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Details

Stereochemistry ACHIRAL
Molecular Formula C25H34FN3O2
Molecular Weight 427.5548
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIMAVANSERIN

SMILES

CC(C)COC1=CC=C(CNC(=O)N(CC2=CC=C(F)C=C2)C3CCN(C)CC3)C=C1

InChI

InChIKey=RKEWSXXUOLRFBX-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C25H34FN3O2
Molecular Weight 427.5548
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Pimavanserin, marketed under the trade name Nuplazid, a non-dopaminergic atypical antipsychotic developed by Acadia Pharmaceuticals is the first and only medication approved by the U.S. Food and Drug Administration (FDA) for the treatment of hallucinations and delusions associated with Parkinson’s disease psychosis. The mechanism of action of pimavanserin in the treatment of hallucinations and delusions associated with Parkinson’s disease psychosis is unknown. However, the effect of pimavanserin could be mediated through a combination of inverse agonist and antagonist activity at serotonin 5-HT2A receptors and to a lesser extent at serotonin 5-HT2C receptors. In vitro, pimavanserin acts as an inverse agonist and antagonist at serotonin 5-HT2A receptors with high binding affinity (Ki value 0.087 nM) and at serotonin 5-HT2C receptors with lower binding affinity (Ki value 0.44 nM). Pimavanserin shows low binding to sigma 1 receptors (Ki value 120 nM) and has no appreciable affinity (Ki value >300 nM), to serotonin 5-HT2B, dopaminergic (including D2), muscarinic, histaminergic, or adrenergic receptors, or to calcium channels. Pimavanserin was approved by the FDA to treat hallucinations and delusions associated with psychosis experienced by some people with Parkinson's disease on April 29, 2016.

CNS Activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.087 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Nuplazid
PubMed

PubMed

TitleDatePubMed
The effects of food on the pharmacokinetics of a formulated ACP-103 tablet in healthy volunteers.
2007 Jul
5-HT(2A) inverse-agonists for the treatment of insomnia.
2008
Pimavanserin tartrate: a 5-HT2A inverse agonist with potential for treating various neuropsychiatric disorders.
2008 Dec
Aripiprazole's receptor pharmacology and extrapyramidal side effects.
2008 Mar
PET analysis of the 5-HT2A receptor inverse agonist ACP-103 in human brain.
2008 Mar
A 5-HT2A receptor inverse agonist, ACP-103, reduces tremor in a rat model and levodopa-induced dyskinesias in a monkey model.
2008 Oct
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.
2010 Feb
Parkinson's disease dementia.
2010 Jul
Serotonin 5-HT(2A) receptor antagonists in the treatment of insomnia: present status and future prospects.
2010 Mar
Pimavanserin, a serotonin(2A) receptor inverse agonist, for the treatment of parkinson's disease psychosis.
2010 Mar
Pimavanserin for the treatment of Parkinson's disease psychosis.
2013 Oct
Patents

Sample Use Guides

In Vivo Use Guide
The recommended dose of NUPLAZID (Pimavanserin) is 34 mg, taken orally as two 17 mg strength tablets once daily, without titration. Pimavanserin can be taken with or without food.
Route of Administration: Oral
In Vitro Use Guide
In vitro, pimavanserin acts as an inverse agonist and antagonist at serotonin 5-HT2A receptors with high binding affinity (Ki value 0.087 nM) and at serotonin 5-HT2C receptors with lower binding affinity (Ki value 0.44 nM).
Substance Class Chemical
Created
by admin
on Tue Oct 22 01:43:41 UTC 2019
Edited
by admin
on Tue Oct 22 01:43:41 UTC 2019
Record UNII
JZ963P0DIK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIMAVANSERIN
DASH   INN   WHO-DD  
INN  
Official Name English
PIMAVANSERIN [INN]
Common Name English
PIMAVANSERIN [WHO-DD]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175430
Created by admin on Tue Oct 22 01:43:41 UTC 2019 , Edited by admin on Tue Oct 22 01:43:41 UTC 2019
WHO-ATC N05AX17
Created by admin on Tue Oct 22 01:43:41 UTC 2019 , Edited by admin on Tue Oct 22 01:43:41 UTC 2019
NCI_THESAURUS C66885
Created by admin on Tue Oct 22 01:43:41 UTC 2019 , Edited by admin on Tue Oct 22 01:43:41 UTC 2019
Code System Code Type Description
CAS
706779-91-1
Created by admin on Tue Oct 22 01:43:41 UTC 2019 , Edited by admin on Tue Oct 22 01:43:41 UTC 2019
PRIMARY
RXCUI
1791685
Created by admin on Tue Oct 22 01:43:41 UTC 2019 , Edited by admin on Tue Oct 22 01:43:41 UTC 2019
PRIMARY
NCI_THESAURUS
C76444
Created by admin on Tue Oct 22 01:43:41 UTC 2019 , Edited by admin on Tue Oct 22 01:43:41 UTC 2019
PRIMARY
EVMPD
SUB183869
Created by admin on Tue Oct 22 01:43:41 UTC 2019 , Edited by admin on Tue Oct 22 01:43:41 UTC 2019
PRIMARY
INN
8877
Created by admin on Tue Oct 22 01:43:41 UTC 2019 , Edited by admin on Tue Oct 22 01:43:41 UTC 2019
PRIMARY
PUBCHEM
10071196
Created by admin on Tue Oct 22 01:43:41 UTC 2019 , Edited by admin on Tue Oct 22 01:43:41 UTC 2019
PRIMARY
WIKIPEDIA
PIMAVANSERIN
Created by admin on Tue Oct 22 01:43:41 UTC 2019 , Edited by admin on Tue Oct 22 01:43:41 UTC 2019
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
EXCRETED UNCHANGED
FECAL
TARGET->INVERSE AGONIST
AGONIST
Ki
TARGET->INVERSE AGONIST
AGONIST
Ki
METABOLIC ENZYME -> SUBSTRATE
MINOR
METABOLIC ENZYME -> SUBSTRATE
EXCRETED UNCHANGED
URINE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
MAJOR
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE ACTIVE -> PARENT
MAJOR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC