Mesoridazine

{{MCN|date=April 2024}}

{{Short description|Typical antipsychotic medication}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 462249027

| IUPAC_name = 10-[2-(1-methylpiperidin-2-yl)ethyl]-2-methylsulfinylphenothiazine

| image = Mesoridazine.svg

| image_class = skin-invert-image

| tradename = Serentil

| Drugs.com = {{drugs.com|CONS|mesoridazine}}

| MedlinePlus = a682306

| pregnancy_US = N

| legal_AU =

| legal_BR = C1

| legal_BR_comment = {{Cite web |last=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control |url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

| legal_CA =

| legal_DE =

| legal_NZ =

| legal_UK =

| legal_US =

| legal_EU =

| legal_UN =

| legal_status = Rx-only

| routes_of_administration = Oral, intravenous

| class = Typical antipsychotic

| bioavailability =

| protein_bound = 4%

| metabolism = Hepatic/renal

| elimination_half-life = 24 to 48 hours

| excretion = Biliary and renal

| IUPHAR_ligand = 7227

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 5588-33-0

| ATC_prefix = N05

| ATC_suffix = AC03

| ATC_supplemental =

| PubChem = 4078

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00933

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 3936

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 5XE4NWM740

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D02671

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 6780

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1088

| C=21 | H=26 | N=2 | O=1 | S=2

| smiles = O=S(c2cc1N(c3c(Sc1cc2)cccc3)CCC4N(C)CCCC4)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = SLVMESMUVMCQIY-UHFFFAOYSA-N

| melting_point = 130

| solubility = insoluble

}}

Mesoridazine (Serentil) is a phenothiazine class drug that is used in the treatment of schizophrenia.{{Cite journal |vauthors=Gershon S, Sakalis G, Bowers PA |date=December 1981 |title=Mesoridazine -- a pharmacodynamic and pharmacokinetic profile |journal=The Journal of Clinical Psychiatry |volume=42 |issue=12 |pages=463–9 |pmid=7031039}} 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.{{Cite web |last=American Society of Health-System Pharmacists (AHFS) |title=Mesoridazine |url=https://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a682306.html |website=Medline Plus |publisher=U.S. National Library of Medicine}}

Mesoridazine is on the FDA's Discontinued Drug Product List.{{Cite web | last=Food and Drug Administration |title=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 |url=https://www.federalregister.gov/documents/2021/04/01/2021-06722/determination-that-serentil-mesoridazine-besylate-tablets-10-milligrams-25-milligrams-50-milligrams |website=National Register |date=April 2021 |publisher=U.S. Government}}