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Related CAS#:
5588-33-0 147-73-9
32672-69-8

5588-33-0

5588-33-0 structure
5588-33-0 structure
  • Name: Mesoridazine
  • Chemical Name: mesoridazine
  • CAS Number: 5588-33-0
  • Molecular Formula: C21H26N2OS2
  • Molecular Weight: 386.57400
  • Catalog: Pharmaceutical intermediate Heterocyclic compound Pyridazine
  • Create Date: 2018-06-28 19:35:26
  • Modify Date: 2024-01-09 07:12:00
  • Mesoridazine (TPS-23) , a metabolite of Thioridazine (HY-B0965A), acts as an orally active phenothiazine antipsychotic agent. Mesoridazine is a potent and rapid open-channel blocker of human ether-a-go-go related gene (hERG) channels and blocks hERG currents with an IC50 of 550 nM (at 0 mV) in human embryonic kidney 293 cells[1].Mesoridazine can be used for the research of schizophrenia, as well as certain other psychiatric disorders[1][2].
Name mesoridazine
Synonyms Mesoridazina
Thioridazine-2-sulfoxide
Lidanar
10-[2-(1-methylpiperidin-2-yl)ethyl]-2-methylsulfinylphenothiazine
Tps23
10-[2-(1-methylpiperidin-2-yl)ethyl]-2-(methylsulfinyl)-10H-phenothiazine
Mesoridazinum
10-[2-(1-methyl-2-piperidyl)ethyl]-2-methylsulphinylphenothiazine
Lidanil
Calodal
Serentil
Thioridazine thiomethyl sulfoxide
10-{2-[(RS)1-methylpiperidin-2-yl]ethyl}-2-methylsulfinyl-10H-phenothiazine
Description Mesoridazine (TPS-23) , a metabolite of Thioridazine (HY-B0965A), acts as an orally active phenothiazine antipsychotic agent. Mesoridazine is a potent and rapid open-channel blocker of human ether-a-go-go related gene (hERG) channels and blocks hERG currents with an IC50 of 550 nM (at 0 mV) in human embryonic kidney 293 cells[1].Mesoridazine can be used for the research of schizophrenia, as well as certain other psychiatric disorders[1][2].
Related Catalog
Target

IC50: hERG currents[1]
In Vitro Mesoridazine blocks human ether-a-go-go-related gene (HERG) currents in a concentration-dependent manner (IC50 = 550 nM at 0 mV), block increased significantly over the voltage range where HERG activates and saturates at voltages eliciting maximal HERG channel activation[1]. Mesoridazine (15 mM; 24 h) shows total absorption of 15.94 ± 4.04% and 39.24 ± 5.11% in nude mouse and pig skin, respectively[3].
In Vivo Mesoridazine (15 mM; topical administration; once or daily for 7 consecutive days) displays potent activity and a long period of analgesia at blocking cutaneous pain[3]. Mesoridazine (15 mM) shows intradermal concentration of 0.34 0.74 nmol/mg after topical application on nude mouse back for 6 h[3]. Animal Model: Eight-week-old female nude mice[3] Dosage: 15 mM Administration: Topical administration, once (analgesia test) or daily for 7 consecutive days (irritation test) Result: Showed analgesic effect. A slight transepidermal water loss (TEWL) increased from 7.8 to 9.9 g/m2/h was observed.
References

[1]. Zhi Su, et al. Mesoridazine: an open-channel blocker of human ether-a-go-go-related gene K+ channel. J Mol Cell Cardiol. 2004 Jan;36(1):151-60.

[2]. I S M Salih, et al. Comparison of the effects of thioridazine and mesoridazine on the QT interval in healthy adults after single oral doses. Clin Pharmacol Ther. 2007 Nov;82(5):548-54.

[3]. Liu KS, et al. Topically applied mesoridazine exhibits the strongest cutaneous analgesia and minimized skin disruption among tricyclic antidepressants: The skin absorption assessment. Eur J Pharm Biopharm. 2016 Aug;105:59-68.
Density 1.3g/cm3
Boiling Point 570.5ºC at 760mmHg
Molecular Formula C21H26N2OS2
Molecular Weight 386.57400
Flash Point 298.9ºC
Exact Mass 386.14900
PSA 68.06000
LogP 5.76970
Index of Refraction 1.694

CHEMICAL IDENTIFICATION

RTECS NUMBER :
SP1880000
CHEMICAL NAME :
Phenothiazine, 10-(2-(1-methyl-2-piperidyl)ethyl)-2-(methylsulfinyl) -
CAS REGISTRY NUMBER :
5588-33-0
LAST UPDATED :
199512
DATA ITEMS CITED :
10
MOLECULAR FORMULA :
C21-H26-N2-O-S2
MOLECULAR WEIGHT :
386.61
WISWESSER LINE NOTATION :
T C666 BN ISJ ESO&1 B2- BT6NTJ A

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
86 mg/kg
TOXIC EFFECTS :
Cardiac - arrhythmias (including changes in conduction)
REFERENCE :
JCPYDR Journal of Clinical Pyschopharmacology. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1981- Volume(issue)/page/year: 2,222,1982
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
42 mg/kg
TOXIC EFFECTS :
Vascular - regional or general arteriolar or venous dilation Lungs, Thorax, or Respiration - chronic pulmonary edema Blood - hemorrhage
REFERENCE :
ARGPAQ Archives of General Psychiatry. (AMA, 535 N. Dearborn St., Chicago,IL 60610) V.3- 1960- Volume(issue)/page/year: 34,955,1977
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
644 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 19,363,1971
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
509 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 19,363,1971
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
560 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,29,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
26 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,29,1972
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
800 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 19,363,1971
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
405 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 19,363,1971 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
60480 mg/kg/72W-I
TOXIC EFFECTS :
Brain and Coverings - recordings from specific areas of CNS Skin and Appendages - dermatitis, other (after systemic exposure) Related to Chronic Data - death
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 19,363,1971 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4738 No. of Facilities: 7 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 103 (estimated) No. of Female Employees: 52 (estimated)
Precursor  1

DownStream  1


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