CAS 50-52-2|THIORIDAZINE
Introduction：Basic information about CAS 50-52-2|THIORIDAZINE, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | THIORIDAZINE | ||
|---|---|---|---|
| CAS Number | 50-52-2 | Molecular Weight | 370.574 |
| Density | 1.2±0.1 g/cm3 | Boiling Point | 515.7±50.0 °C at 760 mmHg |
| Molecular Formula | C21H26N2S2 | Melting Point | 72-74° |
| MSDS | / | Flash Point | 265.7±30.1 °C |
| Symbol | GHS02, GHS06, GHS08 | Signal Word | Danger |
Names
| Name | thioridazine |
|---|---|
| Synonym | More Synonyms |
THIORIDAZINE BiologicalActivity
| Description | Thioridazine, an antagonist of the dopamine receptor D2 family proteins, exhibits potent anti-psychotic and anti-anxiety activities. Thioridazine is also a potent inhibitor of PI3K-Akt-mTOR signaling pathways with anti-angiogenic effect. Thioridazine shows antiproliferative and apoptosis induction effects in various types of cancer cells, with specificity on targeting cancer stem cells (CSCs)[1][2][3][4]. |
|---|---|
| Related Catalog | Signaling Pathways >>Apoptosis >>ApoptosisSignaling Pathways >>Autophagy >>AutophagySignaling Pathways >>GPCR/G Protein >>Dopamine ReceptorSignaling Pathways >>Neuronal Signaling >>Dopamine ReceptorResearch Areas >>Neurological DiseaseSignaling Pathways >>GPCR/G Protein >>5-HT ReceptorSignaling Pathways >>Neuronal Signaling >>5-HT ReceptorSignaling Pathways >>Anti-infection >>Bacterial |
| In Vitro | Thioridazine (0.01-100 μM; 48 h) reduces the cell viability of NCI-N87 and AGS cells in a concentration-dependent manner[2]. Thioridazine (15 μM; 24 h) reduces cell viability of the cervical (HeLa, Caski and C33A) and endometrial (HEC-1-A and KLE) cancer cells[4]. Thioridazine (1-15 μM; 24-48 h) induces gastric cancer cell death via the mitochondrial apoptosis pathway and mitochondrial pathway[2]. Thioridazine (15 μM; 24 h) modulates the regulation of cell cycle progression by interfering with the PI3K/Akt pathway and induces G1 cell cycle arrest in cervical and endometrial cancer cells [4]. Thioridazine inhibits the growth of antibiotic-sensitive and multidrug-resistant strains of A. baumannii[3]. Cell Viability Assay[1] Cell Line: NCI-N87 and AGS cells. Concentration: 0.01, 0.1, 0.5, 1, 5, 10, 20, 50, 100 μM. Incubation Time: 48 hours. Result: Exhibited cytotoxicity in gastric cancer cells. Western Blot Analysis[1] Cell Line: NCI-N87 and AGS cells Concentration: 1, 5, 10, 15 μM. Incubation Time: 24, 48 hours. Result: Downregulated the precursors of caspase-9, caspase-8 and caspase-3. |
| In Vivo | Thioridazine (25 mg/kg; i.p. every 3 days for 3 weeks) extends the survival of tumor-bearing mice and reduces the number of pluripotent embryonal carcinoma (EC) cells within tumors[5]. Thioridazine (1.0-5.0 mg/kg; s.c.) reduces oral behavior and selectively blocks repetitive head bobbing[1]. Animal Model: Nude and Rag2KO mice were injected with iPS cells or NT2D1 cells[5] Dosage: 25 mg/kg. Administration: I.p. every 3 days for 3 weeks. Result: Reduced the number of OCT4-expressing cells within malignant teratocarcinomas and extended the survival of tumor-bearing mice. With no effect on fertility. |
| References | [1]. Tschanz JT, et, al. Atypical antipsychotic drugs block selective components of amphetamine-induced stereotypy. Pharmacol Biochem Behav. 1988 Nov;31(3):519-22. [2]. Mu J, et, al. Thioridazine, an antipsychotic drug, elicits potent antitumor effects in gastric cancer. Oncol Rep. 2014 May;31(5):2107-14. [3]. Kang S, et, al. Thioridazine induces apoptosis by targeting the PI3K/Akt/mTOR pathway in cervical and endometrial cancer cells. Apoptosis. 2012 Sep;17(9):989-97. [4]. Loehr AR, et, al. Targeting Cancer Stem Cells with Differentiation Agents as an Alternative to Genotoxic Chemotherapy for the Treatment of Malignant Testicular Germ Cell Tumors. Cancers (Basel). 2021 Apr 23;13(9):2045. |
