Structure of Sertindole
CAS No.: 106516-24-9
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Sertindole, a neuroleptic, is one of the antipsychotic medications available, with a high affinity for dopamine D2, serotonin 5-HT2A, 5-HT2C, and α1-adrenergic receptors.
Synonyms: Lu 23-174
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Silva Franco, Lucas ; Rodrigues, Daniel Alencar ; Baumart, Gabriela Joras ; de Jesus, Bárbara da Silva Mascarenhas ; Gomes, Flávia Carvalho Alcantara ; Lima, Lídia Moreira , et al.
Abstract: ROCK kinases are key players in neurodegenerative diseases such as Alzheimer’s disease (AD), making them attractive therapeutic targets. In this study, we developed a pharmacophoric map of ROCK inhibitors and highlighted the key affinity sites in ROCK1/2 through molecular modeling. Virtual screening led to the identification of six approved drugs as ROCK inhibitors: ruxolitinib (36), baricitinib (37), ponatinib (38), tivozanib (39), nialamide (40), and tucatinib (41). Ruxolitinib (36) (hROCK1 IC50 = 0.025 μM; hROCK2 IC50 = 0.007 μM) and baricitinib (37) (hROCK1 IC50 = 0.019 μM; hROCK2 IC50 = 0.011 μM) showed the highest potency, while tivozanib (39) displayed 15-fold selectivity for ROCK2 over ROCK1. Molecular dynamics revealed that ruxolitinib (36) forms stable bidentate hydrogen bonds with the ROCK hinge region and has selectivity across the AGC kinase family. Biological assays confirmed ruxolitinib’s (36) safety in neuronal and glial cells and its ability to reduce C3 immunolabeling, a glial inflammation marker, in LPS-treated astrocytes. These findings not only highlight ruxolitinib (36) as a promising candidate for AD but also provide a structural basis for designing novel dual JAK-ROCK inhibitors and pave the way for further in vitro and in vivo studies. Moreover, the validated pharmacophoric map for ROCK inhibition highlights the identification of an affinity pocket that can be useful for the design of new ROCK inhibitors.
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Purchased from AmBeed: 937263-43-9 ; 1187594-09-7 ; 518048-05-0 ; 1346242-81-6 ; 941678-49-5 ; 1338225-97-0 ; 943319-70-8 ; 106516-24-9 ; 73963-72-1 ; 1132935-63-7 ; 475108-18-0
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CAS No. : | 106516-24-9 |
Formula : | C24H26ClFN4O |
M.W : | 440.94 |
SMILES Code : | FC1=CC=C(N2C3=CC=C(Cl)C=C3C(C4CCN(CCN5CCNC5=O)CC4)=C2)C=C1 |
Synonyms : |
Lu 23-174
|
MDL No. : | MFCD00867749 |
InChI Key : | GZKLJWGUPQBVJQ-UHFFFAOYSA-N |
Pubchem ID : | 60149 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335-H413 |
Precautionary Statements: | P261-P305+P351+P338 |
In Vitro:
Concentration | Treated Time | Description | References |
Staphylococcus aureus | 50 µM | 24 hours | Evaluate the antibacterial activity of Sertindole against S. aureus, results showed Sertindole significantly inhibited bacterial growth | ACS Omega. 2023 Feb 3;8(6):5415-5425 |
Normal human urothelial cells | 20 µM | 48 hours | To evaluate the cytotoxic effect of Sertindole on normal human urothelial cells, results showed minimal cytotoxicity | Int J Mol Sci. 2023 Jul 24;24(14):11852 |
T24 | 14.79 ± 0.95 µM | 48 hours | To evaluate the cytotoxic effect of Sertindole on bladder cancer cell line T24, results showed significant reduction in cell viability | Int J Mol Sci. 2023 Jul 24;24(14):11852 |
TCCSUP | 13.43 ± 0.89 µM | 48 hours | To evaluate the cytotoxic effect of Sertindole on bladder cancer cell line TCCSUP, results showed significant reduction in cell viability | Int J Mol Sci. 2023 Jul 24;24(14):11852 |
J82 | 11.43 ± 0.63 µM | 48 hours | To evaluate the cytotoxic effect of Sertindole on bladder cancer cell line J82, results showed significant reduction in cell viability | Int J Mol Sci. 2023 Jul 24;24(14):11852 |
MDA-MB-231 | 4.1 µM (IC50) | 48 hours | Evaluate the antiproliferative activity of Sertindole on MDA-MB-231 cells, showing an IC50 of 4.1 µM | Sci Rep. 2018 Oct 25;8(1):15753 |
