Mesoridazine(Serentil) is a phenothiazine class drug that is used in the treatment of schizophrenia.[2] It is one of the active metabolites of thioridazine. The drug's name is derived from the methylsulfoxy and piperidine functional groups in its chemical structure.
Mesoridazine was withdrawn from the United States market in 2004 due to dangerous side effects, namely irregular heart beat and QT-prolongation of the electrocardiogram.[3]
2-Methylthiophenothiazine [7643-08-5] (1) is treated with acetic anhydride] to give the protected amide, ie 10-acetyl-2-methylthiophenothiazine, CID:69367526. Oxidation of this by means of hydrogen peroxide and removal of the acetyl protecting group with potassium carbonate in methanol solution gives 2-methylsulfonylphenothiazine [23503-68-6] (3). Introduction of the sidechain by alkylation with 2-(2-chlorethyl)-1-methylpiperidine [50846-01-0] (6) in the presence of sodamide, afforded the desired mesoridazine (5).
Referencesedit
^Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). from the original on 2023-08-03. Retrieved 2023-08-16.
^Gershon S, Sakalis G, Bowers PA (December 1981). "Mesoridazine -- a pharmacodynamic and pharmacokinetic profile". The Journal of Clinical Psychiatry. 42 (12): 463–9. PMID 7031039.
^American Society of Health-System Pharmacists (AHFS). "Mesoridazine". Medline Plus. U.S. National Library of Medicine.
mesoridazine, this, article, needs, additional, citations, verification, please, help, improve, this, article, adding, citations, reliable, sources, unsourced, material, challenged, removed, find, sources, news, newspapers, books, scholar, jstor, april, 2024, . This article needs additional citations for verification Please help improve this article by adding citations to reliable sources Unsourced material may be challenged and removed Find sources Mesoridazine news newspapers books scholar JSTOR April 2024 Learn how and when to remove this message Mesoridazine Serentil is a phenothiazine class drug that is used in the treatment of schizophrenia 2 It is one of the active metabolites of thioridazine The drug s name is derived from the methylsulfoxy and piperidine functional groups in its chemical structure MesoridazineClinical dataTrade namesSerentilAHFS Drugs comMicromedex Detailed Consumer InformationMedlinePlusa682306Routes ofadministrationOral intravenousDrug classTypical antipsychoticATC codeN05AC03 WHO Legal statusLegal statusBR Class C1 Other controlled substances 1 In general Prescription only Pharmacokinetic dataProtein binding4 MetabolismHepatic renalElimination half life24 to 48 hoursExcretionBiliary and renalIdentifiersIUPAC name 10 2 1 methylpiperidin 2 yl ethyl 2 methylsulfinylphenothiazineCAS Number5588 33 0 YPubChem CID4078IUPHAR BPS7227DrugBankDB00933 YChemSpider3936 YUNII5XE4NWM740KEGGD02671 YChEBICHEBI 6780 YChEMBLChEMBL1088 YCompTox Dashboard EPA DTXSID3023265Chemical and physical dataFormulaC 21H 26N 2O S 2Molar mass386 57 g mol 13D model JSmol Interactive imageMelting point130 C 266 F Solubility in waterinsoluble mg mL 20 C SMILES O S c2cc1N c3c Sc1cc2 cccc3 CCC4N C CCCC4 CInChI InChI 1S C21H26N2OS2 c1 22 13 6 5 7 16 22 12 14 23 18 8 3 4 9 20 18 25 21 11 10 17 26 2 24 15 19 21 23 h3 4 8 11 15 16H 5 7 12 14H2 1 2H3 YKey SLVMESMUVMCQIY UHFFFAOYSA N Y verify It has central antiadrenergic antidopaminergic antiserotonergic and weak muscarinic anticholinergic effects Serious side effects include akathisia tardive dyskinesia and the potentially fatal neuroleptic malignant syndrome Mesoridazine was withdrawn from the United States market in 2004 due to dangerous side effects namely irregular heart beat and QT prolongation of the electrocardiogram 3 It currently appears to be unavailable worldwide Synthesis edit nbsp Thieme Synthesis 4 5 Patent 6 2 Methylthiophenothiazine 7643 08 5 1 is treated with acetic anhydride to give the protected amide ie 10 acetyl 2 methylthiophenothiazine CID 69367526 Oxidation of this by means of hydrogen peroxide and removal of the acetyl protecting group with potassium carbonate in methanol solution gives 2 methylsulfonylphenothiazine 23503 68 6 3 Introduction of the sidechain by alkylation with 2 2 chlorethyl 1 methylpiperidine 50846 01 0 6 in the presence of sodamide afforded the desired mesoridazine 5 References edit Anvisa 2023 03 31 RDC Nº 784 Listas de Substancias Entorpecentes Psicotropicas Precursoras e Outras sob Controle Especial Collegiate Board Resolution No 784 Lists of Narcotic Psychotropic Precursor and Other Substances under Special Control in Brazilian Portuguese Diario Oficial da Uniao published 2023 04 04 Archived from the original on 2023 08 03 Retrieved 2023 08 16 Gershon S Sakalis G Bowers PA December 1981 Mesoridazine a pharmacodynamic and pharmacokinetic profile The Journal of Clinical Psychiatry 42 12 463 9 PMID 7031039 American Society of Health System Pharmacists AHFS Mesoridazine Medline Plus U S National Library of Medicine Bourquin J P Schwarb G Gamboni G Fischer R Ruesch L Guldimann S Theus V Schenker E Renz J 1958 Synthesen auf dem Phenothiazin Gebiet 1 Mitteilung Mercaptophenothiazin Derivate Helvetica Chimica Acta 41 4 1061 1072 doi 10 1002 hlca 19580410419 Bourquin J P Schwarb G Gamboni G Fischer R Ruesch L Guldimann S Theus V Schenker E Renz J 1958 Synthesen auf dem Phenothiazin Gebiet 2 Mitteilung N substituierte Mercaptophenothiazin Derivate Helvetica Chimica Acta 41 4 1072 1108 doi 10 1002 hlca 19580410420 Schwarb Gustav Renz Jany Bourquin Jean Pierre U S patent 3 084 161 1963 to Sandoz Ltd nbsp This drug article relating to the nervous system is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Mesoridazine amp oldid 1217236480, wikipedia, wiki, book, books, library,
