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Compound Detail

CHEMBL360328

LORCASERIN
💊 Approved Drug
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💊 Approved Drug
C[C@H]1CNCCc2ccc(Cl)cc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL360328
Name LORCASERIN
Phase Approved
Structure Type MOL
InChI Key XTTZERNUQAFMOF-QMMMGPOBSA-N
Therapeutic ✓ Yes

Known Names

ADP-356 ADP356 Lorcaserin Lorcaserina Lorcaserine
7
Targets
70
Activities
2
Assay Types
8
PK Parameters
20
Publications
5
Known Names
11
Indications

Molecular Properties

195.7
MW (Da)
2.59
ALogP
1
HBA
1
HBD
12.0
PSA (Ų)
0.67
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2012
Availability Withdrawn
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Withdrawn Natural Product First in Class
USAN Stem -caserin
USAN Year 2005

Extended Properties

Molecular Formula C11H14ClN
MW 195.69
Aromatic Rings 1
Heavy Atoms 13
NP-Likeness -0.33

Indications

Obesity Cocaine-Related Disorders Opioid-Related Disorders Opioid-Related Disorders Peripheral Nervous System Diseases Tobacco Use Disorder Cardiovascular Diseases Kidney Diseases Liver Diseases Marijuana Abuse Substance-Related Disorders

ATC Classification

A08AA11
lorcaserin
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: ANTIOBESITY PREPARATIONS, EXCL. DIET PRODUCTS

Drug Warnings

Withdrawn
carcinogenicity
Carcinogenicity
Country: United States   Year: 2020

Activity Summary

EC50 50 meas. best 8.74
Ki 20 meas. best 8.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 8.89 7.158 1.3 5
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 8.89 7.072 1.3 5
5-hydroxytryptamine receptor 2C
CHEMBL225
 EC50 8.74 8.115 1.8 22
Serotonin 2 receptors; 5-HT2a & 5-HT2c
CHEMBL2096662
 Ki 8.12 8.12 7.5 1
Unchecked
CHEMBL612545
 Ki 7.92 7.92 12.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 7.82 7.4957 15.0 7
5-hydroxytryptamine receptor 2C
CHEMBL1770041
 EC50 7.79 7.79 16.2 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 EC50 7.49 6.6731 32.4 13
5-hydroxytryptamine receptor 2B
CHEMBL1833
 EC50 7.1 6.3964 79.4 14
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 5.58 5.58 2606.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 800.0 ng.hr.mL-1 Rattus norvegicus
AUC 1400.0 ng.hr.mL-1 Rattus norvegicus
CL 101.67 mL.min-1.kg-1 Rattus norvegicus
Cmax 1328.63 nM Rattus norvegicus
F 86.0 % Rattus norvegicus
T1/2 3.1 hr Rattus norvegicus
T1/2 3.7 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
5-hydroxytryptamine receptor 2A Ki = 1.3 nM 8.89 Agonist activity at 5-HT2A receptor (unknown origin) 23177783
5-hydroxytryptamine receptor 2B Ki = 1.3 nM 8.89 Agonist activity at 5-HT2B receptor (unknown origin) 23177783
5-hydroxytryptamine receptor 2C EC50 = 1.82 nM 8.74 Agonist activity at recombinant human 5HT2C-INI receptor expressed in Flp-In-293... 26704965
5-hydroxytryptamine receptor 2C EC50 = 2.1 nM 8.68 Agonist activity at human 5-HT2C-INI receptor isoform expressed in Flp-IN HEK293... 28657744
5-hydroxytryptamine receptor 2C EC50 = 2.63 nM 8.58 Agonist activity at human 5-HT2C receptor expressed in human Flp-In-293 cells as... 27726356
5-hydroxytryptamine receptor 2C EC50 = 2.63 nM 8.58 Agonist activity at human 5-HT2C-INI receptor isoform expressed in Flp-IN HEK293... 28657744
5-hydroxytryptamine receptor 2C EC50 = 2.64 nM 8.58 Agonist activity at human 5-HT2C receptor expressed in human Flp-In-293 cells as... 27726356
5-hydroxytryptamine receptor 2C EC50 = 2.7 nM 8.57 Agonist activity at human 5HT2C receptor expressed in HEK293 cells assessed as c... 19284718
5-hydroxytryptamine receptor 2C EC50 = 2.7 nM 8.57 Agonist activity at recombinant human 5HT2C-INI receptor expressed in Flp-In-293... 26704965
5-hydroxytryptamine receptor 2C EC50 = 3.4 nM 8.47 Agonist activity at human 5-HT2C INI receptor expressed in human Flp-In-293 cell... 27726356
5-hydroxytryptamine receptor 2C EC50 = 3.467 nM 8.46 Agonist activity at human 5-HT2C INI receptor expressed in human Flp-In-293 cell... 27726356
5-hydroxytryptamine receptor 2C EC50 = 3.6 nM 8.44 Agonist activity at human 5-HT2C receptor expressed in HEK293 cells assessed as ... 25633969
5-hydroxytryptamine receptor 2C EC50 = 4.786 nM 8.32 Agonist activity at recombinant human unedited 5HT2C receptor isoform INI expres... 31445232
5-hydroxytryptamine receptor 2C EC50 = 4.77 nM 8.32 Agonist activity at recombinant human unedited 5HT2C receptor isoform INI expres... 31445232
5-hydroxytryptamine receptor 2C EC50 = 7.6 nM 8.12 Agonist activity at recombinant human 5HT2C receptor expressed in HEK293 cells a... 31952960
Serotonin 2 receptors; 5-HT2a & 5-HT2c Ki = 7.5 nM 8.12 Selectivity ratio of Ki for displacement of [3H]DOI from recombinant human 5HT2A... 30545651
5-hydroxytryptamine receptor 2C EC50 = 7.943 nM 8.1 Agonist activity at human 5HT2C receptor expressed in HEK293 cells assessed as i... 18095642
5-hydroxytryptamine receptor 2C EC50 = 9.0 nM 8.05 Agonist activity at 5-HT2C receptor (unknown origin) 23177783
5-hydroxytryptamine receptor 2C EC50 = 9.0 nM 8.05 Agonist activity at human 5HT2C receptor expressed in HEK293 cells by inositol p... 21195614
5-hydroxytryptamine receptor 2C EC50 = 11.0 nM 7.96 Effective concentration towards 5-hydroxytryptamine 2C receptors transfected in ... 15713408

