Details
Stereochemistry | MIXED |
Molecular Formula | C21H26N2OS2 |
Molecular Weight | 386.5769 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 0 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCCCC1CCN2c3ccccc3Sc4ccc(cc42)S(=O)C
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
Molecular Formula | C21H26N2OS2 |
Molecular Weight | 386.5769 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
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 |
---|---|---|---|
Target ID: P14416 Gene ID: 1813.0 Gene Symbol: DRD2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15357957 |
3.0 nM [Ki] | ||
Target ID: P28223 Gene ID: 3356.0 Gene Symbol: HTR2A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15357957 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | SERENTIL Approved UseIndicated for treatment severely ill schizophrenic patients who have failed to respond adequately to treatment with other antipsychotic drugs Launch Date4.9248E9 |
|||
Primary | SERENTIL Approved UsePsychosis Launch Date4.9248E9 |
Cmax
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 |
T1/2
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 |
Funbound
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 |
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
AE | Significance | Dose | Population |
---|---|---|---|
Ventricular arrhythmias and cardiac arrest | grade 4, 1 patient Disc. AE |
3.1 g single, oral Overdose |
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: |
PubMed
Title | Date | PubMed |
---|---|---|
Neuroleptics and neurologic reactions. | 1973 Mar |
|
Drug-induced dystonia. | 1975 May |
|
Death attributed to ventricular arrhythmia induced by thioridazine in combination with a single Contac C capsule. | 1978 Oct 7 |
|
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 |
|
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 May |
|
Inverse agonist actions of typical and atypical antipsychotic drugs at the human 5-hydroxytryptamine(2C) receptor. | 2001 Oct |
|
Medications that prolong the QT interval. | 2003 Aug 27 |
|
The relevance of prolonged QTc measurement to pediatric psychopharmacology. | 2003 Jun |
|
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 |
|
Mesoridazine: an open-channel blocker of human ether-a-go-go-related gene K+ channel. | 2004 Jan |
|
Diastereotopic analysis of mesoridazine besylate (Serentil). | 2004 Oct |
|
Synthesis, receptor binding and functional studies of mesoridazine stereoisomers. | 2004 Sep 6 |
|
Schizophrenia, antipsychotic drugs, and cardiovascular disease. | 2005 |
|
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 |
|
Time to discontinuation of atypical versus typical antipsychotics in the naturalistic treatment of schizophrenia. | 2006 Feb 21 |
|
Effect of thioridazine on gap junction intercellular communication in connexin 43-expressing cells. | 2006 Jul |
|
Frequency of high-risk use of QT-prolonging medications. | 2006 Jun |
|
Altering extracellular potassium concentration does not modulate drug block of human ether-a-go-go-related gene (hERG) channels. | 2006 Nov |
|
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 |
|
Factors affecting drug concentrations and QT interval during thioridazine therapy. | 2007 Nov |
|
Comparison of the effects of thioridazine and mesoridazine on the QT interval in healthy adults after single oral doses. | 2007 Nov |
|
Using molecular similarity to highlight the challenges of routine immunoassay-based drug of abuse/toxicology screening in emergency medicine. | 2009 Apr 28 |
|
Iatrogenic QT Abnormalities and Fatal Arrhythmias: Mechanisms and Clinical Significance. | 2009 Aug |
|
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 Dec |
|
Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions. | 2010 Apr 7 |
|
Oncologic outcomes of robotic-assisted total mesorectal excision for the treatment of rectal cancer. | 2010 May |
|
Phenothiazines inhibit hepatitis C virus entry, likely by increasing the fluidity of cholesterol-rich membranes. | 2013 Jun |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10991983
[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
Edited
Sat Jun 26 03:18:46 UTC 2021
by
admin
on
Sat Jun 26 03:18:46 UTC 2021
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Record UNII |
5XE4NWM740
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000007544
Created by
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WHO-VATC |
QN05AC03
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NDF-RT |
N0000007544
Created by
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NCI_THESAURUS |
C29710
Created by
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NDF-RT |
N0000007544
Created by
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NDF-RT |
N0000175746
Created by
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NCI_THESAURUS |
C66883
Created by
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WHO-ATC |
N05AC03
Created by
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Code System | Code | Type | Description | ||
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4078
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PRIMARY | |||
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CHEMBL1088
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PRIMARY | |||
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7227
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PRIMARY | |||
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5XE4NWM740
Created by
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PRIMARY | |||
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MESORIDAZINE
Created by
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PRIMARY | |||
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Mesoridazine
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PRIMARY | |||
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1712
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2019
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PRIMARY | |||
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M7250
Created by
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PRIMARY | Merck Index | ||
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5588-33-0
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PRIMARY | |||
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3357
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SUB08786MIG
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DB00933
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5588-33-0
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C66100
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D008653
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6779
Created by
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PRIMARY | RxNorm |
Related Record | Type | Details | ||
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TARGET -> INHIBITOR | |||
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BINDER->LIGAND |
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Related Record | Type | Details | ||
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PARENT -> METABOLITE ACTIVE |
Related Record | Type | Details | ||
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PARENT -> IMPURITY |
For the calculation of contents, multiply the peak areas by 2.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
For the calculation of contents, multiply the peak areas by 2.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |