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Details

Stereochemistry ACHIRAL
Molecular Formula C29H31F2N3O
Molecular Weight 475.5727
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUSPIRILENE

SMILES

FC1=CC=C(C=C1)C(CCCN2CCC3(CC2)N(CNC3=O)C4=CC=CC=C4)C5=CC=C(F)C=C5

InChI

InChIKey=QOYHHIBFXOOADH-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Molecular Formula C29H31F2N3O
Molecular Weight 475.5727
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Fluspirilene, a neuroleptic drug, which is used clinically to treat schizophrenic patients, by blocking of dopamine receptors, especially the dopamine D2 receptors. Fluspirilene also displays calcium channel-blocking activity; it inhibits glutamate release primarily by reducing presynaptic Ca2+ influx via N-type Ca2+ channels that also may contribute to the antischizophrenic action of the drug. Recently in the frame of a project of drugs repositioning, fluspirilene was studied as an anti-cancer drug. It was found, that fluspirilene demonstrates a significant inhibitory effect on the proliferation and invasion of glioma cells. Thus, it can be a promising drug for the treatment of glioblastoma. In addition, fluspirilene, as a potential cyclin-dependent kinase 2 inhibitor, was investigated in animal models for the treatment of human hepatocellular carcinoma. Taken into account that fluspirilene has a long history of safe human use, the drug can be applicable in clinical therapy for cancer’s disease immediately.

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
D(2) dopamine receptor
58
Target ID: P14416
Gene ID: 1813.0
Gene Symbol: DRD2
Target Organism: Homo sapiens (Human)
Antagonist
2849
Voltage-dependent N-type calcium channel subunit alpha-1B
2
Target ID: Q00975
Gene ID: 774.0
Gene Symbol: CACNA1B
Target Organism: Homo sapiens (Human)
Inhibitor
8504
Cyclin-dependent kinase 2
23
Target ID: P24941
Gene ID: 1017.0
Gene Symbol: CDK2
Target Organism: Homo sapiens (Human)
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
23 mg 1 times / week multiple, intramuscular
Highest studied dose
Dose: 23 mg, 1 times / week
Route: intramuscular
Route: multiple
Dose: 23 mg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/3512622/
https://pubmed.ncbi.nlm.nih.gov/17253464/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/3512622/
https://pubmed.ncbi.nlm.nih.gov/17253464/
Other AEs: Drowsiness, Dizziness...
Other AEs:
Drowsiness
Dizziness
Dry mouth
Parkinsonism
Sources:
https://pubmed.ncbi.nlm.nih.gov/3512622/
https://pubmed.ncbi.nlm.nih.gov/17253464/
3 mg 1 times / week multiple, intramuscular
Studied dose
Dose: 3 mg, 1 times / week
Route: intramuscular
Route: multiple
Dose: 3 mg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/2224229/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/2224229/
Other AEs: Dysphagia...
Other AEs:
Dysphagia
Sources:
https://pubmed.ncbi.nlm.nih.gov/2224229/
AEs

AEs

AESignificanceDosePopulation
Dizziness
23 mg 1 times / week multiple, intramuscular
Highest studied dose
Dose: 23 mg, 1 times / week
Route: intramuscular
Route: multiple
Dose: 23 mg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/3512622/
https://pubmed.ncbi.nlm.nih.gov/17253464/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/3512622/
https://pubmed.ncbi.nlm.nih.gov/17253464/
Drowsiness
23 mg 1 times / week multiple, intramuscular
Highest studied dose
Dose: 23 mg, 1 times / week
Route: intramuscular
Route: multiple
Dose: 23 mg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/3512622/
https://pubmed.ncbi.nlm.nih.gov/17253464/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/3512622/
https://pubmed.ncbi.nlm.nih.gov/17253464/
Dry mouth
23 mg 1 times / week multiple, intramuscular
Highest studied dose
Dose: 23 mg, 1 times / week
Route: intramuscular
Route: multiple
Dose: 23 mg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/3512622/
https://pubmed.ncbi.nlm.nih.gov/17253464/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/3512622/
https://pubmed.ncbi.nlm.nih.gov/17253464/
Parkinsonism
23 mg 1 times / week multiple, intramuscular
Highest studied dose
Dose: 23 mg, 1 times / week
Route: intramuscular
Route: multiple
Dose: 23 mg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/3512622/
https://pubmed.ncbi.nlm.nih.gov/17253464/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/3512622/
https://pubmed.ncbi.nlm.nih.gov/17253464/
Dysphagia
3 mg 1 times / week multiple, intramuscular
Studied dose
Dose: 3 mg, 1 times / week
Route: intramuscular
Route: multiple
Dose: 3 mg, 1 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/2224229/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/2224229/
PubMed

