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Fluspirilene

July 24, 2017
Common Name

Fluspirilene Description

Fluspirilene is only found in individuals that have used or taken this drug. It is a long-acting injectable antipsychotic agent used for chronic schizophrenia. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source ImapKegg Hexal brand OF fluspirileneMeSH Hormosan brand OF fluspirileneMeSH Fluspirilen lindoMeSH Fluspirilen betaMeSH RedeptinMeSH SpirodiflamineMeSH Betapharm brand OF fluspirileneMeSH FluspiMeSH Janssen brand OF fluspirileneMeSH Lindopharm brand OF fluspirileneMeSH KivatMeSH

Chemical Formlia

C29H31F2N3O Average Molecliar Weight

475.5727 Monoisotopic Molecliar Weight

475.243519039 IUPAC Name

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

fluspirilene CAS Registry Number

1841-19-6 SMILES

FC1=CC=C(C=C1)C(CCCN1CCC2(CC1)N(CNC2=O)C1=CC=CC=C1)C1=CC=C(F)C=C1

InChI Identifier

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)

InChI Key

QOYHHIBFXOOADH-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Benzene and substituted derivatives Direct Parent

Diphenylmethanes Alternative Parents

  • Phenylbutylamines
  • Phenylimidazolidines
  • Alpha amino acids and derivatives
  • Azaspirodecane derivatives
  • Dialkylarylamines
  • Aniline and substituted anilines
  • Fluorobenzenes
  • Aralkylamines
  • Imidazolidinones
  • Aryl fluorides
  • Piperidines
  • Trialkylamines
  • Lactams
  • Secondary carboxylic acid amides
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organofluorides
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Diphenylmethane
  • Phenylbutylamine
  • Phenylimidazolidine
  • Alpha-amino acid or derivatives
  • Azaspirodecane
  • Aniline or substituted anilines
  • Dialkylarylamine
  • Aralkylamine
  • Halobenzene
  • Fluorobenzene
  • Imidazolidinone
  • Aryl fluoride
  • Aryl halide
  • Piperidine
  • Imidazolidine
  • Secondary carboxylic acid amide
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboxamide group
  • Amino acid or derivatives
  • Lactam
  • Azacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antipsychotic Agents
  • Dopamine Antagonists

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility1.67e-03 g/LNot Available LogP5.86HANSCH,C ET AL. (1995)

    Predicted Properties

    Property Value Source Water Solubility0.0017 mg/mLALOGPS logP5.18ALOGPS logP5.78ChemAxon logS-5.5ALOGPS pKa (Strongest Acidic)11.99ChemAxon pKa (Strongest Basic)9.31ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area35.58 Å2ChemAxon Rotatable Bond Count7ChemAxon Refractivity135.27 m3·mol-1ChemAxon Polarizability50.88 Å3ChemAxon Number of Rings5ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-006t-9636300000-e318745a9958ecf316e7View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04842

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04842

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB04842 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    3279 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Fluspirilene NuGOwiki Link

    HMDB15590 Metagene Link

    HMDB15590 METLIN ID

    Not Available PubChem Compound

    3396 PDB ID

    Not Available ChEBI ID

    166238

    Product: Pemirolast (potassium)

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
    Gene Name:
    DRD2
    Uniprot ID:
    P14416
    Molecular weight:
    50618.9
    References
    1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
    2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
    3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
    4. Wang SJ: Inhibition of glutamate release by fluspirilene in cerebrocortical nerve terminals (synaptosomes). Synapse. 2002 Apr;44(1):36-41. [PubMed:11842444 ]
    5. Schotte A, Janssen PF, Gommeren W, Luyten WH, Van Gompel P, Lesage AS, De Loore K, Leysen JE: Risperidone compared with new and reference antipsychotic drugs: in vitro and in vivo receptor binding. Psychopharmacology (Berl). 1996 Mar;124(1-2):57-73. [PubMed:8935801 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
    Gene Name:
    HTR2A
    Uniprot ID:
    P28223
    Molecular weight:
    52602.6
    References
    1. Schotte A, Janssen PF, Gommeren W, Luyten WH, Van Gompel P, Lesage AS, De Loore K, Leysen JE: Risperidone compared with new and reference antipsychotic drugs: in vitro and in vivo receptor binding. Psychopharmacology (Berl). 1996 Mar;124(1-2):57-73. [PubMed:8935801 ]
    General function:
    Involved in voltage-gated calcium channel activity
    Specific function:
    This protein is a subunit of the dihydropyridine (DHP) sensitive calcium channel. Plays a role in excitation-contraction coupling. The skeletal muscle DHP-sensitive Ca(2+) channel may function only as a multiple subunit complex
    Gene Name:
    CACNG1
    Uniprot ID:
    Q06432
    Molecular weight:
    25028.1
    References
    1. Kenny BA, Fraser S, Kilpatrick AT, Spedding M: Selective antagonism of calcium channel activators by fluspirilene. Br J Pharmacol. 1990 Jun;100(2):211-6. [PubMed:1696149 ]
    2. Wang SJ: Inhibition of glutamate release by fluspirilene in cerebrocortical nerve terminals (synaptosomes). Synapse. 2002 Apr;44(1):36-41. [PubMed:11842444 ]

    PMID: 20208034

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