Identification
- Summary
Thioridazine is a phenothiazine antipsychotic used to treat schizophrenia and generalized anxiety disorder.
- Generic Name
- Thioridazine
- DrugBank Accession Number
- DB00679
- Background
A phenothiazine antipsychotic used in the management of psychoses, including schizophrenia, and in the control of severely disturbed or agitated behavior. It has little antiemetic activity. Thioridazine has a higher incidence of antimuscarinic effects, but a lower incidence of extrapyramidal symptoms, than chlorpromazine. (From Martindale, The Extra Pharmacopoeia, 30th ed, p618).
Thioridazine was withdrawn worldwide in 2005 due to its association with cardiac arrythmias.
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Structure
Structure for Thioridazine (DB00679)
- Weight
- Average: 370.575
Monoisotopic: 370.153740222 - Chemical Formula
- C21H26N2S2
- Synonyms
- 10-[2-(1-methyl-2-piperidyl)ethyl]-2-methylsulfanyl-phenothiazine
- 2-Methylmercapto-10-(2-(N-methyl-2-piperidyl)ethyl)phenothiazine
- 3-Methylmercapto-N-(2'-(N-methyl-2-piperidyl)ethyl)phenothiazine
- Thioridazin
- Thioridazine
- Thioridazinum
- Tioridazina
- External IDs
- TP-21
Pharmacology
- Indication
For the treatment of schizophrenia and generalized anxiety disorder.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Psychosis ••• ••••• Management of Schizophrenia •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Thioridazine is a trifluoro-methyl phenothiazine derivative intended for the management of schizophrenia and other psychotic disorders. Thioridazine has not been shown effective in the management of behaviorial complications in patients with mental retardation.
- Mechanism of action
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.
Target Actions Organism ADopamine D2 receptor antagonistHumans ADopamine D1 receptor antagonistHumans AAlpha-1A adrenergic receptor antagonistHumans AAlpha-1B adrenergic receptor antagonistHumans A5-hydroxytryptamine receptor 2A antagonistHumans UPotassium voltage-gated channel subfamily H member 2 inhibitorHumans - Absorption
60%
- Volume of distribution
Not Available
- Protein binding
95%
- Metabolism
Hepatic
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- Route of elimination
Not Available
- Half-life
21-25 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
LD50=956-1034 mg/kg (Orally in rats); Agitation, blurred vision, coma, confusion, constipation, difficulty breathing, dilated or constricted pupils, diminished flow of urine, dry mouth, dry skin, excessively high or low body temperature, extremely low blood pressure, fluid in the lungs, heart abnormalities, inability to urinate, intestinal blockage, nasal congestion, restlessness, sedation, seizures, shock
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Cytochrome P450 2D6 CYP2D6*3 Not Available C allele ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*4 Not Available C allele ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*5 Not Available Whole-gene deletion ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*6 Not Available 1707delT ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*7 Not Available 2935A>C ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*8 Not Available 1758G>T ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*11 Not Available 883G>C ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*12 Not Available 124G>A ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*13 Not Available CYP2D7/2D6 hybrid gene structure ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*14A Not Available 1758G>A ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*15 Not Available 137insT, 137_138insT ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*19 Not Available 2539_2542delAACT ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*20 Not Available 1973_1974insG ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*21 Not Available 2573insC ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*31 Not Available -1770G>A / -1584C>G … show all ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*36 Not Available 100C>T / -1426C>T … show all ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*38 Not Available 2587_2590delGACT ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*40 Not Available 1863_1864ins(TTT CGC CCC)2 ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*42 Not Available 3259_3260insGT ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*44 Not Available 2950G>C ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*47 Not Available 100C>T / -1426C>T … show all ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*51 Not Available -1584C>G / -1235A>G … show all ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*56 Not Available 3201C>T ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*57 Not Available 100C>T / 310G>T … show all ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*62 Not Available 4044C>T ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*68A Not Available -1426C>T / -1235A>G … show all ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*68B Not Available Similar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4. ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*69 Not Available 2988G>A / -1426C>T … show all ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*92 Not Available 1995delC ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*100 Not Available -1426C>T / -1235A>G … show all ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*101 Not Available -1426C>T / -1235A>G … show all ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*9 Not Available 2615-2617delAAG ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*10 Not Available 100C>T / 1661G>C … show all ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*14B Not Available 1758G>A ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*17 Not Available 1023C>T / 2850C>T ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*18 Not Available 4133dupGTGCCCACT ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*29 Not Available 1659G>A / 1661G>C … show all ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*41 Not Available 2988G>A ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*49 Not Available 100C>T / -1426C>T … show all ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*50 Not Available 1720A>C ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*54 Not Available 100C>T / 1039C>T … show all ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*55 Not Available 1661G>C / 2850C>T … show all ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*59 Not Available 1661G>C / 2291G>A … show all ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details Cytochrome P450 2D6 CYP2D6*72 Not Available -1426C>T / -1235A>G … show all ADR Inferred Reduced CYP2D6 activity associated with Torsades de pointes and/or sudden death. Details
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Thioridazine is combined with 1,2-Benzodiazepine. Abaloparatide The risk or severity of adverse effects can be increased when Thioridazine is combined with Abaloparatide. Abatacept The metabolism of Thioridazine can be increased when combined with Abatacept. Abiraterone The metabolism of Thioridazine can be decreased when combined with Abiraterone. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Thioridazine. - Food Interactions
- Avoid alcohol. Ingesting alcohol may potentiate the CNS depressant actions of thioridazine.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Thioridazine hydrochloride 4WCI67NK8M 130-61-0 NZFNXWQNBYZDAQ-UHFFFAOYSA-N - International/Other Brands
- Aldazine / Mallorol / Malloryl / Meleril / Mellaril-S / Mellerets / Mellerette / Melleretten / Melleril / Novoridazine / Orsanil / Ridazin / Ridazine / Sonapax / Thioril
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Mellaril Liquid 30 mg / mL Oral Novartis 1997-08-15 2001-07-30 Canada 
Mellaril Suspension 10 mg / 5 mL Oral Novartis 1964-12-31 2001-07-30 Canada Mellaril Tab 100mg Tablet 100 mg / tab Oral Sandoz 1959-12-31 1996-09-05 Canada Mellaril Tab 10mg Tablet 10 mg / tab Oral Sandoz 1959-12-31 1997-08-12 Canada Mellaril Tab 200mg Tablet 200 mg / tab Oral Sandoz 1959-12-31 1996-09-05 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Novo-ridazine (thioridazine Oral Suspension) - 2 mg/ml Suspension 2 mg / mL Oral Novopharm Limited 1996-09-18 2005-08-10 Canada Novo-ridazine 100mg Tablet 100 mg Oral Novopharm Limited 1972-12-31 2005-08-10 Canada Novo-ridazine 10mg Tablet 10 mg Oral Novopharm Limited 1972-12-31 2005-08-10 Canada Novo-ridazine 25mg Tablet 25 mg Oral Novopharm Limited 1972-12-31 2005-08-10 Canada Novo-ridazine 50mg Tablet 50 mg Oral Novopharm Limited 1972-12-31 2005-08-10 Canada
Categories
- ATC Codes
- N05AC02 — Thioridazine
- Drug Categories
- Adrenergic alpha-1 Receptor Antagonists
- Adrenergic alpha-Antagonists
- Adrenergic Antagonists
- Agents that produce hypertension
- Antidepressive Agents
- Antipsychotic Agents