Chemical & Physical Properties
| Density | 1.2±0.1 g/cm3 |
|---|---|
| Boiling Point | 515.7±50.0 °C at 760 mmHg |
| Melting Point | 72-74° |
| Molecular Formula | C21H26N2S2 |
| Molecular Weight | 370.574 |
| Flash Point | 265.7±30.1 °C |
| Exact Mass | 370.153748 |
| PSA | 57.08000 |
| LogP | 6.13 |
| Vapour Pressure | 0.0±1.3 mmHg at 25°C |
| Index of Refraction | 1.677 |
| InChIKey | KLBQZWRITKRQQV-UHFFFAOYSA-N |
| SMILES | CSc1ccc2c(c1)N(CCC1CCCCN1C)c1ccccc1S2 |
| Storage condition | ?20°C |
| Water Solubility | Practically insoluble in water, very soluble in methylene chloride, freely soluble in methanol, soluble in ethanol (96 per cent). |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - man
- DOSE/DURATION :
- 43 mg/kg
- TOXIC EFFECTS :
- Cardiac - other changes Lungs, Thorax, or Respiration - acute pulmonary edema Lungs, Thorax, or Respiration - cyanosis
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - child
- DOSE/DURATION :
- 28 mg/kg/2W-I
- TOXIC EFFECTS :
- Behavioral - muscle contraction or spasticity
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - woman
- DOSE/DURATION :
- 14500 mg/kg/15Y-I
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - visual field changes Sense Organs and Special Senses (Eye) - retinal changes (pigmentary depositions, retinitis, other)
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human
- DOSE/DURATION :
- 43 mg/kg
- TOXIC EFFECTS :
- Vascular - regional or general arteriolar or venous dilation Lungs, Thorax, or Respiration - chronic pulmonary edema Blood - hemorrhage
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - child
- DOSE/DURATION :
- 25 mg/kg
- TOXIC EFFECTS :
- Cardiac - change in rate Behavioral - toxic psychosis
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human
- DOSE/DURATION :
- 24 mg/kg
- TOXIC EFFECTS :
- Autonomic Nervous System - parasympatholytic
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - man
- DOSE/DURATION :
- 5214 mg/kg/5Y-I
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - retinal changes (pigmentary depositions, retinitis, other)
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 995 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 150 mg/kg
- TOXIC EFFECTS :
- Behavioral - anticonvulsant Behavioral - antipsychotic
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 640 mg/kg
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - ptosis Autonomic Nervous System - central sympatholytic Behavioral - alteration of classical conditioning
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 71 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 385 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 65 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 310 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 53 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rabbit
- DOSE/DURATION :
- 1200 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rabbit
- DOSE/DURATION :
- 26 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 3040 mg/kg/22W-I
- TOXIC EFFECTS :
- Cardiac - EKG changes not diagnostic of specified effects
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 10 mg/kg
- SEX/DURATION :
- male 7 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Paternal Effects - impotence
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 30 mg/kg
- SEX/DURATION :
- male 7 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Paternal Effects - impotence
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 3214 ug/kg
- SEX/DURATION :
- male 3 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Paternal Effects - impotence
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- DOSE :
- 80 mg/kg
- SEX/DURATION :
- female 1-18 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Unreported
- DOSE :
