Thioridazine (CHEM002246)

Record Information
Version1.0
Creation Date2009-07-21 20:27:24 UTC
Update Date2026-05-14 16:45:52 UTC
Accession NumberCHEM002246
Identification
Common NameThioridazine
ClassSmall Molecule
Description
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)
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Antipsychotic Agent
  • Dopamine Antagonist
  • Drug
  • Ether
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Phenothiazine
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
10-[2-(1-Methyl-2-piperidyl)ethyl]-2-methylsulfanyl-phenothiazineChEBI
2-Methylmercapto-10-(2-(N-methyl-2-piperidyl)ethyl)phenothiazineChEBI
3-Methylmercapto-N-(2'-(N-methyl-2-piperidyl)ethyl)phenothiazineChEBI
MallorolChEBI
MallorylChEBI
MelerilChEBI
MellarilChEBI
Mellaril-SChEBI
MelleretsChEBI
MelleretteChEBI
MellerilChEBI
OrsanilChEBI
SonapaxChEBI
ThioridazinChEBI
ThioridazinumChEBI
TioridazinaChEBI
10-[2-(1-Methyl-2-piperidyl)ethyl]-2-methylsulphanyl-phenothiazineGenerator
Thioridazine chlorideHMDB
ApoThioridazineHMDB
MellerylHMDB
Pinewood brand OF thioridazine hydrochlorideHMDB
Thioridazine hydrochlorideHMDB
Neurazpharm brand OF thioridazine hydrochlorideHMDB
AWD.pharma brand OF thioridazine hydrochlorideHMDB
AldazineHMDB
Arzneimittelwerk dresden brand OF thioridazineHMDB
DDSA brand OF thioridazine hydrochlorideHMDB
RiderilHMDB
ThiozineHMDB
Alphapharm brand OF thioridazine hydrochlorideHMDB
Apo thioridazineHMDB
Clonmel brand OF thioridazine hydrochlorideHMDB
MellerettenHMDB
Thioridazine HCLHMDB
Thioridazine novartis brandHMDB
Thioridazine neurazpharmHMDB
Apo-thioridazineHMDB
Apotex brand OF thioridazine hydrochlorideHMDB
MelzineHMDB
Novartis brand OF thioridazineHMDB
Roxane brand OF thioridazine hydrochlorideHMDB
Thioridazine-neurazpharmHMDB
ThioridazineneurazpharmHMDB
Chemical FormulaC21H26N2S2
Average Molecular Mass370.575 g/mol
Monoisotopic Mass370.154 g/mol
CAS Registry Number50-52-2
IUPAC Name10-[2-(1-methylpiperidin-2-yl)ethyl]-2-(methylsulfanyl)-10H-phenothiazine
Traditional Namethioridazine
SMILESCSC1=CC2=C(SC3=CC=CC=C3N2CCC2CCCCN2C)C=C1
InChI IdentifierInChI=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
InChI KeyKLBQZWRITKRQQV-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassPhenothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Aryl thioether
  • Tertiary aliphatic/aromatic amine
  • Thiophenol ether
  • Alkylarylthioether
  • Piperidine
  • Para-thiazine
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Thioether
  • Azacycle
  • Sulfenyl compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organosulfur compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point73°C
Boiling Point230°C at 2.00E-02 mm Hg
Solubility0.0336 mg/L
Predicted Properties
PropertyValueSource
Water Solubility0.00086 g/LALOGPS
logP5.93ALOGPS
logP5.47ChemAxon
logS-5.6ALOGPS
pKa (Strongest Basic)8.93ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity113.52 m³·mol⁻¹ChemAxon
Polarizability43.26 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral
Mechanism of ToxicityThioridazine 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.
MetabolismHepatic Half Life: 21-25 hours
Toxicity ValuesLD50=956-1034 mg/kg (Orally in rats).
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of schizophrenia and generalized anxiety disorder.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsLD50=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
TreatmentAn airway must be established and maintained. Adequate oxygenation and ventilation must be ensured. Cardiovascular monitoring should commence immediately and should include continuous electrocardiographic monitoring to detect possible arrhythmias. Treatment may include one or more of the following therapeutic interventions: correction of electrolyte abnormalities and acid-base balance, lidocaine, phenytoin, isoproterenol, ventricular pacing, and defibrillation. Disopyramide, procainamide, and quinidine may produce additive QT-prolonging effects when administered to patients with acute overdosage of Mellaril and should be avoided. Caution must be exercised when administering lidocaine, as it may increase the risk of developing seizures. Treatment of hypotension may require intravenous fluids and vasopressors. Phenylephrine, levarterenol, or metaraminol are the appropriate pressor agents for use in the management of refractory hypotension. Gastric lavage and repeated doses of activated charcoal should be considered. Induction of emesis is less preferable to gastric lavage because of the risk of dystonia and the potential for aspiration of vomitus. Acute extrapyramidal symptoms may be treated with diphenhydramine hydrochloride or benztropine mesylate. Forced diuresis, hemoperfusion, hemodialysis and manipulation of urine pH are of unlikely benefit in the treatment of phenothiazine overdose due to their large volume of distribution and extensive plasma protein binding. (2)
Concentrations
Not Available
External Links
DrugBank IDDB00679
HMDB IDHMDB0014817
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkThioridazine
Chemspider ID5253
ChEBI ID9566
PubChem Compound ID5452
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10796547
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11686961
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=1650428
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17764469
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=17876580
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19747949
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=20825390
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=26956010
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=27023487
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=27068340
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=9352572