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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:02 UTC
HMDB IDHMDB0015590
Secondary Accession Numbers
  • HMDB15590
Metabolite Identification
Common NameFluspirilene
DescriptionFluspirilene, also known as fluspirilen lindo or imap, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Fluspirilene is a drug which is used for the treatment of schizophrenia. Fluspirilene is a very strong basic compound (based on its pKa). It is administered intramuscularly.
Structure
Data?1582753313
Synonyms
ValueSource
ImapKegg
Hexal brand OF fluspirileneHMDB
Hormosan brand OF fluspirileneHMDB
Fluspirilen lindoHMDB
Fluspirilen betaHMDB
RedeptinHMDB
SpirodiflamineHMDB
Betapharm brand OF fluspirileneHMDB
FluspiHMDB
Janssen brand OF fluspirileneHMDB
Lindopharm brand OF fluspirileneHMDB
KivatHMDB
Beta, FluspirilenHMDB
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 KeyQOYHHIBFXOOADH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes 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
  • 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
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0017 g/LNot Available
LogP5.86HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0017 g/LALOGPS
logP5.18ALOGPS
logP5.78ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)11.99ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area35.58 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity135.27 m³·mol⁻¹ChemAxon
Polarizability50.88 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+209.70330932474
DeepCCS[M-H]-207.30830932474
DeepCCS[M-2H]-240.19230932474
DeepCCS[M+Na]+215.77130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FluspirileneFC1=CC=C(C=C1)C(CCCN1CCC2(CC1)N(CNC2=O)C1=CC=CC=C1)C1=CC=C(F)C=C14908.6Standard polar33892256
FluspirileneFC1=CC=C(C=C1)C(CCCN1CCC2(CC1)N(CNC2=O)C1=CC=CC=C1)C1=CC=C(F)C=C13818.7Standard non polar33892256
FluspirileneFC1=CC=C(C=C1)C(CCCN1CCC2(CC1)N(CNC2=O)C1=CC=CC=C1)C1=CC=C(F)C=C13780.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Fluspirilene,1TMS,isomer #1C[Si](C)(C)N1CN(C2=CC=CC=C2)C2(CCN(CCCC(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)C1=O3634.6Semi standard non polar33892256
Fluspirilene,1TMS,isomer #1C[Si](C)(C)N1CN(C2=CC=CC=C2)C2(CCN(CCCC(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)C1=O3493.5Standard non polar33892256
Fluspirilene,1TMS,isomer #1C[Si](C)(C)N1CN(C2=CC=CC=C2)C2(CCN(CCCC(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)C1=O4461.9Standard polar33892256
Fluspirilene,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CN(C2=CC=CC=C2)C2(CCN(CCCC(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)C1=O3797.4Semi standard non polar33892256
Fluspirilene,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CN(C2=CC=CC=C2)C2(CCN(CCCC(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)C1=O3663.7Standard non polar33892256
Fluspirilene,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CN(C2=CC=CC=C2)C2(CCN(CCCC(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)C1=O4532.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Fluspirilene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-3291000000-a0c47d195769b3a523c12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fluspirilene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fluspirilene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluspirilene , positive-QTOFsplash10-006t-9636300000-e318745a9958ecf316e72017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluspirilene 10V, Positive-QTOFsplash10-004i-0010900000-445f0f5ef841e744b3902016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluspirilene 20V, Positive-QTOFsplash10-014i-0062900000-1d96122fc707f00d958f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluspirilene 40V, Positive-QTOFsplash10-00kb-2591100000-640dbe28579f85dbe8fc2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluspirilene 10V, Negative-QTOFsplash10-00di-0000900000-9ea0fb21918b9cb7a0ae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluspirilene 20V, Negative-QTOFsplash10-00di-1000900000-b893d74c06dfaad2e89a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluspirilene 40V, Negative-QTOFsplash10-0006-9551100000-90dc4923365c246569082016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluspirilene 10V, Positive-QTOFsplash10-004i-0000900000-e17d4cfb65c9a92777242021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluspirilene 20V, Positive-QTOFsplash10-004i-0013900000-020aa814fa4820d246a82021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluspirilene 40V, Positive-QTOFsplash10-0fft-2891400000-86e79efdd575803664822021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluspirilene 10V, Negative-QTOFsplash10-00di-0000900000-245f8510e2d5c2b15d202021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluspirilene 20V, Negative-QTOFsplash10-00di-1020900000-e32f7aef2656752f1d462021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluspirilene 40V, Negative-QTOFsplash10-00ke-5132900000-e98f1388a2d05b36c3ec2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04842 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04842 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04842
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3279
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFluspirilene
METLIN IDNot Available
PubChem Compound3396
PDB IDNot Available
ChEBI ID166238
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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. [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 ]