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 |
DescriptionSources: https://www.drugbank.ca/drugs/DB06144Curator'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
Sources: https://www.drugbank.ca/drugs/DB06144
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from 1996, but its marketing authorization was suspended by the European Medicines Agency in 1998 and the drug was withdrawn from the market.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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23218776 |
0.45 nM [Ki] | ||
Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12747773 |
0.6 nM [Ki] | ||
Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20857909 |
0.2 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Sertindole Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
[Sertindole, a novel alpha 1A-adrenoceptor selective antagonist]. | 1997 Jul |
|
Sertindole (Serdolect): preclinical and clinical findings of a new atypical antipsychotic. | 1997 Nov |
|
Quinpirole, 8-OH-DPAT and ketanserin modulate catalepsy induced by high doses of atypical antipsychotics. | 1999 Nov |
|
Inverse agonist activity of atypical antipsychotic drugs at human 5-hydroxytryptamine2C receptors. | 2000 Oct |
|
The antipsychotic drugs sertindole and pimozide block erg3, a human brain K(+) channel. | 2001 Aug 24 |
|
Novel antipsychotics and acute dystonic reactions. | 2001 Dec |
|
Agonist, antagonist, and inverse agonist properties of antipsychotics at human recombinant 5-HT(1A) receptors expressed in HeLa cells. | 2001 Dec 14 |
|
Effects of newer atypical antipsychotics on autonomic neurocardiac function: a comparison between amisulpride, olanzapine, sertindole, and clozapine. | 2001 Feb |
|
Development and evaluation of high throughput functional assay methods for HERG potassium channel. | 2001 Oct |
|
The potential cardiotoxicity of antipsychotic drugs as assessed by heart rate variability. | 2002 Dec |
|
Atypical antipsychotics: mechanism of action. | 2002 Feb |
|
Variations in prescribing atypical antipsychotic drugs in primary care: cross-sectional study. | 2002 Jun |
|
Low striatal and extra-striatal D2 receptor occupancy during treatment with the atypical antipsychotic sertindole. | 2002 Jun |
|
Effects of antipsychotic drugs on operant responding after acute and repeated administration. | 2002 Mar |
|
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 |
|
Gateways to clinical trials. | 2003 Jan-Feb |
|
Antipsychotic medication and seizures: a review. | 2003 Jul |
|
Dealing with uncertainty in drug safety: lessons for the future from 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 |
|
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 |
|
Enhancement of latent inhibition by two 5-HT2A receptor antagonists only when given at both pre-exposure and conditioning. | 2003 Sep |
|
A review of the efficacy, tolerability and safety of sertindole in clinical trials. | 2004 |
|
Determination of myocardium to plasma concentration ratios of five antipsychotic drugs: comparison with their ability to induce arrhythmia and sudden death in clinical practice. | 2004 Aug 15 |
|
[Current pharmacotherapy of schizophrenia]. | 2004 Jan 18 |
|
Possible induction of mania or hypomania by atypical antipsychotics: an updated review of reported cases. | 2004 Nov |
|
Atypical antipsychotics: from potassium channels to torsade de pointes and sudden death. | 2005 |
|
QTc interval prolongation and antipsychotic drug treatments: focus on sertindole. | 2005 Dec |
|
Inhibition of rat liver CYP2D in vitro and after 1-day and long-term exposure to neuroleptics in vivo-possible involvement of different mechanisms. | 2005 Jan |
|
Simplified ultraviolet liquid chromatographic method for determination of sertindole, dehydrosertindole and norsertindole, in human plasma. | 2005 Jan 5 |
|
Current therapy issues and unmet clinical needs in the treatment of schizophrenia: a review of the new generation antipsychotics. | 2005 Jul |
|
Sertindole for schizophrenia. | 2005 Jul 20 |
|
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 |
|