- Antipsychotic Agents (First Generation [Typical])
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strong)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP2E1 Inhibitors
- Cytochrome P-450 CYP2E1 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Dopamine Agents
- Dopamine Antagonists
- Dopamine D2 Receptor Antagonists
- Drugs causing inadvertant photosensitivity
- Heterocyclic Compounds, Fused-Ring
- Highest Risk QTc-Prolonging Agents
- Hypotensive Agents
- Nervous System
- Neurotoxic agents
- Neurotransmitter Agents
- Phenothiazines
- Phenothiazines With Piperidine Structure
- Photosensitizing Agents
- Psycholeptics
- Psychotropic Drugs
- QTc Prolonging Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin 5-HT2 Receptor Antagonists
- Serotonin 5-HT2A Receptor Antagonists
- Serotonin Agents
- Serotonin Receptor Antagonists
- Sulfur Compounds
- Tranquilizing Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzothiazines
- Sub Class
- Phenothiazines
- Direct Parent
- Phenothiazines
- Alternative Parents
- Alkyldiarylamines / Diarylthioethers / Thiophenol ethers / Alkylarylthioethers / Piperidines / 1,4-thiazines / Trialkylamines / Sulfenyl compounds / Azacyclic compounds / Organopnictogen compounds show 1 more
- Substituents
- Alkylarylthioether / Alkyldiarylamine / Amine / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Benzenoid / Diarylthioether / Hydrocarbon derivative / Organic nitrogen compound show 12 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- phenothiazines, piperidines (CHEBI:9566)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- N3D6TG58NI
- CAS number
- 50-52-2
- InChI Key
- KLBQZWRITKRQQV-UHFFFAOYSA-N
- InChI
- 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
- IUPAC Name
- 10-[2-(1-methylpiperidin-2-yl)ethyl]-2-(methylsulfanyl)-10H-phenothiazine
- SMILES
- CSC1=CC2=C(SC3=CC=CC=C3N2CCC2CCCCN2C)C=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014817
- KEGG Drug
- D00373
- PubChem Compound
- 5452
- PubChem Substance
- 46509070
- ChemSpider
- 5253
- BindingDB
- 50002338
- 10502
- ChEBI
- 9566
- ChEMBL
- CHEMBL479
- Therapeutic Targets Database
- DAP000476
- PharmGKB
- PA451666
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Thioridazine
- MSDS
- Download (44.7 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Schizoaffective Disorders / Schizophrenia / Schizophrenia and Disorders With Psychotic Features 1 3 Terminated Treatment Anxiety Disorders / Dementia / Depression / Psychosomatic Disorders / Schizophrenia 1 1 Completed Treatment Acute Myeloid Leukemia 1 0 Terminated Not Available Healthy Subjects (HS) 1 Not Available Completed Not Available Bipolar Disorder (BD) / Psychosis / Schizoaffective Disorders / Schizophrenia / Type 2 Diabetes Mellitus 1
Pharmacoeconomics
- Manufacturers
- Novartis pharmaceuticals corp
- Actavis mid atlantic llc
- Alpharma us pharmaceuticals division
- Hi tech pharmacal co inc
- Pharmaceutical assoc inc div beach products
- Sandoz inc
- Teva pharmaceuticals usa
- Wockhardt eu operations (swiss) ag
- Roxane laboratories inc
- Ivax pharmaceuticals inc
- Mutual pharmaceutical co inc
- Mylan pharmaceuticals inc
- Par pharmaceutical inc
- Superpharm corp
- Teva pharmaceuticals usa inc
- Watson laboratories inc
- West ward pharmaceutical corp
- Packagers
- Advanced Pharmaceutical Services Inc.
- Direct Dispensing Inc.
- Dispensing Solutions
- Heartland Repack Services LLC
- Interpharm Pharmaceutical Products Inc.
- Major Pharmaceuticals
- Murfreesboro Pharmaceutical Nursing Supply
- Mutual Pharmaceutical Co.
- Mylan
- Novartis AG
- Pharmaceutical Packaging Center
- Pharmedix
- Physicians Total Care Inc.
- Professional Co.
- Qualitest
- Remedy Repack
- Roxane Labs
- Sandhills Packaging Inc.
- Sandoz
- Southwood Pharmaceuticals
- UDL Laboratories
- United Research Laboratories Inc.
- Dosage Forms
Form Route Strength Liquid Oral 30 mg / mL Suspension Oral 10 mg / 5 mL Tablet Oral 100 mg / tab Tablet Oral 10 mg / tab Tablet Oral 200 mg / tab Tablet Oral 25 mg / tab Tablet Oral 50 mg / tab Pill Tablet Oral Tablet Oral 100 mg Tablet Oral 10 mg Tablet Oral 25 mg Tablet Oral 50 mg Tablet Oral 200 mg Tablet, coated Oral 10 mg Solution Oral 30 mg / mL Solution Oral 5 mg / mL Tablet, film coated Oral 200 MG Tablet Oral 25 mg/1 Tablet Oral 50 mg/1 Tablet, film coated Oral 10 mg/1 Tablet, film coated Oral 100 mg/1 Tablet, film coated Oral 25 mg/1 Tablet, film coated Oral 50 mg/1 Suspension Oral 2 mg / mL Tablet, extended release Tablet, coated Oral Tablet, film coated Oral 25 mg Tablet, film coated Oral 50 mg Tablet, film coated Oral 100 mg Tablet, sugar coated Oral 10 mg Tablet, sugar coated Oral 25 mg Tablet, film coated Oral 10 mg Tablet, sugar coated Oral 100 mg Tablet, sugar coated Oral 50 mg - Prices
