CHEBI:133017 - pimavanserin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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
Download Molfile XML SDF
Wikipedia License
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.
Read full article at Wikipedia
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.
View more via ChEBI Ontology
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
Traynor K (2016)
Pimavanserin approved for Parkinson's-related hallucinations, delusions.
American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 73, 853 [PubMed:27261226]
Stahl SM (2016)
Mechanism of action of pimavanserin in Parkinson's disease psychosis: targeting serotonin 5HT2A and 5HT2C receptors.
CNS spectrums 21, 271-275 [PubMed:27503570]
[show Abstract]
Banks ML (2016)
Effects of 7-day repeated treatment with the 5-HT2A inverse agonist/antagonist pimavanserin on methamphetamine vs. food choice in male rhesus monkeys.
Drug and alcohol dependence 165, 260-264 [PubMed:27242287]
[show Abstract]
Markham A (2016)
Pimavanserin: First Global Approval.
Drugs 76, 1053-1057 [PubMed:27262680]
[show Abstract]
Hermanowicz S, Hermanowicz N (2016)
The safety, tolerability and efficacy of pimavanserin tartrate in the treatment of psychosis in Parkinson's disease.
Expert review of neurotherapeutics 16, 625-633 [PubMed:26908168]
[show Abstract]
Howland RH (2016)
Pimavanserin: An Inverse Agonist Antipsychotic Drug.
Journal of psychosocial nursing and mental health services 54, 21-24 [PubMed:27245248]
[show Abstract]
(2016)
Pimavanserin (Nuplazid) for Parkinson's disease psychosis.
The Medical letter on drugs and therapeutics 58, 74-75 [PubMed:27249096]
Andersen VL, Hansen HD, Herth MM, Dyssegaard A, Knudsen GM, Kristensen JL (2015)
(11)C-labeling and preliminary evaluation of pimavanserin as a 5-HT2A receptor PET-radioligand.
Bioorganic & medicinal chemistry letters 25, 1053-1056 [PubMed:25655720]
[show Abstract]
Hunter NS, Anderson KC, Cox A (2015)
Pimavanserin.
Drugs of today (Barcelona, Spain : 1998) 51, 645-652 [PubMed:26744739]
[show Abstract]
Cummings J, Isaacson S, Mills R, Williams H, Chi-Burris K, Corbett A, Dhall R, Ballard C (2014)
Pimavanserin for patients with Parkinson's disease psychosis: a randomised, placebo-controlled phase 3 trial.
Lancet (London, England) 383, 533-540 [PubMed:24183563]
[show Abstract]
Fox SH (2014)
Pimavanserin as treatment for Parkinson's disease psychosis.
Lancet (London, England) 383, 494-496 [PubMed:24183566]
Hacksell U, Burstein ES, McFarland K, Mills RG, Williams H (2014)
On the discovery and development of pimavanserin: a novel drug candidate for Parkinson's psychosis.
Neurochemical research 39, 2008-2017 [PubMed:24682754]
[show Abstract]
Hubbard D, Hacksell U, McFarland K (2013)
Behavioral effects of clozapine, pimavanserin, and quetiapine in rodent models of Parkinson's disease and Parkinson's disease psychosis: evaluation of therapeutic ratios.
Behavioural pharmacology 24, 628-632 [PubMed:23969614]
[show Abstract]
Friedman JH (2013)
Pimavanserin for the treatment of Parkinson's disease psychosis.
Expert opinion on pharmacotherapy 14, 1969-1975 [PubMed:24016069]
[show Abstract]
Kingwell K (2013)
Parkinson disease: Pimavanserin could be useful for treating psychosis in Parkinson disease.
Nature reviews. Neurology 9, 658 [PubMed:24247322]
Meltzer HY, Roth BL (2013)
Lorcaserin and pimavanserin: emerging selectivity of serotonin receptor subtype-targeted drugs.
The Journal of clinical investigation 123, 4986-4991 [PubMed:24292660]
[show Abstract]
Price DL, Bonhaus DW, McFarland K (2012)
Pimavanserin, a 5-HT2A receptor inverse agonist, reverses psychosis-like behaviors in a rodent model of Alzheimer's disease.
Behavioural pharmacology 23, 426-433 [PubMed:22750845]
[show Abstract]
Meltzer HY, Elkis H, Vanover K, Weiner DM, van Kammen DP, Peters P, Hacksell U (2012)
Pimavanserin, a selective serotonin (5-HT)2A-inverse agonist, enhances the efficacy and safety of risperidone, 2mg/day, but does not enhance efficacy of haloperidol, 2mg/day: comparison with reference dose risperidone, 6mg/day.
Schizophrenia research 141, 144-152 [PubMed:22954754]
[show Abstract]
McFarland K, Price DL, Bonhaus DW (2011)
Pimavanserin, a 5-HT2A inverse agonist, reverses psychosis-like behaviors in a rodent model of Parkinson's disease.
Behavioural pharmacology 22, 681-692 [PubMed:21921840]
[show Abstract]
Ancoli-Israel S, Vanover KE, Weiner DM, Davis RE, van Kammen DP (2011)
Pimavanserin tartrate, a 5-HT(2A) receptor inverse agonist, increases slow wave sleep as measured by polysomnography in healthy adult volunteers.
Sleep medicine 12, 134-141 [PubMed:21256805]
[show Abstract]
Meltzer HY, Mills R, Revell S, Williams H, Johnson A, Bahr D, Friedman JH (2010)
Pimavanserin, a serotonin(2A) receptor inverse agonist, for the treatment of parkinson's disease psychosis.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 35, 881-892 [PubMed:19907417]
[show Abstract]
Snigdha S, Horiguchi M, Huang M, Li Z, Shahid M, Neill JC, Meltzer HY (2010)
Attenuation of phencyclidine-induced object recognition deficits by the combination of atypical antipsychotic drugs and pimavanserin (ACP 103), a 5-hydroxytryptamine(2A) receptor inverse agonist.
The Journal of pharmacology and experimental therapeutics 332, 622-631 [PubMed:19864614]
[show Abstract]
Abbas A, Roth BL (2008)
Pimavanserin tartrate: a 5-HT2A inverse agonist with potential for treating various neuropsychiatric disorders.
Expert opinion on pharmacotherapy 9, 3251-3259 [PubMed:19040345]
[show Abstract]
Vanover KE, Weiner DM, Makhay M, Veinbergs I, Gardell LR, Lameh J, Del Tredici AL, Piu F, Schiffer HH, Ott TR, Burstein ES, Uldam AK, Thygesen MB, Schlienger N, Andersson CM, Son TY, Harvey SC, Powell SB, Geyer MA, Tolf BR, Brann MR, Davis RE (2006)
Pharmacological and behavioral profile of N-(4-fluorophenylmethyl)-N-(1-methylpiperidin-4-yl)-N'-(4-(2-methylpropyloxy)phenylmethyl) carbamide (2R,3R)-dihydroxybutanedioate (2:1) (ACP-103), a novel 5-hydroxytryptamine(2A) receptor inverse agonist.
The Journal of pharmacology and experimental therapeutics 317, 910-918 [PubMed:16469866]
[show Abstract]
Last Modified
22 February 2017