You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameFluspirilene
Accession NumberDB04842
TypeSmall Molecule
GroupsApproved
Description

A long-acting injectable antipsychotic agent used for chronic schizophrenia.

Structure
Thumb
Synonyms
Fluspirileno
Fluspirilenum
Imap
External Identifiers
  • Lopac-F-100
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Imap Forte Inj 10mg/mlsuspension10 mgintramuscularMcneil Pharmaceutical, Division Of Ortho Mcneil Inc.1982-12-311998-08-13Canada
Imap Inj 2mg/mlsuspension2 mgintramuscularMcneil Pharmaceutical, Division Of Ortho Mcneil Inc.1977-12-311998-03-12Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ImapJanssen
lmapMcNeil
RedeptinSKF
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIC5QA4GLR9M
CAS number1841-19-6
WeightAverage: 475.5727
Monoisotopic: 475.243519039
Chemical FormulaC29H31F2N3O
InChI KeyInChIKey=QOYHHIBFXOOADH-UHFFFAOYSA-N
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)
IUPAC Name
8-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
SMILES
FC1=CC=C(C=C1)C(CCCN1CCC2(CC1)N(CNC2=O)C1=CC=CC=C1)C1=CC=C(F)C=C1
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
Pharmacology
IndicationUsed for the treatment of schizophrenia.
PharmacodynamicsFluspirilene 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.
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9807
Blood Brain Barrier+0.9713
Caco-2 permeable-0.68
P-glycoprotein substrateSubstrate0.7042
P-glycoprotein inhibitor IInhibitor0.9082
P-glycoprotein inhibitor IIInhibitor0.8257
Renal organic cation transporterInhibitor0.5978
CYP450 2C9 substrateNon-substrate0.835
CYP450 2D6 substrateNon-substrate0.5726
CYP450 3A4 substrateSubstrate0.645
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9209
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorInhibitor0.6989
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7201
Ames testNon AMES toxic0.5428
CarcinogenicityNon-carcinogens0.8871
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6387 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8401
hERG inhibition (predictor II)Inhibitor0.9014
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Suspensionintramuscular10 mg
Suspensionintramuscular2 mg
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point187.5-190Janssen, P.A.J.; U.S. Patent 3,238,216; March 1, 1966; assigned to Research Laboratorium Dr. C. Janssen NV, Belgium.
water solubility10 mg/L (at 25 °C)MERCK INDEX (1996)
logP5.86HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.00167 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
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Janssen, P.A.J.; U.S. Patent 3,238,216; March 1, 1966; assigned to Research Laboratorium Dr. C. Janssen NV, Belgium.

US3238216
General ReferencesNot Available
External Links
ATC CodesN05AG01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Fluspirilene.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Fluspirilene.
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Fluspirilene.
AmphetamineFluspirilene may decrease the stimulatory activities of Amphetamine.
BenzphetamineFluspirilene may decrease the stimulatory activities of Benzphetamine.
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Fluspirilene.
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Fluspirilene.
CitalopramThe risk or severity of adverse effects can be increased when Citalopram is combined with Fluspirilene.
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Fluspirilene.
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Fluspirilene.
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Fluspirilene.
DesvenlafaxineThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with Fluspirilene.
DextroamphetamineFluspirilene may decrease the stimulatory activities of Dextroamphetamine.
DextromethorphanThe risk or severity of adverse effects can be increased when Dextromethorphan is combined with Fluspirilene.
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Fluspirilene.
DonepezilDonepezil may increase the central neurotoxic activities of Fluspirilene.
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Fluspirilene.
DuloxetineThe risk or severity of adverse effects can be increased when Duloxetine is combined with Fluspirilene.
EletriptanThe risk or severity of adverse effects can be increased when Eletriptan is combined with Fluspirilene.
Ergoloid mesylateThe risk or severity of adverse effects can be increased when Ergoloid mesylate is combined with Fluspirilene.
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Fluspirilene.
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Fluspirilene.
EscitalopramThe risk or severity of adverse effects can be increased when Escitalopram is combined with Fluspirilene.
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Fluspirilene.
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Fluspirilene.
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Fluspirilene.
FrovatriptanThe risk or severity of adverse effects can be increased when Frovatriptan is combined with Fluspirilene.
GalantamineGalantamine may increase the central neurotoxic activities of Fluspirilene.
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Fluspirilene.
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Fluspirilene.
LevomilnacipranThe risk or severity of adverse effects can be increased when Levomilnacipran is combined with Fluspirilene.
LinezolidThe risk or severity of adverse effects can be increased when Linezolid is combined with Fluspirilene.
LisdexamfetamineFluspirilene may decrease the stimulatory activities of Lisdexamfetamine.
LithiumLithium may increase the neurotoxic activities of Fluspirilene.
LorcaserinThe risk or severity of adverse effects can be increased when Lorcaserin is combined with Fluspirilene.
MaprotilineThe risk or severity of adverse effects can be increased when Maprotiline is combined with Fluspirilene.
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Fluspirilene.
MethamphetamineFluspirilene may decrease the stimulatory activities of Methamphetamine.
MethylphenidateThe risk or severity of adverse effects can be increased when Fluspirilene is combined with Methylphenidate.
MetoclopramideThe risk or severity of adverse effects can be increased when Metoclopramide is combined with Fluspirilene.
MetyrosineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Fluspirilene.
MilnacipranThe risk or severity of adverse effects can be increased when Milnacipran is combined with Fluspirilene.
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Fluspirilene.
NaratriptanThe risk or severity of adverse effects can be increased when Naratriptan is combined with Fluspirilene.
NefazodoneThe risk or severity of adverse effects can be increased when Nefazodone is combined with Fluspirilene.
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Fluspirilene.
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Fluspirilene.
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Fluspirilene.
PhendimetrazineFluspirilene may decrease the stimulatory activities of Phendimetrazine.
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Fluspirilene.
PhentermineFluspirilene may decrease the stimulatory activities of Phentermine.
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Fluspirilene.
PromethazineThe risk or severity of adverse effects can be increased when Promethazine is combined with Fluspirilene.
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Fluspirilene.
QuinagolideThe therapeutic efficacy of Quinagolide can be decreased when used in combination with Fluspirilene.
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Fluspirilene.
RivastigmineRivastigmine may increase the central neurotoxic activities of Fluspirilene.
RizatriptanThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Fluspirilene.
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Fluspirilene.
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Fluspirilene.
SumatriptanThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Fluspirilene.
Tedizolid PhosphateThe risk or severity of adverse effects can be increased when Tedizolid Phosphate is combined with Fluspirilene.
TetrabenazineThe risk or severity of adverse effects can be increased when Tetrabenazine is combined with Fluspirilene.
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Fluspirilene.
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Fluspirilene.
TrazodoneThe risk or severity of adverse effects can be increased when Trazodone is combined with Fluspirilene.
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Fluspirilene.
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Fluspirilene.
VilazodoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Fluspirilene.
VortioxetineThe risk or severity of adverse effects can be increased when Vortioxetine is combined with Fluspirilene.
ZolmitriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Fluspirilene.
Food Interactions
  • Avoid alcohol.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Potassium channel regulator activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular Weight:
50618.91 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Virus receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates...
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular Weight:
52602.58 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
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:
25028.105 Da
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 ]
Comments
comments powered by Disqus
Drug created on September 27, 2007 07:56 / Updated on April 23, 2014 18:26