Unit description Cost Unit Thioridazine hcl powder 11.16USD g Thioridazine HCl 200 mg tablet 1.14USD tablet Thioridazine HCl 150 mg tablet 1.01USD tablet Thioridazine HCl 100 mg tablet 0.69USD tablet Thioridazine 100 mg tablet 0.67USD tablet Thioridazine HCl 50 mg tablet 0.61USD tablet Thioridazine 50 mg tablet 0.58USD tablet Thioridazine HCl 25 mg tablet 0.49USD tablet Thioridazine 25 mg tablet 0.47USD tablet Thioridazine HCl 15 mg tablet 0.45USD tablet Thioridazine HCl 10 mg tablet 0.35USD tablet Thioridazine 10 mg tablet 0.33USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 73 °C PhysProp boiling point (°C) 230 °C at 2.00E-02 mm Hg PhysProp water solubility 0.0336 mg/L Not Available logP 5.90 HANSCH,C ET AL. (1995) pKa 9.5 EL TAYAR,N ET AL. (1985) - Predicted Properties
Property Value Source Water Solubility 0.000855 mg/mL ALOGPS logP 5.93 ALOGPS logP 5.47 Chemaxon logS -5.6 ALOGPS pKa (Strongest Basic) 8.93 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 6.48 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 113.52 m3·mol-1 Chemaxon Polarizability 43.26 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9068 Blood Brain Barrier + 0.9901 Caco-2 permeable + 0.7912 P-glycoprotein substrate Substrate 0.7863 P-glycoprotein inhibitor I Inhibitor 0.8564 P-glycoprotein inhibitor II Inhibitor 0.9115 Renal organic cation transporter Inhibitor 0.7943 CYP450 2C9 substrate Non-substrate 0.7981 CYP450 2D6 substrate Substrate 0.8919 CYP450 3A4 substrate Non-substrate 0.5068 CYP450 1A2 substrate Inhibitor 0.9106 CYP450 2C9 inhibitor Non-inhibitor 0.908 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Non-inhibitor 0.7697 CYP450 3A4 inhibitor Non-inhibitor 0.8308 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5826 Ames test Non AMES toxic 0.8703 Carcinogenicity Non-carcinogens 0.9528 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.5395 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.906 hERG inhibition (predictor II) Inhibitor 0.8384
Spectra
- Mass Spec (NIST)
- Download (8.15 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 196.5719702 predictedDarkChem Lite v0.1.0 [M-H]- 186.02287 predictedDeepCCS 1.0 (2019) [M+H]+ 197.2427702 predictedDarkChem Lite v0.1.0 [M+H]+ 188.38087 predictedDeepCCS 1.0 (2019) [M+Na]+ 197.2573702 predictedDarkChem Lite v0.1.0 [M+Na]+ 194.474 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Potassium channel regulator activity
- Specific Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
- Gene Name
- DRD2
- Uniprot ID
- P14416
- Uniprot Name
- D(2) dopamine receptor
- Molecular Weight
- 50618.91 Da
References
- Seeman P: Atypical neuroleptics: role of multiple receptors, endogenous dopamine, and receptor linkage. Acta Psychiatr Scand Suppl. 1990;358:14-20. [Article]
- Assie MB, Sleight AJ, Koek W: Biphasic displacement of [3H]YM-09151-2 binding in the rat brain by thioridazine, risperidone and clozapine, but not by other antipsychotics. Eur J Pharmacol. 1993 Jun 24;237(2-3):183-9. [Article]
- Dimpfel W, Spuler M, Wessel K: Different neuroleptics show common dose and time dependent effects in quantitative field potential analysis in freely moving rats. Psychopharmacology (Berl). 1992;107(2-3):195-202. [Article]
- Barth VN, Chernet E, Martin LJ, Need AB, Rash KS, Morin M, Phebus LA: Comparison of rat dopamine D2 receptor occupancy for a series of antipsychotic drugs measured using radiolabeled or nonlabeled raclopride tracer. Life Sci. 2006 May 22;78(26):3007-12. Epub 2006 Jan 24. [Article]
- Carey GJ, Bergman J: Discriminative-stimulus effects of clozapine in squirrel monkeys: comparison with conventional and novel antipsychotic drugs. Psychopharmacology (Berl). 1997 Aug;132(3):261-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- G-protein coupled amine receptor activity
- Specific Function
- Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
- Gene Name
- DRD1
- Uniprot ID
- P21728
- Uniprot Name
- D(1A) dopamine receptor
- Molecular Weight
- 49292.765 Da
References
- Hammock RG, Schroeder SR, Levine WR: The effect of clozapine on self-injurious behavior. J Autism Dev Disord. 1995 Dec;25(6):611-26. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Protein heterodimerization activity
- Specific Function
- This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
