106516-24-9 Usage
Description
Sertindole, also known as Serlect, is an atypical antipsychotic medication that is synthetically derived in three steps from 5-chloro-1-(4-fluorophenyl)-1H-indole. It selectively targets the limbic areas of the brain and exhibits high affinity for the serotonin 5-HT2 receptor, acting as an antagonist. Sertindole has weak affinity for the α1-adrenergic receptor and no affinity for dopamine D2 receptors. It is characterized by its non-sedating properties, long-lasting effects (several days after a single dose), and an atypical mode of action. It is used in the treatment of schizophrenia and related psychoses, offering efficacy similar to haloperidol without the extrapyramidal symptoms.
Uses
Used in Pharmaceutical Industry:
Sertindole is used as an antipsychotic agent for the treatment of schizophrenia and schizoaffective psychoses. It modulates various neurotransmitter systems, including dopamine D2, serotonin (5-HT) receptor subtypes 5-HT1D, 5-HT2A, and 5-HT2C, histamine H1, and α1and α2-adrenergic receptors. This multi-receptor action contributes to its effectiveness in managing the symptoms of schizophrenia.
Used in Research and Development:
Sertindole is used as a research compound for studying the effects of atypical antipsychotic medications on neurotransmitter systems and their role in the treatment of psychiatric disorders. It has been shown to increase extracellular dopamine, acetylcholine (ACh), and glutamate levels in the medial prefrontal cortex in conscious rats, as well as reverse ketamine-induced impairments in the extradimensional shift stage of the attentional set-shifting task (ASST) in rats.
Used in Clinical Trials:
Sertindole is used in clinical trials to evaluate its efficacy and safety in treating various psychiatric conditions, particularly schizophrenia. It has been compared to other antipsychotic medications, such as haloperidol and clozapine, to determine its potential advantages and disadvantages in terms of side effects and treatment outcomes.
Chemical Properties:
Sertindole is an off-white to pale yellow solid with the chemical structure of a phenylindole that is 1H-indole, substituted on the nitrogen by a p-chlorophenyl group, at position 5 by chlorine, and at position 3 by a piperidin-4-yl group, which is itself substituted on the nitrogen by a 2-(2-oxoimidazolidin-1-yl)ethyl group.
Originator
Lundbeck (Denmark)
Side effects
Sertindole is an indole-containing compound that behaves as a high-affinity serotonin 5-HT2 receptor antagonist,
with weak affinity for adrenergic α1 receptors and almost no affinity for dopaminergic D2 receptors. It is about as
effective as haloperidol in the treatment of acute and chronic schizophrenia, but with much lower incidence of
extrapyramidal side effects. Sertindole is relatively nonsedating, and its effects are long lasting (several days).
Check Digit Verification of cas no
The CAS Registry Mumber 106516-24-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,6,5,1 and 6 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 106516-24:
(8*1)+(7*0)+(6*6)+(5*5)+(4*1)+(3*6)+(2*2)+(1*4)=99
99 % 10 = 9
So 106516-24-9 is a valid CAS Registry Number.
InChI:InChI=1/C24H26ClFN4O/c25-18-1-6-23-21(15-18)22(16-30(23)20-4-2-19(26)3-5-20)17-7-10-28(11-8-17)13-14-29-12-9-27-24(29)31/h1-6,15-17H,7-14H2,(H,27,31)
106516-24-9Relevant articles and documents
Combination treatment for anxiety, depression, obsessive compulsive disorder and psychosis
-
, (2008/06/13)
The present invention relates to a method of treating depression, obsessive compulsive disorder and psychosis in a mammal, including a human, by administering to the mammal an atypical antipsychotic in combination with an antidepressant agent with improvement in efficiency. It also relates to pharmaceutical compositions containing a pharmaceutically acceptable carrier, an atypical antipsychotic, and an SRI.
Noncataleptogenic, centrally acting dopamine D-2 and serotonin 5-HT2 antagonists within a series of 3-substituted 1-(4-fluorophenyl)-1H-indoles
Perregaard,Arnt,Bogeso,Hyttel,Sanchez
, p. 1092 - 1101 (2007/10/02)
A series of 1-(4-fluorophenyl)-1H-indoles substituted at the 3-position with 1-piperazinyl, 1,2,3,6-tetrahydro-4-pyridinyl, and 4-piperidinyl was synthesized. Within all three subseries potent dopamine D-2 and serotonin 5- HT2 receptor affinity was found in ligand binding studies. Quipazine-induced head twitches in rats were inhibited by most derivatives as a measure of central 5-HT2 receptor antagonism. Piperazinyl and tetrahydropyridyl indoles were cataleptogenic, while piperidyl substituted indoles surprisingly were found to be noncataleptogenic or only weakly cataleptogenic. Noncataleptogenic piperidyl derivatives also failed to block dopaminergic- mediated stereotypies, that is methyl phenidate-induced gnawing behavior in mice. These profiles resemble that of the atypical neuroleptic clozapine. 1- Ethyl-2-imidazolidinone was found to be the optimal substituent of the basic nitrogen atom in order to avoid catalepsy. The atypical neuroleptic 1-[2-[4- [5-chloro-1-(4-fluorophenyl)-1H-indol-3-yl]-1-piperidinyl]ethyl]-2- imidazolidinone (sertindole, compound 14c) was selected for further development as a result of these structure/activity studies.
