Sertindole

Base Information

• Chemical Name: Sertindole
• CAS No.: 106516-24-9
• Molecular Formula: C24H26ClFN4O
• Molecular Weight: 440.948
• European Community (EC) Number: 634-595-9
• UNII: GVV4Z879SP
• DSSTox Substance ID: DTXSID6048967
• Nikkaji Number: J380.356B
• Wikipedia: Sertindole
• Wikidata: Q418050
• NCI Thesaurus Code: C73295
• Pharos Ligand ID: 35RZCSF6U2YR
• Metabolomics Workbench ID: 43657
• ChEMBL ID: CHEMBL12713
• Mol file: 106516-24-9.mol

Synonyms:1-(2-(4-(5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl)-1-piperidinyl)ethyl)-2-imidazolidinone;Lu 23-174;Lu-23-174;Serdolect;Serlect;sertindole;sertindole hydrochloride

Chemical Property of Sertindole

Chemical Property:

• Appearance/Colour: off-white to Pale yellow solid
• Vapor Pressure: 5.44E-14mmHg at 25°C
• Melting Point: 95-100 °C
• Refractive Index: 1.67
• Boiling Point: 592.065 °C at 760 mmHg
• PKA: 14.53±0.20(Predicted)
• Flash Point: 311.87 °C
• PSA: 40.51000
• Density: 1.367 g/cm³
• LogP: 4.83220
• Storage Temp.: 2-8°C
• Solubility.: DMSO: >10mg/mL
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 440.1779173
• Heavy Atom Count: 31
• Complexity: 623

Purity/Quality:

98%,99%, ^*data from raw suppliers

Sertindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CN(CCC1C2=CN(C3=C2C=C(C=C3)Cl)C4=CC=C(C=C4)F)CCN5CCNC5=O
• Recent ClinicalTrials: An Observational Drug Utilization Study of Asenapine in the United Kingdom (P08308)
• Recent EU Clinical Trials: HAMLETT. Handling Antipsychotic Medication: Long-term Evaluation of Targeted Treatment. A pragmatic single blind RCT of continuation versus discontinuation/ dose reduction of antipsychotic medication in patients remitted after a first episode of psychosis
• Description: Serdolect was launched in the UK for acute and chronic schizophrenia and schizoaffective psychoses. It is synthetically available in three steps from 5chloro-l- (4-fluorophenyl)-l H-indole. Sertindole is selective for the limbic areas of the brain and has a high affinity for the serotinin 5-HT2 receptor where it behaves as an antagonist. It has weak affinity for the α1-adrenergic receptor and no affinity for dopamine D2 receptors. It is as effective as haloperidol but without the extrapyramidal symptoms. This may be a consequence of the fact that it expresses the c-fos protein in a manner different for haloperidol but similar to clozapine. It is non-sedating, long lasting (several days after a single dose) and has an atypical mode of action. Sertindole is an atypical antipsychotic that binds to dopamine D2 receptors and the serotonin (5-HT) receptor subtypes 5-HT1D, 5-HT2A, and 5-HT2C (Kds = 2.7, 20, 0.14, and 6 nM, respectively). It also binds to histamine H1 and α1- and α2-adrenergic receptors (Kds = 320, 3.9, and 190 nM, respectively). In vivo, sertindole (10 mg/kg) increases extracellular dopamine, acetylcholine (ACh), and glutamate levels in the medial prefrontal cortex in conscious rats. Sertindole (2.5 mg/kg) reverses ketamine-induced impairments in the extradimensional shift stage of the attentional set-shifting task (ASST) in rats. It reverses phencyclidine (PCP)-induced selective reversal learning deficits in rats and subchronic PCP-induced deficits in the novel object recognition task in mice. Sertindole (0.02-0.32 mg/kg) also prevents accuracy deficits and anticipatory over-responding in the 5-choice serial reaction time task (5CSRTT) induced by the NMDA receptor antagonist (R)-CPP in rats. Formulations containing sertindole have been used in the treatment of schizophrenia.
• Uses: Antipsychotic used in the treatment of schizophrenia. antipsychotic;Dopamine D2/Serotonin 5-HT2 receptor antagonist

Technology Process of Sertindole

There total 9 articles about Sertindole 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: 87.0%

1-(2-chloroethyl)imidazolidin-2-one (2387-20-4) + 5-chloro-1-(4-fluorophenyl)-3-(4-piperidinyl)-1H-indole (138900-27-3) → Sertindole (106516-24-9)

Guidance literature:

With potassium carbonate; potassium iodide; In various solvent(s); for 16h; Heating;

DOI:10.1021/jm00084a014

Reference yield: 83.2%

1-[2-[4-[5-chloro-1-(4-fluorophenyl)-1-H-indol-3-yl]-1-piperidinyl]ethyl]-2-imidazolidinone, tartrate → Sertindole (106516-24-9)

Guidance literature:

With sodium hydroxide; In dichloromethane; water; for 1h; pH=9;

Reference yield:

4-piperidone hydrochloride (41979-39-9) → Sertindole (106516-24-9)

Guidance literature:

Multi-step reaction with 3 steps

1: TFA, AcOH / 0.5 h / Heating

2: H₂, AcOH / PtO₂ / ethanol / 16 h / 1900 - 2280 Torr

3: 87 percent / K₂CO₃, KI / various solvent(s) / 16 h / Heating

With hydrogen; potassium carbonate; acetic acid; trifluoroacetic acid; potassium iodide; platinum(IV) oxide; In ethanol;

DOI:10.1021/jm00084a014

upstream raw materials:

1-(2-chloroethyl)imidazolidin-2-one

5-chloro-1-(4-fluorophenyl)-3-(4-piperidinyl)-1H-indole

4-piperidone hydrochloride

1-(4-fluorophenyl)-5-chloroindole

Downstream raw materials:

5-Chloro-1-(4-fluorophenyl)-3-[1-[2-(3-hydroxymethyl-2-imidazolidinon-1-yl)ethyl]-4-piperidyl]-1H-indole

1-[2-[4-[5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl]-1-oxo-1-piperidinyl]ethyl]-imidazolidin-2-one

5-chloro-1-(4-fluorophenyl)-3-{1,1-bis[2-(2-imidazolidon-1-yl)ethyl]-piperidin-1-ium-4-yl}-1H-indole

Refernces

• 1、 -. "Combination treatment for anxiety, depression, obsessive compulsive disorder and psychosis". . . Retrieved 2008/06/13.