- Gene Name
- ADRA1A
- Uniprot ID
- P35348
- Uniprot Name
- Alpha-1A adrenergic receptor
- Molecular Weight
- 51486.005 Da
References
- Sleight AJ, Koek W, Bigg DC: Binding of antipsychotic drugs at alpha 1A- and alpha 1B-adrenoceptors: risperidone is selective for the alpha 1B-adrenoceptors. Eur J Pharmacol. 1993 Jul 20;238(2-3):407-10. [Article]
- Cahir M, King DJ: Antipsychotics lack alpha 1A/B adrenoceptor subtype selectivity in the rat. Eur Neuropsychopharmacol. 2005 Mar;15(2):231-4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Protein heterodimerization activity
- Specific Function
- This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
- Gene Name
- ADRA1B
- Uniprot ID
- P35368
- Uniprot Name
- Alpha-1B adrenergic receptor
- Molecular Weight
- 56835.375 Da
References
- Cahir M, King DJ: Antipsychotics lack alpha 1A/B adrenoceptor subtype selectivity in the rat. Eur Neuropsychopharmacol. 2005 Mar;15(2):231-4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Virus receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
- Gene Name
- HTR2A
- Uniprot ID
- P28223
- Uniprot Name
- 5-hydroxytryptamine receptor 2A
- Molecular Weight
- 52602.58 Da
References
- Andree TH, Mikuni M, Tong CY, Koenig JI, Meltzer HY: Differential effect of subchronic treatment with various neuroleptic agents on serotonin2 receptors in rat cerebral cortex. J Neurochem. 1986 Jan;46(1):191-7. [Article]
- Canton H, Verriele L, Millan MJ: Competitive antagonism of serotonin (5-HT)2C and 5-HT2A receptor-mediated phosphoinositide (PI) turnover by clozapine in the rat: a comparison to other antipsychotics. Neurosci Lett. 1994 Nov 7;181(1-2):65-8. [Article]
- Burki HR: Binding of psychoactive drugs to rat brain amine receptors, measured ex vivo, and their effects on the metabolism of biogenic amines. Naunyn Schmiedebergs Arch Pharmacol. 1986 Mar;332(3):258-66. [Article]
- Costall B, Naylor RJ: Behavioural interactions between 5-hydroxytryptophan, neuroleptic agents and 5-HT receptor antagonists in modifying rodent responding to aversive situations. Br J Pharmacol. 1995 Dec;116(7):2989-99. [Article]
- Morisset S, Sahm UG, Traiffort E, Tardivel-Lacombe J, Arrang JM, Schwartz JC: Atypical neuroleptics enhance histamine turnover in brain via 5-Hydroxytryptamine2A receptor blockade. J Pharmacol Exp Ther. 1999 Feb;288(2):590-6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
- Specific Function
- Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the ...
- Gene Name
- KCNH2
- Uniprot ID
- Q12809
- Uniprot Name
- Potassium voltage-gated channel subfamily H member 2
- Molecular Weight
- 126653.52 Da
References
- Milnes JT, Witchel HJ, Leaney JL, Leishman DJ, Hancox JC: hERG K+ channel blockade by the antipsychotic drug thioridazine: An obligatory role for the S6 helix residue F656. Biochem Biophys Res Commun. 2006 Dec 8;351(1):273-80. Epub 2006 Oct 23. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- Monostory K, Hazai E, Vereczkey L: Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors. Chem Biol Interact. 2004 Apr 15;147(3):331-40. doi: 10.1016/j.cbi.2004.03.003. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Otani K, Aoshima T: Pharmacogenetics of classical and new antipsychotic drugs. Ther Drug Monit. 2000 Feb;22(1):118-21. [Article]
- Yasui N, Tybring G, Otani K, Mihara K, Suzuki A, Svensson JO, Kaneko S: Effects of thioridazine, an inhibitor of CYP2D6, on the steady-state plasma concentrations of the enantiomers of mianserin and its active metabolite, desmethylmianserin, in depressed Japanese patients. Pharmacogenetics. 1997 Oct;7(5):369-74. [Article]
- Flockhart Table of Drug Interactions [Link]
- Health Canada Approved Drug Products: Manerix (Moclobemide) tablets [Link]
- Thioridazine Therapy and CYP2D6 Genotypes [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Li-Wan-Po A, Girard T, Farndon P, Cooley C, Lithgow J: Pharmacogenetics of CYP2C19: functional and clinical implications of a new variant CYP2C19*17. Br J Clin Pharmacol. 2010 Mar;69(3):222-30. doi: 10.1111/j.1365-2125.2009.03578.x. [Article]
- Wu Z, Lee D, Joo J, Shin JH, Kang W, Oh S, Lee do Y, Lee SJ, Yea SS, Lee HS, Lee T, Liu KH: CYP2J2 and CYP2C19 are the major enzymes responsible for metabolism of albendazole and fenbendazole in human liver microsomes and recombinant P450 assay systems. Antimicrob Agents Chemother. 2013 Nov;57(11):5448-56. doi: 10.1128/AAC.00843-13. Epub 2013 Aug 19. [Article]
Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:54