Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C24H26ClFN4O |
| Molecular Weight | 440.941 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
FC1=CC=C(C=C1)N2C=C(C3CCN(CCN4CCNC4=O)CC3)C5=C2C=CC(Cl)=C5
InChI
InChIKey=GZKLJWGUPQBVJQ-UHFFFAOYSA-N
InChI=1S/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)
| Molecular Formula | C24H26ClFN4O |
| Molecular Weight | 440.941 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugs.com/international/sertindole.html | https://www.ncbi.nlm.nih.gov/pubmed/23218776 | https://www.ncbi.nlm.nih.gov/pubmed/12747773 | https://www.ncbi.nlm.nih.gov/pubmed/20857909 | https://www.ncbi.nlm.nih.gov/pubmed/22791154 | https://www.ncbi.nlm.nih.gov/pubmed/22850268
Curator's Comment: description was created based on several sources, including
https://www.drugs.com/international/sertindole.html | https://www.ncbi.nlm.nih.gov/pubmed/23218776 | https://www.ncbi.nlm.nih.gov/pubmed/12747773 | https://www.ncbi.nlm.nih.gov/pubmed/20857909 | https://www.ncbi.nlm.nih.gov/pubmed/22791154 | https://www.ncbi.nlm.nih.gov/pubmed/22850268
Sertindole (brand names: "Serdolect" and "Serlect") is an antipsychotic medication. Sertindole was developed by the Danish pharmaceutical company Lundbeck and marketed under license by Abbott Labs. Like other atypical antipsychotics, it has activity at dopamine and serotonin receptors in the brain. It is used in the treatment of schizophrenia. Sertindole is not approved for use in the United States and was discontinued in Australia in January 2014. In Europe, sertindole was approved and marketed in 19 countries from 1996, but its marketing authorization was suspended by the European Medicines Agency in 1998 and the drug was withdrawn from the market. In 2002, based on new data, the EMA's CHMP suggested that Sertindole could be reintroduced for restricted use in clinical trials, with strong safeguards including extensive contraindications and warnings for patients at risk of cardiac dysrhythmias, a recommended reduction in maximum dose from 24 mg to 20 mg in all but exceptional cases, and extensive ECG monitoring requirement before and during treatment.
CNS Activity
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Novel antipsychotics and acute dystonic reactions. | 2001 Dec |
|
| Cost effectiveness of the newer atypical antipsychotics: a review of the pharmacoeconomic research evidence. | 2001 Jan |
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| Effects of acute versus chronic treatment with typical or atypical antipsychotics on d-amphetamine-induced sensorimotor gating deficits in rats. | 2001 Jul |
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| Comparative study of mortality rates and cardiac dysrhythmias in post-marketing surveillance studies of sertindole and two other atypical antipsychotic drugs, risperidone and olanzapine. | 2001 Jun |
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| [Schizoaffective disorder: clinical symptoms and present-day approach to treatment]. | 2002 |
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| Investigation of the potential of clozapine to cause torsade de pointes. | 2002 |
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| Effects of the 5-HT(6) receptor antagonist, SB-271046, in animal models for schizophrenia. | 2002 Apr |
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| The potential cardiotoxicity of antipsychotic drugs as assessed by heart rate variability. | 2002 Dec |
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| Low striatal and extra-striatal D2 receptor occupancy during treatment with the atypical antipsychotic sertindole. | 2002 Jun |
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| Psychotropic drugs and the ECG: focus on the QTc interval. | 2002 May |
|
| Obesity and related metabolic abnormalities during antipsychotic drug administration: mechanisms, management and research perspectives. | 2002 Nov |
|
| [Relationship between clozapine plasma levels and withdrawal symptoms]. | 2002 Nov-Dec |
|
| QTc prolongation due to propranolol overdose. | 2003 |
|
| Synthesis and structure-affinity relationship investigations of 5-heteroaryl-substituted analogues of the antipsychotic sertindole. A new class of highly selective alpha(1) adrenoceptor antagonists. | 2003 Jan 16 |
|
| Gateways to clinical trials. | 2003 Jan-Feb |
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| Antipsychotic medication and seizures: a review. | 2003 Jul |
|
| Biases affecting the proportional reporting ratio (PPR) in spontaneous reports pharmacovigilance databases: the example of sertindole. | 2003 Jun |
|
| Alpha(1) adrenoceptor subtype selectivity. 3D-QSAR models for a new class of alpha(1) adrenoceptor antagonists derived from the novel antipsychotic sertindole. | 2003 Jun |
|
| Detection of proarrhythmia in the female rabbit heart: blinded validation. | 2003 Mar |
