Phenothiazines

chemical compound

Chlorpromazine (CPZ), marketed under the brand names Thorazine and Largactil among others, is an antipsychotic medication. It is primarily used to treat psychotic disorders such as schizophrenia. Other uses include the treatment of bipolar disorder, severe behavioral problems in children including those with attention deficit hyperactivity disorder, nausea and vomiting, anxiety before surgery, and hiccups that do not improve following other measures. It can be given orally (by mouth), by intramuscular injection (injection into a muscle), or intravenously (injection into a vein).

Phenothiazine, abbreviated PTZ, 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.

Perphenazine is a typical antipsychotic drug. Chemically, it is classified as a piperazinyl phenothiazine. Originally marketed in the United States as Trilafon, it has been in clinical use for decades.

Levomepromazine, also known as methotrimeprazine, is a phenothiazine neuroleptic drug. Brand names include Nozinan, Levoprome, Detenler, Hirnamin, Levotomin and Neurocil. It is a low-potency antipsychotic (approximately half as potent as chlorpromazine) with strong analgesic, hypnotic and antiemetic properties that are primarily used in palliative care.

Thioridazine (sold under the brand names Mellaril or Melleril) is a first-generation antipsychotic drug belonging to the phenothiazine drug group and was previously widely used in the treatment of schizophrenia and psychosis. The branded product was withdrawn worldwide in 2005 because it caused severe cardiac arrhythmias. However, generic versions are still available in the United States.

Prochlorperazine, formerly sold under the brand name Compazine among others, is a medication used to treat nausea, migraines, schizophrenia, psychosis and anxiety. It is a less preferred medication for anxiety. It may be taken by mouth, rectally, injection into a vein, or injection into a muscle.

Promazine (brand name Sparine among others), is used as a short-term add-on treatment for psychomotor agitation. Its approved uses in people is limited, but is used as a tranquilizer in veterinary medicine. It has weak antipsychotic effects but is generally not used to treat psychosis.

Acepromazine, acetopromazine, or acetylpromazine (commonly known as ACP, Ace, or by the trade names Atravet or Acezine 2, number depending on mg/ml dose) is a phenothiazine derivative antipsychotic drug. It was used in humans during the 1950s as an antipsychotic, but is now almost exclusively used on animals as a sedative and antiemetic. A closely related analogue, chlorpromazine, is still used in humans.

Alimemazine (INN), also known as trimeprazine, commonly provided as a tartrate salt, is a phenothiazine derivative that is used as an antipruritic (it prevents itching from causes such as eczema or poison ivy, by acting as an antihistamine). It also acts as a sedative, hypnotic, and antiemetic for prevention of motion sickness.

Thiethylperazine (Torecan, Norzine) is an antiemetic of the phenothiazine class. It is an antagonist of dopamine receptors (DRD1, DRD2, DRD4) as well as of 5-HT2A, 5-HT2C receptors, mAChRs (1 through 5), α1 adrenergic receptor and H1 receptor.

chemical compound

Pipotiazine (Piportil), also known as pipothiazine, is a typical antipsychotic of the phenothiazine class used in the United Kingdom and other countries for the treatment of schizophrenia. Its properties are similar to those of chlorpromazine. A 2004 systematic review investigated its efficacy for people with schizophrenia: {| class="wikitable" |+ Pipotiazine palmitate compared to oral antipsychotics for schizophrenia |- ! Summary |- |Although well-conducted and reported randomized trials are still needed to fully inform practice (no trial data exists reporting hospital and services outcomes,

Oxomemazine is an antihistamine and anticholinergic of the phenothiazine chemical class for the treatment of cough.

Cyamemazine (Tercian), also known as cyamepromazine, is a typical antipsychotic drug of the phenothiazine class which was introduced by Theraplix in France in 1972 and later in Portugal as well.

Periciazine (INN), also known as pericyazine (BAN) or propericiazine, is a drug that belongs to the phenothiazine class of typical antipsychotics.

Mequitazine (trade name Primalan) is an H1 antagonist and anticholinergic of the phenothiazine chemical class. It is used to treat allergies and rhinitis.

Methdilazine (Dilosyn, Tacaryl) is a first-generation antihistamine with anticholinergic properties of the phenothiazine class.

Dixyrazine, also known as dixypazin (oxalate), sold under the brand names Ansiolene, Esocalm, Esucos, Metronal, and Roscal, is a typical antipsychotic of the phenothiazine group described as a neuroleptic and antihistamine. It was first introduced in Germany in 1969. It is used as a neuroleptic, anxiolytic, and antihistamine in doses between 12.5 and 75 mg a day. ==Synthesis== class=skin-invert-image|thumb|center|500px|Synthesis of dixyrazine

Propiomazine, sold under the brand name Propavan among others, is an antihistamine which is used to treat insomnia and to produce sedation and relieve anxiety before or during surgery or other procedures and in combination with analgesics as well as during labor. Propiomazine is a phenothiazine, but is not used therapeutically as a neuroleptic because it does not block dopamine receptors well.

Thioproperazine, sold under the brand name Majeptil, is a typical antipsychotic of the phenothiazine group which is used as a tranquilizer, antiemetic, sedative, and in the treatment of schizophrenia and manic phase of bipolar disorder. Majeptil is available in 10 mg tablets.

Mesoridazine (Serentil) is a phenothiazine class drug that is used in the treatment of schizophrenia. It is one of the active metabolites of thioridazine. The drug's name is derived from the methylsulfoxy and piperidine functional groups in its chemical structure.

