10-[3-(4-methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)-10H-phenothiazine

• ChemBase ID: 710
• Molecular Formular: C21H24F3N3S
• Molecular Mass: 407.4955696
• Monoisotopic Mass: 407.16430344
• SMILES: S1c2c(N(CCCN3CCN(CC3)C)c3c1cccc3)cc(cc2)C(F)(F)F
• Canonical SMILES: CN1CCN(CC1)CCCN1c2ccccc2Sc2c1cc(cc2)C(F)(F)F
• InChI: InChI=1S/C21H24F3N3S/c1-25-11-13-26(14-12-25)9-4-10-27-17-5-2-3-6-19(17)28-20-8-7-16(15-18(20)27)21(22,23)24/h2-3,5-8,15H,4,9-14H2,1H3
• InChIKey: ZEWQUBUPAILYHI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 10-[3-(4-methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)-10H-phenothiazine
• IUPAC Traditional name: trifluoperazine
• Brand Name: Eskazine; Eskazinyl; Fluoperazine; Jatroneural; Modalina; Novo-Trifluzine; Stelazine; Stellazine; Synklor; Terfluzine; Trazine; Triflurin; Triftazin; Triftazine; Triperazine; Triphtazin; Triphtazine; Triphthasine; Triphthazine; Tryptazine
• Synonyms: 10-[3-(4-Methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-10H-phenothiazine Dihydrochloride; Triftazin; Triphthasine; Eskazinyl; Eskazine; Modalina; Stelazine; Trifluoperazine Dihydrochloride; Trifluoperazine Dihydrochloride; Trifluoperazine HCl; Trifluoroperazine Hydrochloride; Trifluoroperazine Dihydrochloride; Trifluoperazine Hydrochloride; Trifluoromethylperazine; Trifluoroperazine; Triphthazine Dihydrochloride; Tryptazine Dihydrochloride; Trifluoperazin; Trifluoperazina; Trifluperazine; Trifluroperizine; Trifluoperazine

Database IDs

• CAS Number: 440-17-5; 117-89-5
• PubChem SID: 46507961; 160964173
• PubChem CID: 5566
• CHEBI ID: 45951
• ATC CODE: N05AB06
• CHEMBL: 422
• Chemspider ID: 5365
• DrugBank ID: DB00831
• IUPHAR ligand ID: 214
• Unique Ingredient Identifier: 214IZI85K3
• Wikipedia Title: Trifluoperazine
• Medline Plus: a682121

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.8602431
• LogD (pH = 7.4): 3.6257002
• Log P: 4.655924
• Molar Refractivity: 110.9753 cm^3
• Polarizability: 41.350826 Å^3
• Polar Surface Area: 9.72 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.87
• LOG S: -4.67
• Solubility (Water): 8.76e-03 g/l

PROPERTIES

Physical Property

• Solubility: 0.0122 mg/mL at 24 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; Water
• Apperance: Off-White Solid
• Melting Point: 236-238°C
• Hydrophobicity(logP): 4.9

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Hygroscopic

Pharmacology Properties

• Admin Routes: oral, IM
• Half Life: 10–20 hours
• Metabolism: Hepatic
• Legal Status: POM (UK); Rx-only (US)
• Pregnancy Category: C (Australia); C (US)

DETAILS

DrugBank - DB00831

• Drug Groups: approved
• Description: A phenothiazine with actions similar to chlorpromazine. It is used as an antipsychotic and an antiemetic. [PubChem]
• Indication: For the treatment of anxiety disorders, depressive symptoms secondary to anxiety and agitation.
• Pharmacology: Trifluoperazine is a trifluoro-methyl phenothiazine derivative intended for the management of schizophrenia and other psychotic disorders. Trifluoperazine has not been shown effective in the management of behaviorial complications in patients with mental retardation.
• Toxicity: Symptoms of overdose include agitation, coma, convulsions, difficulty breathing, difficulty swallowing, dry mouth, extreme sleepiness, fever, intestinal blockage, irregular heart rate, low blood pressure, and restlessness.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Half Life: 10-20 hours
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - T779200

Antipsychotic.

REFERENCES

• Flanagan, T.L., et al.: J. Pharm. Sci., 51, 996 (1962)
• Post., A., et al.: Anal. Profiles Drug Subs., 9, 543 (1980)