MCF-10A | 27.6 µM (IC50) | 48 hours | Evaluate the toxicity of Sertindole on MCF-10A cells, showing an IC50 of 27.6 µM | Sci Rep. 2018 Oct 25;8(1):15753 |
SUM159 | 9.2 µM | 48 hours | Evaluate the antiproliferative activity of Sertindole on SUM159 cells, showing an IC50 of 9.2 µM | Sci Rep. 2018 Oct 25;8(1):15753 |
In Vivo:
Administration | Dosage | Frequency | Description | References |
Wistar rats | Rat brain dopamine D1, D2 and 5-HT2A receptor study model | Intraperitoneal injection | 0.5 mg/kg or 2.0 mg/kg | Single dose, EEDQ administered 1 hour later | To study the in vivo occupation of D1, D2 and 5-HT2A receptors by Sertindole. Results showed that Sertindole had little or no effect on D1 and D2 receptors but occupied 5-HT2A receptors more extensively and firmly. | J Psychiatry Neurosci. 1998 May;23(3):157-62 |
Balb/c mice | MDA-MB-231 orthotopic model | Oral gavage | 10 mg/kg | Once daily for 12 days | Evaluate the antitumor effect of Sertindole on MDA-MB-231 orthotopic model, showing a 22.7% reduction in tumor volume | Sci Rep. 2018 Oct 25;8(1):15753 |
Rats | Conscious rats | Subcutaneous injection | 2.5 mg/kg | Single dose, recorded for 165 minutes | To evaluate the effects of Sertindole on EEG in the prefrontal cortex of conscious rats. Results showed that Sertindole increased the power spectra in the 6-14 Hz frequency band, indicating EEG synchronization. | Br J Pharmacol. 1999 Nov;128(5):1055-63 |
Rats | Ketamine-induced schizophrenia-like behaviors model | Oral | 2.5 mg/kg | Once daily for 14 days | To investigate the effects of Sertindole on the NRG1/ErbB4 and PI3K/AKT/mTOR signaling pathways in ketamine-induced schizophrenia. Results showed that Sertindole significantly ameliorated behavioral deficits, oxidative stress, and neurotransmitter level changes, and activated the NRG1/ErbB4 and PI3K/AKT/mTOR signaling pathways. | Inflammopharmacology. 2022 Oct;30(5):1891-1907 |
Clinical Trial:
NCT Number | Conditions | Phases | Recruitment | Completion Date | Locations |
NCT02374567 | Dementia Depr... More >>ession Schizophrenia Psychosomatic Disorders Anxiety Disorders Less << | Phase 3 | Terminated | - | Germany ... More >> Bezirkskrankenhaus Augsburg Augsburg, Germany Krankenhaus Hedwigshöhe Berlin, Germany Hannover Medical School Hannover, Germany, 30625 Asklepios Fachklinikum Lübben Lübben, Germany Asklepios Fachklinikum Teupitz Teupitz, Germany Less << |
NCT02307396 | Schizophrenia ... More >> Schizophrenia and Disorders With Psychotic Features Schizoaffective Disorders Less << | Phase 4 | Completed | - | Germany ... More >> Psychiatrische Klinik und Poliklinik fuer Psychiatrie und Psychotherapie der Technischen Universitaet Muenchen am Klinikum rechts der Isar Munich, Bavaria, Germany, 81675 Less << |
NCT01765829 | Psychosis Nos/Other | Phase 3 | Unknown | November 2015 | Spain ... More >> Mental Health Unit Villamartín Recruiting Villamartín, Cádiz, Spain, 11650 Contact: José María Mongil San Juan, MD 0034956040209 cheman45@gmail.com Principal Investigator: José María Mongil San Juan, MD Mental Health Unit Baza Recruiting Baza, Granada, Spain, 18800 Contact: Eva Bravo Barba, MD eva.bravo.barba@gmail.com Principal Investigator: Eva Bravo Barba, MD Mental Health Unit Motril Recruiting Motril, Granada, Spain, 18600 Contact: María Luisa Barrigón Estévez, MD 0034958038849 marial.barrigon.sspa@juntadeandalucia.es Principal Investigator: María Luisa Barrigón Estévez, MD Mental Health Unit Andújar Recruiting Andújar, Jaén, Spain, 23740 Contact: Fernando Sarramea Crespo, MD, PhD 0034953021717 fernandosarramea@hotmail.com Principal Investigator: Farnando Sarramea Crespo, MD, PhD Mental Health Unit Martos Recruiting Martos, Jaén, Spain, 23600 Contact: Miguel Ortigosa Luque, MD migueortigosa@hotmail.com Principal Investigator: Miguel Ortigosa Luque, MD Mental Health Unit Miraflores Not yet recruiting Alcobendas, Madrid, Spain, 28100 Contact: María Luisa Zamarro Arraz, MD, PhD 0034916530108 