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MedKoo Cat#: 318691 | Name: Sertindole
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Description:

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

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

Theoretical Analysis

MedKoo Cat#: 318691

Name: Sertindole

CAS#: 106516-24-9

Chemical Formula: C24H26ClFN4O

Exact Mass: 440.1779

Molecular Weight: 440.94

Elemental Analysis: C, 65.37; H, 5.94; Cl, 8.04; F, 4.31; N, 12.71; O, 3.63

Price and Availability

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10mg USD 400.00
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Related CAS #
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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
More Info
Product Data
Product Data
Instruction
View handling instruction
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/
Solvent mg/mL mM comments
Solubility
DMF 15.0 34.02
DMSO 5.0 11.34
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

Recalculate based on batch purity %
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.
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 Res. 2016 May 15;305:140-7. doi: 10.1016/j.bbr.2016.02.032. Epub 2016 Mar 3. 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 15;153:422-7. doi: 10.1016/j.saa.2015.08.040. Epub 2015 Sep 1. PubMed PMID: 26356788. 4: Zoccali RA, Bruno A, Muscatello MR. Efficacy and safety of sertindole in schizophrenia: a clinical review. J Clin Psychopharmacol. 2015 Jun;35(3):286-95. doi: 10.1097/JCP.0000000000000305. Review. PubMed PMID: 25830594. 5: Nielsen J, Wang F, Graff C, Kanters JK. QT dynamics during treatment with sertindole. Ther Adv Psychopharmacol. 2015 Feb;5(1):26-31. doi: 10.1177/2045125314560738. PubMed PMID: 25653828; PubMed Central PMCID: 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 Neuropsychopharmacol. 2015 Mar;25(3):303-11. doi: 10.1016/j.euroneuro.2014.12.005. Epub 2015 Jan 3. PubMed PMID: 25583364. 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: 10.1097/YIC.0b013e328354dcda. PubMed PMID: 22609816. 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. J Clin Psychopharmacol. 2012 Apr;32(2):173-8. doi: 10.1097/JCP.0b013e318248dfb8. 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.