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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:33:30 UTC
HMDB IDHMDB15590
Secondary Accession NumbersNone
Metabolite Identification
Common NameFluspirilene
DescriptionFluspirilene 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
Thumb
Synonyms
ValueSource
ImapKegg
Chemical FormulaC29H31F2N3O
Average Molecular Weight475.5727
Monoisotopic Molecular Weight475.243519039
IUPAC Name8-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
Traditional Namefluspirilene
CAS Registry Number1841-19-6
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 KeyInChIKey=QOYHHIBFXOOADH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Phenylimidazolidine
  • Phenylbutylamine
  • Azaspirodecane
  • Dialkylarylamine
  • Aralkylamine
  • Halobenzene
  • Fluorobenzene
  • Piperidine
  • Imidazolidinone
  • Aryl halide
  • Aryl fluoride
  • Imidazolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antipsychotic Agents
  • Dopamine Antagonists
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.67e-03 g/LNot Available
LogP5.86HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04842
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04842
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04842
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3279
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFluspirilene
NuGOwiki LinkHMDB15590
Metagene LinkHMDB15590
METLIN IDNot Available
PubChem Compound3396
PDB IDNot Available
ChEBI ID166238
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot 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. [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. [17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
  4. Wang SJ: Inhibition of glutamate release by fluspirilene in cerebrocortical nerve terminals (synaptosomes). Synapse. 2002 Apr;44(1):36-41. [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. [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. [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. [1696149 ]
  2. Wang SJ: Inhibition of glutamate release by fluspirilene in cerebrocortical nerve terminals (synaptosomes). Synapse. 2002 Apr;44(1):36-41. [11842444 ]