MESORIDAZINE BESYLATE

Details

Stereochemistry	MIXED
Molecular Formula	C21H26N2OS2.C6H6O3S
Molecular Weight	544.749
Optical Activity	UNSPECIFIED
Defined Stereocenters	0 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(=O)(=O)C1=CC=CC=C1.CN2CCCCC2CCN3C4=C(SC5=C3C=C(C=C5)[S+](C)[O-])C=CC=C4

InChI

InChIKey=CRJHBCPQHRVYBS-UHFFFAOYSA-N

InChI=1S/C21H26N2OS2.C6H6O3S/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;7-10(8,9)6-4-2-1-3-5-6/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3;1-5H,(H,7,8,9)

HIDE SMILES / InChI

Molecular Formula	C6H6O3S
Molecular Weight	158.175
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C21H26N2OS2
Molecular Weight	386.574
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/16-774S073.pdf

Mesoridazine (brand name Serentil) is a phenothiazine antipsychotic. It was marketed in the U.S. for the treatment of schizophrenia, behavioral problems in mental deficiency and chronic brain syndrome, alcoholism and psychoneurotic symptoms, such as anxiety and tension. Due to the risk of serious cardiac events the indicated use of Serentil was limited to severely ill schizophrenic patients who fail other therapies. Based upon animal studies, mesoridazine acts indirectly on reticular formation, whereby neuronal activity into reticular formation is reduced without affecting its intrinsic ability to activate the cerebral cortex. Mesoridazine shows a moderate adrenergic blocking activity in vitro and in vivo and antagonizes 5-hydroxytryptamine in vivo.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
D(2) dopamine receptor 58 Target ID: P14416 Gene ID: 1813.0 Gene Symbol: DRD2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15357957	Antagonist 2849		3.0 nM [Ki]
5-hydroxytryptamine receptor 2A 73 Target ID: P28223 Gene ID: 3356.0 Gene Symbol: HTR2A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15357957	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 305 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/16-774S073.pdf	Primary		Approved 8583	SERENTIL Approved Use Indicated for treatment severely ill schizophrenic patients who have failed to respond adequately to treatment with other antipsychotic drugs Launch Date 1970
Psychosis 16 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/16-774S073.pdf	Primary		Approved 8583	SERENTIL Approved Use Psychosis Launch Date 1970

C_max

Value	Dose	Co-administered	Analyte	Population
240 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17410120/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		MESORIDAZINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
2400 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17410120/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		MESORIDAZINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
12.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17410120/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		MESORIDAZINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
75% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17410120/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		MESORIDAZINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
3.1 g single, oral Overdose Dose: 3.1 g Route: oral Route: single Dose: 3.1 g Sources: https://pubmed.ncbi.nlm.nih.gov/3177997/	healthy, 20 years Health Status: healthy Age Group: 20 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/3177997/	Disc. AE: Ventricular arrhythmias and cardiac arrest... AEs leading to discontinuation/dose reduction: Ventricular arrhythmias and cardiac arrest (grade 4, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/3177997/
16 ug/mL single, oral Overdose Dose: 16 ug/mL Route: oral Route: single Dose: 16 ug/mL Sources: https://pubmed.ncbi.nlm.nih.gov/3824877/	unhealthy, 23 years Health Status: unhealthy Age Group: 23 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/3824877/	Disc. AE: Death... AEs leading to discontinuation/dose reduction: Death (grade 5, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/3824877/
10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1140909/	healthy, 48-62 years Health Status: healthy Age Group: 48-62 years Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/1140909/	Sources: https://pubmed.ncbi.nlm.nih.gov/1140909/

