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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C25H34FN3O2.C4H6O6
Molecular Weight 1005.1964
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIMAVANSERIN TARTRATE

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O.CC(C)COC1=CC=C(CNC(=O)N(CC2=CC=C(F)C=C2)C3CCN(C)CC3)C=C1.CC(C)COC4=CC=C(CNC(=O)N(CC5=CC=C(F)C=C5)C6CCN(C)CC6)C=C4

InChI

InChIKey=RGSULKHNAKTFIZ-CEAXSRTFSA-N
InChI=1S/2C25H34FN3O2.C4H6O6/c2*1-19(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;5-1(3(7)8)2(6)4(9)10/h2*4-11,19,23H,12-18H2,1-3H3,(H,27,30);1-2,5-6H,(H,7,8)(H,9,10)/t;;1-,2-/m..1/s1

HIDE SMILES / InChI

Molecular Formula C4H6O6
Molecular Weight 150.0868
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C25H34FN3O2
Molecular Weight 427.5548
Charge 0
Count
MOL RATIO 2 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.087 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Nuplazid

Cmax

ValueDoseCo-administeredAnalytePopulation
151.8 ng/mL
300 mg single, nasogastric
PIMAVANSERIN TARTRATE plasma
Homo sapiens
20.3 ng/mL
50 mg single, oral
PIMAVANSERIN TARTRATE plasma
Homo sapiens
92.9 ng/mL
50 mg 1 times / day steady-state, oral
PIMAVANSERIN TARTRATE plasma
Homo sapiens
49.7 ng/mL
100 mg single, nasogastric
PIMAVANSERIN TARTRATE plasma
Homo sapiens
193.4 ng/mL
100 mg 1 times / day steady-state, oral
PIMAVANSERIN TARTRATE plasma
Homo sapiens
247.5 ng/mL
150 mg 1 times / day steady-state, oral
PIMAVANSERIN TARTRATE plasma
Homo sapiens
9.2 ng/mL
20 mg single, oral
PIMAVANSERIN TARTRATE plasma
Homo sapiens
111.3 ng/mL
200 mg single, nasogastric
PIMAVANSERIN TARTRATE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
10798 ng × h/mL
300 mg single, nasogastric
PIMAVANSERIN TARTRATE plasma
Homo sapiens
1315 ng × h/mL
50 mg single, oral
PIMAVANSERIN TARTRATE plasma
Homo sapiens
1838.7 ng × h/mL
50 mg 1 times / day steady-state, oral
PIMAVANSERIN TARTRATE plasma
Homo sapiens
3742 ng × h/mL
100 mg single, nasogastric
PIMAVANSERIN TARTRATE plasma
Homo sapiens
3804.6 ng × h/mL
100 mg 1 times / day steady-state, oral
PIMAVANSERIN TARTRATE plasma
Homo sapiens
4680.3 ng × h/mL
150 mg 1 times / day steady-state, oral
PIMAVANSERIN TARTRATE plasma
Homo sapiens
706 ng × h/mL
20 mg single, oral
PIMAVANSERIN TARTRATE plasma
Homo sapiens
7335 ng × h/mL
200 mg single, nasogastric
PIMAVANSERIN TARTRATE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
53.5 h
300 mg single, nasogastric
PIMAVANSERIN TARTRATE plasma
Homo sapiens
53 h
50 mg single, oral
PIMAVANSERIN TARTRATE plasma
Homo sapiens
54.6 h
50 mg 1 times / day steady-state, oral
PIMAVANSERIN TARTRATE plasma
Homo sapiens
58.3 h
100 mg single, nasogastric
PIMAVANSERIN TARTRATE plasma
Homo sapiens
60.1 h
100 mg 1 times / day steady-state, oral
PIMAVANSERIN TARTRATE plasma
Homo sapiens
48 h
150 mg 1 times / day steady-state, oral
PIMAVANSERIN TARTRATE plasma
Homo sapiens
57 h
20 mg single, oral
PIMAVANSERIN TARTRATE plasma
Homo sapiens
55.4 h
200 mg single, nasogastric
PIMAVANSERIN TARTRATE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
3.2%
300 mg single, nasogastric
PIMAVANSERIN TARTRATE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

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
Record UNII
NA83F1SJSR
Record Status Validated (UNII)
Record Version