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MedKoo Cat#: 598835 | Name: Mesoridazine free base

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Mesoridazine, also know as thioridazine EP impurity B is a phenothiazine antipsychotic with effects similar to CHLORPROMAZINE.

Chemical Structure

Mesoridazine free base
CAS#5588-33-0 (free base)

Theoretical Analysis

MedKoo Cat#: 598835

Name: Mesoridazine free base

CAS#: 5588-33-0 (free base)

Chemical Formula: C21H26N2OS2

Exact Mass: 386.1487

Molecular Weight: 386.57

Elemental Analysis: C, 65.25; H, 6.78; N, 7.25; O, 4.14; S, 16.59

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Related CAS #
5588-33-0 (free base) 32672-69-8 (besylate) 59884-26-3 (HCl)
Synonym
Mesoridazine; NC-123; NSC 186066; NSC-186066; NSC186066; TPS23; TPS 23; TPS-23; Thioridazine thiomethyl sulfoxide;
IUPAC/Chemical Name
10-(2-(1-methylpiperidin-2-yl)ethyl)-2-(methylsulfinyl)-10H-phenothiazine
InChi Key
SLVMESMUVMCQIY-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H26N2OS2/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)25-21-11-10-17(26(2)24)15-19(21)23/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3
SMILES Code
O=S(C(C=C1N2CCC3N(C)CCCC3)=CC=C1SC4=C2C=CC=C4)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
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.
In vitro activity:
Mesoridazine blocked HERG currents in a concentration-dependent manner (IC50 550 nM at 0 mV); block increased significantly over the voltage range where HERG activates and saturated at voltages eliciting maximal HERG channel activation. Reference: J Mol Cell Cardiol. 2004 Jan;36(1):151-60. https://pubmed.ncbi.nlm.nih.gov/14734057/
In vivo activity:
Using a subcutaneous injection model in rats, this study tested the cutaneous analgesic effects of six phenothiazine-type antipsychotics (mesoridazine, promazine, chlorpromazine, fluphenazine, perphenazine and triflupromazine) at a dose of 0.6 mumol, and compared them with those of bupivacaine and lidocaine. Mesoridazine had a longer duration of action than bupivacaine (p<0.001). In terms of ED(50) values, mesoridazine was more potent and longer-acting than bupivacaine and lidocaine (p<0.01 for each comparison). Reference: Acta Anaesthesiol Taiwan. 2010 Mar;48(1):3-7. https://pubmed.ncbi.nlm.nih.gov/20434106/