|
| H1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs. | 2003 Mar |
|
| Synthesis and structure-affinity relationship investigations of 5-aminomethyl and 5-carbamoyl analogues of the antipsychotic sertindole. A new class of selective alpha1 adrenoceptor antagonists. | 2003 Mar 20 |
|
| New generation antipsychotics versus low-potency conventional antipsychotics: a systematic review and meta-analysis. | 2003 May 10 |
|
| Characterization of HERG potassium channel inhibition using CoMSiA 3D QSAR and homology modeling approaches. | 2003 May 19 |
|
| Effects of imatinib mesylate (STI571, Glivec) on the pharmacokinetics of simvastatin, a cytochrome p450 3A4 substrate, in patients with chronic myeloid leukaemia. | 2003 Nov 17 |
|
| Influence of classic and atypical neuroleptics on caffeine oxidation in rat liver microsomes. | 2003 Nov-Dec |
|
| Enhancement of latent inhibition by two 5-HT2A receptor antagonists only when given at both pre-exposure and conditioning. | 2003 Sep |
|
| Cardiovascular side effects of new antidepressants and antipsychotics: new drugs, old concerns? | 2004 |
|
| Atypical antipsychotics: pharmacokinetics, therapeutic drug monitoring and pharmacological interactions. | 2004 Feb |
|
| [Current pharmacotherapy of schizophrenia]. | 2004 Jan 18 |
|
| Evidence-based pharmacotherapy of schizophrenia. | 2004 Jun |
|
| Possible induction of mania or hypomania by atypical antipsychotics: an updated review of reported cases. | 2004 Nov |
|
| Current therapy issues and unmet clinical needs in the treatment of schizophrenia: a review of the new generation antipsychotics. | 2005 Jul |
|
| Choice of cardiac tissue plays an important role in the evaluation of drug-induced prolongation of the QT interval in vitro in rabbit. | 2005 Jul-Aug |
|
| Antipsychotics lack alpha 1A/B adrenoceptor subtype selectivity in the rat. | 2005 Mar |
|
| Unbiased descriptor and parameter selection confirms the potential of proteochemometric modelling. | 2005 Mar 10 |
|
| Exploring blocker binding to a homology model of the open hERG K+ channel using docking and molecular dynamics methods. | 2005 May 23 |
|
| Generalization to atypical antipsychotic drugs depends on training dose in rats trained to discriminate 1.25 mg/kg clozapine versus 5.0 mg/kg clozapine versus vehicle in a three-choice drug discrimination task. | 2005 Nov |
|
| A dopaminergic deficit hypothesis of schizophrenia: the path to discovery. | 2006 |
|
| The German Research Network on Schizophrenia--impact on the management of schizophrenia. | 2006 |
|
| Sertindole : a review of its use in schizophrenia. | 2006 |
|
| Pharmacological treatment of primary negative symptoms in schizophrenia: a systematic review. | 2006 Dec |
|
| Comparing sertindole to other new generation antipsychotics on preferential dopamine output in limbic versus striatal projection regions: mechanism of action. | 2006 Dec 1 |
|
| A double-blind, controlled study of sertindole versus risperidone in the treatment of moderate-to-severe schizophrenia. | 2006 Jan |
|
| Effects of antipsychotic drugs on I(to), I (Na), I (sus), I (K1), and hERG: QT prolongation, structure activity relationship, and network analysis. | 2006 Jun |
|
| Comparative evaluation of HERG currents and QT intervals following challenge with suspected torsadogenic and nontorsadogenic drugs. | 2006 Mar |
|
| New insights about HERG blockade obtained from protein modeling, potential energy mapping, and docking studies. | 2006 May 1 |
|
| Pharmacological treatment of ambulatory schizophrenic patients in Belgium. | 2006 May 30 |
|
| Sertindole: efficacy and safety in schizophrenia. | 2006 Sep |
|
| Chlorpromazine, clozapine and olanzapine inhibit anionic amino acid transport in cultured human fibroblasts. | 2006 Sep |
|
| Metabolic drug interactions with newer antipsychotics: a comparative review. | 2007 Jan |
Patents
Sample Use Guides
The sertindole treatment period consisted of a 16-day up-titration period (initiated at 4 mg/day and the dose was increased by 4 mg every fourth day to reach the effective target dose of 16 mg/day at the 16th day), followed by a flexible-dose maintenance period (12, 16, or 20 mg/day according to the investigator’s judgment).
Route of Administration:
Oral
| Substance Class |
Chemical
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| Record UNII |
GVV4Z879SP
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Validated (UNII)
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QN05AE03
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C66883
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C66885
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N05AE03
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SERTINDOLE
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CHEMBL12713
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