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

• ChemBase ID: 561
• Molecular Formular: C21H26N2S2
• Molecular Mass: 370.57454
• Monoisotopic Mass: 370.15374084
• SMILES: S1c2c(N(CCC3N(CCCC3)C)c3c1cccc3)cc(SC)cc2
• Canonical SMILES: CSc1ccc2c(c1)N(CCC1CCCCN1C)c1c(S2)cccc1
• InChI: InChI=1S/C21H26N2S2/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)25-21-11-10-17(24-2)15-19(21)23/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3
• InChIKey: KLBQZWRITKRQQV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 10-[2-(1-methylpiperidin-2-yl)ethyl]-2-(methylsulfanyl)-10H-phenothiazine
• IUPAC Traditional name: thioridazine
• Brand Name: Aldazine; Mallorol; Malloryl; Meleril; Mellaril; Mellaril Hydrochloride; Mellaril-S; Mellarit; Mellerets; Mellerette; Melleretten; Melleril; Metlaril; Novoridazine; Orsanil; Ridazin; Ridazine; Sonapax; Sonapax Hydrochloride; Stalleril; Thioridazine Hcl Intensol; Thioridazine, Prolongatum; Tioridazin
• Synonyms: Thioridazine Hydrochloride; Thioridazine Chloride; Thioridazin; Thoridazine Hydrochloride; Thioridazine Hcl; Thioridazine

Database IDs

• CAS Number: 50-52-2
• PubChem SID: 160964024; 46509070
• PubChem CID: 5452

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.3070333
• LogD (pH = 7.4): 3.9332237
• Log P: 5.469306
• Molar Refractivity: 113.5226 cm^3
• Polarizability: 43.827343 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.93
• LOG S: -5.64
• Solubility (Water): 8.55e-04 g/l

PROPERTIES

Physical Property

• Solubility: 0.0336 mg/L
• Hydrophobicity(logP): 5.9

DETAILS

DrugBank - DB00679

• Drug Groups: approved
• Description: A phenothiazine antipsychotic used in the management of psychoses, including schizophrenia, and in the control of severely disturbed or agitated behavior. It has little antiemetic activity. Thioridazine has a higher incidence of antimuscarinic effects, but a lower incidence of extrapyramidal symptoms, than chlorpromazine. (From Martindale, The Extra Pharmacopoeia, 30th ed, p618)
• Indication: For the treatment of schizophrenia and generalized anxiety disorder.
• Pharmacology: Thioridazine is a trifluoro-methyl phenothiazine derivative intended for the management of schizophrenia and other psychotic disorders. Thioridazine has not been shown effective in the management of behaviorial complications in patients with mental retardation.
• Toxicity: LD₅₀=956-1034 mg/kg (Orally in rats); Agitation, blurred vision, coma, confusion, constipation, difficulty breathing, dilated or constricted pupils, diminished flow of urine, dry mouth, dry skin, excessively high or low body temperature, extremely low blood pressure, fluid in the lungs, heart abnormalities, inability to urinate, intestinal blockage, nasal congestion, restlessness, sedation, seizures, shock
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: 60%
• Half Life: 21-25 hours
• Protein Binding: 95%
• External Links: Wikipedia; RxList; Drugs.com