CHEBI:133017 - pimavanserin

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ChEBI Name pimavanserin
ChEBI ID CHEBI:133017
Definition A member of the class of ureas in which three of the four hydrogens are replaced by 4-fluorobenzyl, 1-methylpiperidin-4-yl, and 4-(isopropyloxy)benzyl groups. An atypical antipsychotic that is used (in the form of its tartrate salt) for treatment of hallucinations and delusions associated with Parkinson's disease.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB8966229, eMolecules:23018935, ZINC000016159083
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Pimavanserin, sold under the brand name Nuplazid, is an atypical antipsychotic which is approved for the treatment of Parkinson's disease psychosis. It is taken by mouth. Side effects of pimavanserin include peripheral edema and confusion. Unlike other antipsychotics, pimavanserin is not a dopamine receptor antagonist, but rather is a selective antagonist or inverse agonist of the serotonin 5-HT2A receptor and to a lesser extent of the serotonin 5-HT2C receptor. Pimavanserin was first approved for medical use in 2016. It was approved as a generic medication in 2024.
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Formula C25H34FN3O2
Net Charge 0
Average Mass 427.556
Monoisotopic Mass 427.26351
InChI InChI=1S/C25H34FN3O2/c1-19(2)18-31-24-10-6-20(7-11-24)16-27-25(30)29(23-12-14-28(3)15-13-23)17-21-4-8-22(26)9-5-21/h4-11,19,23H,12-18H2,1-3H3,(H,27,30)
InChIKey RKEWSXXUOLRFBX-UHFFFAOYSA-N
SMILES C1=C(C=CC(=C1)CNC(N(C2CCN(CC2)C)CC3=CC=C(C=C3)F)=O)OCC(C)C
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): 5-hydroxytryptamine 2A receptor inverse agonist
An inverse agonist that binds to the same receptor as a 5-hydroxytryptamine 2A receptor agonist, but which induces a pharmacological response opposite to that agonist.
serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
Application(s): antipsychotic agent
Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.
serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
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ChEBI Ontology
Outgoing pimavanserin (CHEBI:133017) has role 5-hydroxytryptamine 2A receptor inverse agonist (CHEBI:133016)
pimavanserin (CHEBI:133017) has role antipsychotic agent (CHEBI:35476)
pimavanserin (CHEBI:133017) has role serotonergic antagonist (CHEBI:48279)
pimavanserin (CHEBI:133017) is a aromatic ether (CHEBI:35618)
pimavanserin (CHEBI:133017) is a monofluorobenzenes (CHEBI:83575)
pimavanserin (CHEBI:133017) is a piperidines (CHEBI:26151)
pimavanserin (CHEBI:133017) is a tertiary amino compound (CHEBI:50996)
pimavanserin (CHEBI:133017) is a ureas (CHEBI:47857)
pimavanserin (CHEBI:133017) is conjugate base of pimavanserin(1+) (CHEBI:133020)
Incoming pimavanserin(1+) (CHEBI:133020) is conjugate acid of pimavanserin (CHEBI:133017)
IUPAC Name
N-[(4-fluorophenyl)methyl]-N-(1-methylpiperidin-4-yl)-N'-{[4-(2-methylpropoxy)phenyl]methyl}urea
INN Source
pimavanserin ChemIDplus
Synonym Source
N-(4-Fluorophenylmethyl)-N-(1-methylpiperidin-4-yl)-N'-(4-(2-methylpropyloxy)phenylmethyl) carbamide ChemIDplus
Manual Xrefs Databases
5142 DrugCentral
CA2652300 Patent
Pimavanserin Wikipedia
View more database links
Registry Numbers Types Sources
10386699 Reaxys Registry Number Reaxys
706779-91-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations
Last Modified
22 February 2017