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    Chemistry

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    Also known as: 706779-91-1, Acp-103, 1-(4-fluorobenzyl)-3-(4-isobutoxybenzyl)-1-(1-methylpiperidin-4-yl)urea, Pimavanserin [inn], Pimavanserin free base, Jz963p0dik
    Molecular Formula
    C25H34FN3O2
    Molecular Weight
    427.6  g/mol
    InChI Key
    RKEWSXXUOLRFBX-UHFFFAOYSA-N
    FDA UNII
    JZ963P0DIK
    Pimavanserin Tartrate
    Psychotic symptoms associated with Parkinson's disease (PD) are relatively common, reducing quality of life and prognosis for individuals with PD. Pimavanserin (ACP-103), marketed under the trade name Nuplazid, is a drug developed by Acadia Pharmaceuticals for the treatment of psychosis related to Parkinson's disease. Due to its actions at serotonin receptors and lack of effects on dopamine receptors, pimavanserin treats hallucinations and delusions without causing extrapyramidal symptoms. It was initially approved by the FDA in 2016 and is now under review as a potential treatment for dementia related psychosis. As of April 2021, FDA approval has not been granted for this indication, despite previous breakthrough designation.
    Pimavanserin is an Atypical Antipsychotic.
    1 2D Structure

    Pimavanserin Tartrate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-[(4-fluorophenyl)methyl]-1-(1-methylpiperidin-4-yl)-3-[[4-(2-methylpropoxy)phenyl]methyl]urea
    2.1.2 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)
    2.1.3 InChI Key
    RKEWSXXUOLRFBX-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(C)COC1=CC=C(C=C1)CNC(=O)N(CC2=CC=C(C=C2)F)C3CCN(CC3)C
    2.2 Other Identifiers
    2.2.1 UNII
    JZ963P0DIK
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Acp 103

    2. Acp-103

    3. Acp103

    4. Bis(1-(4-fluorobenzyl)-1-(1-methylpiperidin-4-yl)-3-(4-(2-methylpropoxy)benzyl)urea) (2r,3r)-2,3-dihydroxybutanedioate

    5. N-(4-fluorophenylmethyl)-n-(1-methylpiperidin-4-yl)-n'-(4-(2-methylpropyloxy)phenylmethyl)carbamide

    6. Nuplazid

    7. Pimavanserin Tartrate

    8. Urea, N-((4-fluorophenyl)methyl)-n-(1-methyl-4-piperidinyl)-n'-((4-(2-methylpropoxy)phenyl)methyl)-, (2r,3r)-2,3-dihydroxybutanedioate (2:1)

    2.3.2 Depositor-Supplied Synonyms

    1. 706779-91-1

    2. Acp-103

    3. 1-(4-fluorobenzyl)-3-(4-isobutoxybenzyl)-1-(1-methylpiperidin-4-yl)urea

    4. Pimavanserin [inn]

    5. Pimavanserin Free Base

    6. Jz963p0dik

    7. 706779-91-1 (free Base)

    8. 1-[(4-fluorophenyl)methyl]-1-(1-methylpiperidin-4-yl)-3-[[4-(2-methylpropoxy)phenyl]methyl]urea

