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Compound Detail

CHEMBL2111101

PIMAVANSERIN
💊 Approved Drug
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💊 Approved Drug
CC(C)COc1ccc(CNC(=O)N(Cc2ccc(F)cc2)C2CCN(C)CC2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2111101
Name PIMAVANSERIN
Phase Approved
Structure Type MOL
InChI Key RKEWSXXUOLRFBX-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Pimavanserin Pimavanserina Pimavanserine
11
Targets
27
Activities
2
Assay Types
20
PK Parameters
20
Publications
3
Known Names
6
Indications

Molecular Properties

427.6
MW (Da)
4.67
ALogP
3
HBA
1
HBD
44.8
PSA (Ų)
0.67
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2016
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning
USAN Stem -anserin
USAN Year 2005

Extended Properties

Molecular Formula C25H34FN3O2
MW 427.56
Aromatic Rings 2
Heavy Atoms 31
NP-Likeness -1.63

Indications

Psychotic Disorders Depressive Disorder, Major Neurodegenerative Diseases Schizophrenia Parkinson Disease Tourette Syndrome

ATC Classification

N05AX17
pimavanserin
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOLEPTICS

Activity Summary

IC50 19 meas. best 8.73
Ki 8 meas. best 10.2

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 10.2 9.514 0.1 5
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 8.82 8.3533 1.5 3
5-hydroxytryptamine receptor 2A
CHEMBL224
 IC50 8.73 7.8333 1.9 9
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 6.48 6.435 330.0 2
CX3C chemokine receptor 1
CHEMBL4843
 IC50 5.49 5.49 3258.2 1
Apelin receptor
CHEMBL1628481
 IC50 5.46 5.46 3436.7 1
Psychosine receptor
CHEMBL3714081
 IC50 5.45 5.45 3540.2 1
G-protein coupled receptor 183
CHEMBL3259470
 IC50 5.36 5.36 4329.7 1
Beta-2 adrenergic receptor
CHEMBL210
 IC50 5.34 5.34 4549.7 1
G-protein coupled receptor 35
CHEMBL1293267
 IC50 5.25 5.25 5642.3 1
Cytochrome P450 2C19
CHEMBL3622
 IC50 4.3 4.3 49800.0 1
Cytochrome P450 1A2
CHEMBL3356
 IC50 4.28 4.28 52000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 4460.0 ng.hr.mL-1 Mus musculus
AUC 3250.0 ng.hr.mL-1 Rattus norvegicus
AUC 7730.0 ng.hr.mL-1 Macaca mulatta
AUC 836.0 ng.hr.mL-1 Homo sapiens
AUC 8210.0 ng.hr.mL-1 Mus musculus
AUC 4320.0 ng.hr.mL-1 Rattus norvegicus
AUC 4800.0 ng.hr.mL-1 Macaca mulatta
AUC 527.0 ng.hr.mL-1 Homo sapiens
AUC 2730.0 ng.hr.mL-1 Mus musculus
AUC 18577.0 ng.hr.mL-1 Rattus norvegicus
AUC 2411.0 ng.hr.mL-1 Macaca mulatta
AUC 112.0 ng.hr.mL-1 Homo sapiens
AUC 388.0 ng.hr.mL-1 Mus musculus
AUC 1976.0 ng.hr.mL-1 Rattus norvegicus
AUC 1289.0 ng.hr.mL-1 Macaca mulatta
AUC 236.0 ng.hr.mL-1 Homo sapiens
CL 23.2 mL.min-1.kg-1 Rattus norvegicus
CL 11.0 mL.min-1.kg-1 Homo sapiens
T1/2 1.777 hr Rattus norvegicus
T1/2 1.958 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2A Ki = 0.0631 nM 10.2 Displacement of [3H]ketanserin from human 5-HT2A receptor incubated for 120 mins... 37378639
5-hydroxytryptamine receptor 2A Ki = 0.1995 nM 9.7 Displacement of [3H]ketanserin from 5-HT2A receptor (unknown origin) transfected... 39137033
5-hydroxytryptamine receptor 2A Ki = 0.5012 nM 9.3 Displacement of [3H]ketanserin from postmortem human brain membrane homogenate 5... 37378639
5-hydroxytryptamine receptor 2A Ki = 0.5 nM 9.3 Inverse agonist activity at 5-HT2A receptor (unknown origin) 35939391
