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HCID 3372Erstellt: 4. November 2026

Fluphenazin

Permitil · Fluphenazine Decanoate EP Impurity B · s94 · S 94 · Elinol · sq4918 · Pacinol · Sevinol

https://huagongshe.com/de/chemical/3372

Molekülstruktur von Fluphenazin

Identifikatoren & physikalische Daten

CAS No.146-56-5
SummenformelC22H26F3N3OS
Durchschnittliche Molmasse437,5 g/mol
Monoisotopische Masse437,17486812 g/mol
SMILESOCCN1CCN(CCCN2c3ccccc3Sc3ccc(C(F)(F)F)cc32)CC1
InChIKeyPLDUPXSUYLZYBN-UHFFFAOYSA-N
PubChem CID3372
ChEMBLCHEMBL726
ChEBICHEBI:5123
EC No.200-702-9
DTXSIDDTXSID2023068
Lokaler NameFluphenazin

Chemische & physikalische Eigenschaften

XLogP4,4
Polarare Oberfläche (TPSA)55,3
H-Brücken-Donoren1
H-Brücken-Akzeptoren8
Frei drehbare Bindungen6
Schwere Atome30
Formalladung0
Komplexität544
ArzneimittelDEA NFLIS-Drug Category -> Depressants and TranquilizersPharmaceuticalsPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Nervous system -> Antipsychotics
LogP (Verteilungskoeffizient)log Kow = 4.364.24.55
Color/FormDark brown viscous oil
LöslichkeitIn water, 31.1 g/L (31.3 mg/L) at 37 °C1.90e-02 g/LDMSO (Slightly), Methanol (Slightly)31.06mg/L(37 ºC)
Human DrugsBreast FeedingLactationMilk, HumanAntipsychotic AgentsPhenothiazinesPharmaceuticalsMedicines for psychotic disorders
Siedepunkt268-274 °C at 5.00E-01 mm HgBP: 250-252 °C at 0.3 mm Hg268-274 °C at 0.5 mm Hgbp0.5 268-274°bp0.3 250-252°
DecompositionWhen heated to decomposition it emits very toxic fumes of /hydrogen fluoride/, /nitroge and sulfur/ oxides.
Schmelzpunkt224-226 (Salt)Crystals from absolute alcohol. MP: 235-237 °C, also reported as 224.5-226 °C /Fluphenazine dihydrochloride/Pale yellow-orange, viscous liquid. Slowly crystallizes at room temperature. MP: 30-32 °C. Very soluble in chloroform, ether, cyclohexane, methanol, ethanol. Insoluble in water /Fluphenazine decanoate/< 25 °C268-274℃
Physical DescriptionSolid
Stability/Shelf LifeLight sensitive. /Fluphenazine Decanoate/Unstable in strong light, but stable in air at room temperature. /Fluphenazine Enanthate/
Dissociation Constants7.9pKa = 7.90
Collision Cross Section196.04 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]198.1 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated]
Dichte1.2156 (estimate)
Flammpunkt9℃
Lagerbedingungen-20°C
AggregatzustandSticky Solid
pKa (Säurekonstante)pKa 7.98±0.03(H2O t=20±0.5) (Uncertain)
FarbeDark-brown viscous oil
StabilitätHygroscopic

Sicherheit & Vorschriften

GHS-EinstufungDangerH301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P260, P264, P264+P265, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P305+P354+P338, P308+P316, P316, P317, P320, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 48 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Regulatorische InformationenFluphenazine: Does not have an individual approval but may be used under an appropriate group standard
FDA-AnforderungenThe Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including fluphenazine hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including fluphenazine decanoate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Fluphenazine decanoate/
Special ReportsJann MW, Richards ALUS Pharm 10 (Jan): PH1-5, H9, H12-H13 (1985). A review of the pharmacology, pharmacokinetics, dosage and side effects of haloperidol, loxapine, thiothixene and fluphenazine is presented along with the role of clinical pharmacists in the appropriate use and selection of antipsychotics in emergency medical situations and psychiatric crises.
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Skin, Eye, and Respiratory IrritationsMay cause irritation /to the eyes, skin, and mucous membranes/. Avoid inhalation. Remove to fresh air. Avoid contact. Flush /eyes/ with copious quantities of water. Avoid /skin/ contact. Flush with copious quantities of soap and water.
Hazardous Reactivities and IncompatibilitiesFluphenazine hydrochloride oral concentrate solution should not be mixed with beverages containing caffeine (eg, coffee, cola), tannic acid (eg, tea), or pectinates (eg, apple juice), since physical incompatibility may result.