PubMed

TitleDatePubMed
A repurposing approach identifies off-patent drugs with fungicidal cryptococcal activity, a common structural chemotype, and pharmacological properties relevant to the treatment of cryptococcosis.
2013-02
Transcriptional analysis implicates endoplasmic reticulum stress in bovine spongiform encephalopathy.
2010-12-03
An initial comparative map of copy number variations in the goat (Capra hircus) genome.
2010-11-17
Clinical application and outcome of the internal mammary artery perforator (IMAP) free flap for soft tissue reconstructions of the upper head and neck region in three patients.
2010-11
The atypical anxiolytic drug, tofisopam, selectively blocks phosphodiesterase isoenzymes and is active in the mouse model of negative symptoms of psychosis.
2010-11
IKKβ inhibitor identification: a multi-filter driven novel scaffold.
2010-10-15
Making sense of listening: the IMAP test battery.
2010-10-11
Prediction of PKCθ inhibitory activity using the Random Forest Algorithm.
2010-09-20
Gill transcriptome response to changes in environmental calcium in the green spotted puffer fish.
2010-08-17
Characterization of the biological effects of a novel protein kinase D inhibitor in endothelial cells.
2010-08-01
Chronic deep brain stimulation in patients with tardive dystonia without a history of major psychosis.
2010-07-30
Anticipating forest and range land development in central Oregon (USA) for landscape analysis, with an example application involving mule deer.
2010-05
Chemical inducers of autophagy that enhance the clearance of mutant proteins in neurodegenerative diseases.
2010-04-09
Psychosocial outcomes of three triage methods for the management of borderline abnormal cervical smears: an open randomised trial.
2010-02-23
Comparative gene expression profiling between human cultured myotubes and skeletal muscle tissue.
2010-02-22
The anatomic basis of the internal mammary artery perforator flap: a cadaver study.
2010-02
Temporal proteome and lipidome profiles reveal hepatitis C virus-associated reprogramming of hepatocellular metabolism and bioenergetics.
2010-01
Control of basal autophagy by calpain1 mediated cleavage of ATG5.
2010-01
GIMAP Proteins in T-Lymphocytes.
2010
Internal mammary artery perforator flap for head and neck reconstruction.
2009-11
A single molecule scaffold for the maize genome.
2009-11
Continuing professional development and revalidation: an analysis of general practitioners' recorded learning.
2009-07
Differential gene expression patterns of EBV infected EBNA-3A positive and negative human B lymphocytes.
2009-07
Identification of novel Notch target genes in T cell leukaemia.
2009-06-09
[Anatomic study on internal mammary artery perforator flap].
2009-06
Type 1 diabetes genes in rats: few or many?
2009-04
Regulation of Cellular Metabolism and Cytokines by the Medicinal Herb Feverfew in the Human Monocytic THP-1 Cells.
2009-03
Gene expression profiling of the tumor microenvironment during breast cancer progression.
2009
Neurological and behavioral abnormalities, ventricular dilatation, altered cellular functions, inflammation, and neuronal injury in brains of mice due to common, persistent, parasitic infection.
2008-10-23
Transcriptional response of Mexican axolotls to Ambystoma tigrinum virus (ATV) infection.
2008-10-20
Antigen stimulation of peripheral blood mononuclear cells from Mycobacterium bovis infected cattle yields evidence for a novel gene expression program.
2008-09-29
Differentiation of two types of mobilized peripheral blood stem cells by microRNA and cDNA expression analysis.
2008-07-22
Level of expression of the nonmutant Ferrochelatase allele is a determinant of biochemical phenotype in a mouse model of erythropoietic protoporphyria.
2008-05-29
Merging microarray data from separate breast cancer studies provides a robust prognostic test.
2008-02-27
Hepatitis C virus infection protein network.
2008
Development, validation and implementation of immobilized metal affinity for phosphochemicals (IMAP)-based high-throughput screening assays for low-molecular-weight compound libraries.
2008
[Trichoma (Plica polonica) - a contemporary case with a historical disease].
2008
Integrative microarray analysis of pathways dysregulated in metastatic prostate cancer.
2007-11-01
Normal values and incidence of cardiorespiratory complications in dogs during general anaesthesia. A review of 1281 cases.
2007-11
Identification of a Bis-guanylhydrazone [4,4'-Diacetyldiphenylurea-bis(guanylhydrazone); NSC 109555] as a novel chemotype for inhibition of Chk2 kinase.
2007-10
Forty years of antipsychotic Drug research--from haloperidol to paliperidone--with Dr. Paul Janssen.
2007
Sex-dependent modulation of treatment response.
2004-03
Risperidone compared with new and reference antipsychotic drugs: in vitro and in vivo receptor binding.
1996-03
[Severe "late" dystonia after neuroleptic anxiolysis with fluspirilene].
1994-01
[Severe late-onset dystonia while on fluspirilene].
1991-06-21
Dystonic dysphagia associated with fluspirilene.
1990-09-29
A controlled clinical trial of fluspirilene, a long-acting injectable neuroleptic, in schizophrenic patients with acute exacerbation.
1986-02
[Depression following use of Imap 1.5 mg].
1981-04-10
Fluspirilene (Imap) in the treatment of psychosomatic complaints in hypochondriacal patients.
1980-05-01
Double-blind therapeutic evaluation of fluspirilene compared with fluphenazine decanoate in chronic schizophrenics.
1978-05
Patents

