Details
Stereochemistry | RACEMIC |
Molecular Formula | C21H26N2S2 |
Molecular Weight | 370.5775 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCCCC1CCN2c3ccccc3Sc4ccc(cc42)SC
InChI
InChIKey=KLBQZWRITKRQQV-UHFFFAOYSA-N
InChI=1S/C21H26N2S2/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)25-21-11-10-17(24-2)15-19(21)23/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3
Molecular Formula | C21H26N2S2 |
Molecular Weight | 370.5775 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionSources: https://www.drugs.com/pro/thioridazine.html
Sources: https://www.drugs.com/pro/thioridazine.html
Thioridazine (Mellaril or Melleril) is a piperidine typical antipsychotic drug belonging to the phenothiazine drug group and was previously widely used in the treatment of schizophrenia and psychosis. Thioridazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the brain; blocks alpha-adrenergic effect depresses the release of hypothalamic and hypophyseal hormones and is believed to depress the reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis. Thioridazine primary use in medicine was the treatment of schizophrenia. Thioridazine was also tried with some success as a treatment for various psychiatric symptoms seen in people with dementia, but chronic use of thioridazine and other antipsychotics in people with dementia is not recommended. Thioridazine prolongs the QTc interval in a dose-dependent manner. It produces significantly less extrapyramidal side effects than most first-generation antipsychotics. Its use, along with the use of other typical antipsychotics, has been associated with degenerative retinopathies. It has a higher propensity for causing anticholinergic side effects coupled with a lower propensity for causing extrapyramidal side effects and sedation than chlorpromazine but also has a higher incidence of hypotension and cardiotoxicity. It is also known to possess a relatively high liability for causing orthostatic hypotension compared to other antipsychotics. Similarly to other first-generation antipsychotics, it has a relatively high liability for causing prolactin elevation. It is the moderate risk of causing weight gain.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12747773 |
27.0 nM [Ki] | ||
Target ID: CHEMBL265 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2888897 |
17.3 nM [IC50] | ||
Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7898773 |
6.06 null [pIC50] | ||
Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7898773 |
6.32 null [pIC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | MELLARIL-S Approved UseThioridazine hydrochloride tablets are indicated for the management of schizophrenic patients who fail to respond adequately to treatment with other antipsychotic drugs. Due to the risk of significant, potentially life threatening, proarrhythmic effects with thioridazine treatment, thioridazine hydrochloride tablets should be used only in patients who have failed to respond adequately to treatment with appropriate courses of other antipsychotic drugs, either because of insufficient effectiveness or the inability to achieve an effective dose due to intolerable adverse effects from those drugs. Consequently, before initiating treatment with thioridazine hydrochloride tablets, it is strongly recommended that a patient be given at least two trials, each with a different antipsychotic drug product, at an adequate dose, and for an adequate duration (see WARNINGS and CONTRAINDICATIONS). However, the prescriber should be aware that thioridazine hydrochloride tablets have not been systematically evaluated in controlled trials in treatment refractory schizophrenic patients and its efficacy in such patients is unknown. Launch Date2.77516812E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
131 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10952475 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
THIORIDAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
117 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2007317 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
THIORIDAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1338 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10952475 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
THIORIDAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
709 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2007317 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
THIORIDAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10952475 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
THIORIDAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
4.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2007317 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
THIORIDAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5% |
THIORIDAZINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: lithium Sources: |
unhealthy |
Disc. AE: Torsade de pointes... AEs leading to discontinuation/dose reduction: Torsade de pointes (1 patient) Sources: |
400 mg 1 times / day multiple, oral Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy |
