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CAS NUMBER: 92-84-2
EC NUMBER: 202-196-5
MOLECULAR FORMULA: C12H9NS
MOLECULAR WIGHT: 199.27
Phenothiazine, widely used anthelmintic (worming agent) in veterinary medicine.
Phenothiazine is an organic compound effective against a broad range of parasites in cattle, horses, poultry, sheep, and swine.
Phenothiazine is not recommended for human use and is not effective in dogs or cats.
Some of the most useful antipsychotic drugs are derivatives of phenothiazine.
Phenothiazines are widely used to treat the symptoms of persons suffering from schizophrenia, psychotic depression, the manic phase of manic-depression, and organic psychoses.
The phenothiazines suppress or eliminate such symptoms as hallucinations, delusions, agitation, and disordered thinking.
The drugs apparently achieve their tranquillizing effect by blocking the transmission of dopamine in the brain.
Among the most widely used phenothiazines are chlorpromazine
Phenothiazine is an organic compound that has the formula S(C6H4)2NH and is related to the thiazine-class of heterocyclic compounds.
Derivatives of phenothiazine are highly bioactive and have widespread use and rich history.
The derivatives chlorpromazine and promethazine revolutionized the fields of psychiatry and allergy treatment, respectively.
An earlier derivative, methylene blue, was one of the first antimalarial drugs, and derivatives are under investigation as possible anti-infective drugs.
Phenothiazine is a prototypical pharmaceutical lead structure in medicinal chemistry.
Phenothiazine is a class of agents exhibiting antiemetic, antipsychotic, antihistaminic, and anticholinergic activities.
Phenothiazines antagonize the dopamine D2-receptor in the chemoreceptor trigger zone (CTZ) of the brain, potentially preventing chemotherapy-induced emesis.
In addition, these agents have peripherally or centrally antagonistic activity against alpha adrenergic, serotonergic, histaminic, and muscarinic receptors.
Phenothiazine is a light green to steel-blue powder.
Acquires a greenish-brown tint under exposure to sunlight.
Phenothiazine antipsychotics are a type of antipsychotic.
Antipsychotics are medicines that are used to reduce hallucinations and delusions associated with psychosis.
Phenothiazine antipsychotics are thought to work by blocking the action of dopamine in the brain; however, their exact mechanism of action is unknown.
Phenothiazine antipsychotics are classed as typical antipsychotics.
Typical antipsychotics (also called first-generation antipsychotics) are commonly associated with extrapyramidal side effects (these are drug-induced movement disorders and include dystonia, Parkinson's-like symptoms, restlessness, rigidity, tardive dyskinesia, tremor, and other unwanted movements) and tend to be less effective than atypical antipsychotics at helping symptoms such as lack of motivation and social withdrawal.
Phenothiazine antipsychotics may be used in the treatment of psychotic symptoms associated with schizophrenia or bipolar disorder.
Phenothiazines are important classes of compounds with a variety of biological activities and are useful for many classes of drug discovery.
The syntheses of these compounds have been developed using several strategies.
The most common synthetic methods are shown here, along with some recent catalytic synthesis of the tricyclic ring system.
Fused tricyclic benzothiazine derivatives are also included in this section since they can be considered to be analogs of phenothiazines.
Some are used also to control agitation in certain patients, severe nausea and vomiting, severe hiccups, and moderate to severe pain in some hospitalized patients.
Chlorpromazine is used also in the treatment of certain types of porphyria, and with other medicines in the treatment of tetanus.
Phenothiazines may also be used for other conditions as determined by your doctor.
Phenothiazines may cause unwanted, unattractive, and uncontrolled face or body movements that may not go away when you stop taking the medicine.
They may also cause other serious unwanted effects. You and your doctor should talk about the good this medicine will do as well as the risks of using it.
Phenothiazines are a class of first-generation heterocyclic anti-psychotic medications, which display antagonistic activity towards dopamine receptors and recently have been shown to have potential anti-neoplastic properties.
This activity illustrates the indications, action, and contraindications for phenothiazine as a valuable agent in treating and managing severe mental disorders such as schizophrenia, cancer, and other manifestations of psychosis.
Also, this activity will highlight the mechanism of action, adverse event profile, and other key factors such as pharmacodynamics and relevant interactions pertinent for members of the interprofessional healthcare team charged with the care of patients with schizophrenia and other related conditions.
Phenothiazines are a group of nitrogen and sulfur-containing heterocyclic compounds, labeled as the first-generation typical antipsychotic medications used for the treatment of schizophrenia, bipolar disorders, control nausea and vomiting, and other psychotic disorders with delusional manifestations.