Anwendungen & Verwendung

Verwenden

Fluphenazine is an extremely strong antipsychotic drug. A stimulatory effect accompanies the neuroleptic effect. It is used in psychiatry for treating various forms of schizophrenia and other mental illnesses.

BrandbekämpfungsverfahrenWater spray, dry chemical, carbon dioxide or foam as appropriate for surrounding fire and materials.As with all fires, evacuate personnel to a safe area. Firefighters should use self-contained breathing equipment and protective clothing.
LagerbedingungenCommercially available preparations of fluphenazine should be protected from light and stored at room temperatureoral preparations should be stored in tightly closed containers. Freezing of the oral solution and injections should be avoided. Slight yellowish discoloration of fluphenazine hydrochloride injection will not affect potency or efficacy, but the injection should not be used if markedly discolored or if a precipitate is present.At the time of manufacture, air in the vials of the commercially available fluphenazine decanoate and fluphenazine hydrochloride injections is replaced with nitrogen to avoid oxidation and discoloration.Store in tight, light-resistant container as defined in the USP-NF. This material should be handled and stored per label instructions to ensure product integrity.
ReinigungsverfahrenWear approved respiratory protection, chemically compatible gloves and protective clothing. Wipe up spillage or collect spillage using a high efficiency vacuum cleaner. Avoid breathing dust. Place spillage in appropriately labeled container for disposal. Wash spill site.
EntsorgungsverfahrenSRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.
Preventive MeasuresSRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.This material is assumed to be combustible. As with all dry powders it is advisable to ground mechanical equipment in contact with dry material to dissipate the potential buildup of static electricity.As a general rule, when handling USP Reference Standards avoid all contact and inhalation of dust, mists, and/or vapors associated with the material. Wash thoroughly after handling.Use safety glasses or goggles and protect exposed skin.
Personal Protective Equipment (PPE)Engineering controls such as exhaust ventilation are recommended.Use a NIOSH approved respirator, if it is determined to be necessary by an industrial hygiene survey involving air monitoring. In the event that a respirator is not required, an approved dust mask should be used.
WechselwirkungenAn increase in insulin dosage or decrease in chlorpromazine dosage may be necessary to maintain control of blood glucose levels in patients receiving insulin ... Other phenothiazines that may increase blood glucose levels include fluphenazine ... .Concurrent use of imipramine and chlorpromazine may result in increased serum levels of either drug. ... Chlorpromazine inhibits the metabolism of imipramine and nortriptyline. Similar precaution should be observed when other ... phenothiazines are used concurrently ... . /Phenothiazines/A drug interaction involving ascorbic acid and fluphenazine hydrochloride was reported in a 23 yr old male manic depressive patient. During 13 days patient received replacement ascorbic acid steady state fluphenazine hydrochloride plasma levels declined 25% from baseline. This reduction was associated with escalation of manic behavior. Mechanism by which ascorbic acid replacement lowers fluphenazine hydrochloride plasma levels might involve not only liver enzyme induction but also interactions at the absorptive phase. /Fluphenazine hydrochloride/QT interval-prolonging medications, including cisapride, erythromycin, and quinidine /may produce/ additive QT interval prolongation increasing the risk of developing cardiac arrhythmias when /concurrently administered with phenothiazines/. /Phenothiazines/For more Interactions (Complete) data for Fluphenazine (31 total), please visit the HSDB record page.
