Sertindole | CAS#106516-24-9 | D2 Receptor Antagonist

Sertindole
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 318691

CAS#: 106516-24-9

Description: Sertindole is one of the newer antipsychotic medications and a neuroleptic. Like the other atypical antipsychotics, it has activity at dopamine and serotonin receptors in the brain. It is used in the treatment of schizophrenia.

Chemical Structure

Sertindole

CAS# 106516-24-9

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318691
Name: Sertindole
CAS#: 106516-24-9
Chemical Formula: C24H26ClFN4O
Exact Mass: 440.18
Molecular Weight: 440.940
Elemental Analysis: C, 65.37; H, 5.94; Cl, 8.04; F, 4.31; N, 12.71; O, 3.63

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 250
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Sertindole;SerLect; Serdolect; Sertindol; Sertindolum; Lu 23-174; Lu-23-174; Serdolect; Serlect; sertindole; sertindole hydrochloride;

IUPAC/Chemical Name: 1-[2-[4-[5-chloro-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]imidazolidin-2-one

InChi Key: GZKLJWGUPQBVJQ-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: C1CN(CCC1C2=CN(C3=C2C=C(C=C3)Cl)C4=CC=C(C=C4)F)CCN5CCNC5=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO and DMF

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

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Product Data:

Product Data

Instruction:

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Biological target:	Sertindole binds to dopamine D2 receptors and the serotonin (5-HT) receptor subtypes 5-HT1D, 5-HT2A, and 5-HT2C (Kds = 2.7, 20, 0.14, and 6 nM, respectively). It also binds to histamine H1 and α1- and α2-adrenergic receptors. It also binds to histamine H1 and α1- and α2-adrenergic receptors (Kds = 320, 3.9, and 190 nM, respectively).
In vitro activity:	The use of sertindole as an antipsychotic drug may have adverse effects on the cardiovascular system. In native VSMCs from rabbit coronary arteries, sertindole induced dose-dependent inhibition of Kv channels, with an IC50 of 3.13 ± 0.72 μM. Sertindole did not cause a change in the steady-state activation curve, but it did lead to a negative shift in the steady-state inactivation curve. The inhibitory response to sertindole was significantly diminished by pretreatment with a Kv1.5 inhibitor but not by Kv2.1 and Kv7 subtype inhibitors. Reference: J Appl Toxicol. 2023 Oct 3. https://pubmed.ncbi.nlm.nih.gov/37786982/
In vivo activity:	Sertindole has the potential to improve cognition in the context of schizophrenia. This study investigated the impact of second-generation antipsychotics, one being sertindole, on visual recognition memory in both naive and MK-801-treated mice. Sertindole did not have effect on locomotion in naïve mice. However, it did reverse MK-801-induced cognitive impairment. Sertindole had no effect on anxiety in naive mice, but reversed the MK-801-induced effects on locomotion and anxiety. Reference: Pharmacol Biochem Behav. 2011 Oct;99(4):557-65. https://pubmed.ncbi.nlm.nih.gov/21693127/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	15.0	34.02
	DMSO	5.0	11.34

Preparing Stock Solutions

The following data is based on the product molecular weight 440.94 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Zhuang W, Mun SY, Park M, Jeong J, Kim HR, Na S, Lee SJ, Park H, Park WS. Inhibition of voltage-dependent K+ channels in rabbit coronary arterial smooth muscle cells by the atypical antipsychotic agent sertindole. J Appl Toxicol. 2023 Oct 3. doi: 10.1002/jat.4549. Epub ahead of print. PMID: 37786982. 2. Hsu CY, Yang WT, Lin JH, Lu CH, Hu KC, Lan TH, Chang CC. Sertindole, an Antipsychotic Drug, Curbs the STAT3/BCL-xL Axis to Elicit Human Bladder Cancer Cell Apoptosis In Vitro. Int J Mol Sci. 2023 Jul 24;24(14):11852. doi: 10.3390/ijms241411852. PMID: 37511611; PMCID: PMC10380261. 3. Zhang W, Zhang C, Liu F, Mao Y, Xu W, Fan T, Sun Q, He S, Chen Y, Guo W, Tan Y, Jiang Y. Antiproliferative activities of the second-generation antipsychotic drug sertindole against breast cancers with a potential application for treatment of breast-to-brain metastases. Sci Rep. 2018 Oct 25;8(1):15753. doi: 10.1038/s41598-018-33740-0. PMID: 30361678; PMCID: PMC6202417. 4. Mutlu O, Ulak G, Celikyurt IK, Akar FY, Erden F, Tanyeri P. Effects of olanzapine, sertindole and clozapine on MK-801 induced visual memory deficits in mice. Pharmacol Biochem Behav. 2011 Oct;99(4):557-65. doi: 10.1016/j.pbb.2011.06.011. Epub 2011 Jun 15. PMID: 21693127.
In vitro protocol:	1. Zhuang W, Mun SY, Park M, Jeong J, Kim HR, Na S, Lee SJ, Park H, Park WS. Inhibition of voltage-dependent K+ channels in rabbit coronary arterial smooth muscle cells by the atypical antipsychotic agent sertindole. J Appl Toxicol. 2023 Oct 3. doi: 10.1002/jat.4549. Epub ahead of print. PMID: 37786982. 2. Hsu CY, Yang WT, Lin JH, Lu CH, Hu KC, Lan TH, Chang CC. Sertindole, an Antipsychotic Drug, Curbs the STAT3/BCL-xL Axis to Elicit Human Bladder Cancer Cell Apoptosis In Vitro. Int J Mol Sci. 2023 Jul 24;24(14):11852. doi: 10.3390/ijms241411852. PMID: 37511611; PMCID: PMC10380261.
In vivo protocol:	1. Zhang W, Zhang C, Liu F, Mao Y, Xu W, Fan T, Sun Q, He S, Chen Y, Guo W, Tan Y, Jiang Y. Antiproliferative activities of the second-generation antipsychotic drug sertindole against breast cancers with a potential application for treatment of breast-to-brain metastases. Sci Rep. 2018 Oct 25;8(1):15753. doi: 10.1038/s41598-018-33740-0. PMID: 30361678; PMCID: PMC6202417. 2. Mutlu O, Ulak G, Celikyurt IK, Akar FY, Erden F, Tanyeri P. Effects of olanzapine, sertindole and clozapine on MK-801 induced visual memory deficits in mice. Pharmacol Biochem Behav. 2011 Oct;99(4):557-65. doi: 10.1016/j.pbb.2011.06.011. Epub 2011 Jun 15. PMID: 21693127.

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1: Remezova IP, Lazaryan DS, Voronkov AV, Avramenko NS, Maksimenko TI, Sanzhieva
DY. [The chemical toxicological analysis of sertindole]. Sud Med Ekspert.
2016;59(1):35-39. Russian. PubMed PMID: 27030096.

2: Ihalainen J, Savolainen K, Tanila H, Forsberg MM. Comparison of
phencyclidine-induced spatial learning and memory deficits and reversal by
sertindole and risperidone between Lister Hooded and Wistar rats. Behav Brain
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PubMed PMID: 26940605.

3: El-Kosasy AM, Hussein LA, Sedki NG, Salama NN. Micelle enhanced and native
spectrofluorimetric methods for determination of sertindole using sodium dodecyl
sulfate as sensitizing agent. Spectrochim Acta A Mol Biomol Spectrosc. 2016 Jan
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4: Zoccali RA, Bruno A, Muscatello MR. Efficacy and safety of sertindole in
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5: Nielsen J, Wang F, Graff C, Kanters JK. QT dynamics during treatment with
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PMC4315672.

6: Nielsen J, Matz J, Mittoux A, Polcwiartek C, Struijk JJ, Toft E, Kanters JK,
Graff C. Cardiac effects of sertindole and quetiapine: analysis of ECGs from a
randomized double-blind study in patients with schizophrenia. Eur
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7: Muscatello MR, Bruno A, Micali Bellinghieri P, Pandolfo G, Zoccali RA.
Sertindole in schizophrenia: efficacy and safety issues. Expert Opin
Pharmacother. 2014 Sep;15(13):1943-53. doi: 10.1517/14656566.2014.947960. Epub
2014 Aug 1. Review. PubMed PMID: 25084209.

8: Ernst Nielsen R, Odur F, Ostergaard T, Munk-Jørgensen P, Nielsen J. Comparison
of the effects of Sertindole and Olanzapine on Cognition (SEROLA): a double-blind
randomized 12-week study of patients diagnosed with schizophrenia. Ther Adv
Psychopharmacol. 2014 Feb;4(1):4-14. doi: 10.1177/2045125313499065. PubMed PMID:
24490025; PubMed Central PMCID: PMC3896130.

