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from 1996, but its marketing authorization was suspended by the European Medicines Agency in 1998 and the drug was withdrawn from the market.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

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
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
DRUG CENTRAL
2435
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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
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
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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