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Mesoridazine

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	N05AC03 (WHO)
Legal status
Legal status	BR: Class C1 (Other controlled substances) In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding	4%
Metabolism	Hepatic/renal
Elimination half-life	24 to 48 hours
Excretion	Biliary and renal
Identifiers
IUPAC name 10--2-methylsulfinylphenothiazine
CAS Number	5588-33-0
PubChem CID	4078
IUPHAR/BPS	7227
DrugBank	DB00933
ChemSpider	3936
UNII	5XE4NWM740
KEGG	D02671
ChEBI	CHEBI:6780
ChEMBL	ChEMBL1088
CompTox Dashboard (EPA)	DTXSID3023265
Chemical and physical data
Formula	C21H26N2OS2
Molar mass	386.57 g·mol
3D model (JSmol)	Interactive image
Melting point	130 °C (266 °F)
Solubility in water	insoluble mg/mL (20 °C)
SMILES O=S(c2cc1N(c3c(Sc1cc2)cccc3)CCC4N(C)CCCC4)C
InChI 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 Key:SLVMESMUVMCQIY-UHFFFAOYSA-N
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Mesoridazine (Serentil) is a phenothiazine class drug that is used in the treatment of schizophrenia. 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.

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Mesoridazine was withdrawn from the United States market in 2004 due to dangerous side effects, namely irregular heart beat and QT-prolongation of the electrocardiogram.

Mesoridazine is on the FDA's Discontinued Drug Product List.

Synthesis

2-Methylthiophenothiazine (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 (3). Introduction of the sidechain by alkylation with 2-(2-chlorethyl)-1-methylpiperidine (6) in the presence of sodamide, afforded the desired mesoridazine (5).

References

1. 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). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
2. 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.
3. American Society of Health-System Pharmacists (AHFS). "Mesoridazine". Medline Plus. U.S. National Library of Medicine.
4. Food and Drug Administration (April 2021). "Determination That SERENTIL (Mesoridazine Besylate) Tablets, 10 Milligrams, 25 Milligrams, 50 Milligrams, and 100 Milligrams, Were Not Withdrawn From Sale for Reasons of Safety or Effectiveness". National Register. U.S. Government.
5. 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.
6. 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.
7. Schwarb Gustav, Renz Jany, Bourquin Jean-Pierre, U.S. patent 3,084,161 (1963 to Sandoz Ltd).

• M1 receptor antagonists
• M2 receptor antagonists
• M3 receptor antagonists
• M4 receptor antagonists
• M5 receptor antagonists
• Phenothiazines
• Piperidines
• Sulfoxides
• Tertiary amines
• Typical antipsychotics
• Withdrawn drugs