HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
Huagongshe Open Program:[email protected]AI access: llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.7.8
  1. Home
  2. /Compound

Thioridazine Hydrochloride

HCID 66062
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
130-61-0
Standard SMILES
CSc1ccc2c(c1)N(CCC1CCCCN1C)c1ccccc1S2.Cl
InChIKey
NZFNXWQNBYZDAQ-UHFFFAOYSA-N
Molecular formula
C21H27ClN2S2
Average molar mass
407 g/mol
Monoisotopic mass
406.1304189

Overview

Thioridazine hydrochloride is a hydrochloride. It has a role as a geroprotector and a first generation antipsychotic. It contains a thioridazine.

Names & identifiers

Preferred name
Thioridazine Hydrochloride
IUPAC
10-[2-(1-methylpiperidin-2-yl)ethyl]-2-methylsulfanylphenothiazine;hydrochloride
English name
Thioridazine hydrochloride
Molecular formula
C21H27ClN2S2
Molecular weight
407.04

Names & synonyms

Thioridazine hydrochloride130-61-0Thioridazine HclSonapax hydrochlorideMellaril hydrochlorideRidazineDTXSID90494014WCI67NK8MNSC-186060Thioridazine hydrochloride intensol2-Methylmercapto-10-(2-(N-methyl-2-piperidyl)ethyl)phenothiazine hydrochlorideDTXCID3029360
Show more names
L-714RidazinOrsanilusafsz-3USAF SZ-BStallerilNSC 186060Novoridazine465 (Maleate)
CHEBI:48566NSC1860602-Methylmercapto-10-[2-(N-methyl-2-piperidyl)ethyl]phenothiazine hydrochlorideRefChem:5661210-(2-((2RS)-1-Methylpiperidin-2-yl)ethyl)-2-methylsulfanyl-10H-phenothiazine monohydrochloride204-992-8Thioridazine.HClThioridazine chloride

Database identifiers

CAS
130-61-0
PubChem CID
66062
DTXSID

Properties

Computed structural properties

Topological polar surface area
57.1 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
4
Heavy atoms
26
Formal charge
0
Complexity
432

Experimental & physicochemical properties

Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Collision Cross Section185 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
158 · 158-1600C
Boiling point
230 °C · 230°C (rough estimate)
Density
1.1227 · 1.1227 (rough estimate)
refractive index
1.561 · 1.5610 (estimate)
storage temp.
2 · 2-8°C
solubility
2 O: · H2O: soluble250 mg plus 5 ml of solvent, clear, colorless to faintly yellow
form
Off-white solid
color
White to Almost white
Water Solubility
Soluble in water (75 mM), DMSO (100 mM), chloroform, ethanol, and methanol.
Sensitive
Light Sensitive & Hygroscopic

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H302 (98%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 49 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information10H-Phenothiazine, 10-2-(1-methyl-2-piperidinyl)ethyl-2-(methylthio)-, monohydrochloride: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 10H-Phenothiazine, 10-[2-(1-methyl-2-piperidinyl)ethyl]-2-(methylthio)-, monohydrochloride: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (98%)

Toxicology

Treatment · 1 item

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. (L1712)

Chemistry & industry

Pharmacology

Metabolism/MetabolitesHepatic Half Life: 21-25 hours
FDA Pharmacological Classification · 2 items

THIORIDAZINE HYDROCHLORIDE

Phenothiazines [CS]; Phenothiazine [EPC]

MeSH Pharmacological Classification · 2 items

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus.

Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME.

Uses & manufacturing

UsesFor the treatment of schizophrenia and generalized anxiety disorder.
Applications · 4 items

UsesThioridazine hydrochloride has been used as an intercalating agent for analyzing the integrity of double-stranded DNA (dsDNA) using square-wave voltammetry (SWV) techniques. Thioridazine hydrochloride has also been used as a positive control for the inhibition of hepatic enzyme cytochrome P4502D6 (CYP2D6) in human liver microsomes.

Related reactions

0 records
New reaction record

No reaction records under the current filter.

