Benzamides
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Benzamides
Benzamide is an organic compound with the chemical formula of C7H7NO. It is the simplest amide derivative of benzoic acid. In powdered form, it appears as a white solid, while in crystalline form, it appears as colourless crystals. It is slightly soluble in water, and soluble in many organic solvents. It is a natural alkaloid Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids. Alkaloids are produced by a large varie ... found in the herbs of '' Berberis pruinosa''. Chemical derivatives A number of substituted benzamides are commercial drugs, including: See also * References External links Physical characteristics {{Authority control Phenyl compounds ...
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Sulpiride
Sulpiride, sold under the brand name Dogmatil among others, is an atypical antipsychotic (although some texts have referred to it as a typical antipsychotic) medication of the benzamide class which is used mainly in the treatment of psychosis associated with schizophrenia and major depressive disorder, and is sometimes used in low dosage to treat anxiety and dysthymia. The drug is chemically and clinically similar to amisulpride. Levosulpiride is its purified levo-isomer and is sold in some countries for similar purposes. Sulpiride is commonly used in Asia, Central America, Europe, South Africa and South America. It is not approved in the United States, Canada, or Australia. Medical uses Schizophrenia Sulpiride's primary use in medicine is in the management of the symptoms of schizophrenia. It has been used as both a monotherapy and adjunctive therapy (in case of treatment-resistance) in schizophrenia. Depression and anxiety It has also been used in the treatment of dy ...
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Itopride
Itopride (International Nonproprietary Name, INN; brand name Ganaton) is a prokinetic benzamide derivative. These drugs inhibit dopamine and acetylcholine esterase enzyme and have a gastrokinetic effect. Itopride is indicated for the treatment of functional dyspepsia and other gastrointestinal conditions. It is a combined D2 receptor, D2 receptor receptor antagonist, antagonist and acetylcholinesterase inhibitor. Itopride is the dimethoxy analog of trimethobenzamide. Medical uses Typically, itopride is indicated in the treatment of GI symptoms caused by reduced GI motility: *dyspepsia of a non-ulcer/dysmotility type (gastric "fullness", discomfort, and possible pain) *Gastroparesis, gastroparesis (delayed gastric emptying) *anorexia (symptom), anorexia *heartburn *regurgitation *bloating *nausea and vomiting *other possible gastric, prolactin, or dopamine related conditions Itopride was shown to significantly improve symptoms in patients with functional dyspepsia and motility ...
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Remoxipride
Remoxipride (Roxiam) is an atypical antipsychotic (although according to some sources it is a typical antipsychotic) which was previously used in Europe for the treatment of schizophrenia and acute mania but was withdrawn due to toxicity concerns (incidence of aplastic anemia in 1/10,000 patients). It was initially launched by AstraZeneca in 1990 and suspension of its use began in 1993. Remoxipride acts as a selective D2 and D3 receptor antagonist and also has high affinity for the sigma receptor, possibly playing a role in its atypical neuroleptic action. Due to its short half-life twice daily (bid) dosing is required, although a once-daily controlled-release tablet has been developed. There was some interest in its use in the treatment of treatment-resistant schizophrenia. See also * Typical antipsychotic * Benzamide Benzamide is an organic compound with the chemical formula of C7H7NO. It is the simplest amide derivative of benzoic acid. In powdered form, it appears as a ...
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Nemonapride
Nemonapride, also previously known as emonapride and sold under the brand name Emilace, is an atypical antipsychotic which is used in the treatment of schizophrenia. It is taken by mouth. Side effects of nemonapride include akathisia, dystonia, hypokinesia, tremor, hypersalivation, and hyperprolactinemia, among others. The drug acts as a dopamine D2, D3, and D4 receptor antagonist. To a lesser extent, it is also a serotonin 5-HT1A receptor partial agonist. Structurally, nemonapride is a benzamide derivative and is related to sulpiride and other benzamides. Nemonapride was introduced for medical use in either 1991 or 1997. It was developed and marketed by Yamanouchi Pharmaceuticals. The drug is approved only in Japan and China. Medical uses Nemonapride is used in the treatment of schizophrenia. It is described as being effective in treating the positive symptoms of schizophrenia. It is also said to have some antidepressant and anxiolytic effects. However, clinical data ...
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Levosulpiride
Levosulpiride, sold under the brand names Dislep and Sulpepta among others, is a dopamine antagonist medication which is used in the treatment of psychotic disorders like schizophrenia, major depressive disorder, nausea and vomiting, and gastroparesis. It is taken by mouth. It is a selective antagonist of the dopamine D2 receptor and an agonist of the serotonin 5-HT4 receptor. Chemically, it is a benzamide and the (''S'')-(−)-enantiomer of sulpiride. Levosulpiride is marketed widely throughout the world, including in Europe, South Korea, Latin America, India, and Pakistan. It is not available in the United States or the United Kingdom. Medical uses Levosulpiride is used in the treatment of: * Psychosis * Negative symptoms of schizophrenia * Major depressive disorder * Anxiety disorders * Dysthymia * Vertigo * Nausea and vomiting * Gastroparesis * Dyspepsia * Irritable bowel syndrome * Premature ejaculation Levosulpiride is not currently licensed for treatment of prema ...
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Amisulpride
Amisulpride, sold under the brand names Socian and Barhemsys, is a medication used in the treatment of schizophrenia, acute psychotic episodes, depression, and nausea and vomiting. It is specifically used at lower doses intravenously to prevent and treat postoperative nausea and vomiting; at low doses by mouth to treat depression; and at higher doses by mouth to treat psychosis. It is usually classed with the atypical antipsychotics. Chemically it is a benzamide and like other benzamide antipsychotics, such as sulpiride, it is associated with a high risk of elevating blood levels of the lactation hormone, prolactin (thereby potentially causing the absence of the menstrual cycle, breast enlargement, even in males, breast milk secretion not related to breastfeeding, impaired fertility, impotence, breast pain, etc.), and a low risk, relative to the typical antipsychotics, of causing movement disorders. Amisulpride is indicated for use in the United States in adults fo ...
