(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
Lurasidone
CAS: 367514-87-2
Molecular Formula: C28H36N4O2S
(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 - Names and Identifiers
| Name | Lurasidone |
| Synonyms | urasidone lurasidone Lurasidone Lurasidone Base Lurasidone (SM13496) (3aR,4S,7R,7aS)-2-((1R,2R)-2-(4-(1,2-Benzothiazol-3-yl)piperazin-1-ylmethyl)cyclohexylmethyl)hexahydro-4,7-methano-2H-isoindole-1,3-dione (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 (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 (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 |
| CAS | 367514-87-2 |
| EINECS | 696-042-8 |
| 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 |
(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 - Physico-chemical Properties
| Molecular Formula | C28H36N4O2S |
| Molar Mass | 492.68 |
| Density | 1.273 |
| Melting Point | 146-149°C |
| Boling Point | 623.4±55.0 °C(Predicted) |
| Flash Point | 330.8°C |
| Solubility | Chloroform (Slightly), DMSO (Slightly, Heated), Methanol (Slightly, Heated) |
| Vapor Presure | 1.85E-15mmHg at 25°C |
| Appearance | Powder |
| Color | White to Off-White |
| pKa | 8.41±0.50(Predicted) |
| Storage Condition | -20°C Freezer |
| Refractive Index | 1.636 |
| In vitro study | Lurasidone (SM-13496) is an antagonist of dopamine D 2 and 5-HT 7 with IC 50 s of 1.68±0.09 and 0.495±0.090 nM, respectively. Lurasidone (SM-13496) is also a partial agonist of 5-HT 1A receptor with an IC 50 of 6.75±0.97 nM. In vitro receptor binding experiments reveal that Lurasidone (SM-13496) demonstrates affinity for dopamine D 2 and 5-HT 2A receptors higher than other tested antipsychotics. Lurasidone (SM-13496) does not increase [ 35 S]GTPγS binding to the membrane preparations for dopamine D 2 receptors by itself, but it antagonizes dopamine-stimulated [ 35 S]GTPγS binding in a concentration-dependent manner with a K B value of 2.8±1.1 nM. |
| In vivo study | Lurasidone (SM-13496) dose-dependently increases the ratio of DOPAC/dopamine in frontal cortex and striatum, but it shows a preferential effect on the frontal cortex compare with the striatum, especially at higher doses. Lurasidone (SM-13496) (ED 50 values 2.3 to 5.0 mg/kg) shows a comparable potency with olanzapine (ED 50 values 1.1 to 5.1 mg/kg), higher potency than clozapine (ED 50 9.5 to 290 mg/kg), and slightly lower potency than haloperidol (ED 50 values 0.44 to 1.7 mg/kg). Lurasidone (SM-13496) (1 to 10 mg/kg) dose-dependently inhibits conditioned avoidance response (CAR) in rats, and the ED 50 values are 6.3 mg/kg. Lurasidone (SM-13496) dose-dependently inhibits tryptamine (TRY)-induced forepaw clonic seizure and p-chloroamphetamine (p-CAMP)-induced hyperthermia with ED 50 values of 5.6 and 3.0 mg/kg, respectively. Lurasidone (SM-13496) (0.3 to 30 mg/kg) dose-dependently and significantly increases the number of shocks received by rats in the conflict test with MED of 10 mg/kg (p<0.01). |
(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 - Reference
| Reference Show more | 1. [IF=3.119] Jinrui Zhang et al."In silico study on identification of novel MALT1 allosteric inhibitors."Rsc Adv. 2019 Nov;9(67):39338-39347 2. [IF=4.411] Xin Meng et al."Drug Repurposing for Influenza Virus Polymerase Acidic (PA) Endonuclease Inhibitor."Molecules. 2021 Jan;26(23):7326 |
(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 - Reference Information
| drug for schizophrenia | Lurasidone is an atypical antipsychotic drug developed by Dainippon sumitmo pharmaceutical company, Japan, it belongs to the 3.1 class of chemical drug registration classification, which is suitable for the treatment of patients with schizophrenia. Efficacy was determined in four controlled studies of 6-week adult schizophrenic patients. Its exact mechanism for the treatment of schizophrenia, like other atypical antipsychotics, is not well understood and may be related to antagonism of dopamine D2 and serotonin 2A(5-HT2A) receptors. It is used in the treatment of schizophrenia, and studies have reported that lurasidone can improve cognitive function. on October 28, 2010, the US FDA approved lurasidone hydrochloride (lurasidone HCI) once daily tablet for the first-line treatment of patients with schizophrenia, and its trade name is Latuda. usage and dosage: The recommended initial dose is 40 mg · d, the effective dose range is 40-120 mg · d, and the maximum recommended dose is 80 mg · d. Should be taken with food. Adverse Reactions: The most common adverse reactions were somnolence, akathisia, Nausea, parkinsonism-like symptoms and Anxiety emotional agitation. Lurasidone is not physically dependent and causes less weight gain and does not cause changes in glucose, lipids (lipids), ECG and QT interval. |
| biological activity | Lurasidone (SM-13496) is an antagonist of dopamine D2 and 5-HT7 with IC50 values of 1.68 and 0.495 nM, respectively. Lurasidone (SM-13496) is also a partial agonist of the 5-HT1A receptor with an IC50 value of 6.75 nM. |
| Target | TargetValue 5-HT2A (Cell-free assay) 0.5 nM(Ki) 5-HT7 receptor (Cell-free assay) 0.5 nM(Ki) D2 receptor (Cell-free assay) 1 nM(Ki) 5-HT1A receptor (Cell-free assay) 6.4 nM(Ki) |
| Target | Value |
| 5-HT2A (Cell-free assay) | 0.5 nM(Ki) |
| 5-HT7 receptor (Cell-free assay) | 0.5 nM(Ki) |
| D2 receptor (Cell-free assay) | 1 nM(Ki) |
| 5-HT1A receptor (Cell-free assay) | 6.4 nM(Ki) |
| in vitro study | Lurasidone (SM-13496) is an angialist of dopamin D 2 and 5-HT 7 with IC 50 s of 1.68±0.09 and 0.495±0.090 nM, reviewatively. Lurasidone (SM-13496) is also a partial agnist of 5-HT 1A receptor with an IC 50 of 6.75±0.97 nM. In vitro receptor binding experts reveal that Lurasidone (SM-13496) demonstrates affinity for dopamine D 2 and 5-HT 2A receptors higher than other tested antipsychotics. Lurasidone (SM-13496) does not increase [ 35 S]GTPγS binding to the membrane preparations for dopamine D 2 receptors by itself, but it antagonizes dopamine-stimulated [ 35 S]GTPγS binding in a concentration-dependent manner with a K B value of 2.8±1.1 nM. |
| in vivo studies | Lurasidone (SM-13496) dose-dependently, but it shows a preferred effect on the frontal cortex compare. Lurasidone (SM-13496) (ED 50 values 2.3 to 5.0 mg/kg) shows (ED 50 values 1.1 to 5.1 mg/kg), higher potency than clozapine (ED 50 9.5 to 290 mg/kg), and slightly lower potency than haloperidol (ED 50 values 0.44 to 1.7 mg/kg). Lurasidone (SM-13496) (1 to 10 mg/kg) dose-dependently inhibits conditioned avoidance response (CAR) in rats and the ED 50 values are 6.3 mg/kg. Lurasidone (SM-13496) dose-dependently inhibits tryptamine (TRY)-induced forepaw clonic seizure and p-chloroamphetamine (p-CAMP)-induced hyperthermia with ED 50 values of 5.6 and 3.0 mg/kg, respectively. Lurasidone (SM-13496) (0.3 to 30 mg/kg) dose-dependently and significantly increases the number of shocks received by rats in the conflict test with MED of 10 mg/kg (p<0.01). |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:32:00
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