Butyrophenone Antipsychotics
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Butyrophenone Antipsychotics
Butyrophenone is an organic compound with the formula C6H5C(O)C3H7. It is a colorless liquid. The butyrophenone structure—a ketone flanked by a phenyl ring and a butyl chain—forms the basis for many other chemicals containing various substituents. Some of these butyrophenones are used to treat various psychiatric disorders such as schizophrenia, as well as acting as antiemetics. Examples of butyrophenone-derived pharmaceuticals include: * Benperidol‡‡ denotes drugs that are no longer (or were never to begin with) marketed in the United States. Some antipsychotics are not firmly placed in either first-generation or second-generation classes. (200 times more potent than chlorpromazine) * Bromperidol†† indicates drugs that are no longer (or were never) marketed in English-speaking countries. * Droperidol‡, Antiemetic for postoperative nausea and vomiting * Haloperidol, the most widely used classical antipsychotic drug in this class * Lumateperone, an atypical ant ...
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Organic Compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-containing compounds such as alkanes (e.g. methane ) and its derivatives are universally considered organic, but many others are sometimes considered inorganic, such as certain compounds of carbon with nitrogen and oxygen (e.g. cyanide ion , hydrogen cyanide , chloroformic acid , carbon dioxide , and carbonate ion ). Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, and even ...
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Antiemetic
An antiemetic is a drug that is effective against vomiting and nausea. Antiemetics are typically used to treat motion sickness and the side effects of opioid analgesics, general anaesthetics, and chemotherapy directed against cancer. They may be used for severe cases of gastroenteritis, especially if the patient is dehydrated. Some antiemetics previously thought to cause birth defects appear safe for use by pregnant women in the treatment of morning sickness and the more serious hyperemesis gravidarum. __TOC__ Types * 5-HT3 receptor antagonists block serotonin receptors in the central nervous system and gastrointestinal tract. As such, they can be used to treat post-operative and cytotoxic drug nausea & vomiting. However, they can also cause constipation, dry mouth, and fatigue. ** Dolasetron (Anzemet) can be administered in tablet form or in an injection. ** Granisetron (Kytril, Sancuso) can be administered in tablet (Kytril), oral solution (Kytril), injection (Kyt ...
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Melperone
Melperone (Bunil ( PT), Buronil ( AT, BE, CZ, DK, FI†, NL†, NO†, SE), Eunerpan ( DE)) is an atypical antipsychotic of the butyrophenone chemical class, making it structurally related to the typical antipsychotic haloperidol. It first entered clinical use in 1960s. Marketing and indications It has been tried in treatment-resistant cases of schizophrenia with some (albeit limited) success. It has also been reported effective in the treatment of L-DOPA and other forms of psychosis in Parkinson's disease (although a multicentre, double-blind, placebo-controlled study conducted in 2012 failed to support these findings). It is also known to possess anxiolytic properties. It is marketed in the following countries: * Austria * Czech Republic * Denmark * Estonia * Finland * Germany * Iceland * Lithuania * Latvia * Portugal * Sweden Adverse effects Melperone is reported to produce significantly less weight gain than clozapine and approximately as much weight gain as typical ...
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Lenperone
Lenperone (Elanone-V) is a typical antipsychotic of the butyrophenone chemical class. It was first reported as an anti-emetic in 1974, and its use in treatment of acute schizophrenia was reported in 1975. Related early antipsychotic agents include declenperone and milenperone. Lenperone was never approved by the FDA for use in humans in the United States, but prior to 1989 it was approved for use in veterinary medicine for sedation. Synthesis The alkylation between 2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane [3308-94-9] (1) and 4-(4-fluorobenzoyl)piperidine [56346-57-7] (2) gives 2-(p-fluorophenyl)-2--1,3-dioxolaneCID:20318874(3). Deprotection of the ketal function completes the synthesis of lenperone (4). See also * Glemanserin * Pruvanserin * Roluperidone * Volinanserin Chemically related drugs containing the same 4-(''p''-fluorobenzoyl)piperidine group: * Altanserin * Ketanserin * Setoperone * Lidanserin References

Butyrophenone antipsychotics 4-Fl ...
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Timiperone
Timiperone, sold under the brand name Tolopelon, is a typical antipsychotic of the butyrophenone class which is marketed in Japan for the treatment of schizophrenia. It is similar in chemical structure to benperidol, but has a thiourea group instead of a urea group. It acts as an antagonist An antagonist is a character in a story who is presented as the main enemy or rival of the protagonist and is often depicted as a villain.D2 and 5-HT2A receptors.