9: Waldman W, Kaletha K, Sein Anand J. [Acute poisoning with sertindole--a case
report]. Przegl Lek. 2013;70(8):669-70. Polish. PubMed PMID: 24466716.

10: Wang SM, Han C, Lee SJ, Patkar AA, Masand PS, Pae CU. Asenapine, blonanserin,
iloperidone, lurasidone, and sertindole: distinctive clinical characteristics of
5 novel atypical antipsychotics. Clin Neuropharmacol. 2013 Nov-Dec;36(6):223-38.
doi: 10.1097/WNF.0b013e3182aa38c4. Review. PubMed PMID: 24201235.

11: El-Ragehy NA, Hassan NY, Abdelkawy M, Tantawy MA. Stability-indicating
chromatographic methods for the determination of sertindole. J Chromatogr Sci.
2014 Jul;52(6):559-65. doi: 10.1093/chromsci/bmt066. Epub 2013 Jun 2. PubMed
PMID: 23733912.

12: Pae CU. Sertindole: dilemmas for its use in clinical practice. Expert Opin
Drug Saf. 2013 May;12(3):321-6. doi: 10.1517/14740338.2013.773971. Epub 2013 Feb
25. PubMed PMID: 23432404.

13: Kállmán J, Pákáski M, Szucs S, Kálmán S, Fazekas O, Santha P, Szabó G, Janka
Z, Kálmán J. [The role of immobilization stress and sertindole on the expression
of APP, MAPK-1 and beta-actin genes in rat brain]. Ideggyogy Sz. 2012 Nov
30;65(11-12):394-400. Hungarian. PubMed PMID: 23289174.

14: Jørgensen M, Jørgensen PN, Christoffersen CT, Jensen KG, Balle T,
Bang-Andersen B. Discovery of novel α₁-adrenoceptor ligands based on the
antipsychotic sertindole suitable for labeling as PET ligands. Bioorg Med Chem.
2013 Jan 1;21(1):196-204. doi: 10.1016/j.bmc.2012.10.049. Epub 2012 Nov 15.
PubMed PMID: 23218776.

15: Karamatskos E, Lambert M, Mulert C, Naber D. Drug safety and efficacy
evaluation of sertindole for schizophrenia. Expert Opin Drug Saf. 2012
Nov;11(6):1047-62. doi: 10.1517/14740338.2012.726984. Epub 2012 Sep 19. Review.
PubMed PMID: 22992213.

16: Kwon JS, Mittoux A, Hwang JY, Ong A, Cai ZJ, Su TP. The efficacy and safety
of 12 weeks of treatment with sertindole or olanzapine in patients with chronic
schizophrenia who did not respond successfully to their previous treatments: a
randomized, double-blind, parallel-group, flexible-dose study. Int Clin
Psychopharmacol. 2012 Nov;27(6):326-35. PubMed PMID: 22850268.

17: Shin JH, Park SJ, Kim ES, Jo YK, Hong J, Cho DH. Sertindole, a potent
antagonist at dopamine D₂ receptors, induces autophagy by increasing reactive
oxygen species in SH-SY5Y neuroblastoma cells. Biol Pharm Bull.
2012;35(7):1069-75. PubMed PMID: 22791154.

18: Hale AS, Azorin JM, Lemming OM, Mæhlum E. Sertindole in the long-term
treatment of schizophrenia. Int Clin Psychopharmacol. 2012 Jul;27(4):231-7. doi:
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19: Nielsen J, Emborg C, Gydesen S, Dybbro J, Aagaard J, Haderup K, Glyngdal P,
Fabricius S, Thode D, Lublin H, Andersen T, Damkier P, Taylor D. Augmenting
clozapine with sertindole: a double-blind, randomized, placebo-controlled study.
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PubMed PMID: 22367659.

20: Nielsen RE, Levander S, Thode D, Nielsen J. Effects of sertindole on
cognition in clozapine-treated schizophrenia patients. Acta Psychiatr Scand. 2012
Jul;126(1):31-9. doi: 10.1111/j.1600-0447.2012.01840.x. Epub 2012 Feb 22. PubMed
PMID: 22356584.

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