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Typical antipsychotic
Mesoridazine
Другие языки:

Mesoridazine

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Mesoridazine
Mesoridazine.svg
Clinical data
Trade names Serentil
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a682306
Routes of
administration		 Oral, intravenous
Drug class Typical antipsychotic
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding 4%
Metabolism Hepatic/renal
Elimination half-life 24 to 48 hours
Excretion Biliary and renal
Identifiers
  • 10-[2-(1-methylpiperidin-2-yl)ethyl]-2-methylsulfinylphenothiazine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C21H26N2OS2
Molar mass 386.57 g·mol−1
3D model (JSmol)
Melting point 130 °C (266 °F)
Solubility in water insoluble mg/mL (20 °C)
  • O=S(c2cc1N(c3c(Sc1cc2)cccc3)CCC4N(C)CCCC4)C
  • 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 checkY
  • Key:SLVMESMUVMCQIY-UHFFFAOYSA-N checkY
  (verify)

Mesoridazine (Serentil) is a piperidine neuroleptic drug belonging to the class of drugs called phenothiazines, used in the treatment of schizophrenia. It is a metabolite of thioridazine. The drug's name is derived from the methylsulfoxy and piperidine functional groups in its chemical structure.

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Mesoridazine was withdrawn from the United States market in 2004 due to dangerous side effects, namely irregular heart beat and QT-prolongation of the electrocardiogram.

It currently appears to be unavailable worldwide.

Synthesis

Thieme Synthesis: Patent:

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).


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