Phenothiazines were synthesized in 1883 and served as the first commercial antipsychotic therapy in the USA during the 1950s.
In cases of schizophrenia that are resistant to therapy, clinicians can use phenothiazines in combination along with second-generation antipsychotics such as clozapine.
However, this combination therapy exposes the patient to multiple antipsychotic medications and may increase the risk of serious side effects, so this approach is preferable in later stages of treatment.
Patients who undertook pharmacological therapy as an avenue of treatment showcased an 18% to 32% relapse, while patients that did not elect to incorporate pharmacological therapy showcased 60% to 80% relapse in their symptoms.
Phenothiazines produce the most optimal results when combined with non-pharmacological psychotherapeutic therapy, such as narrative, meta-cognitive, and mindfulness therapy.
Also, recent studies have investigated the anti-cancer properties of phenothiazines in glioblastoma as Phenothiazine produced an arrest in the G1 cycle of cancer cells, pointing to a reduction in cyclins stimulating DNA replication along with an increase in Cycline inhibiting compounds.
Furthermore, phenothiazines have shown anti-helminths properties such as Trypanosoma brucei by inhibiting trypanothione reductase and causing cell cycle abnormalities.
Specifically, a decrease in the Phenothiazine phase, an accumulation of the parasite in the G2 phase, and a lack of nucleus creation in the parasite.
Phenothiazine will primarily focus on phenothiazines as antipsychotic medications.
Phenothiazines are medicines used to treat serious mental and emotional disorders, and to reduce nausea.
Phenothiazine discusses an overdose of phenothiazines.
Overdose occurs when someone takes more than the normal or recommended amount of a certain substance.
Phenothiazine can be by accident or on purpose.
Phenothiazine is a class of agents exhibiting antiemetic, antipsychotic, antihistaminic, and anticholinergic activities.
Phenothiazines antagonize the dopamine D2-receptor in the chemoreceptor trigger zone (CTZ) of the brain, potentially preventing chemotherapy-induced emesis.
In addition, these agents have peripherally or centrally antagonistic activity against alpha adrenergic, serotonergic, histaminic, and muscarinic receptors.
Phenothiazines are used to treat serious mental and emotional disorders, including schizophrenia and other psychotic disorders.
Some are used also to control agitation in certain patients, severe nausea and vomiting, severe hiccups, and moderate to severe pain in some hospitalized patients.
Phenothiazine is used also in the treatment of certain types of porphyria, and with other medicines in the treatment of tetanus.
Phenothiazine was initially synthesized in 1883 by Bernthsen.
Phenothiazine was the basis for the development of other drugs including the phenothiazine class of antipsychotics or neuroleptics.
Phenothiazines are the largest class of neuroleptics and include agents such as chlorpromazine, thioridazine, and prochlorperazine.
In 1933, a derivative of phenothiazine, promethazine, was synthesized.
Phenothiazine was found to have much more significant sedative and antihistaminic effects than previous derivatives of phenothiazine and it was used to induce sedation for surgical patients.
After promethazine was developed, a series of agents, including chlorpromazine, was synthesized and tested in France at a military hospital by the French physician Laborit.
Phenothiazine found that chlorpromazine induced calm in patients and had other effects that might be useful clinically.
Phenothiazine, known colloquially as ‘Laborit’s drug’ was released into the market in 1953 after a trial published in 1952 showed efficacy in treatment of psychosis in 38 individuals who received daily injections of chlorpromazine.
Phenothiazine is the prototypical drug for the phenothiazine class of antipsychotics.
The phenothiazines are classified as low-potency antipsychotics and have more side effects at standard doses than the newer agents used as neuroleptics.
For example, they are more anticholinergic and have more extrapyramidal effect than newer agents.
Phenothiazines are neuroleptic agents that affect a variety of receptors including dopaminergic receptor sites.
Phenothiazines are used to treat psychosis including schizophrenia; violent, agitated, disturbed behavior; and mania secondary to bipolar disorder.
Other uses include treatment of pain, headache, hiccups, acute severe anxiety, idiopathic dystonia, withdrawal, taste disorders, leishmaniasis, acute intermittent porphyria, and alleviation of nausea and vomiting.
Phenothiazines allow smoother induction of anesthesia, potentiate anesthetic agents, and treat behavioral symptoms secondary to Alzheimer disease and senile dementia.
