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Merck
CN

S8072

Sertindole

≥97.5% (HPLC)

Synonym(s):

1-[2-[4-[5-Chloro-1-(4-fluorophenyl)-1h-indol-3-yl]-1-piperidinyl]ethyl]-2-imidazolidinone

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About This Item

Empirical Formula (Hill Notation):
C24H26ClFN4O
CAS Number:
106516-24-9
Molecular Weight:
440.94
NACRES:
NA.77
PubChem Substance ID:
329824596
UNSPSC Code:
12352200
MDL number:
MFCD00867749

Key Documents

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InChI key

GZKLJWGUPQBVJQ-UHFFFAOYSA-N

SMILES string

Fc1ccc(cc1)-n2cc(C3CCN(CC3)CCN4CCNC4=O)c5cc(Cl)ccc25

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)

assay

≥97.5% (HPLC)

form

solid

color

off-white

solubility

DMSO: >10 mg/mL, H2O: <2 mg/mL

originator

Abbott

storage temp.

2-8°C

Gene Information

human ... ADRA1A(148), ADRA1B(147), ADRA1D(146), DRD2(1813)

Application

Sertindole was used to study the role of 5-HT2C receptor in antipsychotic-induced body weight gain in rats.3

Biochem/physiol Actions

Sertindole is a 5-HT2 serotonin and D2 dopamine receptor antagonist and antipsychotic.
Sertindole readily passes the blood-brain barrier and is metabolized into compounds that show greater affinity for 5-HT2 receptors and less for D2 receptors. It is an effective treatment agent for schizophrenia as it improves cognitive impairment.1 Sertindole also acts as antagonist to human cardiac potassium channel, HERG and produces prolonged QT interval.2

Features and Benefits

This compound is featured on the Dopamine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Abbott. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Aquatic Chronic 4 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000100531
0000056972
0000056983
0000049060
0000012635

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D Rampe et al.
The Journal of pharmacology and experimental therapeutics, 286(2), 788-793 (1998-08-08)
Acquired long QT syndrome is a side effect seen with some pharmacological agents, including antipsychotic drugs, and is associated with the development of ventricular arrhythmias. This syndrome is often caused by the blockade of repolarizing potassium channels the human heart.
Dominique H Holstein et al.
Journal of psychopharmacology (Oxford, England), 25(12), 1600-1613 (2011-09-06)
Sensory gating, indexed by P50 suppression, and sensorimotor gating, indexed by prepulse inhibition (PPI), are impaired in schizophrenia spectrum disorders. There is considerable evidence that schizophrenia patients treated with atypical antipsychotics exhibit relatively less gating deficits than do other patients
A S Hale
International clinical psychopharmacology, 13 Suppl 3, S65-S70 (1998-08-05)
The safety and efficacy of sertindole have been established in three double-blind randomized controlled studies conducted in the United States, North America and Europe. In these three studies the tendency for sertindole to cause extrapyramidal side effects (EPS), a critical
Morten Jørgensen et al.
Bioorganic & medicinal chemistry, 21(1), 196-204 (2012-12-12)
The synthesis and in vitro preclinical profile of a series of 5-heteroaryl substituted analogs of the antipsychotic drug sertindole are presented. Compounds 1-(4-fluorophenyl)-3-(1-methylpiperidin-4-yl)-5-(pyrimidin-5-yl)-1H-indole (Lu AA27122, 3i) and 1-(4-fluorophenyl)-5-(1-methyl-1H-1,2,4-triazol-3-yl)-3-(1-methylpiperidin-4-yl)-1H-indole (3l) were identified as high affinity α(1A)-adrenoceptor ligands with K(i) values of
Lowijs Perquin et al.
CNS drugs, 18 Suppl 2, 19-30 (2004-10-06)
Sertindole is a non-sedating atypical antipsychotic agent with high selectivity for dopaminergic neurons in the mesolimbic system. In pivotal clinical trials, sertindole has demonstrated significantly greater efficacy than placebo against both the positive and negative symptoms of schizophrenia. In addition
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