8-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one

• ChemBase ID: 4386
• Molecular Formular: C29H31F2N3O
• Molecular Mass: 475.5727464
• Monoisotopic Mass: 475.24351907
• SMILES: Fc1ccc(C(CCCN2CCC3(N(CNC3=O)c3ccccc3)CC2)c2ccc(F)cc2)cc1
• Canonical SMILES: Fc1ccc(cc1)C(c1ccc(cc1)F)CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1
• InChI: InChI=1S/C29H31F2N3O/c30-24-12-8-22(9-13-24)27(23-10-14-25(31)15-11-23)7-4-18-33-19-16-29(17-20-33)28(35)32-21-34(29)26-5-2-1-3-6-26/h1-3,5-6,8-15,27H,4,7,16-21H2,(H,32,35)
• InChIKey: QOYHHIBFXOOADH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
• IUPAC Traditional name: 8-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one; fluspirilene; imap
• Brand Name: Imap; Lopac-F-100; Redeptin
• Synonyms: Redeptin; 8-[4,4-Bis(4-fluorophenyl)butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one; Fluspirilen; Fluspiriline; Imap; McN-JR 6218; 8-[4,4-bis(p-Fluorophenyl)butyl]-1-phenyl-1,3,8-triazino[4.5]decan-4-one; R 6218; Fluspirilene; Spirodiflamin; R6218; 8-[4,4-bis (p-fluorophenyl)butyl]-1-phenyl-1,3,8-triazino[4,5]decan-4-one; Fluspirileno [inn-spanish]; Fluspirilenum [inn-latin]; Fluspirilene

Database IDs

• CAS Number: 1841-19-6
• EC Number: 217-418-6
• MDL Number: MFCD00055137
• PubChem SID: 24277915; 160967818; 46508202
• PubChem CID: 3396
• ATC CODE: N05AG01
• CHEMBL: 46516
• Chemspider ID: 3279
• DrugBank ID: DB04842
• IUPHAR ligand ID: 85
• KEGG ID: D02629
• Unique Ingredient Identifier: C5QA4GLR9M
• Wikipedia Title: Fluspirilene

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.987693
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.4489284
• LogD (pH = 7.4): 3.8700993
• Log P: 5.778034
• Molar Refractivity: 135.2675 cm^3
• Polarizability: 51.41223 Å^3
• Polar Surface Area: 35.58 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.18
• LOG S: -5.45
• Solubility (Water): 1.67e-03 g/l

PROPERTIES

Physical Property

• Solubility: 0.01 mg/mL at 25 oC [MERCK INDEX (1996)]; DMSO: ≥20 mg/mL; ethanol: soluble; H2O: insoluble
• Apperance: white solid
• Melting Point: 187.5-190°C
• Hydrophobicity(logP): 5.86 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: XX8750000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: room temp

Pharmacology Properties

• Admin Routes: IM
• Legal Status: Rx-only
• Gene Information: human ... DRD1(1812), DRD2(1813), DRD3(1814), DRD4(1815), DRD5(1816)
• Mechanism of Action: Calcium channel antagonist; Dopamine antagonist

Product Information

• Purity: ≥98% (HPLC)
• Grade: USP
• Application(s): Neuroleptic; Psychosedatives

DETAILS

MP Biomedicals - 02153707

A dopamine antagonist.

DrugBank - DB04842

• Drug Groups: approved
• Description: A long-acting injectable antipsychotic agent used for chronic schizophrenia.
• Indication: Used for the treatment of schizophrenia.
• Pharmacology: Fluspirilene is a relatively long-acting injectable depot antipsychotic drug used for schizophrenia. Fluspirilene does not differ greatly from other depot antipsychotics (fluphenazine decanoate, fluphenazine enathate, perphenazine onanthat, pipotiazine undecylenate) with respect to treatment efficacy, response or tolerability. Outcomes suggest that fluspirilene does not differ significantly from oral antipsychotics or in different weekly regimens, although much cannot be inferred because of the shortage of trials.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia

Sigma Aldrich - F100

Biochem/physiol Actions
Dopamine receptor antagonist; antipsychotic; calcium channel blocker.

Toronto Research Chemicals - F599800

Fluspirilene is a diphenylbutylpiperidine antipsychotic drug, used for the treatment of schizophrenia.

REFERENCES

• Janssen, P.A.J., et al.: Arzneim.-Forsch., 20, 1689 (1970)
• Cox, D., et al.: J. Cardiovasc. Pharmacol., 21, 595 (1970)
• Toenjes, K., et al.: Antimicrob. Agents Chemother., 49, 963 (1970)
• ,Agarwal, V., et al.: J. Biotechnol., 136, S451 (1970)
• U.S. Pat., 1966, Janssen, 3 238 216; CA, 65, 8924d, (synth)
• Janssen, P.A.J. et al., Arzneim.-Forsch., 1970, 20, 1689, (pharmacol)
• Blessington, B., Org. Mass Spectrom., 1971, 5, 1113, (ms)
• Kenny, B.A. et al., Br. J. Pharmacol., 1990, 100, 211, (pharmacol)
• Grantham, C.J. et al., Br. J. Pharmacol., 1994, 111, 483, (pharmacol)
• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 713
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PFU250