367514-87-2

Basic information

• Product Name: lurasidone
• Synonyms: lurasidone;(3aR,4S,7R,7aS)-2-[[(1R,2R)-2-[[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl]methyl]cyclohexyl]methyl]hexahydro-4,7-methano-1H-isoindole-1,3(2H)-dione;4-{[(1R,2R)-2-{[4-(2$l^{4}-thia-6-azatricyclo[5.4.0.0^{2,6}]undeca-1(11),2,4,7,9-pentaen-5-yl)piperazin-1-yl]Methyl}cyclohexyl]Methyl}-4-azatricyclo[5.2.1.0^{2,6}]deca-1(9),2(6),7-triene-3,5-dione;Lurasidone (SM13496);(3aR,4S,7R,7aS)-2-{[(1R,2R)-2-{[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]Methyl}cyclohexyl]Methyl}hexahydro-1H-4,7-Methanoisoindole-1,3(2H)-dione;urasidone;Lurasidone, >=98%;Lurasidone Base
• CAS NO: 367514-87-2
• Molecular Formula: C28H36N4O2S
• Molecular Weight: 492.67604
• EINECS: 1308068-626-2
• Product Categories: Pharmaceutical intermediate
• Mol File: 367514-87-2.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 623.377 °C at 760 mmHg
• Flash Point: 330.807 °C
• Appearance: white crystal powder
• Density: 1.273
• Vapor Pressure: 1.85E-15mmHg at 25°C
• Refractive Index: 1.636
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• PKA: 8.41±0.50(Predicted)
• CAS DataBase Reference: lurasidone(CAS DataBase Reference)
• NIST Chemistry Reference: lurasidone(367514-87-2)
• EPA Substance Registry System: lurasidone(367514-87-2)

Safety Data

• Hazardous Substances Data: 367514-87-2(Hazardous Substances Data)

Usage

Description

Lurasidone, also known as SM-13496, is an atypical antipsychotic medication approved in the United States in 2010 for the treatment of schizophrenia. It is characterized by its potent affinity for D2 (Ki= 1.7 nM) and 5-HT2A (Ki= 2.0 nM) receptors, acting as an antagonist at both receptors. Lurasidone is also a partial agonist at the 5-HT1A receptor and a potent antagonist at the 5-HT7 receptor, which are believed to contribute to its beneficial cognitive properties. It is further differentiated by its lack of affinity for muscarinic and histamine H1 receptors and its weak affinity for the 5-HT2C receptor, which may help reduce weight gain and cognitive deficits associated with other atypical antipsychotic agents.

Uses

Used in Pharmaceutical Industry:
Lurasidone is used as an atypical antipsychotic for the treatment of schizophrenia. Its unique receptor profile, including potent antagonism at D2 and 5-HT2A receptors, partial agonism at 5-HT1A receptor, and potent antagonism at 5-HT7 receptor, contributes to its efficacy in managing the symptoms of schizophrenia while potentially reducing side effects such as weight gain and cognitive deficits.
Used in Research and Development:
Lurasidone is used as a research compound for studying the mechanisms of schizophrenia and the role of various receptors in the pathophysiology of the disease. Its unique receptor binding profile makes it a valuable tool in understanding the complex interactions between neurotransmitter systems and the development of psychotic symptoms.
Brand name: Latuda

Drug for the treatment of schizophrenia

Lurasidone is developed by Japan's Dainippon Sumitomo Pharma which is an atypical antipsychotic,and is a classification of drug registration 3.1 class, it is suitable for the treatment of patients with schizophrenia. Its efficacy is Determined in four six weeks in adult patients with schizophrenia controlled studies. The exact mechanism of the treatment of schizophrenia, like other atypical antipsychotics ,is not very clear,and may be related to the antagonism of the dopamine D2 and serotonin 2A (5-HT2A) receptors. For the treatment of schizophrenia, a study has reported lurasidone can improve cognitive function. October 28, 2010 ,the FDA approved lurasidone hydrochloride (lurasidone HCI) tablets once a day for the first-line treatment of patients with schizophrenia, the trade name is Latuda. Dosage: The recommended starting dose is 40 mg/d, the effective dose range is 40~120 mg /· d, the maximum recommended dose is 80 mg /· d. It should be taken with food. Adverse reaction: common adverse reactions are somnolence, akathisia, nausea, Parkinson's disease-like symptoms and emotional anxiety. Lurasidone has no physical dependence, less likely to cause weight gain, it does not cause glucose, lipids (lipids), it changs the period between ECG and QT. The above information is edited by the lookchem of Tian Ye.

