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Pimavanserin Tartrate

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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

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 Formula	C₂₅H₃₄FN₃O₂
Molecular Weight	427.6 g/mol
XLogP3	4.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	8
Exact Mass	427.26350550 g/mol
Monoisotopic Mass	427.26350550 g/mol
Topological Polar Surface Area	44.8 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	523
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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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