HepatotoxicityLiver test abnormalities have been reported to occur in up to 40% of patients on long term therapy with phenothiazines, but elevations are uncommonly above 3 times the upper limit of normal. The aminotransferase abnormalities are usually mild, asymptomatic and transient, reversing even with continuation of medication. Several instances of clinically apparent acute liver injury have been reported due to fluphenazine, which have resembled the liver injury caused by chlorpromazine and other phenothiazines. The onset of phenothiazide-related jaundice is usually within 1 to 4 weeks, and the pattern of serum enzyme elevations is typically cholestatic or mixed. Immunoallergic features (fever, rash and eosinophilia) are present in some cases, but they are usually mild and self-limitedautoantibodies are rare. Most importantly, phenothiazide induced jaundice can be prolonged and associated with vanishing bile duct syndrome. All phenothiazine antipsychotic agents are probably capable of causing cholestatic liver injury, but the frequency of hepatotoxicity appears to be far greater with chlorpromazine than with others such as fluphenazine.
Unerwünschte WirkungenFluphenazine has an adverse effect profile similar to other first-generation or typical antipsychotics, which is due to its dopamine receptor antagonism as well as its anticholinergic, antihistaminic, and alpha-adrenergic antagonistic properties. Common side effects include sedation, dry mouth, dry eyes, blurred vision, constipation, orthostasis, dizziness, hypotension, and urinary retention. Other possible side effects include rebound tachycardia, urinary retention, and weight gain. Due to dopaminergic antagonism, fluphenazine can cause extrapyramidal symptoms, including akathisia, parkinsonian features such as resting tremor and shuffling gait, acute dystonic reactions, oculogyric crises, opisthotonos, and tardive dyskinesia.
ExpositionspfadeOral, Intramuscular
Milk ConcentrationsPhenothiazines ... may appear in milk of nursing mothers... /phenothiazines, human, oral, im/
ToxizitätsübersichtIn instances of fluphenazine overdose, there is no specific antidote for toxicitytreatment is symptomatic, usually based on the presenting anticholinergic effects.Fluphenazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the braindepresses 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.
Human Toxicity Excerpts/HUMAN EXPOSURE STUDIES/ The growth hormone (hGH) and prolactin (hPRL) response to insulin induced hypoglycaemia was studied in six alcoholics on two occasions before and after treatment with a single intramuscular injection of fluphenazine (Modecate). On both occasions blood samples were taken at intervals before and after the intravenous injection of soluble insulin (0.1 u/kg body weight). The patients were investigated on the first occasion, 2-7 days after cessation of drinking and they all demonstrated an adequate hGH response. They then received an injection of fluphenazine (Modecate 12.5 mg) and were reinvestigated 1 week later. The hGH response to hypoglycaemia was significantly impaired after treatment with fluphenazine. Basal hPRL concentrations were significantly increased and increased concentrations of hPRL in response to hypoglycaemia occurred after treatment. /Investigators/ conclude that a single injection of fluphenazine (Modecate 12.5 mg) has a marked effect on hypothalamic-pituitary mechanisms controlling hGH and hPRL release./SIGNS AND SYMPTOMS/ In general, overdosage of phenothiazines may be expected to produce effects that are extensions of common adverse reactionssevere extrapyramidal reactions, hypotension, and sedation have been the principal effects reported. CNS depression progressing to coma with areflexia or CNS stimulation with convulsions followed by respiratory depression may occurpatients with early or mild intoxication may experience drowsiness, restlessness, disorientation, confusion, and excitement. Other reported effects associated with acute phenothiazine overdosage have included shock (eg, ECG changes and cardiac arrhythmias), increased QT and PR intervals, non-specific ST and T wave changes, bradycardia, sinus tachycardia, bilateral bundle branch block, atrioventricular block, ventricular tachycardia, ventricular fibrillation, torsades de pointes, myocardial depression, agitation, dry skin, nasal congestion, urinary retention, oliguria, uremia, blurred vision, hypothermia, hyperthermia, mydriasis, miosis, tremor, muscle twitching, spasm or rigidity, seizures, muscular hypotonia, constipation, ileus, dry mouth, vomiting, difficulty in swallowing or breathing, cyanosis, and respiratory and/or vasomotor collapse, and pulmonary edema, possibly with sudden apnea. /Phenothiazine general Statement//SIGNS AND SYMPTOMS/ Geriatric patients with dementia-related psychosis treated with either conventional (first-generation) or atypical (second-generation) antipsychotic agents are at an increased risk of mortality./SIGNS AND SYMPTOMS/ Various ECG changes, including nonspecific, usually reversible, Q- and T-wave abnormalities have occurred in some patients receiving phenothiazines. ECG changes may resemble quinidine-like alterations or those induced by hypokalemia. Sudden death, apparently secondary to cardiac arrest, also has occurred. /Phenothiazine General Statement/For more Human Toxicity Excerpts (Complete) data for Fluphenazine (17 total), please visit the HSDB record page.