AEs

AE	Significance	Dose	Population
Ventricular arrhythmias and cardiac arrest	grade 4, 1 patient Disc. AE	3.1 g single, oral Overdose Dose: 3.1 g Route: oral Route: single Dose: 3.1 g Sources: https://pubmed.ncbi.nlm.nih.gov/3177997/	healthy, 20 years Health Status: healthy Age Group: 20 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/3177997/
Death	grade 5, 1 patient Disc. AE	16 ug/mL single, oral Overdose Dose: 16 ug/mL Route: oral Route: single Dose: 16 ug/mL Sources: https://pubmed.ncbi.nlm.nih.gov/3824877/	unhealthy, 23 years Health Status: unhealthy Age Group: 23 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/3824877/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	P-gp 2052

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://jpet.aspetjournals.org/content/jpet/365/2/336.full.pdf?with-ds=yes#page=4 Page: 4.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/14734057/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6780	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6780
ChemicalBook	CB0157447	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0157447
ChemicalBook	CB0875422	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0875422

PubMed

Title	Date	PubMed
Phenothiazines inhibit hepatitis C virus entry, likely by increasing the fluidity of cholesterol-rich membranes.	2013-06	23529728
Oncologic outcomes of robotic-assisted total mesorectal excision for the treatment of rectal cancer.	2010-05	20395863
Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions.	2010-04-07	20396637
Phenothiazine-type antipsychotics elicit cutaneous analgesia in rats.	2010-03	20434106
Identification of novel substrates for human cytochrome P450 2J2.	2010-02	19923256
Mechanisms of action of antipsychotic drugs of different classes, refractoriness to therapeutic effects of classical neuroleptics, and individual variation in sensitivity to their actions: Part II.	2009-12	20514211
Mechanisms of action of antipsychotic drugs of different classes, refractoriness to therapeutic effects of classical neuroleptics, and individual variation in sensitivity to their actions: Part I.	2009-12	20514210
Iatrogenic QT Abnormalities and Fatal Arrhythmias: Mechanisms and Clinical Significance.	2009-08	20676275
Relevance of CYP2D6 -1584C>G polymorphism for thioridazine:mesoridazine plasma concentration ratio in psychiatric patients.	2009-07	19604081
Pediatric thioridazine poisoning as a result of a pharmacy compounding error.	2009-06-08	21589825
Using molecular similarity to highlight the challenges of routine immunoassay-based drug of abuse/toxicology screening in emergency medicine.	2009-04-28	19400959
Hospitalization risk associated with typical and atypical antipsychotic use in community-dwelling elderly patients.	2008-10	19028375
Factors affecting drug concentrations and QT interval during thioridazine therapy.	2007-11	17460606
Comparison of the effects of thioridazine and mesoridazine on the QT interval in healthy adults after single oral doses.	2007-11	17410120
No effect of the CYP1A2*1F genotype on thioridazine, mesoridazine, sulforidazine plasma concentrations in psychiatric patients.	2007-05	17345072
Altering extracellular potassium concentration does not modulate drug block of human ether-a-go-go-related gene (hERG) channels.	2006-11	17042915
Efficacy of typical and atypical antipsychotics for primary and comorbid anxiety symptoms or disorders: a review.	2006-09	17017818
Effect of thioridazine on gap junction intercellular communication in connexin 43-expressing cells.	2006-07	16685461
Frequency of high-risk use of QT-prolonging medications.	2006-06	16178046
Time to discontinuation of atypical versus typical antipsychotics in the naturalistic treatment of schizophrenia.	2006-02-21	16504026
Intrinsic efficacy of antipsychotics at human D2, D3, and D4 dopamine receptors: identification of the clozapine metabolite N-desmethylclozapine as a D2/D3 partial agonist.	2005-12	16135699
Expert Canadian consensus suggestions on the rational, clinical use of ziprasidone in the treatment of schizophrenia and related psychotic disorders.	2005-06	18568067
Schizophrenia, antipsychotic drugs, and cardiovascular disease.	2005	16107178
Diastereotopic analysis of mesoridazine besylate (Serentil).	2004-10	15290689
Synthesis, receptor binding and functional studies of mesoridazine stereoisomers.	2004-09-06	15357957
Physical health monitoring of patients with schizophrenia.	2004-08	15285957
Mesoridazine: an open-channel blocker of human ether-a-go-go-related gene K+ channel.	2004-01	14734057
Medications that prolong the QT interval.	2003-08-27	12941670
The relevance of prolonged QTc measurement to pediatric psychopharmacology.	2003-06	12921471
Thioridazine steady-state plasma concentrations are influenced by tobacco smoking and CYP2D6, but not by the CYP2C9 genotype.	2003-05	12682803
Effect of thioridazine dosage on the debrisoquine hydroxylation phenotype in psychiatric patients with different CYP2D6 genotypes.	2001-12	11802093
Inverse agonist actions of typical and atypical antipsychotic drugs at the human 5-hydroxytryptamine(2C) receptor.	2001-10	11561066
Activity of phenothiazines against antibiotic-resistant Mycobacterium tuberculosis: a review supporting further studies that may elucidate the potential use of thioridazine as anti-tuberculosis therapy.	2001-05	11328759
Thioridazine (Mellaril) and mesoridazine (Serentil): prolongation of the QTc interval.	2001-01-09	11202679
Cardiac arrhythmia following rapid imipramine withdrawal.	1989-02-15	2467692
Complete heart block associated with mesoridazine and lithium combination.	1987-03	3102462
Rapid death resulting from mesoridazine overdose.	1987-02	3824877
Death attributed to ventricular arrhythmia induced by thioridazine in combination with a single Contac C capsule.	1978-10-07	709472
Drug-induced dystonia.	1975-05	1119613
Neuroleptics and neurologic reactions.	1973-03	4144147