References

Benzimidazolines
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Pipamperone
Pipamperone (International Nonproprietary Name, INN, United States Adopted Name, USAN, British Approved Name, BAN), sold under the brand name Dipiperon, is a typical antipsychotic of the butyrophenone family used in the treatment of schizophrenia and as a sleep aid for depression. It is or has been marketed under brand names including Dipiperon, Dipiperal, Piperonil, Piperonyl, and Propitan. Pipamperone was discovered at Janssen Pharmaceutica in 1961, and entered clinical trials in the United States in 1963. Medical uses Pipamperone was developed for use as an antipsychotic in the treatment of schizophrenia. Pipamperone might be useful as a trip killer, hallucinogen antidote or "trip killer" in blocking the effects of serotonergic psychedelics like psilocybin. Pharmacology Pipamperone acts as an receptor antagonist, antagonist of the 5-HT2A receptor, 5-HT2A, 5-HT2B receptor, 5-HT2B, 5-HT2C receptor, 5-HT2C D2 receptor, D2, D3 receptor, D3, D4 receptor, D4, Alpha-1 adrenergic ...
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Moperone
Moperone (Luvatren, since discontinued) is a typical antipsychotic of the butyrophenone class which is marketed in Japan for the treatment of schizophrenia. It is an antagonist An antagonist is a character in a story who is presented as the main enemy or rival of the protagonist and is often depicted as a villain.D2 (''Ki'' 0.7–1.9 nM), D3 (''Ki'' 0.1–1 nM), and 5-HT2A (''Ki'' 52 nM) receptors. It also has a high binding affinity for the
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Lumateperone
Lumateperone, sold under the brand name Caplyta, is an atypical antipsychotic medication of the butyrophenone class. It is approved for the treatment of schizophrenia as well as bipolar depression, as either monotherapy or adjunctive therapy (with lithium or valproate). It is developed by Intra-Cellular Therapies, licensed from Bristol-Myers Squibb. Lumateperone was approved for medical use in the United States in December 2019 with an initial indication for schizophrenia, and became available in February 2020. It has since demonstrated efficacy in bipolar depression and received FDA approval in December 2021 for depressive episodes associated with both bipolar I and II disorders. Part of the drug shows structural similarity to Pirlindole. Medical uses Schizophrenia On December 20, 2019, the United States Food and Drug Administration (FDA) approved lumateperone for the treatment of schizophrenia in adults. Bipolar depression In December 2021, the FDA approved lumatep ...
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Haloperidol
Haloperidol, sold under the brand name Haldol among others, is a typical antipsychotic medication. Haloperidol is used in the treatment of schizophrenia, tics in Tourette syndrome, mania in bipolar disorder, delirium, agitation, acute psychosis, and hallucinations from alcohol withdrawal. It may be used by mouth or injection into a muscle or a vein. Haloperidol typically works within 30 to 60 minutes. A long-acting formulation may be used as an injection every four weeks for people with schizophrenia or related illnesses, who either forget or refuse to take the medication by mouth. Haloperidol may result in movement disorders such as tardive dyskinesia, and akathisia, both of which may be permanent. Neuroleptic malignant syndrome and QT interval prolongation may occur, the latter particularly with IV administration. In older people with psychosis due to dementia it results in an increased risk of death. When taken during pregnancy it may result in problems in the infant. I ...
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Postoperative Nausea And Vomiting
Postoperative nausea and vomiting (PONV) is the common complication of nausea, vomiting, or retching experienced by a person within the first 24 hours following a surgical procedure. Untreated, PONV affects about 30% of people undergoing general anesthesia each year, with rates rising to 70–80% among those considered high-risk. Postoperative nausea and vomiting can be highly distressing for people undergoing surgery and may pose significant barriers towards recovery, cause surgical complications, and result in delayed discharge from the surgical center if not managed properly. Cause Risk factors Risk factors for PONV can be classified into three main categories: patient-related, surgical, and anesthetic-related. Patient-related Patient factors that confer increased risk for PONV include female gender, younger age (<16 years old), , non-smoking status, high le ...
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Droperidol
Droperidol (Inapsine, Droleptan, Dridol, Xomolix, Innovar fentanyl.html" ;"title="ombination with fentanyl">ombination with fentanyl is an antidopaminergic medication, drug used as an antiemetic (that is, to prevent or treat nausea) and as an antipsychotic. Droperidol is also often used as a rapid sedative in intensive care medicine, intensive-care treatment, and where "agitation aggression or violent behavior" are present. History Discovered at Janssen Pharmaceutica in 1961, droperidol is a butyrophenone which acts as a potent D2 (dopamine receptor) antagonist with some histamine and serotonin antagonist activity. Medical use It has a central antiemetic action and effectively prevents postoperative nausea and vomiting in adults using doses as low as 0.625 mg. For treatment of nausea and vomiting, droperidol and ondansetron are equally effective; droperidol is more effective than metoclopramide. It has also been used as an antipsychotic in doses ranging from 5 to 10 ...
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Ketone
In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone (where R and R' are methyl), with the formula . Many ketones are of great importance in biology and industry. Examples include many sugars (ketoses), many steroids, ''e.g.'', testosterone, and the solvent acetone. Nomenclature and etymology The word ''ketone'' is derived from ''Aketon'', an old German word for ''acetone''. According to the rules of IUPAC nomenclature, ketone names are derived by changing the suffix ''-ane'' of the parent alkane to ''-anone''. Typically, the position of the carbonyl group is denoted by a number, but traditional nonsystematic names are still generally used for the most important ketones, for example acetone and benzophenone. These nonsystematic names are considered retained IUPAC names, although some introdu ...
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