Nitroimidazole
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Nitroimidazole
5-Nitroimidazole is an organic compound with the formula O2NC3H2N2H. The nitro group at position 5 on the imidazole ring is the most common positional isomer. The term nitroimidazole also refers to a class of antibiotics that share similar chemical structures. Synthesis Imidazole undergoes a nitration reaction with a mixture of nitric acid and sulfuric acid to give 5-nitroimidazole: :C3H3N2H + HNO3 + H2SO4 → O2NC3H2N2H + H2O Nitroimidazole antibiotics From the chemistry perspective, nitroimidazole antibiotics can be classified according to the location of the nitro functional group. Structures with names 4- and 5-nitroimidazole are equivalent from the perspective of drugs since these tautomers readily interconvert. Drugs of the 5-nitro variety include metronidazole, tinidazole, nimorazole, dimetridazole, pretomanid, ornidazole, megazol, and azanidazole. Drugs based on 2-nitromidazoles include benznidazole. Nitroimidazole antibiotics have been used to combat anaerobic ba ...
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Benznidazole
Benznidazole is an antiparasitic medication used in the treatment of Chagas disease. While it is highly effective in early disease this decreases in those who have long-term infection. It is the first-line treatment given its moderate side effects compared to nifurtimox. It is taken by mouth. Side effects are fairly common. They include rash, numbness, fever, muscle pain, loss of appetite, and trouble sleeping. Rare side effects include bone marrow suppression which can lead to low blood cell levels. It is not recommended during pregnancy or in people with severe liver or kidney disease. Benznidazole is in the nitroimidazole family of medication and works by the production of free radicals. Benznidazole came into medical use in 1971. It is on the World Health Organization's List of Essential Medicines. As of 2012, Laboratório Farmacêutico do Estado de Pernambuco, a government run pharmaceutical company in Brazil was the only producer. Medical uses Benznidazole has a signi ...
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Metronidazole
Metronidazole, sold under the brand name Flagyl among others, is an antibiotic and antiprotozoal medication. It is used either alone or with other antibiotics to treat pelvic inflammatory disease, endocarditis, and bacterial vaginosis. It is effective for dracunculiasis, giardiasis, trichomoniasis, and amebiasis. It is an option for a first episode of mild-to-moderate ''Clostridium difficile'' colitis if vancomycin or fidaxomicin is unavailable. Metronidazole is available by mouth, as a cream, and by injection into a vein. Common side effects include nausea, a metallic taste, loss of appetite, and headaches. Occasionally seizures or allergies to the medication may occur. Some state that metronidazole should not be used in early pregnancy, while others state doses for trichomoniasis are safe. Metronidazole is generally considered compatible with breastfeeding. Metronidazole began to be commercially used in 1960 in France. It is on the World Health Organization's List of Esse ...
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5-Nitroimidazole Antibiotics Examples
5-Nitroimidazole is an organic compound with the formula O2NC3H2N2H. The nitro group at position 5 on the imidazole ring is the most common positional isomer. The term nitroimidazole also refers to a class of antibiotics that share similar chemical structures. Synthesis Imidazole undergoes a nitration reaction with a mixture of nitric acid and sulfuric acid to give 5-nitroimidazole: :C3H3N2H + HNO3 + H2SO4 → O2NC3H2N2H + H2O Nitroimidazole antibiotics From the chemistry perspective, nitroimidazole antibiotics can be classified according to the location of the nitro functional group. Structures with names 4- and 5-nitroimidazole are equivalent from the perspective of drugs since these tautomers readily interconvert. Drugs of the 5-nitro variety include metronidazole, tinidazole, nimorazole, dimetridazole, pretomanid, ornidazole, megazol, and azanidazole. Drugs based on 2-nitromidazoles include benznidazole. Nitroimidazole antibiotics have been used to combat anaerobic ba ...
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Megazol
Megazol (CL 64855) is a nitroimidazole based drug that cures some protozoan infections. A study of nitroimidazoles found the drug extremely effective against '' T. cruzi'' and '' T. brucei'' which cause Chagas disease and African sleeping sickness, respectively. The drug is considerably more effective than standard benznidazole Benznidazole is an antiparasitic medication used in the treatment of Chagas disease. While it is highly effective in early disease this decreases in those who have long-term infection. It is the first-line treatment given its moderate side effe ... therapy (for Chagas) which is considered the gold standard. This is despite that other nitroimidazoles proved ineffective against these pathogens. References Antiprotozoal agents Nitroimidazole antibiotics Thiadiazoles {{antimicrobial-stub ...