Exploring blocker binding to a homology model of the open hERG K+ channel using docking and molecular dynamics methods. | 2005 May 23 |
|
Atypical antipsychotics produce within-session decrements on self-stimulation of the rat medial prefrontal cortex. | 2005 Sep 1 |
|
Sertindole : a review of its use in schizophrenia. | 2006 |
|
Myocardium distribution of sertindole and its metabolite dehydrosertindole in guinea-pigs. | 2006 May |
|
Beat-to-Beat variability of repolarization determines proarrhythmic outcome in dogs susceptible to drug-induced torsades de pointes. | 2006 Sep 19 |
|
Metabolic drug interactions with newer antipsychotics: a comparative review. | 2007 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22850268
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22791154
SH-SY5Y cells stably expressing GFP-LC3 (SY5Y/GFP-LC3) were treated with Sertindole (10 μM) for 24 h. The cells were then fixed and observed by fluorescence microscopy or electron microscopy.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 16:20:02 GMT 2023
by
admin
on
Sat Dec 16 16:20:02 GMT 2023
|
Record UNII |
GVV4Z879SP
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-VATC |
QN05AE03
Created by
admin on Sat Dec 16 16:20:02 GMT 2023 , Edited by admin on Sat Dec 16 16:20:02 GMT 2023
|
||
|
NCI_THESAURUS |
C66883
Created by
admin on Sat Dec 16 16:20:02 GMT 2023 , Edited by admin on Sat Dec 16 16:20:02 GMT 2023
|
||
|
NCI_THESAURUS |
C66885
Created by
admin on Sat Dec 16 16:20:02 GMT 2023 , Edited by admin on Sat Dec 16 16:20:02 GMT 2023
|
||
|
WHO-ATC |
N05AE03
Created by
admin on Sat Dec 16 16:20:02 GMT 2023 , Edited by admin on Sat Dec 16 16:20:02 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
C066304
Created by
admin on Sat Dec 16 16:20:02 GMT 2023 , Edited by admin on Sat Dec 16 16:20:02 GMT 2023
|
PRIMARY | |||
|
DTXSID6048967
Created by
admin on Sat Dec 16 16:20:02 GMT 2023 , Edited by admin on Sat Dec 16 16:20:02 GMT 2023
|
PRIMARY | |||
|
98
Created by
admin on Sat Dec 16 16:20:02 GMT 2023 , Edited by admin on Sat Dec 16 16:20:02 GMT 2023
|
PRIMARY | |||
|
6455
Created by
admin on Sat Dec 16 16:20:02 GMT 2023 , Edited by admin on Sat Dec 16 16:20:02 GMT 2023
|
PRIMARY | |||
|
SUB10498MIG
Created by
admin on Sat Dec 16 16:20:02 GMT 2023 , Edited by admin on Sat Dec 16 16:20:02 GMT 2023
|
PRIMARY | |||
|
9122
Created by
admin on Sat Dec 16 16:20:02 GMT 2023 , Edited by admin on Sat Dec 16 16:20:02 GMT 2023
|
PRIMARY | |||
|
41996
Created by
admin on Sat Dec 16 16:20:02 GMT 2023 , Edited by admin on Sat Dec 16 16:20:02 GMT 2023
|
PRIMARY | RxNorm | ||
|
2435
Created by
admin on Sat Dec 16 16:20:02 GMT 2023 , Edited by admin on Sat Dec 16 16:20:02 GMT 2023
|
PRIMARY | |||
|
100000084340
Created by
admin on Sat Dec 16 16:20:02 GMT 2023 , Edited by admin on Sat Dec 16 16:20:02 GMT 2023
|
PRIMARY | |||
|
DB06144
Created by
admin on Sat Dec 16 16:20:02 GMT 2023 , Edited by admin on Sat Dec 16 16:20:02 GMT 2023
|
PRIMARY | |||
|
GVV4Z879SP
Created by
admin on Sat Dec 16 16:20:02 GMT 2023 , Edited by admin on Sat Dec 16 16:20:02 GMT 2023
|
PRIMARY | |||
|
106516-24-9
Created by
admin on Sat Dec 16 16:20:02 GMT 2023 , Edited by admin on Sat Dec 16 16:20:02 GMT 2023
|
PRIMARY | |||
|
C73295
Created by
admin on Sat Dec 16 16:20:02 GMT 2023 , Edited by admin on Sat Dec 16 16:20:02 GMT 2023
|
PRIMARY | |||
|
EE-14
Created by
admin on Sat Dec 16 16:20:02 GMT 2023 , Edited by admin on Sat Dec 16 16:20:02 GMT 2023
|
PRIMARY | |||
|
60149
Created by
admin on Sat Dec 16 16:20:02 GMT 2023 , Edited by admin on Sat Dec 16 16:20:02 GMT 2023
|
PRIMARY | |||
|
m9875
Created by
admin on Sat Dec 16 16:20:02 GMT 2023 , Edited by admin on Sat Dec 16 16:20:02 GMT 2023
|
PRIMARY | Merck Index | ||
|
SERTINDOLE
Created by
admin on Sat Dec 16 16:20:02 GMT 2023 , Edited by admin on Sat Dec 16 16:20:02 GMT 2023
|
PRIMARY | |||
|
CHEMBL12713
Created by
admin on Sat Dec 16 16:20:02 GMT 2023 , Edited by admin on Sat Dec 16 16:20:02 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
TARGET -> INHIBITOR | |||
|
TARGET -> INHIBITOR | |||
|
TARGET -> INHIBITOR |
|
||
|
TARGET -> INHIBITOR |
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |