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50-52-2

50-52-2 structure
50-52-2 structure
  • Name: THIORIDAZINE
  • Chemical Name: thioridazine
  • CAS Number: 50-52-2
  • Molecular Formula: C21H26N2S2
  • Molecular Weight: 370.574
  • Catalog: API Synthetic anti-infective drugs Sulfonamides and synergists
  • Create Date: 2018-09-22 15:35:20
  • Modify Date: 2024-01-02 15:19:30
  • 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].

Name thioridazine
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)-
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
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.

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
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).

CHEMICAL IDENTIFICATION

RTECS NUMBER :
SP2100000
CHEMICAL NAME :
Phenothiazine, 10-((1-methyl-2-piperidyl)ethyl)-2-(methylthio)-
CAS REGISTRY NUMBER :
50-52-2
LAST UPDATED :
199712
DATA ITEMS CITED :
28
MOLECULAR FORMULA :
C21-H26-N2-S2
MOLECULAR WEIGHT :
370.61
WISWESSER LINE NOTATION :
T C666 BN ISJ ES1 B2- BT6NTJ A1

HEALTH HAZARD DATA

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)
Symbol GHS02 GHS06 GHS08
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

~%

50-52-2 structure

50-52-2

Literature: Bourquin et al. Helvetica Chimica Acta, 1958 , vol. 41, p. 1072,1080

~%

50-52-2 structure

50-52-2

Literature: Bourquin et al. Helvetica Chimica Acta, 1958 , vol. 41, p. 1072,1080

~%

50-52-2 structure

50-52-2

Literature: Bourquin et al. Helvetica Chimica Acta, 1958 , vol. 41, p. 1072,1080

~%

50-52-2 structure

50-52-2

Literature: Bourquin et al. Helvetica Chimica Acta, 1958 , vol. 41, p. 1072,1080

~%

50-52-2 structure

50-52-2

Literature: Bourquin et al. Helvetica Chimica Acta, 1958 , vol. 41, p. 1072,1080

~%

50-52-2 structure

50-52-2

Literature: Bourquin et al. Helvetica Chimica Acta, 1958 , vol. 41, p. 1072,1080

~%

50-52-2 structure

50-52-2

Literature: Bourquin et al. Helvetica Chimica Acta, 1958 , vol. 41, p. 1072,1080