    9. N-(4-fluorophenylmethyl)-n-(1-methylpiperidin-4-yl)-n'-(4-(2-methylpropyloxy)phenylmethyl) Carbamide

    10. Unii-jz963p0dik

    11. N-(4-fluorophenylmethyl)-n-(1-methylpiperidin-4-yl)-n'-(4-(2-methylpropyloxy)phenylmethyl)carbamide

    12. 706782-28-7

    13. Pimanavserin

    14. Methyltrimethylacetate

    15. Ac-5273

    16. Pimavanserin [mi]

    17. Pimavanserin(acp-103)

    18. Pimavanserin [who-dd]

    19. Schembl675165

    20. Nuplazid (proposed Trade Name)

    21. Gtpl8423

    22. Chembl2111101

    23. Dtxsid90990906

    24. Chebi:133017

    25. Bdbm139370

    26. Hms3742a03

    27. Bcp11618

    28. Ex-a4895

    29. Mfcd09953792

    30. Zinc16159083

    31. Akos015902593

    32. Cs-3378

    33. Db05316

    34. Me-0240

    35. Sb16963

    36. Ncgc00390656-01

    37. Ncgc00390656-02

    38. Hy-14557

    39. B8019

    40. Ft-0653701

    41. A14434

    42. 779p911

    43. A836958

    44. J-503297

    45. Q7194603

    46. N-[(4-fluorophenyl)methyl]-n-(1-methyl-4-piperidinyl)-n'-[[4-(2-methylpropoxy)phenyl]methyl]urea;

    47. N-[(4-fluorophenyl)methyl]-n-(1-methylpiperidin-4-yl)-n'-{[4-(2-methylpropoxy)phenyl]methyl}urea

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 427.6 g/mol
    Molecular Formula C25H34FN3O2
    XLogP34.5
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count8
    Exact Mass427.26350550 g/mol
    Monoisotopic Mass427.26350550 g/mol
    Topological Polar Surface Area44.8 Ų
    Heavy Atom Count31
    Formal Charge0
    Complexity523
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Pimavanserin is indicated for the treatment of hallucinations and delusions associated with Parkinsons disease psychosis.

    Treatment of schizophrenia and other psychotic disorders

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Pimavanserin's unique actions on serotonin receptors improve symptoms of hallucinations and delusions associated with Parkinson's disease. In clinical studies, 80.5% of individuals treated with pimavanserin reported improvement in symptoms. Pimavanserin does not worsen motor functioning in patients with Parkinson's disease psychosis.

    5.2 MeSH Pharmacological Classification

    Antiparkinson Agents

    Agents used in the treatment of Parkinson's disease. The most commonly used drugs act on the dopaminergic system in the striatum and basal ganglia or are centrally acting muscarinic antagonists. (See all compounds classified as Antiparkinson Agents.)

    Antipsychotic Agents

    Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus. (See all compounds classified as Antipsychotic Agents.)

    Serotonin 5-HT2 Receptor Antagonists

    Drugs that bind to but do not activate SEROTONIN 5-HT2 RECEPTORS, thereby blocking the actions of SEROTONIN or SEROTONIN 5-HT2 RECEPTOR AGONISTS. Included under this heading are antagonists for one or more specific 5-HT2 receptor subtypes. (See all compounds classified as Serotonin 5-HT2 Receptor Antagonists.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    PIMAVANSERIN
    5.3.2 FDA UNII
    JZ963P0DIK
    5.3.3 Pharmacological Classes
    Established Pharmacologic Class [EPC] - Atypical Antipsychotic
    5.4 ATC Code

    N - Nervous system

    N05 - Psycholeptics

    N05A - Antipsychotics

    N05AX - Other antipsychotics

    N05AX17 - Pimavanserin

    5.5 Absorption, Distribution and Excretion

    Absorption

    The median Tmax of pimavanserin in clinical studies was 6 hours, regardless of the dose. Bioavailability of an oral tablet of pimavanserin and a solution were almost identical. The major active circulating N-desmethylated metabolite, AC-279, has a median Tmax of 6 hours.

    Route of Elimination

    About 0.55% of a 34 mg oral dose was excreted unchanged in the urine and 1.53% was eliminated in feces within 10 days. Less than 1% of the administered dose and its active metabolite AC-279 were recovered in urine during clinical studies.

    Volume of Distribution

    Following administration of a single dose of 34 mg, the average apparent volume of distribution was 2173 L in clinical studies.

    5.6 Metabolism/Metabolites

    Pimavanserin is mainly metabolized CYP3A4 and CYP3A5 hepatic cytochrome enzymes, and to a lesser extent by CYP2J2, CYP2D6, and other cytochrome and flavin-containing monooxygenase enzymes. CYP3A4 metabolizes pimavanserin to its major active metabolite, AC-279.

    5.7 Biological Half-Life

    The average plasma half-lives for pimavanserin and its active metabolite (AC-279) are estimated at 57 hours and 200 hours, respectively.

    5.8 Mechanism of Action

    Parkinson's disease psychosis (PDP) is a imbalance of serotonin and dopamine from disruption of the normal balance between the serotonergic and dopaminergic receptors and neurotransmitters in the brain. The mechanism by which pimavanserin treats hallucinations and delusions associated with Parkinsons disease psychosis is not fully established. It is possible that pimavanserin acts via inverse agonist and antagonist activity at serotonin 5-HT2A receptors with limited effects on serotonin 5-HT2C receptors. Pimavanserin is an inverse agonist and antagonist of serotonin 5-HT2A receptors with high binding affinity, demonstrating low binding affinity to serotonin 5-HT2C receptors. In addition, this drug exhibits low affinity binding to sigma 1 receptors. Pimavanserin lacks activity at muscarinic, dopaminergic, adrenergic, and histaminergic receptors, preventing various undesirable effects typically associated with antipsychotics.

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