Pimavanserin

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Pimavanserin are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Pimavanserin?

The molecule Pimavanserin presents a molecular formula of C25H34FN3O2 and its IUPAC name is 1-[(4-fluorophenyl)methyl]-1-(1-methylpiperidin-4-yl)-3-[[4-(2-methylpropoxy)phenyl]methyl]urea.

Pimavanserin (N-(3-fluorophenyl)-N-(1-(2-methylpiperidin-1-yl)ethyl)methanamine) is a molecule of the phenylpiperidine class that acts as a selective serotonin inverse agonist and antagonist. It was developed by ACADIA Pharmaceuticals for the treatment of psychosis in Parkinson's disease and dementia..

Pimavanserin is a serotonin 5-HT2A receptor inverse agonist/antagonist with high binding affinity (Ki = 3.4 nM). It also has moderate affinity for the serotonin 5-HT2C receptor (Ki = 31 nM) and the serotonin 5-HT7 receptor (Ki = 41 nM). Pimavanserin has no significant affinity for other serotonin, dopamine, adrenergic, histamine, or muscarinic receptors..

In animal models, pimavanserin has demonstrated antipsychotic-like effects in the absence of motor side effects. In a rat model of psychosis, pimavanserin reversed the effects of the non-selective serotonin agonist, quipazine. In another rat model, pimavanserin reversed the effects of the dopamine D2/D3 agonist, quinpirole..

In a phase II clinical trial in patients with Parkinson's disease and psychosis, pimavanserin was associated with a significant reduction in the severity of psychotic symptoms as measured by the Scale for the Assessment of Positive Symptoms (SAPS). Pimavanserin was well-tolerated in this trial, with the most common adverse events being nausea, fatigue, and dizziness..

Pimavanserin is currently in phase III clinical trials for the treatment of psychosis in Parkinson's disease and dementia..

3D structure

Cartesian coordinates

Geometry of Pimavanserin in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Pimavanserin RKEWSXXUOLRFBX-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Pimavanserin

 

Molecule descriptors

 
IUPAC name1-[(4-fluorophenyl)methyl]-1-(1-methylpiperidin-4-yl)-3-[[4-(2-methylpropoxy)phenyl]methyl]urea
InChI codeInChI=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)
InChI KeyRKEWSXXUOLRFBX-UHFFFAOYSA-N
SMILESCC(C)COc1ccc(CNC(=O)N(Cc2ccc(F)cc2)C2CCN(C)CC2)cc1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 1-(4-Fluorobenzyl)-3-(4-isobutoxybenzyl)-1-(1-methylpiperidin-4-yl)urea
  • 1-[(4-fluorophenyl)methyl]-1-(1-methylpiperidin-4-yl)-3-[[4-(2-methylpropoxy)phenyl]methyl]urea
  • 706779-91-1
  • 706779-91-1 (free base)
  • 706782-28-7
  • 779P911
  • A14434
  • A836958
  • AC-5273
  • ACP-103
  • B8019
  • BCP11618
  • BDBM139370
  • CS-3378
  • DB05316
  • EX-A4895
  • FT-0653701
  • GTPL8423
  • HMS3742A03
  • HY-14557
  • J-503297
  • JZ963P0DIK
  • ME-0240
  • MFCD09953792
  • N-(4-Fluorophenylmethyl)-N-(1-methylpiperidin-4-yl)-N'-(4-(2-methylpropyloxy)phenylmethyl) carbamide
  • N-(4-Fluorophenylmethyl)-N-(1-methylpiperidin-4-yl)-N'-(4-(2-methylpropyloxy)phenylmethyl)carbamide
  • N-[(4-Fluorophenyl)Methyl]-N-(1-Methyl-4-piperidinyl)-N'-[[4-(2-Methylpropoxy)phenyl]Methyl]urea;
  • N-[(4-fluorophenyl)methyl]-N-(1-methylpiperidin-4-yl)-N'-{[4-(2-methylpropoxy)phenyl]methyl}urea
  • NCGC00390656-01
  • NCGC00390656-02
  • Nuplazid (proposed trade name)
  • Pimanavserin
  • Pimavanserin
  • Pimavanserin free base
  • Pimavanserin(ACP-103)
  • Q7194603
  • SB16963
  • methyltrimethylacetate

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC16159083
  • UNII-JZ963P0DIK
  • AKOS015902593
  • DTXSID90990906
  • CHEMBL2111101
  • CHEBI:133017
  • SCHEMBL675165

Physico-Chemical properties

IUPAC name1-[(4-fluorophenyl)methyl]-1-(1-methylpiperidin-4-yl)-3-[[4-(2-methylpropoxy)phenyl]methyl]urea
Molecular formulaC25H34FN3O2
Molecular weight427.555
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity126.21
LogP5.0
Topological polar surface area44.8

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.