Disc. AE: Hyperthermia malignant... AEs leading to discontinuation/dose reduction: Hyperthermia malignant (1 patient) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Torsade de pointes | 1 patient Disc. AE |
800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: lithium Sources: |
unhealthy |
Hyperthermia malignant | 1 patient Disc. AE |
400 mg 1 times / day multiple, oral Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/16382211/ Page: 4.0 |
no | |||
Sources: https://dmd.aspetjournals.org/content/27/9/1078.full Page: abstract |
yes [IC50 2.7 uM] | |||
Page: 3.0 |
yes | |||
Page: 3.0 |
yes | |||
Page: abstract |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 10.0 |
weak | |||
Page: 10.0 |
weak | |||
Page: 10.0 |
yes | |||
Page: 3.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 4.0 |
||||
Page: 4.0 |
PubMed
Title | Date | PubMed |
---|---|---|
The bucco-linguo-masticatory syndrome as a side-effect of neuroleptics therapy. | 1967 |
|
Recurrent major ventricular arrhythmias associated with thioridazine therapy. | 1971 Nov |
|
Thioridazine in schizophrenia. | 1971 Sep 20 |
|
Thioridazine incontinence. | 1972 Jan 10 |
|
Hypertensive episodes after adding methylphenidate (Ritalin) to tricyclic antidepressants. (Report of three cases and review of clinical advantages). | 1972 Jul-Aug |
|
Thioridazine toxicity. Agranulocytosis and hepatitis with encephalopathy. | 1973 Apr 23 |
|
The therapeutic use of diazepam for akathisia. | 1973 Jul-Aug |
|
Ventricular arrhythmias associated with use of thioridazine hydrochloride in alcohol withdrawal. | 1973 Nov 24 |
|
Neuroleptic-induced tardiave dyskinesias in nonpsychotic patients. | 1974 Apr |
|
Electrocardiographic changes and cardiac arrhythmias in patients receiving psychotropic drugs. | 1976 Feb |
|
Seven cases of somnambulism induced by drugs. | 1979 Jul |
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Effect of bromocriptine mesylate on induced hyperprolactinemia in stabilized psychiatric outpatients undergoing neuroleptic treatment. | 1985 |
|
Thioridazine toxicity--an experimental cardiovascular study of thioridazine and its major metabolites in overdose. | 1985 Apr |
|
Cardiorespiratory depression and haemolysis due to thioridazine overdose in the rat. | 1985 Jul |
|
Drug-induced torsade de pointes. | 1985 Nov-Dec |
|
The effect of thioridazine on prolactinoma growth in a schizophrenic man: case report. | 1985 Oct |
|
Tics with combined thioridazine-methylphenidate therapy: case report. | 1986 Jan |
|
Tourette-like syndrome following low dose short-term neuroleptic treatment. | 1986 May |
|
Neuroleptic-induced tics in two hyperactive children. | 1986 Sep |
|
Meige's syndrome associated with neuroleptic treatment. | 1988 Apr |
|
Attempted strangulation during phenothiazine-induced sleep-walking and night terrors. | 1988 Nov |
|
A case of secondary mania. | 1988 Winter |
|
Drug-induced tremor of the tongue. | 1989 Feb |
|
Renal and hepatic impairment in association with diclofenac administration. | 1989 Jul |
|
Myxedema coma associated with lithium therapy. | 1989 Sep |
|
Seizure promotion and protection by D-1 and D-2 dopaminergic drugs in the mouse. | 1990 Aug |
|
Neurologic approach to drug-induced movement disorders: a study of 125 patients. | 1990 May |
|
[Ventricular arrhythmia following thioridazine poisoning]. | 1991 Apr |
|
Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1. | 1991 Apr 18 |
|
Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors. | 2004 Apr 15 |
|
Physical health monitoring of patients with schizophrenia. | 2004 Aug |
|
Spasmodic dysphonia, a rare form of tardive dystonia, induced by low-dose risperidone? | 2004 Mar |
|
Automated tight seal electrophysiology for assessing the potential hERG liability of pharmaceutical compounds. | 2004 Oct |
|
[Sonapax use in the clinical practice]. | 2005 Apr |
|
Invited review: fluphenazine augments retinal oxidative stress. | 2005 Aug |
|
A toxicogenomic approach to drug-induced phospholipidosis: analysis of its induction mechanism and establishment of a novel in vitro screening system. | 2005 Feb |
|
Stable expression of constitutively activated mutant h5HT6 and h5HT7 serotonin receptors: inverse agonist activity of antipsychotic drugs. | 2005 May |
|
[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations]. | 2006 Jun |
|
Frequency of high-risk use of QT-prolonging medications. | 2006 Jun |
|
In vitro detection of drug-induced phospholipidosis using gene expression and fluorescent phospholipid based methodologies. | 2007 Sep |
|
Identification of selected therapeutic agents as inhibitors of carboxylesterase 1: potential sources of metabolic drug interactions. | 2010 Apr 11 |
|
Identification of human Ether-à-go-go related gene modulators by three screening platforms in an academic drug-discovery setting. | 2010 Dec |
|
QT alterations in psychopharmacology: proven candidates and suspects. | 2010 Jan |
|
Effects of K openers on the QT prolongation induced by HERG-blocking drugs in guinea-pigs. | 2010 Jul |
|
A gene signature-based approach identifies thioridazine as an inhibitor of phosphatidylinositol-3'-kinase (PI3K)/AKT pathway in ovarian cancer cells. | 2011 Jan |
|
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
|
Comparison of a genomic and a multiplex cell imaging approach for the detection of phospholipidosis. | 2011 Oct |