Patents

Sample Use Guides

In Vivo Use Guide

A starting dose of 50 mg of Serentil (Mesoridazine) three times a day is recommended. The usual optimal total daily dose range is 100-400 mg per day.

Route of Administration: Oral

In Vitro Use Guide

[3H]IP production was measured in COS-7 cells expressing human 5-HT2C-INI receptors at 2.7 pmol/mg of protein. Cells were treated with or without 1 uM Mesoridazine. Basal activity was determined by subtracting [3H]IP produced in cells transfected with vector only.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:22:51 GMT 2025` Edited by `admin` on `Mon Mar 31 18:22:51 GMT 2025`
Record UNII	T4G2I958J2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MESORIDAZINE BESILATE

Preferred Name

English

MESORIDAZINE BESYLATE

Common Name

English

NSC-760073

Code

English

MESORIDAZINE BENZENESULFONATE [MI]

Common Name

English

10H-PHENOTHIAZINE, 10-(2-(1-METHYL-2-PIPERIDINYL)ETHYL)-2-(METHYLSULFINYL)-, (±)-, MONOBENZENESULFONATE

Systematic Name

English

MESORIDAZINE BESYLATE [ORANGE BOOK]

Common Name

English

MESORIDAZINE BENZENESULFONATE

Common Name

English

SERENTIL

Brand Name

English

MESORIDAZINE BESYLATE [VANDF]

Common Name

English

(±)-10-(2-(1-METHYL-2-PIPERIDYL)ETHYL)-2-(METHYLSULPHINYL)PHENOTHIAZINE MONOBENZENESULPHONATE

Systematic Name

English

MESORIDAZINE BESYLATE [USP-RS]

Common Name

English

Mesoridazine besilate [WHO-DD]

Common Name

English

MESORIDAZINE BESYLATE [USP IMPURITY]

Common Name

English

MESORIDAZINE BESILATE [MART.]

Common Name

English

10H-PHENOTHIAZINE, 10-(2-(1-METHYL-2-PIPERIDINYL)ETHYL)-2-(METHYLSULPHINYL)-, (±)-, MONOBENZENESULPHONATE

Systematic Name

English

(±)-10-(2-(1-METHYL-2-PIPERIDYL)ETHYL)-2-(METHYLSULFINYL)PHENOTHIAZINE MONOBENZENESULFONATE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66883