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver InjuryDrug-Induced Liver Injury Severity and Toxicity (DILIst)fluphenazineDILI NegativeOralDOI:10.1016/j.drudis.2019.09.022
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ The enhancement of mammary tumorigenesis by fluphenazine was investigated in Sprague-Dawley rats. Rats were divided into five groups. Two groups were given a single intragastric dose of 5 mg of 7,12-dimethylbenz(a)anthracene. Animals were then given 100 or 200 mg fluphenazine 3 times per week for 30 weeks and were then examined weekly for mammary tumors. All animals that appeared moribund were killed and autopsied. All surviving animals were killed at 30 weeks, autopsied, and examined for tumors. None of the untreated control rats developed mammary tumors. One of 15 rats given 100 ug fluphenazine alone developed a mammary tumor, but none of the 15 rats given 200 ug developed tumors. Of 15 rats given 7,12-dimethylbenz(a)anthracene only, 12 developed mammary tumors for a total of 17 tumors50 percent of the tumors developed within 21 weeks after treatment. All animals treated with the combination of 7,12-dimethylbenz(a)anthracene and fluphenazine developed tumors that appeared in 50 percent of rats within 10 weeks after the secondary treatment. /It was/ concluded that fluphenazine alone does not induce tumors in Sprague-Dawley rats, but repeated fluphenazine treatment increases the number of mammary tumors in rats pretreated with 7,12-dimethylbenz(a)anthracene and shortens the latency period./LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Guinea pigs were administered chronic fluphenazine decanoate for 11 months and oral movements (OMs) were periodically observed using several different paradigms. Shortly after the initiation of neuroleptic treatment, increased OMs were seen in the drugged animals, but these did not persist and may have reflected a decreased fear (freezing) reaction in the tranquilized animals, being correlated with increased locomotion in open field. After 7 months of neuroleptics, twitch-like movements of the orofacial region were observed in the drugged animalsthese dyskinetic movements were enhanced by administration of d-amphetamine. These twitch-like movements appear to be a better model of tardive dyskinesia in the guinea pig than the initially observed and normal-appearing OMs./LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Persistent tardive dyskinesia is a serious side effect of long-term treatment with neuroleptics. Although striatal pathologic changes are believed to underlie this potentially irreversible iatrogenic syndrome, the nature of the neuroleptic-induced neuropathology is unclear. In the present study, we treated rats with either vehicle or fluphenazine decanoate (5 mg/kg, IM) every 2 weeks for 4, 8 or 12 months. Four to nine weeks after the last injection, the animals were sacrificed and the density of cells in the central part of the striatum was measured with a computerized image-analysis system. The control and experimental animals did not differ in body weight with 4 and 8 months of treatment, but the rats treated with fluphenazine for 12 months had significantly lower body weights than comparable controls. Four months of neuroleptic use produced no significant neuropathologic changes. The animals treated with fluphenazine for 8 months had a significantly lower density of the large neurons. In the 12-month-treated group, there was no significant difference between the control and experimental animals, probably because of a 'floor effect': the density of the large neurons was significantly lower in the 12-month-treated compared to the 8-month-treated control rats./LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Five Cebus apella monkeys were treated