1A) dopamine receptor
CHEMBL265
 Ki 8.72 8.72 1.9 1
D(1B) dopamine receptor
CHEMBL1850
 Ki 8.7 8.7 2.0 2
D(2) dopamine receptor
CHEMBL339
 Ki 6.29 6.29 514.0 1
D(2) dopamine receptor
CHEMBL217
 Ki 6.01 5.9767 980.0 3
D(4) dopamine receptor
CHEMBL219
 Ki 5.26 5.26 5515.0 2
Unchecked
CHEMBL612545
 IC50 4.81 4.81 15364.9 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 160.0 ng.hr.mL-1 Rattus norvegicus
AUC 156.0 ng.hr.mL-1 Rattus norvegicus
AUC 156.0 ug ml-1 Rattus norvegicus
Cmax 229.42 nM Rattus norvegicus
Cmax 229.42 nM Rattus norvegicus
F 0.6 % Rattus norvegicus
F 0.6 % Rattus norvegicus
Tmax 0.5 hr Rattus norvegicus
Tmax 0.5 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(1A) dopamine receptor Ki = 0.9 nM 9.05 Binding affinity to human dopamine D1 receptor 32976928
Unchecked Ki = 1.2 nM 8.92 In vitro binding affinity for Dopamine receptor D1 15689153
D(1A) dopamine receptor Ki = 1.2 nM 8.92 Binding affinity to dopamine D1 receptor 20061148
D(1A) dopamine receptor Ki = 1.2 nM 8.92 Displacement of [3H]SCh23390 from dopamine D1 receptor expressed in mouse LTK ce... 20064718
D(1A) dopamine receptor Ki = 1.2 nM 8.92 Binding affinity to D1 receptor (unknown origin) assessed as inhibition constant 39038276
D(1A) dopamine receptor Ki = 1.9 nM 8.72 Binding affinity to displace [3H]-SCH- 23390 against Dopamine receptor D1 1973733
D(1A) dopamine receptor Ki = 1.9 nM 8.72 Inhibition of [3H]SCH-23390 binding to rat striatal homogenate dopamine receptor... 2666667
D(1A) dopamine receptor Ki = 1.9 nM 8.72 Compound was tested for the displacement of [3H]-SCH- 23390 from dopamine recept... 1531365
D(1B) dopamine receptor Ki = 2.0 nM 8.7 Displacement of radioligand from dopamine D5 receptor expressed in mouse LTK cel... 20064718
D(1B) dopamine receptor Ki = 2.0 nM 8.7 Binding affinity to dopamine D5 receptor 20061148
Unchecked Ki = 2.0 nM 8.7 In vitro binding affinity for Dopamine receptor D5 15689153
Unchecked Ki = 80.0 nM 7.1 In vitro binding affinity for 5-HT transporter 15689153
D(2) dopamine receptor Ki = 514.0 nM 6.29 Displacement of [3H]spiperone from rat striatal homogenate dopamine receptor D2 2666667
Unchecked Ki = 731.0 nM 6.14 In vitro binding affinity for Alpha-2a adrenergic receptor 15689153
Unchecked Ki = 980.0 nM 6.01 In vitro binding affinity for Dopamine receptor D2 15689153
D(2) dopamine receptor Ki = 980.0 nM 6.01 Binding affinity to dopamine D2 receptor 20061148
D(2) dopamine receptor Ki = 980.0 nM 6.01 Displacement of [3H]methylspiperon from dopamine D2 receptor expressed in mouse ... 20064718
D(2) dopamine receptor Ki = 1240.0 nM 5.91 Binding affinity to human dopamine D2 receptor 32976928
Unchecked Ki = 5520.0 nM 5.26 In vitro binding affinity for Dopamine receptor D4 15689153
D(4) dopamine receptor Ki = 5515.0 nM 5.26 Binding affinity to dopamine D4 receptor 20061148

Literature References

PubMed DOI Target Context # Activities
15689153 10.1021/jm030614p Unchecked 6
20061148 10.1016/j.bmcl.2009.12.100 Unchecked 5
15689153 10.1021/jm030614p ADMET 4
20064718 10.1016/j.bmcl.2009.12.094 Rattus norvegicus 3
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
20061148 10.1016/j.bmcl.2009.12.100 Rattus norvegicus 2
39038276 10.1021/acs.jmedchem.4c00537 D(1A) dopamine receptor 1
1973733 10.1021/jm00170a025 D(1A) dopamine receptor 1
32976928 10.1016/j.bmcl.2020.127563 ADMET 1
10836148 10.1146/annurev.pharmtox.40.1.581 UDP-glucuronosyltransferase 2B15 1
20064718 10.1016/j.bmcl.2009.12.094 D(4) dopamine receptor 1
20064718 10.1016/j.bmcl.2009.12.094 D(2) dopamine receptor 1
20064718 10.1016/j.bmcl.2009.12.094 D(1B) dopamine receptor 1
20064718 10.1016/j.bmcl.2009.12.094 D(1A) dopamine receptor 1
20061148 10.1016/j.bmcl.2009.12.100 D(4) dopamine receptor 1
20061148 10.1016/j.bmcl.2009.12.100 D(2) dopamine receptor 1
20061148 10.1016/j.bmcl.2009.12.100 D(1B) dopamine receptor 1
20061148 10.1016/j.bmcl.2009.12.100 D(1A) dopamine receptor 1
1531365 10.1021/jm00081a010 D(1A) dopamine receptor 1
2666667 10.1021/jm00128a038 D(2) dopamine receptor 1

Data from ChEMBL 36 via Core Engine