Mesoridazine

Modify Date: 2024-01-09 07:12:00

Mesoridazine Structure
Mesoridazine structure
Common Name Mesoridazine
CAS Number 5588-33-0 Molecular Weight 386.57400
Density 1.3g/cm3 Boiling Point 570.5ºC at 760mmHg
Molecular Formula C21H26N2OS2 Melting Point N/A
MSDS N/A Flash Point 298.9ºC

 Use of Mesoridazine


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].

 Names

Name mesoridazine
Synonym More Synonyms

 Mesoridazine Biological Activity

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.

 Chemical & Physical Properties

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

 Toxicological Information

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 & DownStream

Precursor  1

DownStream  1

 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
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