2-methanesulfinyl-10-[2-(1-methylpiperidin-2-yl)ethyl]-10H-phenothiazine

• ChemBase ID: 809
• Molecular Formular: C21H26N2OS2
• Molecular Mass: 386.57394
• Monoisotopic Mass: 386.14865546
• SMILES: S1c2c(N(CCC3N(CCCC3)C)c3c1cccc3)cc(S(=O)C)cc2
• Canonical SMILES: CN1CCCCC1CCN1c2ccccc2Sc2c1cc(cc2)S(=O)C
• InChI: 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
• InChIKey: SLVMESMUVMCQIY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methanesulfinyl-10-[2-(1-methylpiperidin-2-yl)ethyl]-10H-phenothiazine
• IUPAC Traditional name: mesoridazine
• Brand Name: Calodal; Lidanar; Lidanil; Serentil; Serentil Concentrate
• Synonyms: 10-[2-(1-Methyl-2-piperidinyl)ethyl]-2-(methylsulfinyl)-phenothiazine; 1-Methyl-2-[2-[2-(methylsulfinyl)phenothiazin-10-yl]ethyl]piperidine; 10-[2-(1-Methyl-2-piperidyl)ethyl]-2-(methylsulfinyl)phenothiazine; NSC 186066; Serentil; TPS 23; Thioridazine-2-sulfoxide; Thioridazien Thiomethyl Sulfoxide; Thioridazine Monosulfoxide Analog; Thioridazine Thiomethyl Sulfoxide; TPS-23; TPS23; Mesoridazine

Database IDs

• CAS Number: 5588-33-0
• PubChem SID: 46506724; 160964272
• PubChem CID: 4078
• CHEBI ID: 6780
• ATC CODE: N05AC03
• CHEMBL: 1088
• Chemspider ID: 3936
• DrugBank ID: DB00933
• KEGG ID: D02671
• Unique Ingredient Identifier: 5XE4NWM740
• Wikipedia Title: Mesoridazine
• Medline Plus: a682306

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.359158
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.9448053
• LogD (pH = 7.4): 2.718917
• Log P: 3.5745034
• Molar Refractivity: 115.1253 cm^3
• Polarizability: 44.35003 Å^3
• Polar Surface Area: 23.55 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.83
• LOG S: -3.7
• Solubility (Water): 7.67e-02 g/l

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; insoluble in water; Methanol
• Apperance: Pale Pink Solid
• Melting Point: 130°C (266°F)
• Hydrophobicity(logP): 3.9

Pharmacology Properties

• Admin Routes: oral, intravenous
• Excretion: Biliary and renal
• Half Life: 24 to 48 hours
• Metabolism: Hepatic/Renal
• Protein Bound: 4%
• Legal Status: Rx-only
• Pregnancy Category: C (US)

DETAILS

DrugBank - DB00933

• Drug Groups: approved
• Description: A phenothiazine antipsychotic with effects similar to chlorpromazine. [PubChem]
• Indication: Used in the treatment of schizophrenia, organic brain disorders, alcoholism and psychoneuroses.
• Pharmacology: Mesoridazine, the besylate salt of a metabolite of thioridazine, is a phenothiazine tranquilizer. Pharmacological studies in laboratory animals have established that mesoridazine has a spectrum of pharmacodynamic actions typical of a major tranquilizer. In common with other tranquilizers it inhibits spontaneous motor activity in mice, prolongs thiopental and hexobarbital sleeping time in mice and produces spindles and block of arousal reaction in the EEG of rabbits. It is effective in blocking spinal reflexes in the cut and antagonizes d-amphetamine excitation and toxicity in grouped mice. It shows a moderate adrenergic blocking activity in vitro and in vivo and antagonizes 5-hydroxytryptamine in vivo. Intravenously administered, it lowers the blood pressure of anesthetized dogs. It has a weak antiacetylcholine effect in vitro.
• Toxicity: Oral LD₅₀ is 560 ± 62.5 mg/kg and 644 ± 48 mg/kg in mouse and rat, respectively. Symptoms of overdose may include emesis, muscle tremors, decreased food intake and death associated with aspiration of oral-gastric contents into the respiratory system.
• Affected Organisms: Humans and other mammals
• Absorption: Well absorbed from the gastrointestinal tract.
• Half Life: 24 to 48 hours
• Protein Binding: 4%
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - M225760

Mesoridazine is an antipsychotic.

REFERENCES

• Rossato, G., et al.: ChemMedChem, 5, 2088 (2010)
• Sudeshna, G., et al.: Eur. J. Pharmacol., 648, 6 (2010)
• Hidaka, S., et al.: J. Toxicol. Sci., 35, 393 (2010)