Identification
- Summary
Fluspirilene is an antipsychotic agent used in the treatment of schizophrenia.
- Generic Name
- Fluspirilene
- DrugBank Accession Number
- DB04842
- Background
A long-acting injectable antipsychotic agent used for chronic schizophrenia.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Fluspirilene (DB04842)
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Prevention of Psychosis •••••••••••• ••••••••• - Associated Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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 antagonistHumans U5-hydroxytryptamine receptor 2A antagonistHumans UVoltage-dependent calcium channel gamma-1 subunit inhibitorHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" 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 Integrate drug-drug
interactions in your software1,2-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. - Food Interactions
- Avoid alcohol.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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 
Imap Inj 2mg/ml Suspension 2 mg / mL Intramuscular Mcneil Pharmaceutical, Division Of Ortho Mcneil Inc. 1977-12-31 1998-03-12 Canada
Categories
- ATC Codes
- N05AG01 — Fluspirilene
- Drug Categories
- Agents causing hyperkalemia
- Antiarrhythmic agents
- Antidepressive Agents
- Antipsychotic Agents
- Bradycardia-Causing Agents
- Calcium Channel Blockers
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Diphenylbutylpiperidine Derivatives
- Dopamine Agents
- Dopamine Antagonists
- Dopamine D2 Receptor Antagonists
- Imidazoles
- Moderate Risk QTc-Prolonging Agents
- Nervous System
- Neurotoxic agents
- Neurotransmitter Agents
- Piperidines
- Psycholeptics
- Psychotropic Drugs
- QTc Prolonging Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin 5-HT2 Receptor Antagonists
- Serotonin 5-HT2A Receptor Antagonists
- Serotonin Agents
- Serotonin Receptor Antagonists
- Spiro Compounds
- Tranquilizing Agents
- Chemical TaxonomyProvided by Classyfire
- 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
- Diphenylmethanes
- Direct Parent
- Diphenylmethanes
- 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
- External Links
- Human Metabolome Database
- HMDB0015590
- KEGG Drug
- D02629
- PubChem Compound
- 3396
- PubChem Substance
- 46508202
- ChemSpider
- 3279
- BindingDB
- 26948
- 4507
- ChEBI
- 93369
- ChEMBL
- CHEMBL46516
- ZINC
- ZINC000000537755
- Therapeutic Targets Database
- DAP000980
- PharmGKB
- PA162565878
- Guide to Pharmacology
- GtP Drug Page
- Wikipedia
- Fluspirilene
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Schizoaffective Disorders / Schizophrenia / Schizophrenia and Disorders With 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. water solubility 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 Polarizability 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 221.6054333 predictedDarkChem Lite v0.1.0 [M-H]- 207.308 predictedDeepCCS 1.0 (2019) [M+H]+ 221.6695333 predictedDarkChem Lite v0.1.0 [M+H]+ 209.70357 predictedDeepCCS 1.0 (2019) [M+Na]+ 221.7942333 predictedDarkChem Lite v0.1.0 [M+Na]+ 215.77109 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- 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
- Molecular Weight
- 50618.91 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Wang SJ: Inhibition of glutamate release by fluspirilene in cerebrocortical nerve terminals (synaptosomes). Synapse. 2002 Apr;44(1):36-41. [Article]
- 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]
- 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
- Molecular Weight
- 52602.58 Da
References
- 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]
- 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
- Molecular Weight
- 25028.105 Da
References
- 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]
- Wang SJ: Inhibition of glutamate release by fluspirilene in cerebrocortical nerve terminals (synaptosomes). Synapse. 2002 Apr;44(1):36-41. [Article]
Enzymes
- 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
- Molecular Weight
- 57342.67 Da
References
- 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