Basic information
- CAS
146-56-5- Standard SMILES
Cl.Cl.OCCN1CCN(CCCN2c3ccccc3Sc3ccc(C(F)(F)F)cc32)CC1- InChIKey
MBHNWCYEGXQEIT-UHFFFAOYSA-N- Molecular formula
- C22H28Cl2F3N3OS
- Average molar mass
- 510.4 g/mol
- Monoisotopic mass
- 509.1282236
Overview
Fluphenazine hydrochloride is a member of phenothiazines. It has a role as an anticoronaviral agent.
Names & identifiers
- Preferred name
- Fluphenazine Hydrochloride
- IUPAC
- 2-[4-[3-[2-(trifluoromethyl)phenothiazin-10-yl]propyl]piperazin-1-yl]ethanol;dihydrochloride
- English name
- Fluphenazine hydrochloride
- Molecular formula
- C22H28Cl2F3N3OS
- Molecular weight
- 510.44
Names & synonyms
Fluphenazine dihydrochlorideFluphenazine hydrochloride146-56-5PermitilFLUPHENAZINE HCLDapotumSquibb 4918ZOU145W1XLFluphenazini hydrochloridumNSC-179197DTXSID008929224-(3-(2-(Trifluoromethyl)phenothiazin-10-yl)propyl)-1-piperazineethanol dihydrochloride
Show more names
ProlinateomcaanatensolFluphenazine DiHCla4077liogenmoditen
4-[3-[2-(Trifluoromethyl)phenothiazin-10-yl]propyl]-1-piperazineethanol dihydrochlorideNSC179197RefChem:55217Fluphenazine HydrochorideHydrochloride, FluphenazineDTXCID401284964205-674-1Prolixin
Database identifiers
- CAS
146-56-5- PubChem CID
- 67356
- DTXSID
DTXSID00892922- ChEMBL
CHEMBL1448187- ChEBI
Properties
Computed structural properties
- Topological polar surface area
- 55.3 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 6
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 544
Experimental & physicochemical properties
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antipsychotic Agents; Phenothiazines
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Collision Cross Section197.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 200 · 200-2020C
- storage temp.
- 2 · 2-8°C
- solubility
- Soluble in DMSO and methanol.
- form
- Solid
- color
- White to Light yellow
- Sensitive
- Hygroscopic
- Stability
- Hygroscopic
- Major Application
- pharmaceutical (small molecule)
- InChI
- InChI=1S/C22H26F3N3OS.2ClH/c23-22(24,25)17-6-7-21-19(16-17)28(18-4-1-2-5-20(18)30-21)9-3-8-26-10-12-27(13-11-26)14-15-29;;/h1-2,4-7,16,29H,3,8-15H2;2*1H
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 (68.2%): Toxic if swallowed [Danger Acute toxicity, oral]
P203, P260, P261, P263, P264, P264+P265, P270, P271, P272, P280, P284, P301+P316, P301+P317, P302+P352, P304+P340, P305+P354+P338, P308+P316, P316, P317, P318, P319, P320, P321, P330, P332+P317, P333+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 66 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information1-Piperazineethanol, 4-3-2-(trifluoromethyl)-10H-phenothiazin-10-ylpropyl-, dihydrochloride: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 1-Piperazineethanol, 4-[3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl]-, dihydrochloride: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 3 (68.2%)
Toxicology
Exposure RoutesOral, Intramuscular
Toxicity Summary
Fluphenazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the brain; depresses the release of hypothalamic and hypophyseal hormones and is believed to depress the reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis.
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
FLUPHENAZINE HYDROCHLORIDE
Phenothiazines [CS]; Phenothiazine [EPC]
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.
Uses & manufacturing
UsesFor management of manifestations of psychotic disorders.
Applications
Usesantiandrogen, antineoplastic, Nuclear Hormone receptor antagonist
UsesAntipsychotic
General DescriptionThe member ofthe piperazine subgroup with a trifluoromethyl group at the2-position of the phenothiazine system and the most potentantipsychotic phenothiazine on a milligram basis is fluphenazinehydrochloride, 4-[3-[2-(trifluoromethyl)phenazin-10-yl] propyl]-1-piperazineethanol dihydrochloride, 10[3-[4-(2-hydroxyethyl)piperazinyl]propyl]-2-trifluoromethylphenothiazine dihydrochloride (Permitil, Prolixin). It is alsoavailable as two lipid-soluble esters for depot intramuscularinjection, the enanthate (heptanoic acid ester) and the decanoateester. These long-acting preparations have use intreating psychotic patients who do not take their medicationor are subject to frequent relapse.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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