Originator

Dainippon Sumitomo Pharma (Japan)

InChI:InChI=1/C28H36N4O2S/c33-27-24-18-9-10-19(15-18)25(24)28(34)32(27)17-21-6-2-1-5-20(21)16-30-11-13-31(14-12-30)26-22-7-3-4-8-23(22)35-29-26/h3-4,7-8,18-21,24-25H,1-2,5-6,9-17H2/t18-,19+,20-,21-,24+,25-/m0/s1

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 2746-19-2 (1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 
• 14166-28-0 exo-bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride 
• 87691-87-0 3-(1-piperazinyl)-1,2-benzisothiazole 
• 140459-96-7 (1R,2R)-1,2-cyclohexanedicarboxylic acid dimethyl ester 
• 186204-35-3 (1R,2R)-(-)-trans-cyclohexane-1,2-diylbis(methylene)dimethanesulfonate 
• 14805-29-9 (3aR,4S,7R,7aS)?4,7?methylene?1H?isoindole?1,3(2H)-dione 
• 46022-05-3 (1R,2R)-(-)-trans-cyclohexane-1,2-dicarboxylic acid 
• 194861-74-0 C₂₈H₃₆N₄O₂S 
• 194861-74-0 C₂₈H₃₆N₄O₂S 
• 367514-87-2 C₂₈H₃₆N₄O₂S 
• 186204-37-5 (3aR,7aR)-4’-(benzo[d]isothiazol-3-yl)octahydrospiro[isoindole-2,1’-piperazin]-2-ium methanesulfonate 
• 6713-41-3 endo-bicyclo<2.2.1>heptane-2,3-dicarboximide 
• 133070-64-1 3-(piperazin-1-yl)-1,2-benzisothiazole hydrochloride 

Downstream Products

• 1318074-18-8 C₂₈H₃₆N₄O₂S 
• 1318074-19-9 C₂₈H₃₆N₄O₂S 
• 139563-25-0 Lurasidone hydrochloride 
• 139563-20-5 (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 
• 139563-25-0 (3aR,4S,7R,7aS)-2-{(1R,2R)-2-[4-(1,2-benzisothiazol-3-yl)piperazin-1-ylmethyl]cyclohexylmethyl}hexahydro-1H-4,7-methanisoindol-1,3-dione dihydrochloride 
• 139563-25-0 lurasidone hydrochloride 

Relevant articles and documents

Preparation method of lurasidone

The invention relates to a preparation method of lurasidone. The preparation method comprises the following steps of: reacting a compound as shown in a formula (I) with a compound as shown in a formula (II) under the action of an organic solvent A and a catalyst A, and performing quenching with a weak base solution to obtain a lurasidone crude product. According to the preparation method, the organic solvent A is selected from N-methyl pyrrolidone, N, N-dimethylformamide or a mixture of N-methyl pyrrolidone and N, N-dimethylformamide, preferably N-methyl pyrrolidone; the catalyst A is cesium carbonate; the weak base solution is selected from a cesium carbonate solution, a potassium carbonate solution or a sodium carbonate solution, preferably the potassium carbonate solution. The method is simple to operate, high in product yield, short in reaction time, low in cost and suitable for actual industrial production.

Preparation of west lulalula alkone isomer impurities (by machine translation)

West hydrochloric acid lulalula alkone, chemical name: (3 aR, 4S, 7R, 7 AS) - 2 - {(1R, 2R) - 2 - [4 - (1, 2 - Benzothiazole - 3 - yl) piperazine - 1 - yl methyl] cyclohexyl methyl} hexahydro - 1H- 4, 7 - Methyl isobutyl ketone indole - 1, 3 - dione hydro

Preparation method for lurasidone hydrochloride

The invention discloses a preparation method for lurasidone hydrochloride. According to the preparation method, trans-1,2-cyclohexanedicarboxylic acid (SM-1) is used as a raw material and subjected to resolution, methyl esterification, reduction, methylsulfonylation, condensation, recrystallization and salt formation so as to eventually obtain lurasidone hydrochloride. The preparation method provided by the invention greatly reduces production cost and has the characteristics of high product yield, easy operation, low toxicity and suitability for industrial large-scale production.