Mesoridazine

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Mesoridazine
Mesoridazine.png
Mesoridazine0.gif
Clinical data
Trade namesSerentil
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa682306
Pregnancy
category
  • US: C (Risk not ruled out)
Routes of
administration
oral, intravenous
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding4%
MetabolismHepatic/Renal
Elimination half-life24 to 48 hours
ExcretionBiliary and renal
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number{{#property:P628}}
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Chemical and physical data
FormulaC21H26N2OS2
Molar mass386.576 g/mol
3D model (JSmol)
Melting point130 °C (266 °F)
Solubility in waterinsoluble mg/mL (20 °C)
  (verify)

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [2]

Overview

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Mesoridazine was withdrawn from the United States market in 2004 due to dangerous side effects, namely irregular heart beat and QT-prolongation of the electrocardiogram.[1]

It currently appears to be unavailable worldwide.

Chemistry

Mesoridazine (10-[2-(1-methyl-2-piperidyl)ethyl]-2-(methylsufinyl)phenothiazine) is synthesized by an analogous scheme to that seen already for thioridazine.

Mesoridazine synthesis.png

However, it is also synthesized by alkylating the acidic form of 2-methylthiophenothiazine -methylsulfonylphenothiazine- using 2-(2-chloroethyl)-1-methylpiperidine. 2-methylthiophenothiazine is initially acylated at the nitrogen atom using acetic anhydride, giving 10-acetyl-2-methylthiophenothiazine. The resulting acetyl derivative is further oxidized by hydrogen peroxide into 10-acetyl-2-methylsulfonylpenothiazine. Deacylation of this product in potassium carbonate methanol solution gives 2-methylsulfanylphenothiazine, which is alkylated by 2-(2-chlorethyl)-1-methylpiperidine in the presence of sodamide, affording the desired mesoridazine.

References


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