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Metronidazole

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Metronidazole Basic information
The nitro imidazoles antibiotics Chemical property Uses Methods of production
Product Name:Metronidazole
Synonyms:1-(2-Hydroxy-1-ethyl)-2-methyl-5-nitroimidazole;1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole;1-(beta-Hydroxyethyl)-2-methyl-5-nitroimidazole;1-(beta-Oxyethyl)-2-methyl-5-nitroimidazole;1H-Imidazole-1-ethanol, 2-methyl-5-nitro-;1H-Imidazole-1-ethanol,2-methyl-5-nitro-;1-Hydroxyethyl-2-methyl-5-nitroimidazole;2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethanol
CAS:443-48-1
MF:C6H9N3O3
MW:171.15
EINECS:207-136-1
Product Categories:Active Pharmaceutical Ingredients;API's;Peptide Synthesis/Antibiotics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;FLAGYL;antibiotic
Mol File:443-48-1.mol
Metronidazole Structure
Metronidazole Chemical Properties
mp 159-161 °C(lit.)
storage temp. 2-8°C
solubility acetic acid: 0.1 M, clear, faintly yellow
form crystalline
Water Solubility <0.1 g/100 mL at 20 ºC
Merck 6157
Stability:Stable. Incompatible with strong oxidizing agents.
NIST Chemistry ReferenceMetronidazole(443-48-1)
EPA Substance Registry System1H-Imidazole-1-ethanol, 2-methyl-5-nitro-(443-48-1)
Safety Information
Hazard Codes Xn,T,F
Risk Statements 40-46-45-39/23/24/25-23/24/25-11
Safety Statements 36/37-45-53-16-7
WGK Germany 3
RTECS NI5600000
8
HS Code 29332990
Hazardous Substances Data443-48-1(Hazardous Substances Data)
MSDS Information
ProviderLanguage
Flagyl English
SigmaAldrich English
ACROS English
Metronidazole Usage And Synthesis
The nitro imidazoles antibioticsMetronidazole is a kind of nitroimidazole antibiotics, also called flagyl, has killing effect on anaerobic microorganisms. When it restored in the body, its metabolites also have anti anaerobic bacteria, inhibiting the synthesis of bacterial deoxyribonucleic acid, thus interfering with bacterial growth, reproduction, and ultimately death of bacteria. And general anti anaerobic bacteria including: bacteroides fragilis, fusiform bacilli (it become well-known due to cell shape with sharp spindle shaped ends), tetanus, peptococcus, peptostreptococcus, giardia bacteria. At first, it was used in treatment of vaginal trichomoniasis, clinical effect is very significant. Later it was found that metronidazole can also kill anaerobic bacteria causing oral infection. In 1978, it was determined its anti anaerobic infection effects of drugs by the World Health Organization, widely used in the prevention and treatment of oral anaerobic bacteria infection in hospital. This products are also often used in the prevention and treatment for anaerobic bacteria causing respiratory tract, digestive tract, abdominal cavity and pelvic infection, skin and soft tissue and bone and joint infection, heart meningitis, septicemia and cerebral treatment.
Metronidazole has significant effect on amoebiasis in vivo tissue and the intestines, also is the first choice drug for the treatment of toxoplasmosis in the human body, the mechanism is through inhibition of redox reaction of amoebae, rupturing protozoal nitrogen chain and functioned. In vitro test showed that, drug concentration is 1 ~ 2mg / L, soluble Entamoeba histolytica can change their shapes in 6 to 20 hours, and completely killed in 24 hours. The concentration is 0.2mg/L, can kill Entamoeba histolytica in 72 hours. It has been widely used in treatment of intestinal and extraintestinal amebiasis (such as amoebic liver abscess, pleural o Miba disease, etc.).
Due to the interaction of nitroimidazole antibiotics, alcohol, nicotine, etc. and interference of ethanol oxidation process, can cause disulfiram reaction, resulting in rapid heart rate, decreasing blood pressure and other symptoms, so patients should be to avoid contact with alcoholic drink, smoke less, so as to avoid the occurrence of adverse drug reactions during treatment.
The above information is edited by the Chemicalbook Hanya.
Chemical propertyWhite or milky white crystalline powder. Melting point is 158-160. Soluble in hot water, slightly soluble in ethanol, slightly soluble in water or chloroform, slightly soluble in ether. Bitter and slightly salty.
Uses1.In 1959, the goods were used for the treatment of vaginal trichomoniasis. Since 1970, it has used for the intestine, extraintestinal amebiasis, and it has high efficacy, low toxicity, wide application. it has mutagenic and teratogenic effects on experimental animals.
2.It has strong antibacterial effect on most anaerobic bacteria.
3.It is used for the treatment of amebiasis, trichomoniasis and anaerobic bacteria infection.
Methods of productionIt is synthetized by 2-methyl-5-nitro imidazole (see 25010) and ethylene oxide addition. 2-methyl-5-nitro imidazole dissolved in formic acid and at 30-40℃ successive adding epoxy ethane, and sulfuric acid in the middle of adding feeding. and reaction for 1 h, after that. Decompression to recycle formic acid, water solution is cooled to 10 ℃, filter. The filtrate with sodium hydroxide solution to adjust pH = 10. Set aside to cool, filtering, washing to nearly alterations into neutral, recrystallization in water. Activated carbon decolorization to get metronidazole.
Chemical Propertieswhite to slightly yellow crystalline powder
UsageUsed as an antibacterial in the treatment of rosacea. Antiprotozoal (trichomonas). A potential human carcinogen.
General DescriptionWhite to pale-yellow crystalline powder with a slight odor. Bitter and saline taste. pH (saturated aqueous solution) about 6.5.
Air & Water ReactionsInsoluble in water.
Reactivity ProfileMetronidazole darkens on exposure to light. Metronidazole is incompatible with strong oxidizing agents. .
Fire HazardFlash point data for Metronidazole are not available; however, Metronidazole is probably combustible.
Metronidazole Preparation Products And Raw materials
Raw materialsGlyoxal-->Acetaldehyde-->BENZANILIDE-->2-Methylimidazole-->2-Methyl-5-nitroimidazole
Tag:Metronidazole(443-48-1) Related Product Information
Metronidazole 1-Methylimidazole Methyl nitrotoluene Kresoxim-methyl Bensulfuron methyl Thiophanate-methyl Ethyl acetate 2-Methyl-5-nitroimidazole 2-[[[[(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]benzoic acid methyl ester Methyl bromide 2-Methylimidazole Methyl acrylate Methyl acetate 4-Nitrobenzeneethanol alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol Methylparaben Parathion-methyl