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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
Structure of SERTINDOLE

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)

HIDE SMILES / InChI

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

Description
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from 1996, but its marketing authorization was suspended by the European Medicines Agency in 1998 and the drug was withdrawn from the market.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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.45 nM [Ki]
0.6 nM [Ki]
0.2 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Sertindole

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Sertindole (Serdolect): preclinical and clinical findings of a new atypical antipsychotic.
1997 Nov
QTc prolongation due to propranolol overdose.
2003
Antipsychotic medication and seizures: a review.
2003 Jul
The relevance of prolonged QTc measurement to pediatric psychopharmacology.
2003 Jun
Dealing with uncertainty in drug safety: lessons for the future from sertindole.
2003 Jun
Biases affecting the proportional reporting ratio (PPR) in spontaneous reports pharmacovigilance databases: the example of sertindole.
2003 Jun
New generation antipsychotics versus low-potency conventional antipsychotics: a systematic review and meta-analysis.
2003 May 10
Electrophysiological safety of sertindole in dogs with normal and remodeled hearts.
2003 Nov
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
Impact of atypical antipsychotics on quality of life in patients with schizophrenia.
2004
Case histories illustrating the utility of sertindole in clinical practice.
2004
A review of the efficacy, tolerability and safety of sertindole in clinical trials.
2004
Cardiovascular side effects of new antidepressants and antipsychotics: new drugs, old concerns?
2004
[Psychotropics and weight gain].
2004 Aug 25
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
Intrinsic efficacy of antipsychotics at human D2, D3, and D4 dopamine receptors: identification of the clozapine metabolite N-desmethylclozapine as a D2/D3 partial agonist.
2005 Dec
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
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
Treatment with the new antipsychotic sertindole for late-occurring undesirable movement effects.
2005 Nov
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
Interactions between neuroleptics and CYP2C6 in rat liver--in vitro and ex vivo study.
2005 Nov-Dec
Direct effects of neuroleptics on the activity of CYP2A in the liver of rats.
2005 Nov-Dec
Comparison of methanol and acetonitrile as solvents for the separation of sertindole and its major metabolites by capillary zone electrophoresis.
2005 Sep
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
Classical as well as novel antipsychotic drugs increase self-stimulation threshold in the rat--similar mechanism of action?
2006 Aug 21
Sertindole, in contrast to clozapine and olanzapine, does not disrupt water maze performance after acute or chronic treatment.
2006 Aug 7
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
The effectiveness of atypical antipsychotics for the treatment of aggression and psychosis in Alzheimer's disease.
2006 Jan 25
Haloperidol dose when used as active comparator in randomized controlled trials with atypical antipsychotics in schizophrenia: comparison with officially recommended doses.
2006 Jun
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
Myocardium distribution of sertindole and its metabolite dehydrosertindole in guinea-pigs.
2006 May
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
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

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
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 Sat Dec 16 16:20:02 GMT 2023
Edited
by admin
on Sat Dec 16 16:20:02 GMT 2023
Record UNII
GVV4Z879SP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SERTINDOLE
DASH   INN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
LU-23-174
Code English
SERTINDOLE [USAN]
Common Name English
Sertindole [WHO-DD]
Common Name English
sertindole [INN]
Common Name English
SERTINDOLE [VANDF]
Common Name English
2-IMIDAZOLIDINONE, 1-(2-(4-(5-CHLORO-1-(4-FLUOROPHENYL)-1H-INDOL-3-YL)-1-PIPERIDINYL)ETHYL)-
Systematic Name English
SERDOLECT
Brand Name English
SERTINDOLE [MI]
Common Name English
ZERDOL
Brand Name English
SERLECT
Brand Name English
LU 23-174
Code English
SERTINDOLE [MART.]
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
MESH
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
EPA CompTox
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
IUPHAR
98
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PRIMARY
INN
6455
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PRIMARY
EVMPD
SUB10498MIG
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PRIMARY
CHEBI
9122
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PRIMARY
RXCUI
41996
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PRIMARY RxNorm
DRUG CENTRAL
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
SMS_ID
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
DRUG BANK
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
FDA UNII
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
CAS
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
NCI_THESAURUS
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
USAN
EE-14
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PRIMARY
PUBCHEM
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
MERCK INDEX
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
WIKIPEDIA
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
ChEMBL
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
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