Lurasidone hydrochloride

Base Information

• Chemical Name: Lurasidone hydrochloride
• CAS No.: 367514-88-3
• Deprecated CAS: 441351-20-8
• Molecular Formula: C28H36N4O2S.HCl
• Molecular Weight: 529.146
• European Community (EC) Number: 682-423-6
• UNII: O0P4I5851I
• DSSTox Substance ID: DTXSID401027714
• Wikidata: Q27882070
• NCI Thesaurus Code: C77576
• RXCUI: 1040027
• ChEMBL ID: CHEMBL1615372
• Mol file: 367514-88-3.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 hydrochloride

Chemical Property:

• Melting Point: 198-205°C
• Flash Point: 9℃
• PSA: 84.99000
• LogP: 4.19660
• Storage Temp.: Refrigerator
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 528.2325753
• Heavy Atom Count: 36
• Complexity: 804

Purity/Quality:

99%, ^*data from raw suppliers

LurasidoneHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(C(C1)CN2CCN(CC2)C3=NSC4=CC=CC=C43)CN5C(=O)C6C7CCC(C7)C6C5=O.Cl
• 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.Cl
• Recent ClinicalTrials: The Safety and Effectiveness of Latuda? Post-marketing Surveillance in the Treatment of Chinese Schizophrenia Patients
• 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
• Uses: Lurasidone is an atypical antipsychotic, inhibits Dopamine D2, 5-HT2A, 5-HT7, 5-HT1A and noradrenaline α2C with IC50 of 1.68 nM, 2.03 nM, 0.495 nM, 6.75 nM and 10.8 nM, respectively An antipsychotic used for treatment of schizophrenia.

Technology Process of Lurasidone hydrochloride

There total 21 articles about Lurasidone hydrochloride 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: 98.3%

(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) → (3aR,4S,7R,7aS)-2-[((1R,2R)-2-{[4-(l1,2-benzisothiazol-3-yl)piperazin-1-yl]methyl}cyclohexyl)methyl]hexahydro-1H-4,7-methanisoindol-1,3-dione hydrochloride (367514-88-3,139563-25-0)

Guidance literature:

(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; With potassium carbonate; In toluene; at 105 ℃; for 15h; Industrial scale;

With hydrogenchloride; In isopropyl alcohol; Industrial scale;

Reference yield: 96.1%

lurasidone (194861-74-0,367514-87-2,1318074-25-7) → (3aR,4S,7R,7aS)-2-[((1R,2R)-2-{[4-(l1,2-benzisothiazol-3-yl)piperazin-1-yl]methyl}cyclohexyl)methyl]hexahydro-1H-4,7-methanisoindol-1,3-dione hydrochloride (367514-88-3,139563-25-0)

Guidance literature:

With hydrogenchloride; In water; at 50 ℃; for 2h; Temperature;

Reference yield: 93.0%

hydrogenchloride (7647-01-0,15364-23-5) + lurasidone (194861-74-0,367514-87-2,1318074-25-7) → (3aR,4S,7R,7aS)-2-[((1R,2R)-2-{[4-(l1,2-benzisothiazol-3-yl)piperazin-1-yl]methyl}cyclohexyl)methyl]hexahydro-1H-4,7-methanisoindol-1,3-dione hydrochloride (367514-88-3,139563-25-0)

Guidance literature:

In water; isopropyl alcohol; at 65 - 75 ℃;

upstream raw materials:

lurasidone

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

(3aR,7aR)-2,2-bis(2-hydroxyethyl)octahydro-1H-isoindolium mesylate

3-aminobenzisothiazole

Downstream raw materials:

(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

Refernces

• 1、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF LURASIDONE BASE AND ITS SALT". Paragraph 15. . Retrieved 2017/09/27.
• 2、 -. "Lurasidone key intermediate preparation method". . . Retrieved 2017/09/01.