Patents

Fluspirilene-containing compositions - Google ...
1

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Intramuscular
In Vitro Use Guide
Curator's Comment: The aim of the study was to investigate the effect of fluspirilene on the 4-aminopyridine (4AP)-evoked glutamate release in the cerebrocortical nerve terminals (synaptosomes). Fluspirilene reduced 4AP-evoked glutamate release in a concentration-dependent manner. This inhibitory effect was associated with a decrease in the depolarization-evoked increase in the cytoplasmic free Ca2+ concentration ([Ca2+]C), which could be completely abolished by the Ca2+ channel blocker omega-CgTX GVIA. Furthermore, fluspirilene did not produce any effect on ionomycin-evoked glutamate release. These results suggest that fluspirilene inhibits glutamate release primarily by reducing presynaptic Ca2+ influx via N-type Ca2+ channels in rat cerebrocortical nerve terminals.
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:49:15 GMT 2025
Edited
by admin
on Mon Mar 31 17:49:15 GMT 2025
Record UNII
C5QA4GLR9M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLUSPIRILENE
EP   INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
IMAP
Preferred Name English
FLUSPIRILENE [USAN]
Common Name English
Fluspirilene [WHO-DD]
Common Name English
FLUSPIRILENE [MART.]
Common Name English
1,3,8-TRIAZASPIRO(4.5)DECAN-4-ONE, 8-(4,4-BIS(4-FLUOROPHENYL)BUTYL)-1-PHENYL-
Systematic Name English
MCN-JR-6218
Code English
R-6218
Code English
R 6218
Code English
FLUSPIRILENE [EP MONOGRAPH]
Common Name English
8-(4,4-BIS(P-FLUOROPHENYL)BUTYL)-1-PHENYL-1,3,8-TRIAZASPIRO-(4.5)DECAN-4-ONE
Common Name English
FLUSPIRILENE [MI]
Common Name English
fluspirilene [INN]
Common Name English
Classification Tree Code System Code
WHO-ATC N05AG01
Created by admin on Mon Mar 31 17:49:15 GMT 2025 , Edited by admin on Mon Mar 31 17:49:15 GMT 2025
WHO-VATC QN05AG01
Created by admin on Mon Mar 31 17:49:15 GMT 2025 , Edited by admin on Mon Mar 31 17:49:15 GMT 2025
Code System Code Type Description
MESH
D005484
Created by admin on Mon Mar 31 17:49:15 GMT 2025 , Edited by admin on Mon Mar 31 17:49:15 GMT 2025
PRIMARY
ECHA (EC/EINECS)
217-418-6
