Basic information
- CAS
1841-19-6- Standard SMILES
O=C1NCN(c2ccccc2)C12CCN(CCCC(c1ccc(F)cc1)c1ccc(F)cc1)CC2- InChIKey
QOYHHIBFXOOADH-UHFFFAOYSA-N- Molecular formula
- C29H31F2N3O
- Average molar mass
- 475.6 g/mol
- Monoisotopic mass
- 475.24351894
Overview
8-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one is a diarylmethane.
Names & identifiers
- Preferred name
- Fluspirilene
- IUPAC
- 8-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
- English name
- FLUSPIRILENE
- Molecular formula
- C29H31F2N3O
- Molecular weight
- 475.57
Names & synonyms
Fluspirilene1841-19-6RedeptinImapFluspirilenoMcN-JR-62188-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-oneR 6218FluspirilenumDTXSID7045152R-6218C5QA4GLR9M
Show more names
FluspirilenFluspirilene CRSFluspirilene (R 6218FLUSPIRILENE USP/EP/BPParoxetine EP IMpurity C
8-(4,4-Bis(p-fluorophenyl)butyl)-1-phenyl-1,3,8-triazaspiro-(4.5)decan-4-one1,3,8-Triazaspiro(4.5)decan-4-one, 8-(4,4-bis(4-fluorophenyl)butyl)-1-phenyl-SpirodiflamineDTXCID50251521,3,8-Triazaspiro[4.5]decan-4-one, 8-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-Beta, Fluspirilen8-(4,4-bis(4-fluorophenyl)butyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one8-(4,4-bis(4-fluorophenyl)butyl)-1-phenyl-1,3,8-triazaspiro(4.5)decan-4-one
Database identifiers
- CAS
1841-19-6- PubChem CID
- 3396
- DTXSID
DTXSID7045152- ChEMBL
CHEMBL46516- ChEBI
CHEBI:93369
Properties
Computed structural properties
- XLogP
- 5.6
- Topological polar surface area
- 35.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 7
- Heavy atoms
- 35
- Formal charge
- 0
- Complexity
- 653
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Nervous system -> Antipsychotics
LogP
5.86
5.86
Solubility1.67e-03 g/L
Melting Point187.5-190
Physical DescriptionSolid
Dissociation Constants
8.66
7.7
Physicochemical properties
- Melting point
- 187.5 · 187.5-190°
- Boiling point
- 668.9 · 668.9±55.0 °C(Predicted)
- Density
- 1.1634 · 1.1634 (estimate)
- storage temp.
- room temp
- solubility
- DMSO: soluble
- form
- amorphous solid
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P273, P301+P316, P321, P330, P391, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Other Safety InformationIMAP assessments - 1,3,8-Triazaspiro[4.5]decan-4-one, 8-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
fluspirilene
DILI Positive
Intramuscular
DOI:10.1016/j.drudis.2019.09.022
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- XX8750000
- ridadr
- 3249
- Toxicity
- LD50 i.m. in rats: 146 ±14 mg/kg (Janssen)
- Signal word
- Danger
- Symbol(GHS)
- GHS09,GHS06
- hazard_class
- 6.1(b)
- Storage Class
Chemistry & industry
Pharmacology
ATC Code
N05AG01
N - Nervous system
QN - Nervous system
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.
MeSH Pharmacological Classification
Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus.
Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME.
Cellular LocationsMembrane
Applications
DescriptionFluspirilene is a potent, non-competitive antagonist of agonist-activated L-type calcium channels (IC50 = 0.03 μM). In addition to its use in research as a calcium channel blocker, fluspirilene has potential application as an antipsychotic in schizophrenia.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…