|
Refining the human iPSC-cardiomyocyte arrhythmic risk assessment model. | 2013 Dec |
|
Phenothiazines inhibit hepatitis C virus entry, likely by increasing the fluidity of cholesterol-rich membranes. | 2013 Jun |
|
HepG2 cells simultaneously expressing five P450 enzymes for the screening of hepatotoxicity: identification of bioactivable drugs and the potential mechanism of toxicity involved. | 2013 Jun |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/thioridazine.html
The usual starting dose for adult schizophrenic patients is 50 mg to 100 mg three times a day, with a gradual increment to a maximum of 800 mg daily if necessary. Once effective control of symptoms has been achieved, the dosage may be reduced gradually to determine the minimum maintenance dose. The total daily dosage ranges from 200 mg to 800 mg, divided into two to four doses.
For pediatric patients with schizophrenia who are unresponsive to other agents, the recommended initial dose is 0.5 mg/kg/day given in divided doses. Dosage may be increased gradually until optimum therapeutic effect is obtained or the maximum dose of 3 mg/kg/day has been reached.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7898773
Slices of female Wistar rats frontal cortex were prepared by 350 x 350-/.tm crosschopping. These were preincubated for 1 h in Krebsbicarbonate buffer at 37°C in the presence of O2/CO2 (95:5). Aliquots of gravity-packed slices (50 mkl) were dispensed into 13 x 100 glass tubes containing 250 mk1 of 5 mkCi [3H]myo-inositol (Amersham, Les Ulis, France; specific activity 80-120 Ci/mmol) and, after 20 min incubation, antagonist (Thioridazine) or buffer, each containing pargyline and lithium chloride (final concentrations 10 mkM and 10 mM) were added and incubation continued for 10 min. Serotonin (0.6 mkM final) or buffer was added for a stimulation period of 60 min. The reaction was stopped by three volumes of chloroform/methanol (1:2). Extraction and separation of phosphoinositol was by anion-exchange chromatography
Substance Class |
Chemical
Created
by
admin
on
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Fri Jun 25 20:55:14 UTC 2021
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on
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Record UNII |
N3D6TG58NI
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000007544
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NDF-RT |
N0000007544
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NDF-RT |
N0000007544
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NDF-RT |
N0000175746
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WHO-VATC |
QN05AC02
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WHO-ATC |
N05AC02
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NCI_THESAURUS |
C29710
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LIVERTOX |
954
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5452
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200-044-2
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818
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CHEMBL479
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DB00679
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N3D6TG58NI
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50-52-2
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THIORIDAZINE
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3189
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100
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10502
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1662504
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D013881
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50-52-2
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C61971
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Thioridazine
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2637
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SUB10984MIG
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M10782
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
---|---|---|---|---|
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
|
||
|
METABOLIC ENZYME -> INHIBITOR |
IC50
|
||
|
BINDER->LIGAND |
|
||
|
SALT/SOLVATE -> PARENT | |||
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE ACTIVE -> PARENT | |||
|
METABOLITE -> PARENT | |||
|
METABOLITE ACTIVE -> PARENT |
Metabolite to parent drug ratio in non-uraemic human plasma.
Mesoridazine is twice as potent as the parent drug in man and has been introduced into clinical use as an antipsychotic.
METABOLITE TO PARENT DRUG RATIO
PLASMA; URINE
|
||
|
METABOLITE INACTIVE -> PARENT | |||
|
METABOLITE ACTIVE -> PARENT |
Amount excreted in 24 hour period. Percent of dose excreted in urine as metabolite.
AMOUNT EXCRETED
URINE
|
||
|
METABOLITE ACTIVE -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 1.5
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 2.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 0.5
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 1.9
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
Related Record | Type | Details | ||
---|---|---|---|---|
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ACTIVE MOIETY |