Created by admin on Mon Mar 31 17:49:15 GMT 2025 , Edited by admin on Mon Mar 31 17:49:15 GMT 2025
PRIMARY
PUBCHEM
3396
Created by admin on Mon Mar 31 17:49:15 GMT 2025 , Edited by admin on Mon Mar 31 17:49:15 GMT 2025
PRIMARY
DRUG CENTRAL
1222
Created by admin on Mon Mar 31 17:49:15 GMT 2025 , Edited by admin on Mon Mar 31 17:49:15 GMT 2025
PRIMARY
WIKIPEDIA
FLUSPIRILENE
Created by admin on Mon Mar 31 17:49:15 GMT 2025 , Edited by admin on Mon Mar 31 17:49:15 GMT 2025
PRIMARY
MERCK INDEX
m5507
Created by admin on Mon Mar 31 17:49:15 GMT 2025 , Edited by admin on Mon Mar 31 17:49:15 GMT 2025
PRIMARY Merck Index
INN
1801
Created by admin on Mon Mar 31 17:49:15 GMT 2025 , Edited by admin on Mon Mar 31 17:49:15 GMT 2025
PRIMARY
CAS
1841-19-6
Created by admin on Mon Mar 31 17:49:15 GMT 2025 , Edited by admin on Mon Mar 31 17:49:15 GMT 2025
PRIMARY
RXCUI
4507
Created by admin on Mon Mar 31 17:49:15 GMT 2025 , Edited by admin on Mon Mar 31 17:49:15 GMT 2025
PRIMARY RxNorm
FDA UNII
C5QA4GLR9M
Created by admin on Mon Mar 31 17:49:15 GMT 2025 , Edited by admin on Mon Mar 31 17:49:15 GMT 2025
PRIMARY
NCI_THESAURUS
C171733
Created by admin on Mon Mar 31 17:49:15 GMT 2025 , Edited by admin on Mon Mar 31 17:49:15 GMT 2025
PRIMARY
ChEMBL
CHEMBL46516
Created by admin on Mon Mar 31 17:49:15 GMT 2025 , Edited by admin on Mon Mar 31 17:49:15 GMT 2025
PRIMARY
IUPHAR
85
Created by admin on Mon Mar 31 17:49:15 GMT 2025 , Edited by admin on Mon Mar 31 17:49:15 GMT 2025
PRIMARY
DRUG BANK
DB04842
Created by admin on Mon Mar 31 17:49:15 GMT 2025 , Edited by admin on Mon Mar 31 17:49:15 GMT 2025
PRIMARY
EVMPD
SUB07755MIG
Created by admin on Mon Mar 31 17:49:15 GMT 2025 , Edited by admin on Mon Mar 31 17:49:15 GMT 2025
PRIMARY
EPA CompTox
DTXSID7045152
Created by admin on Mon Mar 31 17:49:15 GMT 2025 , Edited by admin on Mon Mar 31 17:49:15 GMT 2025
PRIMARY
SMS_ID
100000080973
Created by admin on Mon Mar 31 17:49:15 GMT 2025 , Edited by admin on Mon Mar 31 17:49:15 GMT 2025
PRIMARY
Related Record Type Details
Structure of 8-[(4RS)-4-(4-fluorophenyl)-4-phenylbutyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
IMPURITY -> PARENT
Related Record Type Details
Structure of FLUSPIRILENE
ACTIVE MOIETY
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