Lurasidone

Base Information

• Chemical Name: Lurasidone
• CAS No.: 367514-87-2
• Molecular Formula: C28H36N4O2S
• Molecular Weight: 492.68
• European Community (EC) Number: 696-042-8
• UNII: 22IC88528T
• DSSTox Substance ID: DTXSID40870340
• Nikkaji Number: J2.437.646J
• Wikipedia: Lurasidone
• Wikidata: Q416992
• NCI Thesaurus Code: C77575
• RXCUI: 1040028
• Pharos Ligand ID: BAV88W6QFVXP
• Metabolomics Workbench ID: 65224
• ChEMBL ID: CHEMBL1237021
• Mol file: 367514-87-2.mol

Synonyms:13496, SM;HCl, Lurasidone;Hydrochloride, Lurasidone;latuda;lurasidone;Lurasidone HCl;Lurasidone Hydrochloride;N-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinylmethyl)-1-cyclohexylmethyl)-2,3-bicyclo(2.2.1)heptanedicarboximide;SM 13,496;SM 13496;SM-13,496;SM-13496;SM13,496;SM13496

Chemical Property of Lurasidone

Chemical Property:

• Appearance/Colour: white crystal powder
• Vapor Pressure: 1.85E-15mmHg at 25°C
• Refractive Index: 1.636
• Boiling Point: 623.377 °C at 760 mmHg
• PKA: 8.41±0.50(Predicted)
• Flash Point: 330.807 °C
• PSA: 84.99000
• Density: 1.274 g/cm³
• LogP: 4.19660
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 492.25589758
• Heavy Atom Count: 35
• Complexity: 804

Purity/Quality:

99% ^*data from raw suppliers

Lurasidone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antipsychotic Agents
• Canonical SMILES: C1CCC(C(C1)CN2CCN(CC2)C3=NSC4=CC=CC=C43)CN5C(=O)C6C7CCC(C7)C6C5=O
• Isomeric SMILES: C1CC[C@H]([C@@H](C1)CN2CCN(CC2)C3=NSC4=CC=CC=C43)CN5C(=O)[C@H]6[C@@H]7CC[C@@H](C7)[C@H]6C5=O
• Recent ClinicalTrials: Observational Study on the Effect of Switch to Lurasidone in Subjects With Schizophrenia'
• Recent EU Clinical Trials: IMPACT OF STRUCTURAL AND MYELIN ABNORMALITIES ON COGNITIVE IMPAIRMENTS IN RECENT-ONSET SCHIZOPHRENIA – before and after lurasidone treatment
• Recent NIPH Clinical Trials: Valuable interaction with cognitive remediation and optimal antipsychotics for recovery in schizophrenia
• Description: The atypical antipsychotic lurasidone (also known as SM-13496) was approved in the United States in 2010 as an oral agent for the treatment of patients with schizophrenia. Lurasidone has potent affinity for D2 (Ki= 1.7 nM) and 5-HT2A (Ki= 2.0 nM) receptors and acts as an antagonist at both receptors. It is also a partial agonist at the 5-HT1A receptor and, unlike other atypical agents, is a potent antagonist at the 5-HT7 receptor; both of these activities are thought to confer beneficial cognitive properties. Lurasidone is further differentiated by its lack of affinity for muscarinic and histamine H1 receptors and its weak affinity for the 5-HT2C receptor. Antagonism at H1 and 5-HT2C receptors has been implicated in weight gain associated with atypical agents, while muscarinic receptor antagonism is associated with cognitive deficits.

Technology Process of Lurasidone

There total 32 articles about Lurasidone 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: 95.0%

C19H26N3S(1+)*CH3O3S(1-) + (3aR,4S,7R,7aS)?4,7?methylene?1H?isoindole?1,3(2H)-dione (14805-29-9,1318027-24-5) → lurasidone (194861-74-0,367514-87-2,1318074-25-7)

Guidance literature:

With potassium carbonate; In water; for 10h; Reflux;

Reference yield: 94.3%

(3aR,7aR)-4’-(benzo[d]isothiazol-3-yl)octahydrospiro[isoindole-2,1’-piperazin]-2-ium methanesulfonate (186204-37-5) + (3aR,4S,7R,7aS)?4,7?methylene?1H?isoindole?1,3(2H)-dione (14805-29-9,1318027-24-5) → lurasidone (194861-74-0,367514-87-2,1318074-25-7)

Guidance literature:

With potassium carbonate; In water; toluene; for 8h; Product distribution / selectivity; Reflux;

Reference yield: 86.35%

(3aR,7aR)-4’-(benzo[d]isothiazol-3-yl)octahydrospiro[isoindole-2,1’-piperazin]-2-ium methanesulfonate (186204-37-5) + endo-bicyclo<2.2.1>heptane-2,3-dicarboximide (6713-41-3,14805-29-9,28871-95-6,1318027-24-5) → [14C]-Lurasidone (194861-74-0,367514-87-2,1318074-25-7)

Guidance literature:

With potassium carbonate; dibenzo-18-crown-6; In toluene; for 12h; Product distribution / selectivity; Reflux;

upstream raw materials:

(3aR,7aR)-4’-(benzo[d]isothiazol-3-yl)octahydrospiro[isoindole-2,1’-piperazin]-2-ium methanesulfonate

(3aR,4S,7R,7aS)?4,7?methylene?1H?isoindole?1,3(2H)-dione

bicyclo[2.2.1]heptane-2-exo-3-exodicarboximide

(1S,2S)-cyclohexane-1,2-dimethanol bis(methanesulfonate)

Downstream raw materials:

C₂₈H₃₆N₄O₂S

C₂₈H₃₆N₄O₂S

Lurasidone hydrochloride

(3aR,4S,7R,7aS)-2-(((1R,2R)-2-((4-(benzo[d]isothiazol-3-yl)piperazin-1-yl)methyl)cyclohexyl)methyl)hexahydro-1H-4,7-methanoisoindole-1,3(2H)-dione tartrate

Refernces

• 1、 -. "Method for preparing lurasidone and salt thereof". Paragraph 0113-0115; 0118-0119; 0122; 0125-0126; 0129; 0132. . Retrieved 2020/02/10.
• 2、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF LURASIDONE BASE AND ITS SALT". Page/Page column 13-14. . Retrieved 2017/09/27.