Acetophenazine (Tindal) is a typical antipsychotic of the phenothiazine class.

chemical compound

Perazine (Taxilan) is a moderate-potency typical antipsychotic of the phenothiazine class. It is quite similar to chlorpromazine, and acts as a dopamine antagonist. It was very popular in West-Germany. A 2014 systematic review compared it with other antipsychotic drugs: {| class="wikitable" |+ Perazine versus other antipsychotic drugs for schizophrenia |- ! Summary |- | The number, size and reporting of randomized controlled perazine trials are insufficient to present firm conclusions about the properties of this antipsychotic. It is possible that perazine is associated with a similar risk of

Thiopropazate (Artalan, Dartal, Dartalan, Dartan) is a typical antipsychotic of the phenothiazine class. It is a prodrug to perphenazine.

Prothipendyl (brand names Dominal, Timovan, Tolnate), also known as azapromazine or phrenotropin, is an anxiolytic, antiemetic, and antihistamine of the azaphenothiazine group which is marketed in Europe and is used to treat anxiety and agitation in psychotic syndromes. It differs from promazine only by the replacement of one carbon atom with a nitrogen atom in the tricyclic ring system. Prothipendyl is said to not possess antipsychotic effects, and in accordance, appears to be a weaker dopamine receptor antagonist than other phenothiazines.

Metopimazine (, , ), sold under the brand names Vogalen and Vogalene, is an antiemetic of the phenothiazine group which is used to treat nausea and vomiting. It is marketed in Europe, Canada, and South America. As of August 2020, metopimazine has been repurposed and is additionally under development for use in the United States for the treatment of gastroparesis.

chemical compound

Moracizine or moricizine, sold under the trade name Ethmozine, is an antiarrhythmic of class IC. It was used for the prophylaxis and treatment of serious and life-threatening ventricular arrhythmias, but was withdrawn in 2007 for commercial reasons.

Ethacizine (ethacyzine) is a class Ic antiarrhythmic agent, related to moracizine. It is used in Russia and some other CIS countries for the treatment of severe and/or refractory ventricular and supraventricular arrhythmias, especially those accompanied by organic heart disease. It is also indicated as a treatment of refractory tachycardia associated with Wolff–Parkinson–White syndrome.

Chlorproethazine, sold under the brand name Neuriplege, is a drug of the phenothiazine group described as a muscle relaxant or tranquilizer which is or has been marketed in Europe as a topical cream for the treatment of muscle pain. It has been associated with photoallergic contact dermatitis. ==Synthesis== Chlorproethazine can be synthesized from a diphenylsulfide derivative. The general scheme is sufficiently flexible to permit the interchange of the order of some of the steps.

Dimetotiazine (INN) is a phenothiazine drug used for the treatment of migraine. It is a serotonin antagonist and histamine antagonist.

Thionine, also known as '''Lauth's violet, is the salt of a heterocyclic compound. It was firstly synthesised by Charles Lauth. A variety of salts are known including the chloride and acetate, called respectively thionine chloride and thionine acetate'''. The dye is structurally related to methylene blue, which also features a phenothiazine core. The dye's name is frequently misspelled with omission of the e, and is not to be confused with the plant protein thionin. The -ine ending indicates that the compound is an amine.

Sulforidazine (Imagotan, Psychoson, Inofal) a typical antipsychotic and a metabolite of thioridazine; it and mesoridazine are more potent than the parent compound, whose pharmacological effects are believed by some to be largely due to its metabolism into sulforidazine and mesoridazine.

Butaperazine (Repoise, Tyrylen) is a typical antipsychotic of the phenothiazine class. It was approved in 1967, and possibly discontinued in the 1980s.

Dimethylaminopropionylphenothiazine or 10-(alpha-dimethylaminopropionyl)phenothiazine is an antispasmodic.

Profenamine (INN; also known as ethopropazine (BAN); sold under the trade name Parsidol and others) is a phenothiazine derivative used as an antiparkinsonian agent that has anticholinergic, antihistamine, and antiadrenergic actions. It is also used in the alleviation of the extrapyramidal syndrome induced by drugs such as other phenothiazine compounds, but, like other compounds with antimuscarinic properties, is of no value against tardive dyskinesia.

Hydroxyethylpromethazine is an antihistamine with anticholinergic properties. It is structurally analogous to promethazine.

Carfenazine (INN; former development code WY-2445; BAN carphenazine; USAN carphenazine maleate; brand name Proketazine; former development code NSC-71755) is an antipsychotic and tranquilizer of the phenothiazine group that was withdrawn from the market.

Etymemazine is an antipsychotic, antihistamine and anticholinergic drug of the phenothiazine chemical class, structurally related to cyamemazine and methotrimeprazine.

Fenoverine (INN) is an antispasmodic [also known as spasmolytics] drug, which acts by inhibiting calcium channels [much in the same way as traditional calcium channel blockers, which are used as antianginal drugs]. In the case of Fenoverine, the relaxation occurs in abdominal / intestinal smooth muscles, while in case of antianginal drugs, the relaxation occurs in coronary vessels. Notably Fenoverine does not act as an antianginal agent. ==Toxicity== Fenoverine is known to cause rhabdomyolysis. ==References==

Aceprometazine (INN) is a phenothiazine derivative prescription drug with neuroleptic and anti-histamine properties It is not widely prescribed, and may be associated with drug-induced Parkinsonism. It may be used in combination with meprobamate for the treatment of sleep disorders. This combination is available in France under the trade name Mepronizine.