NAV

Fluspirilene

Identification

Summary

Fluspirileneis an antipsychotic agent used in the treatment of schizophrenia.

Generic Name
Fluspirilene
DrugBank Accession Number
DB04842
Background

长效注射抗精神病剂使用for chronic schizophrenia.

Type
Small Molecule
Groups
Approved, Investigational
Structure
 3D
Similar Structures
Weight
Average: 475.5727
Monoisotopic: 475.243519039
Chemical Formula
C29H31F2N3O
Synonyms
  • Fluspirilene
  • Fluspirileno
  • Fluspirilenum
External IDs
  • Lopac-F-100
  • MCN-JR-6218
  • R 6218
  • R-6218

Pharmacology

Indication

Used for the treatment of schizophrenia.

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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

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.

Mechanism of action
Target Actions Organism
ADopamine D2 receptor
antagonist
 Humans
U5-hydroxytryptamine receptor 2A
antagonist
 Humans
UVoltage-dependent calcium channel gamma-1 subunit
inhibitor
 Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRsBrowse all" title="" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug InteractionsLearn More" title="" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction
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1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Fluspirilene is combined with 1,2-Benzodiazepine.
Abametapir The serum concentration of Fluspirilene can be increased when it is combined with Abametapir.
Acarbose The risk or severity of hypoglycemia can be increased when Fluspirilene is combined with Acarbose.
Acebutolol Acebutolol may increase the arrhythmogenic activities of Fluspirilene.
Aceclofenac The risk or severity of hyperkalemia can be increased when Fluspirilene is combined with Aceclofenac.
Acemetacin The risk or severity of hyperkalemia can be increased when Fluspirilene is combined with Acemetacin.
Acenocoumarol The risk or severity of adverse effects can be increased when Fluspirilene is combined with Acenocoumarol.
Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Fluspirilene.
Acetohexamide The risk or severity of hypoglycemia can be increased when Fluspirilene is combined with Acetohexamide.
Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Fluspirilene.
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Food Interactions
  • Avoid alcohol.

Products

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International/Other Brands
Imap (Janssen)/lmap (McNeil)/Redeptin (SKF)
Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image
Imap Forte Inj 10mg/ml Suspension 10 mg / mL Intramuscular Mcneil Pharmaceutical, Division Of Ortho Mcneil Inc. 1982-12-31 1998-08-13 Canada flag
Imap Inj 2mg/ml Suspension 2 mg / mL Intramuscular Mcneil Pharmaceutical, Division Of Ortho Mcneil Inc. 1977-12-31 1998-03-12 Canada flag

Categories

ATC Codes
N05AG01 — Fluspirilene
Drug Categories
Chemical TaxonomyProvided byClassyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
二苯基甲烷s
Direct Parent
二苯基甲烷s
Alternative Parents
Phenylbutylamines/Phenylimidazolidines/Alpha amino acids and derivatives/Azaspirodecane derivatives/Dialkylarylamines/Aniline and substituted anilines/Fluorobenzenes/Aralkylamines/Imidazolidinones/Aryl fluorides
show 10 more
Substituents
Alpha-amino acid or derivatives/Amine/Amino acid or derivatives/Aniline or substituted anilines/Aralkylamine/Aromatic heteropolycyclic compound/Aryl fluoride/Aryl halide/Azacycle/Azaspirodecane
show 26 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
C5QA4GLR9M
CAS number
1841-19-6
InChI Key
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

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 References
Not Available
Human Metabolome Database
HMDB0015590
KEGG Drug
D02629
PubChem Compound
3396
PubChem Substance
46508202
ChemSpider
3279
BindingDB
26948
RxNav
4507
ChEBI
93369
ChEMBL
CHEMBL46516
ZINC
ZINC000000537755
Therapeutic Targets Database
DAP000980
PharmGKB
PA162565878
Guide to Pharmacology
GtP Drug Page
Wikipedia
Fluspirilene