zamarroluisa@yahoo.es Principal Investigator: María Luisa Zamarro Arraz, MD, PhD Hospital Infanta Sofía Not yet recruiting San Sebastian de los Reyes, Madrid, Spain, 28702 Contact: María Rosario Gutiérrez Labrador, MD rosagutierrez@psiquiatra.e.telefonica.net Principal Investigator: María Rosario Guitiérrez Labrador, MD Mental Health Unit Valle del Guadalhorce Not yet recruiting Cártama, Málaga, Spain, 29580 Contact: Daniel Gutiérrez Castillo, MD 0034951033931 dgutierrezcastillo@gmail.com Principal Investigator: Daniel Gutiérrez Castillo, MD Mental Health Unit Las Lagunas Not yet recruiting Fuengiróla, Málaga, Spain, 29650 Contact: María Isabel Osuna Carmona, MD maribelosunac@hotmail.com Principal Investigator: María Isabel Osuna Carmona, MD Fundación Argibide Not yet recruiting Pamplona, Navarra, Spain, 31007 Contact: Ignacio Mata Pastor, MD, PhD 0034948266650 nacho.mata70@gmail.com Principal Investigator: Ignacio Mata Pastor, MD, PhD Hospital El Tomillar Recruiting Dos Hermanas, Seville, Spain, 41700 Contact: Joaquín Carlos Martín Muñoz, MD, PhD 0034955016083 joaquinmartin@hotmail.com Principal Investigator: Joaquín Carlos Martín Muñoz, MD, PhD Hospital Francesc de Borja Recruiting Gandía, Valencia, Spain, 46700 Contact: María Lacruz Silvestre, MD, PhD maria.lacruz.silvestre@gmail.com Principal Investigator: María Lacruz Silvestre, MD, PhD Hospital de Basurto Not yet recruiting Bilbao, Spain, 48013 Contact: Sonia Bustamante Madariaga, MD, Phd 0034944 006137 sonia.bustamantemadariaga@osakidetza.net Principal Investigator: Sonia Bustamante Madariaga, MD, PhD Mental Health Unit Tetuán Not yet recruiting Madrid, Spain, 28003 Contact: Mariano Hernández Monsalve, MD, PhD 0034915347363 hergoico@gmail.com Contact: Ruth Berdún Pe, MD ruthberdun@yahoo.es Principal Investigator: Mariano Hernández Monsalve, MD, PhD Lafora Hospital Not yet recruiting Madrid, Spain, 28049 Contact: Juan Dios Molina Martín, MD, PhD jmolinamar@hotmail.com Principal Investigator: Juan Dios Molina Martín, MD, PhD Hospital Carlos Haya Recruiting Málaga, Spain, 29009 Contact: Fermín Mayoral Cleríes, Md, PhD fermin.mayoral.sspa@juntadeandalucia.es Principal Investigator: Fermín Mayoral Cleríes, MD, PhD Virgen del Rocío Hospital Recruiting Seville, Spain, 41013 Contact: Clara M. Rosso Fernández, MD 0034955013414 claram.rosso.sspa@juntadeandalucia.es Contact: Miguel Ruiz Veguilla, MD, PhD 0034955013414 mruizveguilla@yahoo.com Principal Investigator: Miguel Ruiz Veguilla, MD, PhD Less << |
NCT02435095 | Schizophrenia | Phase 4 | Recruiting | April 2019 | Germany ... More >> RWTH University Hospital Aachen Recruiting Aachen, NRW, Germany, 52074 Contact: Sabrina Schaffrath saschaffrath@ukaachen.de Contact: Sarah Lammertz slammertz@ukaachen.de Alexianer Aachen GmbH Not yet recruiting Aachen, Germany, 52062 Zentrum für Neurologie und Seelische Gesundheit im Kapuziner Karree Aachen Not yet recruiting Aachen, Germany, 52062 Contact: Frank Bergmann, Dr. med. LVR Klinik Bonn Recruiting Bonn, Germany, 53111 LVR Klinik Düren Not yet recruiting Düren, Germany, 52353 Klinik und Poliklinik für Psychiatrie und Psychotherapie der Heinrich-Heine-Universität Düsseldorf Recruiting Düsseldorf, Germany, 40629 LVR Klinik Essen Not yet recruiting Essen, Germany, 45147 ViaNobis Gangelt Recruiting Gangelt, Germany, 52538 Klinik Königshof (Abteilung für Allgemeine Psychiatrie) Recruiting Krefeld, Germany, 47807 LVR Klinik Langenfeld Recruiting Langenfeld, Germany, 40764 LVR Klinik Viersen Not yet recruiting Viersen, Germany, 41749 Less << |
NCT00629252 | Schizophrenia | Not Applicable | Terminated(Not enough subjects... More >> have been recruited in the expected period.) Less << | - | Switzerland ... More >> University Hospital of Psychiatry, Department Neuropsychopharmacology and Brain Imaging Zurich, ZH, Switzerland, CH-8032 Less << |
NCT00612079 | Healthy | Not Applicable | Completed | - | Switzerland ... More >> University of Psychiatry Hospital Zurich, ZH, Switzerland, CH-8032 Less << |