Some phenothiazines exert an antipruritic effect and are useful for the treatment of neurodermatitis and pruriginous eczema, and relieve psychogenic itching.
USES:
Phenothiazine is only of theoretical interest, but its derivatives revolutionized psychiatry, other fields of medicine, and pest management. Other derivatives have been studied for possible use in advanced batteries and fuel cells.
Phenothiazine was formerly used as an insecticide and as a drug to treat infections with parasitic worms (anthelminthic) in livestock and people, but its use for those purposes has been superseded by other chemicals.
Phenothiazine was introduced by DuPont as an insecticide in 1935.
However, because Phenothiazine was degraded by sunlight and air, Phenothiazine was difficult to determine how much to use in the field, and its use waned in the 1940s with the arrival of new pesticides like DDT that were more durable.
Phenothiazine is not registered for pesticide use in the US, Europe, or Australia.
Phenothiazine was introduced as anthelminthic in livestock in 1940 and is considered, with thiabendazole, to be the first modern anthelminthic.
The first instances of resistance were noted in 1961.
Among anthelmintics, Blizzard et al. 1990 found only paraherquamide to have similar activity to phenothiazine.
Phenothiazine is possible that they share the same mode of action.
Uses for this purpose in the US are still described but Phenothiazine has "virtually disappeared from the market.
Phenothiazine also was introduced as antihelminthic for humans; since Phenothiazine was often given to children, the drug was often sold in chocolate, leading to the popular name, "worm chocolate." Phenothiazine was superseded by other drugs in the 1950s.
Phenothiazine is a relatively widely used anthelmintic reagent with excellent efficacy in treating the Haemonchus contortus of cattle, horse and sheep, nodular worm, Bunostomum and Plasmodium chabaudi.
Phenothiazine is the intermediates of fine chemicals such as dyes and drugs with itself being a auxiliary material for synthetic material (the anti-polymerization reagent for production of vinylon), fruit pesticides and veterinary anthelmintic.
Phenothiazine is mainly used as the polymerization inhibitor for acrylic acid, acrylic esters, and methacrylic aicd as well as ester monomer.
PROPERTIES:
-Quality Level: 200
-assay: ≥98%
-bp: 371 °C (lit.)
-mp: 182-187 °C (lit.)
-SMILES string: N1c2ccccc2Sc3ccccc13
-InChI: 1S/C12H9NS/c1-3-7-11-9(5-1)13-10-6-2-4-8-12(10)14-11/h1-8,13H
-InChI key: WJFKNYWRSNBZNX-UHFFFAOYSA-N
CHARACTERISTICS:
-Boiling point: 371°C
-Melting point: 185.1°C
-Density: 1.34 g/cm³
-Solubility in water: none
-Flash point: 202°C
-Auto-ignition temperature: 471°C
-Octanol/water partition coefficient as log Pow: 4.15
CHEMICAL PROPERTIES:
Phenothiazine is clean gray-green powder with the melting point of 185.5 ℃, boiling point of 371 ℃, 290 ℃ (5.33kPa).
Phenothiazine is insoluble in petroleum ether, chloroform and water, and soluble in ether and hot acetic acid.
Phenothiazine will be oxidized upon exposure to light in the air.
STRUCTURE:
Phenothiazine is folded in phenothiazines.
Phenothiazine was originally prepared in 1883 via the reaction of diphenylamine with sulfur, but more recent syntheses rely on the cyclization of 2-substituted diphenyl sulfides.
Few pharmaceutically significant phenothiazines are prepared from phenothiazine,[22] although some of them are.
Phenothiazines are electron donors, forming charge-transfer salts with many acceptors.
STORAGE:
Separated from strong oxidants and strong acids.
Store in an area without drain or sewer access.
Provision to contain effluent from fire extinguishing.
SYNONYM:
10H-Phenothiazine
92-84-2
Thiodiphenylamine
Dibenzo-1,4-thiazine
Feeno
Dibenzothiazine
Nemazine
Phenosan
Phenthiazine
Penthazine
Souframine
Agrazine
Antiverm
Contaverm
Fenoverm
Fentiazin
Helmetina
Lethelmin
Nemazene
Nexarbol
Padophene
Phenegic
Phenoverm
Phenovis
Phenoxur
Phenzeen
Reconox
Orimon
Thiodiphenylamin
Wurm-Thional
Dibenzoparathiazine
Early bird wormer
AFI-Tiazin
10H-Phenothiazin
Dibenzo-p-thiazine
Fenothiazine
Tiodifenilamina
Fenotiazina
Biverm
Thiodifenylamine
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