Clinical Trials

Clinical TrialsLearn More" title="" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
4 Completed Treatment Schizoaffective Disorders/Schizophrenia/精神分裂症和障碍Psychotic Features 1
3 Terminated Treatment Anxiety Disorders/Dementia/Depression/Psychosomatic Disorders/Schizophrenia 1
Not Available Completed Not Available Bipolar Disorder (BD)/Psychosis/Schizoaffective Disorders/Schizophrenia/Type 2 Diabetes Mellitus 1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Form Route Strength
Injection Parenteral 12 mg
Injection Parenteral 1.5 MG
Suspension Intramuscular 10 mg / mL
Suspension Intramuscular 2 mg / mL
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Property Value Source
melting point (°C) 187.5-190 Janssen, P.A.J.; U.S. Patent 3,238,216; March 1, 1966; assigned to Research Laboratorium Dr. C. Janssen NV, Belgium.
水溶度 10 mg/L (at 25 °C) MERCK INDEX (1996)
logP 5.86 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 0.00167 mg/mL ALOGPS
logP 5.18 ALOGPS
logP 5.78 Chemaxon
logS -5.4 ALOGPS
pKa (Strongest Acidic) 11.99 Chemaxon
pKa (Strongest Basic) 9.31 Chemaxon
Physiological Charge 1 Chemaxon
Hydrogen Acceptor Count 3 Chemaxon
Hydrogen Donor Count 1 Chemaxon
Polar Surface Area 35.58 Å2 Chemaxon
Rotatable Bond Count 7 Chemaxon
Refractivity 135.27 m3·mol-1 Chemaxon
极化率 50.88 Å3 Chemaxon
Number of Rings 5 Chemaxon
Bioavailability 1 Chemaxon
Rule of Five No Chemaxon
Ghose Filter No Chemaxon
Veber's Rule Yes Chemaxon
MDDR-like Rule Yes Chemaxon
Predicted ADMET Features
Property Value Probability
Human Intestinal Absorption + 0.9807
Blood Brain Barrier + 0.9713
Caco-2 permeable - 0.68
P-glycoprotein substrate Substrate 0.7042
P-glycoprotein inhibitor I Inhibitor 0.9082
P-glycoprotein inhibitor II Inhibitor 0.8257
Renal organic cation transporter Inhibitor 0.5978
CYP450 2C9 substrate Non-substrate 0.835
CYP450 2D6 substrate Non-substrate 0.5726
CYP450 3A4 substrate Substrate 0.645
CYP450 1A2 substrate Inhibitor 0.9107
CYP450 2C9 inhibitor Non-inhibitor 0.9209
CYP450 2D6 inhibitor Inhibitor 0.8932
CYP450 2C19 inhibitor Inhibitor 0.6989
CYP450 3A4 inhibitor Inhibitor 0.796
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7201
Ames test Non AMES toxic 0.5428
Carcinogenicity Non-carcinogens 0.8871
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 2.6387 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8401
hERG inhibition (predictor II) Inhibitor 0.9014
ADMET data is predicted usingadmetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Spectrum Spectrum Type Splash Key
Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
MS/MS Spectrum - , positive LC-MS/MS splash10-006t-9636300000-e318745a9958ecf316e7

Targets

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Details 1.Dopamine D2 receptor
Kind
Protein
Organism
Humans
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
Uniprot Name
D(2) dopamine receptor
分子量
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. [Article]
  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. [Article]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  4. Wang SJ: Inhibition of glutamate release by fluspirilene in cerebrocortical nerve terminals (synaptosomes). Synapse. 2002 Apr;44(1):36-41. [Article]
  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. [Article]
Details 2.5-hydroxytryptamine receptor 2A
Kind
Protein
Organism
Humans
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-iodop...
Gene Name
HTR2A
Uniprot ID
P28223
Uniprot Name
5-hydroxytryptamine receptor 2A
分子量
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. [Article]
Details 3.Voltage-dependent calcium channel gamma-1 subunit
Kind
Protein
Organism
Humans
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...
Gene Name
CACNG1
Uniprot ID
Q06432
Uniprot Name
Voltage-dependent calcium channel gamma-1 subunit
分子量
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. [Article]
  2. Wang SJ: Inhibition of glutamate release by fluspirilene in cerebrocortical nerve terminals (synaptosomes). Synapse. 2002 Apr;44(1):36-41. [Article]

Enzymes

Details 1.Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
分子量
57342.67 Da
References
  1. Uesawa Y, Takeuchi T, Mohri K: Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17. [Article]

Drug created at September 27, 2007 13:56 / Updated at February 21, 2021 18:51