• Product NameMetronidazole
  • CasNo. 443-48-1
  • MFC6H9N3O3
  • MW171.156
  • Purity
  • Appearancewhite to slightly yellow crystalline powder
  • Packing
  • Contact usInquiry

Product Details

CasNo: 443-48-1

MF: C6H9N3O3

Appearance: white to slightly yellow crystalline powder

Quality Manufacturer Supply High Purity 99% Metronidazole 443-48-1 with Reasonable Price

  • Molecular Formula:C6H9N3O3
  • Molecular Weight:171.156
  • Appearance/Colour:white to slightly yellow crystalline powder 
  • Vapor Pressure:2.67E-07mmHg at 25°C 
  • Melting Point:159-161 °C(lit.) 
  • Refractive Index:1.612 
  • Boiling Point:405.4 °C at 760 mmHg 
  • PKA:pKa 2.62(H2O,t =25±0.2,Iundefined) (Uncertain) 
  • Flash Point:199 °C 
  • PSA:83.87000 
  • Density:1.45 g/cm3 
  • LogP:0.61520 

Metronidazole(Cas 443-48-1) Usage

Description

Metronidazole is an antibiotic medication belonging to the nitroimidazole class. It's used to treat a variety of bacterial and parasitic infections in different parts of the body.
Manufacturer WLP Ingredient Inc was formerly known as Green Valley Biochemical, which was founded in Hong Kong  In 2013, it reached a long-term strategic cooperation agreement with a local factory of plant extrac ,which already got HAHAL,KOSHER,ISO9001,ISO2200,HACCP,cGMP. Now it has developed into a comprehensive enterprise integrating R&D, production and sales. And after years of market accumulation and in response to customer needs, we have close cooperation in various fields and production such as human APIs, veterinary APIs, food additives, feed additives, vitamins, amino acids, etc In the course of business, our company has always adhered to the principle of integrity first and won the praise of our customers. we hope that in the days to come,we can become your important partner and create a better future together.

Indications and Usage

Metronidazole is a nitroimidazole antibiotic, also known as metronidazol and novonidazol. It was initially used to treat vaginal trichomaniasis, with very significant clinical effects. It is broadly used to prevent and treat oral anaerobic infections. In hospitals, it has been used frequently to prevent and treat respiratory, gastrointestinal, peritoneal, pelvic, skin, soft tissue, joint, and brain infections, cardiomyitis, and septicemia caused by anaerobic bacteria. The effectiveness of Metronidazole towards treating body tissue and intestinal amoebiasis is significant, and it the preferred drug to treat parasitosis.

Mechanisms of Action

Metronidazole kills anaerobic microorganisms, and its metabolites in the body during reduction also inhibit them by inhibiting DNA synthesis, thus interfering with bacterial growth and propagation, eventually killing them. Anaerobic bacteria affected include: Bacteroides fragilis, Fusobacterium (so named because of its sharp fusiform shape at both ends,) Clostridium tetani, Peptostreptococcus, and Giardia lamblia. Its mechanism of action in the treatment of parasites is to disrupt protozoans’ nitrogen chains by inhibiting their redox reactions. In vitro experiments have shown that at concentrations of 1-2 mg/L, morphological changes occurred in dissolved amoeba starting at 6-20 hours, killing them all within 24 hours. At a concentration of 0.2 mg/L, dissolved bacteria were killed within 72 hours.

Warnings and Precautions

Interactions with nitroimidazole antibiotics, ethanol, and nicotine interfere with the oxidation of ethanol and can cause disulfiram reactions, causing symptoms like faster heart rate and decreased blood pressure, so patients should avoid contact with alcohol and smoke less during treatment in order to prevent the occurrence of adverse reactions.

Methods of production

It 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.

Indications

Against infections caused by Trichomonas vaginalis, Entamoeba histolytica (acute intestinal type and liver abscesses), Giardia lamblia and Dracunculus medinensis. During treatment of trichomoniasis it is wise to treat the male partner as well. In amoebiasis, a luminal amoebicide is added to eliminate surviving organisms in the colon. Metronidazole is also used for the treatment of infections due to anaerobic bacteria.

Contraindications and precautions

Dosage reductions should be made in patients with severe hepatic failure. Because of its potential neurotoxicity and neutropenia the drug should be given with caution to patients with diseases of the CNS or with a history of blood dyscrasia. Patients should be warned of a disulfiram-like reaction if the drug is taken together with alcohol. Metronidazole should be used with extra caution in patients being treated with warfarin (see interactions).