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
DTXSID9049401
ChEMBL
CHEMBL1200916
ChEBI
CHEBI:48566
UNII
4WCI67NK8M
EC Number
204-992-8
λmax
317 nm · 317nm(EtOH)(lit.)
Merck
14 · 14,9359
InChI
1S/C21H26N2S2.ClH/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;1H
InChIKey
NZFNXWQNBYZDAQ-UHFFFAOYSA-N
SMILES
Cl.CSc1ccc2Sc3ccccc3N(CCC4CCCCN4C)c2c1
CAS DataBase Reference
130 · 130-61-0(CAS DataBase Reference)
FDA UNII
4 WCI67NK8M · 4WCI67NK8M
NIST Chemistry Reference
Thioridazine hydrochloride(130-61-0)
NCI Drug Dictionary
thioridazine hydrochloride
EPA Substance Registry System
10 H-Phenothiazine, · 10H-Phenothiazine, 10-[2-(1-methyl-2-piperidinyl)ethyl]-2-(methylthio)-, monohydrochloride (130-61-0)
UNSPSC Code
41116107 · 41116107
NACRES
77 · NA.77
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
264 · P264-P270-P301+P312-P501
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xn,N
Risk Statements
22 · 22-36/37/38-50/53
Safety Statements
26 · 26-36-60-61
RIDADR
3077 · UN 3077 9/PG 3
WGK Germany
3 · 3
RTECS
2275000 · SP2275000
HazardClass
9 · 9
HS Code
2934302300 · 2934302300
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 Oral · Acute Tox. 4 Oral
Exposure RoutesOral
Toxicity Summary · 1 item

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.

Signs and Symptoms · 1 item

LD<sub>50</sub>=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

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Thioridazine hydrochloride

vLess-DILI-concern

5

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Toxicity DataLD<sub>50</sub>=956-1034 mg/kg (Orally in rats).

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
rtecs
SP2275000
ridadr
UN 3077 9/PG 3
hs_code
2934302300
risk_code
22-36/37/38-50/53
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn,N
safety_code
26-36-60-61
hazard_class
9
Storage Class
11 - Combustible Solids
Hazard statements
H302
Hazard Classifications
Acute Tox. 4 Oral
Precautionary statements
P264-P270-P301+P312-P501

UsesDopamine receptor blocker; parent compound of sulforidazine and mesoridazine. Antipsychotic

UsesThioridazine HCl is a dopamine receptor blocker and antipsychotic. It is the parent compound of sulforidazine and mesoridazine. This compound has been reported to bind strongly to dopamine receptors on cancer stem cells and cause differentiation leaving normal cells alone (see Can. Chem. News 12 July/August 2012).

General DescriptionThioridazine hydrochloride,10-[2-(1-methyl-2-piperidyl)ethyl]-2-(methylthio)phenothiazine monohydrochloride (Mellaril), is amember of the piperidine subgroup of the phenothiazines.The drug has a relatively low tendency to produce EPS. Thedrug has high anticholinergic activity, and this activity in thestriatum, counterbalancing a striatal DA block, may be responsiblefor the low EPS. It also has been suggested thatthere may be increased DA receptor selectivity, which may be responsible. The drug has sedative and hypotensive activityin common with chlorpromazine and less antiemeticactivity. At high doses, pigmentary retinopathy has been observed.Its major metabolites include N-demethylated, ringhydroxylated,and S-oxidized products. Thioridazine isprominently converted to the active metabolite mesoridazine(discussed next), which probably contributes to the antipsychoticactivity of thioridazine.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
湖南韵邦生物科技股份有限公司0731-88532326 13319508186 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
盐城通铭生物科技有限公司15195160625 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
广州纳珑化工有限公司13192879270; 13192879270 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
武汉云尚本草医药有限公司13816696056 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
南京世洲生物科技有限公司025-025-85560043 17301488900 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
湖北威德利化学试剂有限公司17771473825 13385289472 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
广东云星生物技术有限公司0751-18902340975/189023400307 18902340307 · [email protected]
西安泽邦生物科技有限公司[email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
怀化市冰峰化工有限公司0745-2866851 17711757908 · [email protected]
上海相辉医药科技有限公司13761987713 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
湖北广奥生物科技有限公司027-02702759223056 18162699093 · [email protected]
湖北成海化工有限公司027-59220433 18327245847 · [email protected]
ChemeGen 中国18818260767 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
Clearsynth Labs Limited+91-22-26355700 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
南京世洲生物科技有限公司13675144456 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
普善实业(陕西)有限公司029-81310890 18165209495 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
珠海安哲生物科技有限公司13169972583 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
Alfa Chemistry1-516-6625404 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
上海萄普生物医药技术有限公司15900573766 18018507602 · [email protected]
上海波以尔化工有限公司021-50182298 021-50180596 · [email protected]
上海谱振生物科技有限公司4001650900 13817534909 · [email protected]

Additional notes

DefinitionChEBI: Thioridazine hydrochloride is a hydrochloride. It has a role as a first generation antipsychotic and a geroprotector. It contains a thioridazine.