Preparing Stock Solutions

The following data is based on the product molecular weight 386.57 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Su Z, Martin R, Cox BF, Gintant G. 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. doi: 10.1016/j.yjmcc.2003.10.017. PMID: 14734057. 2. Liu KS, Chen YW, Aljuffali IA, Chang CW, Wang JJ, Fang JY. 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. doi: 10.1016/j.ejpb.2016.05.025. Epub 2016 May 31. PMID: 27260201. 3. Chen YW, Chu CC, Chu KS, Shieh JP, Chien CC, Wang JJ, Kao CH. Phenothiazine-type antipsychotics elicit cutaneous analgesia in rats. Acta Anaesthesiol Taiwan. 2010 Mar;48(1):3-7. doi: 10.1016/S1875-4597(10)60002-1. PMID: 20434106.
In vitro protocol:
1. Su Z, Martin R, Cox BF, Gintant G. 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. doi: 10.1016/j.yjmcc.2003.10.017. PMID: 14734057.
In vivo protocol:
1. Liu KS, Chen YW, Aljuffali IA, Chang CW, Wang JJ, Fang JY. 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. doi: 10.1016/j.ejpb.2016.05.025. Epub 2016 May 31. PMID: 27260201. 2. Chen YW, Chu CC, Chu KS, Shieh JP, Chien CC, Wang JJ, Kao CH. Phenothiazine-type antipsychotics elicit cutaneous analgesia in rats. Acta Anaesthesiol Taiwan. 2010 Mar;48(1):3-7. doi: 10.1016/S1875-4597(10)60002-1. PMID: 20434106.
1: Im SH, Park MJ, Seo H, Choi SH, Kim SK, Ahn SH. Determination of mesoridazine by liquid chromatography-tandem mass spectrometry and its application to pharmacokinetic study in rats. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 May 1;958:117-23. doi: 10.1016/j.jchromb.2014.03.020. Epub 2014 Mar 24. PubMed PMID: 24732149. 2: Liu KS, Chen YW, Aljuffali IA, Chang CW, Wang JJ, Fang JY. 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. doi: 10.1016/j.ejpb.2016.05.025. Epub 2016 May 31. PubMed PMID: 27260201. 3: Salih IS, Thanacoody RH, McKay GA, Thomas SH. 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. Epub 2007 Apr 4. PubMed PMID: 17410120. 4: Charalampous KD, Johnson PC, Estevez V. Absorption and excretion of thioridazine and mesoridazine in man. Dis Nerv Syst. 1974 Nov;35(11):494-6. PubMed PMID: 17896456. 5: Gershon S, Sakalis G, Bowers PA. Mesoridazine -- a pharmacodynamic and pharmacokinetic profile. J Clin Psychiatry. 1981 Dec;42(12):463-9. Review. PubMed PMID: 7031039. 6: Vital-Herne J, Gerbino L, Kay SR, Katz IR, Opler LA. Mesoridazine and thioridazine: clinical effects and blood levels in refractory schizophrenics. J Clin Psychiatry. 1986 Jul;47(7):375-9. PubMed PMID: 2873133. 7: Lin G, Hawes EM, McKay G, Korchinski ED, Midha KK. The metabolism of piperidine-type phenothiazine antipsychotic agents. III. Mesoridazine in dog, human and rat. Xenobiotica. 1993 Jan;23(1):37-52. PubMed PMID: 8097900. 8: Su Z, Martin R, Cox BF, Gintant G. 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. PubMed PMID: 14734057. 9: Barnes RJ. Mesoridazine (Serentil) in personality disorders--a controlled trial in adolescent patients. Dis Nerv Syst. 1977 Apr;38(4):258-64. PubMed PMID: 321198. 10: Dinovo EC, Gottschalk LA, Nandi BR, Geddes PG. GLC analysis of thioridazine, mesoridazine, and their metabolites. J Pharm Sci. 1976 May;65(5):667-9. PubMed PMID: 932933. 11: Llerena A, Berecz R, de la Rubia A, Norberto MJ, Benítez J. Use of the mesoridazine/thioridazine ratio as a marker for CYP2D6 enzyme activity. Ther Drug Monit. 2000 Aug;22(4):397-401. PubMed PMID: 10942178. 12: Dorado P, Peñas-LLedó EM, de la Rubia A, LLerena A. Relevance of CYP2D6 -1584C>G polymorphism for thioridazine:mesoridazine plasma concentration ratio in psychiatric patients. Pharmacogenomics. 2009 Jul;10(7):1083-9. doi: 10.2217/pgs.09.57. PubMed PMID: 19604081. 13: Aguilar SJ. An open study of mesoridazine (Serentil) in chronic schizophrenics. Dis Nerv Syst. 1975 Sep;36(9):484-9. PubMed PMID: 1175465. 14: Donlon PT, Tupin JP. Successful suicides with thioridazine and mesoridazine: a result of probable cardiotoxicity. Arch Gen Psychiatry. 1977 Aug;34(8):955-7. PubMed PMID: 889420. 15: Dinovo EC, Pollak H, Gottschalk LA. Partitioning of thioridazine and mesoridazine in human blood fractions. Methods Find Exp Clin Pharmacol. 1984 Mar;6(3):143-6. PubMed PMID: 6748818. 16: Choi S, Haggart D, Toll L, Cuny GD. Synthesis, receptor binding and functional studies of mesoridazine stereoisomers. Bioorg Med Chem Lett. 2004 Sep 6;14(17):4379-82. PubMed PMID: 15357957. 17: Hamid TA, Wertz WJ. Mesoridazine versus chlorpromazine in acute schizophrenia: a double-blind investigation. Am J Psychiatry. 1973 Jun;130(6):689-92. PubMed PMID: 4573820. 18: Gottschalk LA, Dinovo E, Bierner R. Plasma levels of mesoridazine and its metabolites and clinical response in acute schizophrenia after a single intramuscular drug dose. Psychopharmacol Bull. 1975 Oct;11(4):33-4. PubMed PMID: 812135. 19: Niemann JT, Stapczynski JS, Rothstein RJ, Laks MM. Cardiac conduction and rhythm disturbances following suicidal ingestion of mesoridazine. Ann Emerg Med. 1981 Nov;10(11):585-8. PubMed PMID: 7316263. 20: Goldstein SE. The use of mesoridazine in geriatrics. Curr Ther Res Clin Exp. 1974 Apr;16(4):316-23. PubMed PMID: 4208348.