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Ornidazole
Ornidazole is an antibiotic used to treat protozoan infections. A synthetic nitroimidazole, it is commercially obtained from an acid-catalyzed reaction between 2-methyl-5-nitroimidazole and epichlorohydrin. Antimicrobial spectrum is similar to that of metronidazole and is more well tolerated; however there are concerns of lower relative efficacy. It was first introduced for treating trichomoniasis before being recognized for its broad anti-protozoan and anti-anaerobic-bacterial capacities. has also been investigated for use in Crohn's disease Crohn's disease is a type of inflammatory bowel disease (IBD) that may affect any segment of the gastrointestinal tract. Symptoms often include abdominal pain, diarrhea (which may be bloody if inflammation is severe), fever, abdominal distension ... after bowel resection. References Antiprotozoal agents Disulfiram-like drugs Poultry diseases Nitroimidazole antibiotics Organochlorides Halohydrins {{genito-urinary-drug- ...
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Pretomanid
Pretomanid is an antibiotic medication used for the treatment of multi-drug-resistant tuberculosis affecting the lungs. It is generally used together with bedaquiline and linezolid. It is taken by mouth. The most common side effects include nerve damage, acne, vomiting, headache, low blood sugar, diarrhea, and liver inflammation. It is in the nitroimidazole class of medications. Pretomanid was approved for medical use in the United States in August 2019, and in the European Union in July 2020. Text was copied from this source which is © European Medicines Agency. Reproduction is authorized provided the source is acknowledged. Pretomanid was developed by TB Alliance. The U.S. Food and Drug Administration (FDA) considers it to be a first-in-class medication. Medical uses Pretomanid is indicated in combination with bedaquiline and linezolid, in adults, for the treatment of pulmonary extensively drug resistant (XDR), or treatment-intolerant or nonresponsive multidrug-resist ...
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Imidazole 2D Numbered
Imidazole (ImH) is an organic compound with the formula C3N2H4. It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. In chemistry, it is an aromatic heterocycle, classified as a diazole, and has non-adjacent nitrogen atoms in meta-substitution. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam. When fused to a pyrimidine ring, it forms a purine, which is the most widely occurring nitrogen-containing heterocycle in nature. The name "imidazole" was coined in 1887 by the German chemist Arthur Rudolf Hantzsch (1857–1935). Structure and properties Imidazole is a planar 5-membered ri ...
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Imidazole
Imidazole (ImH) is an organic compound with the formula C3N2H4. It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. In chemistry, it is an aromatic heterocycle, classified as a diazole Diazole refers to either one of a pair of isomeric chemical compounds with molecular formula C3H4N2, having a five-membered ring consisting of three carbon atoms and two nitrogen atoms.
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Tinidazole
Tinidazole is a drug used against protozoan infections. It is widely known throughout Europe and the developing world as a treatment for a variety of anaerobic amoebic and bacterial infections. It was developed in 1972 and is a prominent member of the nitroimidazole antibiotic class. It is on the World Health Organization's List of Essential Medicines. Tinidazole is marketed by Mission Pharmacal under the brand name Tindamax, by Pfizer under the names Fasigyn and Simplotan, and in some Asian countries as Sporinex. Uses Tinidazole may be a therapeutic alternative in the setting of metronidazole intolerance. Tinidazole is used to treat ''Helicobacter pylori'', Amoebic dysentery, ''Giardia'' and ''Trichomonas vaginalis''. Side effects Drinking alcohol while taking tinidazole causes an unpleasant disulfiram Disulfiram is a medication used to support the treatment of chronic alcoholism by producing an acute sensitivity to ethanol (drinking alcohol). Disulfiram works by inhibi ...
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Nimorazole
Nimorazole (INN) is a nitroimidazole anti-infective. It is also being investigated for the treatment of head and neck cancer Head and neck cancer develops from tissues in the lip and oral cavity (mouth), larynx (throat), salivary glands, nose, sinuses or the skin of the face. The most common types of head and neck cancers occur in the lip, mouth, and larynx. Symptoms .... References Aromatase inhibitors Nitroimidazole antibiotics Antiprotozoal agents Morpholines {{antiinfective-drug-stub ...
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Dimetridazole
Dimetridazole is a drug that combats protozoan infections. It is a nitroimidazole class drug. It used to be commonly added to poultry feed. This led to it being found in eggs. Because of suspicions of it being carcinogenic its use has been legally limited but it is still found in the eggs. It is now banned as a livestock feed additive in many jurisdictions, for example in the European Union, Canada. and the United States. In the US, the Food and Drug Administration bans it for extralabel useUS Food and Drug Administration, Code of Federal Regulations, Title 21, Volume 6, Revised as of April 1, 202/ref> See also * Metronidazole * Nimorazole Nimorazole (INN) is a nitroimidazole anti-infective. It is also being investigated for the treatment of head and neck cancer Head and neck cancer develops from tissues in the lip and oral cavity (mouth), larynx (throat), salivary glands, nose ... References Antiparasitic agents Nitroimidazole antibiotics {{antimicrobial-stub ...
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Imidazole
Imidazole (ImH) is an organic compound with the formula C3N2H4. It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. In chemistry, it is an aromatic heterocycle, classified as a diazole Diazole refers to either one of a pair of isomeric chemical compounds with molecular formula C3H4N2, having a five-membered ring consisting of three carbon atoms and two nitrogen atoms.
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