Literature References

PubMed DOI Target Context # Activities
18095642 10.1021/jm0709034 Rattus norvegicus 18
27726356 10.1021/acs.jmedchem.6b01194 5-hydroxytryptamine receptor 2C 14
28657744 10.1021/acs.jmedchem.7b00584 5-hydroxytryptamine receptor 2C 8
21195614 10.1016/j.bmcl.2010.11.120 5-hydroxytryptamine receptor 2C 8
25633969 10.1021/jm5019274 5-hydroxytryptamine receptor 2B 4
27726356 10.1021/acs.jmedchem.6b01194 5-hydroxytryptamine receptor 2A 4
27726356 10.1021/acs.jmedchem.6b01194 5-hydroxytryptamine receptor 2B 4
30998358 10.1021/acs.jmedchem.9b00241 Mus musculus 4
19284718 10.1021/jm801354e 5-hydroxytryptamine receptor 2B 3
21195614 10.1016/j.bmcl.2010.11.120 5-hydroxytryptamine receptor 2B 3
26704965 10.1021/acs.jmedchem.5b01153 5-hydroxytryptamine receptor 2B 3
26704965 10.1021/acs.jmedchem.5b01153 5-hydroxytryptamine receptor 2A 3
31445232 10.1016/j.ejmech.2019.111626 5-hydroxytryptamine receptor 2C 3
19284718 10.1021/jm801354e Unchecked 3
28657744 10.1021/acs.jmedchem.7b00584 5-hydroxytryptamine receptor 2B 3
19284718 10.1021/jm801354e 5-hydroxytryptamine receptor 2C 3
19284718 10.1021/jm801354e 5-hydroxytryptamine receptor 2A 3
28657744 10.1021/acs.jmedchem.7b00584 5-hydroxytryptamine receptor 2A 3
26704965 10.1021/acs.jmedchem.5b01153 5-hydroxytryptamine receptor 2C 3
31445232 10.1016/j.ejmech.2019.111626 5-hydroxytryptamine receptor 2B 3

Data from ChEMBL 36 via Core Engine