with biweekly injections of fluphenazine enanthate (0.1-3.2 mg/kg IM). Three of these completed 1 full year of treatment, one injured its leg after 6 months of treatment and was killed, and another died of unknown causes after 9 months of treatment. All monkeys displayed abnormal movements corresponding to the early appearing extrapyramidal symptoms of neuroleptic-treated patients. These consisted initially of slowing or absence of volitional movement, trembling of the hands, trembling of the entire body, and general drowsy behavior. As treatment progressed, a variety of abnormal postures and movements appeared after each injection that were not exacerbated by drug withdrawal and, as tested at the end of the year, could be abolished or prevented with benztropine mesylate (0.2-0.5 mg/kg im). The three monkeys that completed 1 year of treatment with fluphenazine were then withdrawn from the drug. After withdrawal, all three developed movements similar in appearance to those of patients with tardive dyskinesia. Reinstitution of fluphenazine treatment, as tested in one monkey, abolished all movements resembling tardive dyskinesia. /Fluphenazine enanthate/For more Non-Human Toxicity Excerpts (Complete) data for Fluphenazine (8 total), please visit the HSDB record page.
Antidote and Emergency TreatmentTreatment of phenothiazine overdosage generally involves symptomatic and supportive care. There is no specific antidote for phenothiazine intoxicationhowever, anticholinergic antiparkinsonian drugs may be useful in controlling extrapyramidal reactions associated with phenothiazine overdosage. Following acute ingestion of the drugs, the stomach should be emptied by gastric lavage and consideration also should be given to repeated doses of activated charcoal. If the patient is comatose, having seizures or a dystonic reaction, or lacks the gag reflex, gastric lavage may be performed if an endotracheal tube with cuff inflated is in place to prevent aspiration of gastric contents. Gastric lavage may be useful even several hours after the drug has been ingested, since GI motility may be greatly reduced following overdosage of phenothiazines. Induction of emesis should generally not be attempted, since a phenothiazine-induced dystonic reaction of the head or neck may result in aspiration of vomitus during emesis. Administration of a saline cathartic may be beneficial in enhancing evacuation of the drug from the GI tract, especially following ingestion of extended-release preparations (eg, Spansules). /Phenothiazine General Statement/Cardiovascular monitoring should begin immediately and should include continuous ECG monitoring to detect possible arrhythmias. Treatment may include correction of electrolyte abnormalities and acid-base balance, lidocaine, phenytoin, isoproterenol, ventricular pacing, and defibrillation. Antiarrhythmic agents that can prolong the QT interval (eg, class IA [disopyramide, procainamide, quinidine] or III agents) should be avoided in treating overdosage-associated arrhythmias in which prolongation of QTc is a manifestation. Appropriate therapy (IV fluids and a vasopressor) should be instituted if hypotension occursepinephrine, bretylium, or dopamine should not be used. For the management of refractory hypotension, vasopressors such as phenylephrine, levarterenol, or metaraminol may be used. Appropriate therapy should be instituted if excessive sedation occursCNS stimulants that may cause seizures should be avoided. If seizures occur, treatment should not include barbiturates because these drugs may potentiate phenothiazine-induced respiratory depression. Hypothermia is common and sometimes difficult to control. In some patients with acute toxicity, exchange transfusions may be useful, but hemodialysis, forced diuresis, hemoperfusion, or manipulation of urine pH is of little value in enhancing elimination of phenothiazines. /Phenothiazine General Statement//SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B//SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B//SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation◈ What is fluphenazine?
Wassergefährdungsklasse (WGK)1
UN-TransportnummerUN1230 - class 3 - PG 2 - Methanol, solution
R-Sätze (R)11-23/24/25-39/23/24/25
ToxizitätLD50 oral in mouse: 220mg/kg
GefahrensymboleF,T
Sicherheitshinweise (S)16-36/37-45
Gefahrenklasse6.1
Gefahrstoffdaten69-23-8(Hazardous Substances Data)