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Compound Detail

CHEMBL558598

RIMONABANT HYDROCHLORIDE
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Cc1c(C(=O)NN2CCCCC2)nn(-c2ccc(Cl)cc2Cl)c1-c1ccc(Cl)cc1.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL558598
Name RIMONABANT HYDROCHLORIDE
Phase Preclinical
Structure Type MOL
InChI Key REOYOKXLUFHOBV-UHFFFAOYSA-N
Parent Compound CHEMBL111
Active Moiety CHEMBL111
4
Targets
10
Activities
4
Assay Types
0
PK Parameters
10
Publications
0
Known Names

Molecular Properties

463.8
MW (Da)
5.94
ALogP
4
HBA
1
HBD
50.2
PSA (Ų)
0.52
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H22Cl4N4O
MW 500.26
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness -1.37

Activity Summary

Ki 5 meas. best 8.91
IC50 3 meas. best 7.89
EC50 1 meas. best 8.0
Kd 1 meas. best 8.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cannabinoid receptor 1
CHEMBL3571
 Ki 8.91 8.655 1.2 2
Cannabinoid receptor 1
CHEMBL218
 Kd 8.6 8.6 2.5 1
Cannabinoid receptor 1
CHEMBL218
 Ki 8.27 7.935 5.4 2
Cannabinoid receptor 1
CHEMBL218
 EC50 8.0 8.0 10.1 1
Cannabinoid receptor 1
CHEMBL218
 IC50 7.89 7.89 13.0 1
Cannabinoid receptor 2
CHEMBL253
 Ki 5.8 5.8 1580.0 1
Cannabinoid receptor 2
CHEMBL253
 IC50 5.01 5.01 9800.0 1
Acetylcholinesterase
CHEMBL220
 IC50 4.6 4.6 25118.9 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cannabinoid receptor 1 Ki = 1.23 nM 8.91 Displacement of [3H]SR141716A from CB1 receptor in rat cerebellum 16451053
Cannabinoid receptor 1 Kd = 2.512 nM 8.6 Antagonist activity at human CB1 receptor expressed in CHO cells assessed as inh... 20047331
Cannabinoid receptor 1 Ki = 4.0 nM 8.4 Binding affinity for cannabinoid receptor 1 in rat cerebellar membrane 15139773
Cannabinoid receptor 1 Ki = 5.4 nM 8.27 Displacement of [3H]SR141716A from human CB1 receptor 16451053
Cannabinoid receptor 1 EC50 = 10.1 nM 8.0 Potency at human CB1 receptor in a [35S]GTP-gamma-S functional assay 16451053
Cannabinoid receptor 1 IC50 = 13.0 nM 7.89 Antagonist activity at CB1 receptor (unknown origin) expressed in CHO cells up t... 25644673
Cannabinoid receptor 1 Ki = 25.0 nM 7.6 Displacement of [3H]CP-55940 from human CB1 receptor expressed in CHO cells 20047331
Cannabinoid receptor 2 Ki = 1580.0 nM 5.8 Displacement of [3H]CP-55940 from human CB2 receptor expressed in CHO cells 20047331
Cannabinoid receptor 2 IC50 = 9800.0 nM 5.01 Antagonist activity at CB2 receptor (unknown origin) expressed in CHO cells up t... 25644673
Acetylcholinesterase IC50 = 25118.86 nM 4.6 Inhibition of human recombinant AChE expressed in HEK293 cells by photometry 20047331

Literature References

PubMed DOI Target Context # Activities
16451053 10.1021/jm050484f Cannabinoid receptor 1 4
20047331 10.1021/jm901614b Cannabinoid receptor 1 2
15139773 10.1021/jm031099y Cannabinoid receptor 1 1
18207393 10.1016/j.bmcl.2007.12.036 Cannabinoid receptor 1 1
18207393 10.1016/j.bmcl.2007.12.036 Rattus norvegicus 1
20047331 10.1021/jm901614b Cannabinoid receptor 2 1
20047331 10.1021/jm901614b Acetylcholinesterase 1
25644673 10.1016/j.ejmech.2015.01.054 Cannabinoid receptor 1 1
25644673 10.1016/j.ejmech.2015.01.054 Cannabinoid receptor 2 1
25644673 10.1016/j.ejmech.2015.01.054 Unchecked 1

Data from ChEMBL 36 via Core Engine