2-(4-{3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl}piperazin-1-yl)ethan-1-ol

• ChemBase ID: 505
• Molecular Formular: C22H26F3N3OS
• Molecular Mass: 437.5215496
• Monoisotopic Mass: 437.17486813
• SMILES: S1c2c(N(CCCN3CCN(CC3)CCO)c3c1cccc3)cc(cc2)C(F)(F)F
• Canonical SMILES: OCCN1CCN(CC1)CCCN1c2ccccc2Sc2c1cc(cc2)C(F)(F)F
• InChI: InChI=1S/C22H26F3N3OS/c23-22(24,25)17-6-7-21-19(16-17)28(18-4-1-2-5-20(18)30-21)9-3-8-26-10-12-27(13-11-26)14-15-29/h1-2,4-7,16,29H,3,8-15H2
• InChIKey: PLDUPXSUYLZYBN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4-{3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl}piperazin-1-yl)ethan-1-ol
• IUPAC Traditional name: fluphenazine; 2-(4-{3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl}piperazin-1-yl)ethan-1-ol
• Brand Name: Apo-Fluphenazine; Elinol; Modecate; Moditen Enanthate; Moditen Hcl; Permitil Concentrate; Prolixin; Prolixin Concentrate; Prolixin Enanthate; Prolixine; Sevinol; Siqualine; Siqualon; Vespazine; Yespazine
• Synonyms: Triflumethazine; Fluphenazine Hcl; Fluphenazine Decanoate; Fluorphenazine; Fluorophenazine; Fluorfenazine; Fluphenazine; 4-[3-[2-(Trifluoromethyl)-10H-phenothiazin-10-yl]propyl]-1-piperazineethanol Dihydrochloride; 4-[3-[2-(Trifluoromethyl)phenothiazin-10-yl]propyl]-1-piperazineethanol Dihydrochloride; Anatensol; Dapotum; Flufenazin; Tensofin; Fluphenazine Dihydrochloride; Flufenazine; Fluphenazine

Database IDs

• CAS Number: 146-56-5; 69-23-8
• PubChem SID: 160963968; 46506645
• PubChem CID: 3372
• CHEBI ID: 5123
• ATC CODE: N05AB02
• CHEMBL: 726
• Chemspider ID: 3255
• DrugBank ID: DB00623
• IUPHAR ligand ID: 204
• KEGG ID: D07977
• Unique Ingredient Identifier: S79426A41Z
• Wikipedia Title: Fluphenazine
• Medline Plus: a682172

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.593098
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.3181694
• LogD (pH = 7.4): 3.0929255
• Log P: 3.9658215
• Molar Refractivity: 117.2676 cm^3
• Polarizability: 43.838596 Å^3
• Polar Surface Area: 29.95 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.4
• LOG S: -4.36
• Solubility (Water): 1.90e-02 g/l

PROPERTIES

Physical Property

• Solubility: 31.1 mg/L; DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 200-202°C
• Hydrophobicity(logP): 4.2

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Admin Routes: oral, IM, decanoate
• Bioavailability: 40% - 50%
• Excretion: bile/feces
• Half Life: 15 to 30 hours
• Metabolism: Hepatic
• Legal Status: Rx-only
• Pregnancy Category: C (US)
• Mechanism of Action: Calmodulin-antagonist; Dopamine-antagonist; Dopamine-release inhibitor; Dopamine-turnover stimulant in the forebrain; Increases neuronal firing-rate in the midbrain; Mechanism of action not fully understood.; Postsynaptic dopamine-antagonist in: basal ganglia; hypothalamus; limbic-system; brain-stem; medulla

Product Information

• Application(s): Neuroleptic; Psychosedative; Tranquilliser

DETAILS

DrugBank - DB00623

• Drug Groups: approved
• Description: A phenothiazine used in the treatment of psychoses. Its properties and uses are generally similar to those of chlorpromazine. [PubChem]
• Indication: For management of manifestations of psychotic disorders.
• Pharmacology: Fluphenazine is a trifluoro-methyl phenothiazine derivative intended for the management of schizophrenia and other psychotic disorders. Fluphenazine has not been shown effective in the management of behaviorial complications in patients with mental retardation.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - F598400

Antipsychotic.

REFERENCES

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• Dreyfuss, J., et al.: J. Pharm. Sci., 60, 826 (1962)
• Florey, K., et al.: Anal. Profiles Drug Subs., 2, 245 (1962)
• Yale, H.L. et al., J.A.C.S., 1960, 82, 2039, (synth)
• U.K. Pat., 1960, 829 246; CA, 54, 17428
• U.K. Pat., 1960, 833 473; CA, 54, 21143
• Ger. Pat., 1964, 1 165 602; CA, 60, 15886, (deriv)
• U.S. Pat., 1965, 3 194 733; CA, 64, 5114, (derivs)
• Gowda, H.S. et al., Rev. Roum. Chim., 1977, 22, 745; CA, 87, 126635a, (use)
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• Clarke, G., Anal. Profiles Drug Subst., 1980, 9, 275, (rev, decanoate)
• Shetty, H.U. et al., Biomed. Mass Spectrom., 1983, 10, 601, (ms)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6546; 7787; 7963, (synonyms)
• Phenothiazines and 1,4-Benzothiazines, (ed. Gupta, R.R.), Elsevier, Amsterdam, 1988, (book, pharmacol)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 596
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, FMP000; PMI250; TJW500