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S8072

Sigma-Aldrich

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
MDL number:
MFCD00867749
UNSPSC Code:
12352200
PubChem Substance ID:
329824596
NACRES:
NA.77

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

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)

InChI key

GZKLJWGUPQBVJQ-UHFFFAOYSA-N

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 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
Sertindole is a 5-HT2 serotonin and D2 dopamine receptor antagonist and antipsychotic.

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_germany

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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Tomasz Kos et al.
Psychopharmacology, 214(4), 911-921 (2010-12-17)
Cognitive deficits, including an impaired ability to shift perceptual attentional set, belong to the core features of schizophrenia, are associated with prefrontal cortical dysfunctions, and may involve glutamate NMDA receptors. Although phencyclidine disturbs cognitive flexibility, little is known about the
Eva Lindström et al.
The international journal of neuropsychopharmacology, 8(4), 615-629 (2005-06-21)
Since the 1960s, physicians have been aware of electrocardiographic (ECG) abnormalities and cases of sudden death associated with the use of antipsychotic drugs in patients with schizophrenia. Explanations for such deaths have traditionally focused on drug-induced prolongation of the QT
Anna Secher et al.
Neuroendocrinology, 91(2), 155-168 (2009-10-10)
Body weight gain is a common side effect of treatment with antipsychotics, but the mechanisms underlying this weight gain are unknown. Several factors may be involved in antipsychotic-induced body weight gain including the cannabinoid receptor 1 (CB(1)), the serotonin receptor
Katja Komossa et al.
The Cochrane database of systematic reviews, (2)(2), CD006752-CD006752 (2009-04-17)
In many countries of the industrialised world second generation (atypical) antipsychotics have become the first line drug treatment for people with schizophrenia. The question as to whether and, if so, how much the effects of the various second generation antipsychotics
R E Nielsen et al.
Acta psychiatrica Scandinavica, 126(1), 31-39 (2012-02-24)
To assess the cognitive effects of sertindole augmentation in clozapine-treated patients diagnosed with schizophrenia. Cognition is secondary outcome of the trial. A 12-week, double-blinded, randomized, placebo-controlled, augmentation study of patients treated with clozapine. Participants were randomized 1:1 to receive 16
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