U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of MESORIDAZINE

SMILES

CN1CCCCC1CCN2C3=CC(=CC=C3SC4=C2C=CC=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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P14416
Gene ID: 1813.0
Gene Symbol: DRD2
Target Organism: Homo sapiens (Human)
3.0 nM [Ki]
Target ID: P28223
Gene ID: 3356.0
Gene Symbol: HTR2A
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SERENTIL

Approved Use

Indicated for treatment severely ill schizophrenic patients who have failed to respond adequately to treatment with other antipsychotic drugs

Launch Date

4.9248E9
Primary
SERENTIL

Approved Use

Psychosis

Launch Date

4.9248E9
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
240 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
2400 ng × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
12.5 h
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
75%
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

Doses

DosePopulationAdverse events​
3.1 g single, oral
Overdose
Dose: 3.1 g
Route: oral
Route: single
Dose: 3.1 g
Sources:
healthy, 20 years
n = 1
Health Status: healthy
Condition: suicide attempt
Age Group: 20 years
Sex: F
Population Size: 1
Sources:
Disc. AE: Ventricular arrhythmias and cardiac arrest...
AEs leading to
discontinuation/dose reduction:
Ventricular arrhythmias and cardiac arrest (grade 4, 1 patient)
Sources:
16 ug/mL single, oral
Overdose
Dose: 16 ug/mL
Route: oral
Route: single
Dose: 16 ug/mL
Sources:
unhealthy, 23 years
n = 1
Health Status: unhealthy
Condition: mentally retarded
Age Group: 23 years
Sex: F
Population Size: 1
Sources:
Disc. AE: Death...
AEs leading to
discontinuation/dose reduction:
Death (grade 5, 1 patient)
Sources:
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:
healthy, 48-62 years
n = 7
Health Status: healthy
Age Group: 48-62 years
Sex: unknown
Population Size: 7
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
healthy, 20 years
n = 1
Health Status: healthy
Condition: suicide attempt
Age Group: 20 years
Sex: F
Population Size: 1
Sources:
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:
unhealthy, 23 years
n = 1
Health Status: unhealthy
Condition: mentally retarded
Age Group: 23 years
Sex: F
Population Size: 1
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Neuroleptics and neurologic reactions.
1973 Mar
Complete heart block associated with mesoridazine and lithium combination.
1987 Mar
Effect of thioridazine dosage on the debrisoquine hydroxylation phenotype in psychiatric patients with different CYP2D6 genotypes.
2001 Dec
Thioridazine (Mellaril) and mesoridazine (Serentil): prolongation of the QTc interval.
2001 Jan 9
Thioridazine steady-state plasma concentrations are influenced by tobacco smoking and CYP2D6, but not by the CYP2C9 genotype.
2003 May
Physical health monitoring of patients with schizophrenia.
2004 Aug
Diastereotopic analysis of mesoridazine besylate (Serentil).
2004 Oct
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 Dec
Expert Canadian consensus suggestions on the rational, clinical use of ziprasidone in the treatment of schizophrenia and related psychotic disorders.
2005 Jun
Efficacy of typical and atypical antipsychotics for primary and comorbid anxiety symptoms or disorders: a review.
2006 Sep
No effect of the CYP1A2*1F genotype on thioridazine, mesoridazine, sulforidazine plasma concentrations in psychiatric patients.
2007 May
Comparison of the effects of thioridazine and mesoridazine on the QT interval in healthy adults after single oral doses.
2007 Nov
Hospitalization risk associated with typical and atypical antipsychotic use in community-dwelling elderly patients.
2008 Oct
Using molecular similarity to highlight the challenges of routine immunoassay-based drug of abuse/toxicology screening in emergency medicine.
2009 Apr 28
Relevance of CYP2D6 -1584C>G polymorphism for thioridazine:mesoridazine plasma concentration ratio in psychiatric patients.
2009 Jul
Pediatric thioridazine poisoning as a result of a pharmacy compounding error.
2009 Jun 8
Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions.
2010 Apr 7
Phenothiazine-type antipsychotics elicit cutaneous analgesia in rats.
2010 Mar
Oncologic outcomes of robotic-assisted total mesorectal excision for the treatment of rectal cancer.
2010 May
Patents

Sample Use Guides

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
[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.
Name Type Language
MESORIDAZINE
HSDB   INN   MART.   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official 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
LIDANAR
Brand Name 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
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
WHO-VATC QN05AC03
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
NDF-RT N0000007544
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
NCI_THESAURUS C29710
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
NDF-RT N0000007544
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
NDF-RT N0000175746
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
NCI_THESAURUS C66883
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
WHO-ATC N05AC03
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
Code System Code Type Description
PUBCHEM
4078
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
PRIMARY
NSC
186066
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
PRIMARY
ChEMBL
CHEMBL1088
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
PRIMARY
IUPHAR
7227
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
PRIMARY
FDA UNII
5XE4NWM740
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
PRIMARY
WIKIPEDIA
MESORIDAZINE
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
PRIMARY
LACTMED
Mesoridazine
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
PRIMARY
DRUG CENTRAL
1712
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
PRIMARY
CHEBI
6780
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
PRIMARY
INN
2019
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
PRIMARY
MERCK INDEX
m7250
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
PRIMARY Merck Index
CAS
5588-33-0
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
PRIMARY
HSDB
3357
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
PRIMARY
EVMPD
SUB08786MIG
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
PRIMARY
DRUG BANK
DB00933
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
PRIMARY
EPA CompTox
DTXSID3023265
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
PRIMARY
SMS_ID
100000081186
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
PRIMARY
CHEBI
6781
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
PRIMARY
NCI_THESAURUS
C66100
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
PRIMARY
MESH
D008653
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
PRIMARY
RXCUI
6779
Created by admin on Sat Dec 16 17:21:14 UTC 2023 , Edited by admin on Sat Dec 16 17:21:14 UTC 2023
PRIMARY RxNorm