- 100 mg/kg
- SEX/DURATION :
- female 1 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Fertility - other measures of fertility
MUTATION DATA - TEST SYSTEM :
- Insect - Drosophila melanogaster
- DOSE/DURATION :
- 100 mg/L
- REFERENCE :
- IJEBA6 Indian Journal of Experimental Biology. (Publications & Information Directorate, CSIR, Hillside Rd., New Delhi 110 012, India) V.1- 1963- Volume(issue)/page/year: 11,403,1973 *** REVIEWS *** TOXICOLOGY REVIEW JMSCA9 Journal of Mental Science. (London, UK) V.4-108, 1857-1962. For publisher information, see BJPYAJ. Volume(issue)/page/year: 106,755,1960 TOXICOLOGY REVIEW IDPYAK Industrial Pharmacology. (Mount Kisco, NY) V.1-3, 1974-79. Discontinued. Volume(issue)/page/year: 1,203,1974 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5668 No. of Facilities: 35 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 430 (estimated) No. of Female Employees: 239 (estimated)
- TEST SYSTEM :
- Insect - Drosophila melanogaster
- DOSE/DURATION :
- 100 mg/L
- REFERENCE :
- IJEBA6 Indian Journal of Experimental Biology. (Publications & Information Directorate, CSIR, Hillside Rd., New Delhi 110 012, India) V.1- 1963- Volume(issue)/page/year: 11,403,1973 *** REVIEWS *** TOXICOLOGY REVIEW JMSCA9 Journal of Mental Science. (London, UK) V.4-108, 1857-1962. For publisher information, see BJPYAJ. Volume(issue)/page/year: 106,755,1960 TOXICOLOGY REVIEW IDPYAK Industrial Pharmacology. (Mount Kisco, NY) V.1-3, 1974-79. Discontinued. Volume(issue)/page/year: 1,203,1974 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5668 No. of Facilities: 35 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 430 (estimated) No. of Female Employees: 239 (estimated)
Safety Information
| Symbol | GHS02, GHS06, GHS08 |
|---|---|
| Signal Word | Danger |
| Hazard Statements | H225-H301 + H311 + H331-H370-H412 |
| Precautionary Statements | P210-P260-P273-P280-P301 + P310-P311 |
| Hazard Codes | F,T |
| Risk Phrases | 11-23/24/25-39/23/24/25-52/53 |
| Safety Phrases | 16-36/37-45-61 |
| RIDADR | UN1230 - class 3 - PG 2 - Methanol, solution |
Articles38
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| A repurposing approach identifies off-patent drugs with fungicidal cryptococcal activity, a common structural chemotype, and pharmacological properties relevant to the treatment of cryptococcosis. Eukaryotic Cell 12(2) , 278-87, (2013) New, more accessible therapies for cryptococcosis represent an unmet clinical need of global importance. We took a repurposing approach to identify previously developed drugs with fungicidal activity ... | |
| Why and how thioridazine in combination with antibiotics to which the infective strain is resistant will cure totally drug-resistant tuberculosis. Expert Rev. Anti. Infect. Ther. 10(8) , 869-73, (2012) Over a period of 14 years, the authors have studied thioridazine, an old neuroleptic, that has been shown to have in vitro activity against intracellular Mycobacterium tuberculosis, regardless of its ... |
Synonyms
| 3-Methylmercapto-N-[2'-(N'-methyl-2-piperidyl)ethyl]phenothiazine |
| EINECS 200-044-2 |
| MFCD00242875 |
| Phenothiazine, 10-[2-(1-methyl-2-piperidyl)ethyl]-2-(methylthio)- |
| 10H-Phenothiazine, 10-[2-(1-methyl-2-piperidinyl)ethyl]-2-(methylthio)- |
| 2-Methylmercapto-10-[2-(N-methyl-2-piperidyl)ethyl]phenothiazine |
| 10-[2-(1-methylpiperidin-2-yl)ethyl]-2-methylsulfanylphenothiazine |
| 10-[2-(1-methylpiperidin-2-yl)ethyl]-2-(methylthio)-10H-phenothiazine |
| THIORIDAZINE |
| 10-[2-(1-Methyl-2-piperidinyl)ethyl]-2-(methylsulfanyl)-10H-phenothiazine |
| 10-[2-(1-Methyl-2-piperidinyl)ethyl]-2-(methylthio)-10H-phenothiazine |
| 10-[2-(1-Methylpiperidin-2-yl)ethyl]-2-(methylsulfanyl)-10H-phenothiazine |
| UNII:N3D6TG58NI |
| 10H-Phenothiazine, 10-(2-(1-methyl-2-piperidinyl)ethyl)-2-(methylthio)- |
