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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

Signal Word

Warning

Hazard Statements

H315,H319,H335,H413

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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.
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
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
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
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