ContaminantDB: Thioridazine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (15)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:24 UTC

Update Date

2016-11-09 01:08:43 UTC

Accession Number

CHEM002246

Identification

Common Name

Thioridazine

Class

Small 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
Metabolite
Organic Compound
Phenothiazine
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
10-[2-(1-Methyl-2-piperidyl)ethyl]-2-methylsulfanyl-phenothiazine	ChEBI
2-Methylmercapto-10-(2-(N-methyl-2-piperidyl)ethyl)phenothiazine	ChEBI
3-Methylmercapto-N-(2'-(N-methyl-2-piperidyl)ethyl)phenothiazine	ChEBI
Mallorol	ChEBI
Malloryl	ChEBI
Meleril	ChEBI
Mellaril	ChEBI
Mellaril-S	ChEBI
Mellerets	ChEBI
Mellerette	ChEBI
Melleril	ChEBI
Orsanil	ChEBI
Sonapax	ChEBI
Thioridazin	ChEBI
Thioridazinum	ChEBI
Tioridazina	ChEBI
10-[2-(1-Methyl-2-piperidyl)ethyl]-2-methylsulphanyl-phenothiazine	Generator
Thioridazine chloride	HMDB
ApoThioridazine	HMDB
Melleryl	HMDB
Pinewood brand OF thioridazine hydrochloride	HMDB
Thioridazine hydrochloride	HMDB
Neurazpharm brand OF thioridazine hydrochloride	HMDB
AWD.pharma brand OF thioridazine hydrochloride	HMDB
Aldazine	HMDB
Arzneimittelwerk dresden brand OF thioridazine	HMDB
DDSA brand OF thioridazine hydrochloride	HMDB
Rideril	HMDB
Thiozine	HMDB
Alphapharm brand OF thioridazine hydrochloride	HMDB
Apo thioridazine	HMDB
Clonmel brand OF thioridazine hydrochloride	HMDB
Melleretten	HMDB
Thioridazine HCL	HMDB
Thioridazine novartis brand	HMDB
Thioridazine neurazpharm	HMDB
Apo-thioridazine	HMDB
Apotex brand OF thioridazine hydrochloride	HMDB
Melzine	HMDB
Novartis brand OF thioridazine	HMDB
Roxane brand OF thioridazine hydrochloride	HMDB
Thioridazine-neurazpharm	HMDB
Thioridazineneurazpharm	HMDB

Chemical Formula

C₂₁H₂₆N₂S₂

Average Molecular Mass

370.575 g/mol

Monoisotopic Mass

370.154 g/mol

CAS Registry Number

50-52-2

IUPAC Name

10-[2-(1-methylpiperidin-2-yl)ethyl]-2-(methylsulfanyl)-10H-phenothiazine

Traditional Name

thioridazine

SMILES

CSC1=CC2=C(SC3=CC=CC=C3N2CCC2CCCCN2C)C=C1

InChI Identifier

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

InChI Key

KLBQZWRITKRQQV-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazines

Sub Class

Phenothiazines

Direct Parent

Phenothiazines

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenothiazines (CHEBI:9566 )
piperidines (CHEBI:9566 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	73°C
Boiling Point	230°C at 2.00E-02 mm Hg
Solubility	0.0336 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	0.00086 g/L	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

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-9110000000-042dbd4f525abce007c0	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-9112000000-03a53f455eb75bee12b1	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-00di-4539000000-9b298eff08d8aae4d50c	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-9110000000-042dbd4f525abce007c0	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-9112000000-03a53f455eb75bee12b1	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-00di-4539000000-9b298eff08d8aae4d50c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052b-9133000000-5c5d51f787da054d1cd8	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0009000000-72ae3160baada68a101c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-1409000000-ca7f19c9476403b237f6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004j-8920000000-1ac0f55aa083ad77c72b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-002b-9320000000-494b15b3b671ebe76be9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0002-9220000000-e3e4ef2154cbee0f6852	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00di-0109000000-0729d6c8c352282a1d00	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9300000000-7b3f963cdcb2b42af246	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00ba-4904000000-3d19a92d11da4536561a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0002-9220000000-e3e4ef2154cbee0f6852	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0009000000-bff15ad076402d6c8d67	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1409000000-ca7f19c9476403b237f6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0009000000-72ae3160baada68a101c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-004j-8920000000-1ac0f55aa083ad77c72b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-002b-9320000000-494b15b3b671ebe76be9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0109000000-598e54239d6d13ff6dd4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00fr-3529000000-18e24c0e0b54472d7826	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4m-9521000000-43949f1e3ce6dea95cbd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00xs-3009000000-6a6f8dcd7ed070a5e1e3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02mj-2297000000-57d37082170bc3391ec8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9100000000-8657369f1e7405e6943b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0009000000-b5f90a911ff7bb6a25ee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0092-9616000000-cb1233f7b165a2d465ff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9010000000-d79d5f56e64b7d0e6a41	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-e1981bf8caf13296fc86	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0059000000-ba6507d64713944a5b65	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-006t-9552000000-ea4c5c56ee4333d0815a	Spectrum

Toxicity Profile

Route of Exposure

Oral

Mechanism of Toxicity

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.

Metabolism

Hepatic Half Life: 21-25 hours

Toxicity Values

LD₅₀=956-1034 mg/kg (Orally in rats).

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the treatment of schizophrenia and generalized anxiety disorder.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

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

Treatment

An 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 ID

DB00679

HMDB ID

HMDB0014817

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID