Paliperidone Palmitate

Base Information

• Chemical Name: Paliperidone Palmitate
• CAS No.: 199739-10-1
• Molecular Formula: C39H57FN4O4
• Molecular Weight: 664.904
• European Community (EC) Number: 682-873-3
• UNII: R8P8USM8FR
• DSSTox Substance ID: DTXSID70870217
• Wikipedia: Paliperidone_palmitate
• Wikidata: Q27157250
• NCI Thesaurus Code: C83917
• RXCUI: 858045
• Pharos Ligand ID: UVR6CV6HYYZ6
• ChEMBL ID: CHEMBL2107360
• Mol file: 199739-10-1.mol

Synonyms:3-(2-(4-(6-fluoro-3-(1,2-benzisoxazolyl))-1-piperidinyl)ethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido(1,2-a)pyrimidin-4-one;9 Hydroxy risperidone;9 Hydroxyrisperidone;9 OH risperidone;9-hydroxy-risperidone;9-hydroxyrisperidone;9-OH-risperidone;Invega;Invega Sustenna;paliperidone;paliperidone palmitate;Palmitate, Paliperidone;R 76477;R-76477;R76477;Sustenna, Invega

Chemical Property of Paliperidone Palmitate

Chemical Property:

• Boiling Point: 736.308 °C at 760 mmHg
• PKA: 8.07±0.10(Predicted)
• Flash Point: 399.105 °C
• PSA: 90.46000
• Density: 1.196 g/cm³
• LogP: 9.05140
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly, Heated, Sonicated), Methanol (Sl
• XLogP3: 10.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 20
• Exact Mass: 664.43638447
• Heavy Atom Count: 48
• Complexity: 1090

Purity/Quality:

99.0% ^*data from raw suppliers

PaliperidonePalmitate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OC1CCCN2C1=NC(=C(C2=O)CCN3CCC(CC3)C4=NOC5=C4C=CC(=C5)F)C
• Recent ClinicalTrials: Relative Bioavailability of LY03010 Compared to Listed Drug
• Recent EU Clinical Trials: Open, multicenter, randomized clinical trial to evaluate the efficacy and safety of aripiprazole vs paliperidone / risperidone using multi-omics data in patients with a first psychotic episode.
• Recent NIPH Clinical Trials: Qualitative assessment and evaluation for change of patient oriented QOL regarding long-acting injectable antipsychotics for schizophrenia
• Description: Paliperidone palmitate is an atypical long acting antipsychotics，which can fast onset in acute phase and continuously improve the symptoms in maintenance phase． It has the solid efficacy and convenient ad[1]ministration，which offer a new option for schizophrenia treatment and will help patients to adhere the treatment and prevent relapse． As the sole long acting antipsychotics with monthly injection，it was approved by CFDA in 2011 and indicated for the acute and maintenance treatment of schizophrenia．
• Uses: Paliperidone Palmitate is a long-acting injectable atypical antipsychotic used in the treatment of schizophrenia.

Technology Process of Paliperidone Palmitate

There total 7 articles about Paliperidone Palmitate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.5%

palmitic anhydride (623-65-4) + paliperidone (144598-75-4,147663-01-2) → paliperidone palmitate (199739-10-1)

Guidance literature:

palmitic anhydride; paliperidone; With dmap; In toluene; at 20 - 70 ℃; for 3h;

With tert-butyl methyl ether; In toluene; at 10 ℃; for 1h; Product distribution / selectivity;

Reference yield: 80.0%

3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-9-hydroxy-4H-pyrido[1,2-a]pyrimidine-4-one palmitate ester (1415488-05-9) + 6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride (84163-13-3) → paliperidone palmitate (199739-10-1)

Guidance literature:

6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride; With potassium carbonate; In acetonitrile; at 25 - 60 ℃; for 1.16667h;

3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-9-hydroxy-4H-pyrido[1,2-a]pyrimidine-4-one palmitate ester; With tetrabutylammomium bromide; potassium iodide; at 20 - 75 ℃; for 14h;

Reference yield: 80.0%

1-hexadecylcarboxylic acid (57-10-3) + paliperidone (144598-75-4,147663-01-2) → paliperidone palmitate (199739-10-1)

Guidance literature:

With dmap; pivaloyl chloride; triethylamine; In tetrahydrofuran; at 20 ℃; for 24h; Product distribution / selectivity;

upstream raw materials:

1-hexadecylcarboxylic acid

paliperidone

n-hexadecanoyl chloride

palmitic anhydride

Downstream raw materials:

paliperidone

3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7-dihydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-9-pentadecyl-4H-pyrido[1,2-a]pyrimidin-4-one

Refernces

• 1、 -. "PREPARATION OF 3-[2-[4-((6-FLUORO-1, 2-BENZISOXAZOL-3-YL)-L-PIPERIDINYL)-6, 7, 8, 9-TETRAHYDRO-9-HYDROXY-2-METHYL-4H-PYRIDO[ 1, 2-A]-PYRIMIDIN-4-ONE (PALIPERIDONE) AND PALIPERIDONE PALMITATE.". Paragraph 0038; 0039. . Retrieved 2014/03/25.
• 2、 -. "PROCESSES FOR THE PREPARATION AND PURIFICATION OF PALIPERIDONE PALMITATE". Page/Page column 28. . Retrieved 2009/09/04.