Brexpiprazole

Base Information

• Chemical Name: Brexpiprazole
• CAS No.: 913611-97-9
• Molecular Formula: C₂₅H₂₇N₃O₂S
• Molecular Weight: 433.574
• European Community (EC) Number: 811-628-7,945-906-5
• UNII: 2J3YBM1K8C
• DSSTox Substance ID: DTXSID40238527
• Nikkaji Number: J3.002.326I
• Wikipedia: Brexpiprazole
• Wikidata: Q2924764
• NCI Thesaurus Code: C166575
• RXCUI: 1658314
• Pharos Ligand ID: TADN4TTKMGCN
• Metabolomics Workbench ID: 152169
• ChEMBL ID: CHEMBL2105760
• Mol file: 913611-97-9.mol

Synonyms:7-(4-(4-(1-benzothiophen-4-yl)piperazin-1-yl)butoxy)quinolin-2(1H)-one;brexpiprazole;Rexulti

Chemical Property of Brexpiprazole

Chemical Property:

• Melting Point: 179 - 181oC
• Boiling Point: 675.2±55.0 °C(Predicted)
• PKA: 11.22±0.70(Predicted)
• Density: 1.245±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility.: Dichloromethane (Slightly), Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 433.18239829
• Heavy Atom Count: 31
• Complexity: 636

Purity/Quality:

99% ^*data from raw suppliers

Brexpiprazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antipsychotic Agents
• Canonical SMILES: C1CN(CCN1CCCCOC2=CC3=C(C=C2)C=CC(=O)N3)C4=C5C=CSC5=CC=C4
• Recent ClinicalTrials: Brexpiprazole as Combination Therapy With Sertraline in Treatment of Adults With PTSD
• Recent EU Clinical Trials: A Multicenter, Randomized, Flexible-dose, Double-blind Trial of Brexpiprazole Versus Placebo for the Treatment of Adults With Borderline Personality Disorder
• Recent NIPH Clinical Trials: A Clinical Pharmacology Trial of Brexpiprazole Long Acting Injectable (LAI) Administered as a Single Dose in Patients With Schizophrenia
• Description: Brexpiprazole is a kind of atypical antipsychotic. It is a dopamine D2 receptor partial agonist. As a novel serotonin-dopamine activity modulator, it can be used for the treatment of schizophrenia, and for the adjunctive treatment for depression. It can also provide efficacy and tolerability over established adjunctive treatments formajor depressive disorder(MDD).Recent study has also suggested it can ameliorate PCP-induced cognitive deficits in mice via 5-HT1A receptors. Brexpiprazole is a novel antipsychotic drug which serves as a serotonin ? dopamine activity modulator and has demonstrated efficacy as an adjunctive treatment in patients with major depressive disorder (MDD). The drug exhibits a unique pharmacological profile, acting as a partial agonist of serotonin 5-HT1A and dopamine D2 receptors and as a full antagonist of 5-HT2A and noradrenaline α1B/2C receptors, with similar subnanomolar binding affinity. The drug, which was developed by Otsuka and Lundbeck, was approved in 2015 by the FDA for the treatment of schizophrenia and as an adjunctive treatment for depression. Brexpiprazole is widely considered to be a successor to Otsuka’s antipsychotic drug aripiprazole (trade name Abilify) whose patent expired in August 2014.
• Uses: Brexpiprazole is a drug candidate useful in treatment and prevention of mental disorders including CNS disorders.

Technology Process of Brexpiprazole

There total 82 articles about Brexpiprazole 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: 96.1%

brexpiprazole hydrochloride → Brexpiprazole (913611-97-9)

Guidance literature:

With sodium hydroxide; In ethanol; water; at 20 - 80 ℃; for 2h;

Reference yield: 96.0%

7-[4-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)butoxy]-1H-quinolin-2-one hydrochloride → Brexpiprazole (913611-97-9)

Guidance literature:

With potassium carbonate; In dichloromethane; water; for 2h;

Reference yield: 95.5%

7-(4-chlorobutoxy)quinoline-2(1H)-one (913613-82-8) + 1-(benzo[b]thiophen-4-yl)piperazine hydrochloride (1677681-05-8,913614-18-3) → Brexpiprazole (913611-97-9)

Guidance literature:

1-(benzo[b]thiophen-4-yl)piperazine hydrochloride; With sodium carbonate; In methanol; water; at 50 ℃; for 0.5h;

7-(4-chlorobutoxy)quinoline-2(1H)-one; In methanol; water; at 70 ℃; for 16h;

upstream raw materials:

7-(4-chlorobutoxy)quinoline-2(1H)-one

1-(benzo[b]thiophen-4-yl)piperazine hydrochloride

7-hydroxy-1H-quinolin-2-one

4-chlorobenzothiophene

Downstream raw materials:

7-(4-(4-(benzo[b]thiophen-4-yl)piperazin-1-yl)butoxy)-1-(4-((2-oxo-1,2-dihydroquinolin-7-yl)oxy)butyl)quinoline-2(1H)-one

7-[4-(4-benzo[b]thiophene-4-ylpiperazin-1-yl)butoxy]-2-benzyloxymethoxyquinoline

7-{4-[4-(1-benzothiophen-4-yl)piperazin-1-yl]butoxy}quinolin-2-yl cyclohexanecarboxylate

7-(4-(4-(benzo[b]thiophen-4-yl)piperazin-1-yl)butoxy)-1-(cyclohexanecarbonyl)-3,4-dihydroquinolin-2(1H)-one