NCT00759460 | Schizophrenia | Phase 3 | Completed | - | China ... More >> CN002 Beijing, China, 100083 Less << |
NCT00759421 | Schizophrenia | Phase 3 | Completed | - | Taiwan ... More >> TWN001 Tapei, Taiwan, 112 Less << |
NCT00654706 | Schizophrenia ... More >> Cognition Less << | Phase 3 | Completed | - | United States, California ... More >> US017 Garden Grove, California, United States, 92845 US008 National City, California, United States, 91950 US001 Pasadena, California, United States, 91107 US006 Pico Rivera, California, United States, 90660 US011 San Diego, California, United States, 92126 US014 Stanford, California, United States, 94305 US026 Torrance, California, United States, 90502 United States, Colorado US016 Aurora, Colorado, United States, 80045 United States, Florida US015 Orange City, Florida, United States, 32763 US010 Tampa, Florida, United States, 33613 United States, Georgia US007 Atlanta, Georgia, United States, 30308 United States, Illinois US024 Chicago, Illinois, United States, 60640 US002 Joliet, Illinois, United States, 60435 United States, Maryland US012 Baltimore, Maryland, United States, 21204 US027 Glen Burnie, Maryland, United States, 21061 United States, New Hampshire US019 Lebanon, New Hampshire, United States, 03756 United States, New Jersey US021 Clementon, New Jersey, United States, 08021 United States, New York US013 Brooklyn, New York, United States, 11203 US025 Staten Island, New York, United States, 10305 United States, North Carolina US005 Charlotte, North Carolina, United States, 28211 US018 Durham, North Carolina, United States, 27705 United States, Pennsylvania US022 Philadelphia, Pennsylvania, United States, 19139 United States, Texas US023 Austin, Texas, United States, 78754 US020 Dallas, Texas, United States, 75235 US004 Desoto, Texas, United States, 75115 US028 Houston, Texas, United States, 77008 Less << |
NCT00885690 | Schizophrenia | Not Applicable | Terminated(Due to recruitment ... More >>problems) Less << | - | Denmark ... More >> Aalborg Psychiatric Hospital Aalborg, Denmark, 9000 Sweden Universitets Allmänna Sjukhuset, Malmø UMAS Malmø, Sweden Less << |
NCT00345982 | Schizophrenia | Not Applicable | Completed | - | Denmark ... More >> Aalborg Psychiatric Hospital Aalborg, Denmark, 9000 Less << |
NCT00763438 | Schizophrenia | PHASE4 | COMPLETED | 2025-10-10 | FR002, Allonnes, 72703, France |
NCT00856583 | Schizophrenia | Phase 3 | Completed | - | - |
NCT02021201 | Schizophrenia | Phase 4 | Terminated(No suitable patient... More >>s could be recruited in the available time period) Less << | - | Denmark ... More >> Center for Neuropsychiatric Schizophrenia Research, University of Copenhagen, Psychiatric Center Glostrup Glostrup, Denmark, DK-2600 Less << |
NCT00480844 | Schizophrenia | Phase 4 | Unknown | - | Israel ... More >> Department of Psychiatry of the Sheba Medical Center Recruiting Ramat Gan, Tel Hashomer, Israel, 52621 Contact: Mark Weiser, Dr 03-5303773 mweiser@netvision.net.il Principal Investigator: Mark Weiser, Dr Beer-Yaakov Mental Health Center Not yet recruiting Beer-Yaakov, Israel, 70350 Principal Investigator: Yehuda Abramowitz, Dr Kfar Shaul Mental Health Center Not yet recruiting Jerusalem, Israel, 91060 Principal Investigator: Alexander Teitelbaum, Dr Less << |
NCT00864045 | Schizophrenia | Phase 3 | Completed | - | China ... More >> CN001 Beijing, China, 300074 Less << |
NCT01498770 | - | Completed | - | - | |
NCT00856583 | - | Completed | - | - |
Bio Calculators | ||||
Preparing Stock Solutions | ![]() |
1mg | 5mg | 10mg |
1 mM 5 mM 10 mM |
2.27mL 0.45mL 0.23mL |
11.34mL 2.27mL 1.13mL |
22.68mL 4.54mL 2.27mL |
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Dissolving Methods |
in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day; The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound. Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:
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