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

• ChemBase编号: 809
• 分子式: C21H26N2OS2
• 平均质量: 386.57394
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 2-methanesulfinyl-10-[2-(1-methylpiperidin-2-yl)ethyl]-10H-phenothiazine
• IUPAC传统名: mesoridazine
• 商标名: Calodal; Lidanar; Lidanil; Serentil; Serentil Concentrate
• 别名: 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

登记号

• CAS号: 5588-33-0
• PubChem SID: 160964272; 46506724
• PubChem CID: 4078
• CHEBI ID: 6780
• ATC码: N05AC03
• CHEMBL: 1088
• Chemspider ID: 3936
• DrugBank ID: DB00933
• KEGG ID: D02671
• 美国药典/FDA物质标识码: 5XE4NWM740
• 维基百科标题: Mesoridazine
• Medline Plus: a682306

理论计算性质

JChem

• Acid pKa: 19.359158
• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 0.9448053
• LogD (pH = 7.4): 2.718917
• Log P: 3.5745034
• 摩尔折射率: 115.1253 cm^3
• 极化性: 44.35003 Å^3
• 极化表面积: 23.55 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.83
• LOG S: -3.7
• 溶解度: 7.67e-02 g/l

分子性质

理化性质

• 溶解度: Dichloromethane; Ethyl Acetate; insoluble in water; Methanol
• 外观: Pale Pink Solid
• 熔点: 130°C (266°F)
• 疏水性(logP): 3.9

药理学性质

• 给药途径: oral, intravenous
• 排泄: Biliary and renal
• 半衰期: 24 to 48 hours
• 代谢: Hepatic/Renal
• 蛋白结合率: 4%
• 法定药品分级: Rx-only
• 妊娠期药物分类: C (US)

详细说明

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.

参考文献

• 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)