5-hydroxytryptamine receptor 2A Ki = 0.86 nM 9.07 Displacement of [3H]ketanserin from human 5-HT2A receptor transfected in Jump-In... 39137033
5-hydroxytryptamine receptor 2C Ki = 1.5 nM 8.82 Inverse agonist activity at 5-HT2C receptor (unknown origin) 35939391
5-hydroxytryptamine receptor 2A IC50 = 1.862 nM 8.73 Inverse agonist activity at human full-length 5-HT2A 34671731
5-hydroxytryptamine receptor 2A IC50 = 5.01 nM 8.3 Inverse agonist activity at human prefrontal cortex 5-HT2A receptor assessed as ... 37378639
5-hydroxytryptamine receptor 2C Ki = 5.72 nM 8.24 Displacement of [3H]ketanserin from human 5-HT2C receptor transfected in Jump-In... 39137033
5-hydroxytryptamine receptor 2A IC50 = 9.0 nM 8.05 Antagonist activity at human 5-HT2A receptor expressed in CHO-K1 cells co-expres... 29730027
5-hydroxytryptamine receptor 2C Ki = 10.0 nM 8.0 Displacement of [3H]mesulergine from 5-HT2C receptor (unknown origin) transfecte... 39137033
5-hydroxytryptamine receptor 2A IC50 = 12.6 nM 7.9 Inverse agonist activity at human 5-HT2A receptor expressed in cell membrane ass... 37378639
5-hydroxytryptamine receptor 2A IC50 = 12.59 nM 7.9 Inverse agonist activity at human postmortem human brain membrane 5-HT2A recepto... 37378639
5-hydroxytryptamine receptor 2A IC50 = 22.0 nM 7.66 Antagonist activity at 5HT2A receptor (unknown origin) expressed in HEK293 cells... 32285676
5-hydroxytryptamine receptor 2A IC50 = 27.3 nM 7.56 Antagonist activity at 5-HT2A receptor (unknown origin) expressed in CHO-K1 cell... 35279606
5-hydroxytryptamine receptor 2A IC50 = 50.0 nM 7.3 Inverse agonist activity at 5-HT2A receptor (unknown origin) expressed in mouse ... 35279606
5-hydroxytryptamine receptor 2A IC50 = 79.43 nM 7.1 Inverse agonist activity at human 5-HT2A receptor assessed as increase in [35S]G... 37378639
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 330.0 nM 6.48 Inhibition of hERG expressed in CHO cells by automated patch clamp (QPatch) assa... 39137033
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 410.0 nM 6.39 Inhibition of hERG potassium channel expressed in CHO cells at -80 mV holding po... 35279606
CX3C chemokine receptor 1 IC50 = 3258.17 nM 5.49 GPCR PRESTO-Tango dose-response in antagonist mode with target: CX3CR1 -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5724801 U2OS 304
- 10.6019/CHEMBL5724801 Fibroblast 304
- 10.6019/CHEMBL5724801 HEK-293T 304
- 10.6019/CHEMBL5058577 Fibroblast 304
- 10.6019/CHEMBL5058577 U2OS 304
- 10.6019/CHEMBL5058577 HEK-293T 304
35279606 10.1016/j.ejmech.2022.114246 ADMET 29
37378639 10.1021/acs.jmedchem.3c00662 5-hydroxytryptamine receptor 2A 11
- 10.6019/CHEMBL5058564 HEK-293T 8
- 10.6019/CHEMBL5058564 U2OS 8
- 10.6019/CHEMBL5058564 Fibroblast 8
39137033 10.1021/acs.jmedchem.4c01244 Rattus norvegicus 6
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 5
- 10.6019/CHEMBL5209801 N-formyl peptide receptor 2 5
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 5
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 5
- 10.6019/CHEMBL5209801 Type-1 angiotensin II receptor 5
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 5
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 5
- 10.6019/CHEMBL5209801 Glucagon-like peptide 1 receptor 5

Data from ChEMBL 36 via Core Engine