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Zacopride
Zacopride is a potent antagonist at the 5-HT3 receptor and an agonist at the 5-HT4 receptor. It has anxiolytic and nootropic effects in animal models, with the (''R'')-(+)-enantiomer being the more active form. It also has antiemetic and pro-respiratory effects, both reducing sleep apnea and reversing opioid-induced respiratory depression in animal studies. Early animal trials have also revealed that administration of zacopride can reduce preference for and consumption of ethanol. Zacopride was found to significantly increase aldosterone levels in human subjects for 180 minutes at a dose of 400 micrograms. It is thought to do this by stimulating the 5-HT4 receptors on the adrenal glands. Zacopride also stimulated aldosterone secretion when applied to human adrenal glands ''in vitro''. No significant changes were observed in renin, ACTH, or cortisol levels. Zacopride has been tested in clinical trials for the treatment of schizophrenia Schizophrenia () is a mental dis ...
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Ethenzamide
Ethenzamide (2-ethoxybenzamide) is a common analgesic and anti-inflammatory drug that is used for the relief of fever, headaches, and other minor aches and pains. It is also an ingredient in numerous cold medications and many prescription analgesics. It is used as an over-the-counter drug in Japan, often in combination with caffeine and acetaminophen, where it is marketed for uses including toothache, menstrual cramps, headache, and fever. It is metabolized ''in vivo Studies that are ''in vivo'' (Latin for "within the living"; often not italicized in English) are those in which the effects of various biological entities are tested on whole, living organisms or cells, usually animals, including humans, an ...'' into salicylamide. References Nonsteroidal anti-inflammatory drugs Benzamides Phenol ethers {{analgesic-stub ...
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Veralipride
Veralipride (Agreal, Agradil) is an atypical antipsychotic of the benzamide class. It is used for the treatment of vasomotor symptoms associated with menopause. It is a D2 receptor antagonist and it induces prolactin secretion without any estrogenic or progestagenic effects. It was first authorised for use in 1979. However, Veralipride has never gained approval in the United States. The women who took it, in addition to extra-pyramidal effects, experienced an aggressive form of depression that resulted in death by suicide for some. The Sanofi laboratory, despite knowing its side effects, allowed women to continue taking it for a considerable amount of time. For this reason, its sale was banned in all countries except Mexico, which allowed its sale to continue for at least 15 years. In September 2006, veralipride was withdrawn from the Spanish market. As a result, the European Commission referred the matter to the European Medicines Agency (EMA). In July 2007, the EMA recommend ...
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Moclobemide
Moclobemide, sold under the brand names Amira, Aurorix, Clobemix, Depnil and Manerix among others, is a reversible inhibitor of monoamine oxidase A (RIMA) drug primarily used to treat Clinical depression, depression and social anxiety. It is not approved for use in the United States, but is approved in other Western countries such as Canada, the United Kingdom, UK and Australia. It is produced by affiliates of the Hoffmann–La Roche pharmaceutical company. Initially, Aurorix was also marketed by Roche in South Africa, but was withdrawn after its patent rights expired and Cipla Medpro's Depnil and Pharma Dynamic's Clorix became available at half the cost. No significant rise in blood pressure occurs when moclobemide is combined with amines such as tyramine-containing foods or pressor amine drugs, unlike with the older irreversible and non-selective monoamine oxidase inhibitors (MAOIs), which cause a severe rise in blood pressure with such combination. Due to the lack of anticholi ...
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Trimethobenzamide
Trimethobenzamide (trade names Tebamide, Tigan) is an antiemetic used to prevent nausea and vomiting. Mechanism of action Trimethobenzamide is an antagonist of the D2 receptor. It is believed to affect the chemoreceptor trigger zone (CTZ) of the medulla oblongata to suppress nausea and vomiting. Side effects Possible side effects include drowsiness, dizziness, headache, muscle cramps, and blurred vision. More serious adverse effects include skin rash, tremors, parkinsonism, and jaundice. Formulations Trimethobenzamide is marketed under the brand names Tebamide and Tigan, manufactured by GlaxoSmithKline and King Pharmaceuticals, respectively. It is available as oral capsules and injectable formulations. Trimethobenzamide was also available as a rectal suppository, but such formulations were banned by the U.S. Food and Drug Administration on April 6, 2007, due to unproven efficacy. Synthesis Alkylation of the sodium salt of ''p''-hydroxybenzaldehyde (1) with 2-dimethyl ...
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Renzapride
Renzapride is a prokinetic agent and antiemetic which acts as a full 5-HT4 agonist and partial 5-HT3 antagonist. It also functions as a 5-HT2B antagonist and has some affinity for the 5-HT2A and 5-HT2C receptors. Renzapride was being developed by Alizyme plc of the United Kingdom. In May 2016, EndoLogic LLC, a US-based pharmaceutical and medical device company, acquired the US and worldwide patent rights to Renzapride. Endologic confirmed the cardiac safety of renzapride through a “Thorough QTc” study and sold the rights to Atlantic Healthcare plc in 2019, a specialist pharmaceutical company. Ambrose Healthcare acquired renzapride in 2024. It is focusing on the development of renzapride for the management of gastrointestinal (GI) motility in patients with cystic fibrosis, for which there is no approved therapy. Clinical trials In nine diabetic patients with autonomic neuropathy, renzapride reduced the mean lag phase of gastric emptying by 20–26 min at all doses ...
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