MESORIDAZINE

Details

Stereochemistry	MIXED
Molecular Formula	C21H26N2OS2
Molecular Weight	386.574
Optical Activity	UNSPECIFIED
Defined Stereocenters	0 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCCCC1CCN2C3=CC=CC=C3SC4=C2C=C(C=C4)[S+](C)[O-]

InChI

InChIKey=SLVMESMUVMCQIY-UHFFFAOYSA-N

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

HIDE SMILES / InChI

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
Neuroleptics and neurologic reactions.	1973 Mar	4144147
Death attributed to ventricular arrhythmia induced by thioridazine in combination with a single Contac C capsule.	1978 Oct 7	709472
Diastereotopic analysis of mesoridazine besylate (Serentil).	2004 Oct	15290689
Synthesis, receptor binding and functional studies of mesoridazine stereoisomers.	2004 Sep 6	15357957
Schizophrenia, antipsychotic drugs, and cardiovascular disease.	2005	16107178
Time to discontinuation of atypical versus typical antipsychotics in the naturalistic treatment of schizophrenia.	2006 Feb 21	16504026
Frequency of high-risk use of QT-prolonging medications.	2006 Jun	16178046
Efficacy of typical and atypical antipsychotics for primary and comorbid anxiety symptoms or disorders: a review.	2006 Sep	17017818
No effect of the CYP1A2*1F genotype on thioridazine, mesoridazine, sulforidazine plasma concentrations in psychiatric patients.	2007 May	17345072
Hospitalization risk associated with typical and atypical antipsychotic use in community-dwelling elderly patients.	2008 Oct	19028375
Relevance of CYP2D6 -1584C>G polymorphism for thioridazine:mesoridazine plasma concentration ratio in psychiatric patients.	2009 Jul	19604081
Identification of novel substrates for human cytochrome P450 2J2.	2010 Feb	19923256

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 `Wed Apr 02 09:02:16 GMT 2025` Edited by `admin` on `Wed Apr 02 09:02:16 GMT 2025`
Record UNII	5XE4NWM740
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MESORIDAZINE

Official Name

English

LIDANAR

Preferred Name

English

mesoridazine [INN]

Common Name

English

THIORIDAZINE-2-SULFOXIDE

Common Name

English

MESORIDAZINE [MI]

Common Name

English

MESORIDAZINE [VANDF]

Common Name

English

Mesoridazine [WHO-DD]

Common Name

English

NC-123

Code

English

NSC-186066

Code

English

THIORIDAZINE IMPURITY B [EP IMPURITY]

Common Name

English

TPS-23

Code

English

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

Systematic Name

English

MESORIDAZINE [HSDB]

Common Name

English

10-[2(1-Methyl-2-piperidyl)ethyl]-2-(methylsulfinyl)-phenothiazine

Systematic Name

English

MESORIDAZINE [USAN]

Common Name

English

MESORIDAZINE [MART.]

Common Name

English

THIORIDAZINE HYDROCHLORIDE IMPURITY B [EP IMPURITY]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000007544