Interactions

Metronidazole is a weak inhibitor of alcohol dehydrogenase. Simultaneous administration of metronidazole and disulfiram has been reported to cause an acute psychosis or mental confusion. This effect was observed in 6 of 29 chronic alcoholic men given both drugs, but in none of those given placebo plus disulfiram [8]. Metronidazole inhibits the ring oxidation of S (+) warfarin and significant bleeding can occur if the two drugs are taken together [9]. Significant increase of hepatic clearance of metronidazole has been reported when the drug was taken together with phenobarbital [10, 11] or prednisone [11].

Preparations

Many preparations are available apart from those mentioned below. Available as metronidazole ? Elyzol? (Dumex). Solution for infusion 5 mg/ml. Tablets 250 mg, 500 mg. Suppositories 500 mg, 1000 mg. ? Flagyl? (Rh?ne-Poulenc Rorer). Solution for infusion 5 mg/ml. Tablets 200 mg, 400 mg. Suppositories 500 mg, 1000 mg. ? Servizol? (Servipharm). Tablets 200 mg, 250 mg. Available as metronidazole benzoate: 10 mg metronidazole benzoate is equivalent to 6.2 mg metronidazole. ? Elyzol (Dumex)? Oral solution 25 mg metronidazole base/ml. ? Flagyl? (Rh?ne-Poulenc Rorer). Oral solution 40 mg metronidazole base/ml.

Definition

ChEBI: Metronidazole is a member of the class of imidazoles substituted at C-1, -2 and -5 with 2-hydroxyethyl, nitro and methyl groups respectively. It has activity against anaerobic bacteria and protozoa, and has a radiosensitising effect on hypoxic tumour cells. It may be given by mouth in tablets, or as the benzoate in an oral suspension. The hydrochloride salt can be used in intravenous infusions. Metronidazole is a prodrug and is selective for anaerobic bacteria due to their ability to intracellularly reduce the nitro group of metronidazole to give nitroso-containing intermediates. These can covalently bind to DNA, disrupting its helical structure, inducing DNA strand breaks and inhibiting bacterial nucleic acid synthesis, ultimately resulting in bacterial cell death. It has a role as an antitrichomonal drug, a prodrug, an antibacterial drug, an antimicrobial agent, an antiparasitic agent, a xenobiotic, an environmental contaminant, a radiosensitizing agent and an antiamoebic agent. It is a member of imidazoles, a C-nitro compound and a primary alcohol. It is a conjugate base of a metronidazole(1+).

Therapeutic Function

Antiprotozoal

Antimicrobial activity

Metronidazole inhibits E. histolytica, G. lamblia, T. vaginalis, Blastocystis hominis, B. coli, and the helminth Dracunculus medinensis. It is also bactericidal for obligate anaerobic gram-positive and gram-negative bacteria except Actinomyces spp. It is not active against aerobes or facultative anaerobes. Drug resistance is infrequent; the mechanism of resistance is not understood. Tinidazole, a 5-nitroimidazole closely related to metronidazole, is effective against vaginal trichomoniasis resistant to metronidazole.

Acquired resistance

Although resistance in Bacteroides spp. and T. vaginalis is well documented, it is uncommon. Resistance occurs more frequently in H. pylori and failure of treatment with triple drug regimens may be associated with resistance to the metronidazole component.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Metronidazole darkens on exposure to light. Metronidazole is incompatible with strong oxidizing agents. .

Fire Hazard

Flash point data for Metronidazole are not available; however, Metronidazole is probably combustible.

Contact allergens

Metronidazole is a nitro-6-imidazole compound with antiprotozoal and antibacterial properties. Topical exposure may induce allergic contact dermatitis. Sensitization is mainly observed with the treatment of rosacea and rarely occurs from handling of table.

Biochem/physiol Actions

Metronidazole is a prodrug and is selective for anaerobic bacteria due to their ability to intracellularly reduce metronidazole to its active form. Reduced metronidazole covalently binds to DNA which disrupts its helical structure, induces DNA strand breaks and inhibits bacterial nucleic acid synthesis. Bacterial cell death results.

Pharmacology

Absorption from the intestinal tract is usually good. Food delays but does not reduce absorption.The drug is distributed in body fluids and has a half-life of about 8 hours. High levels are found in plasma and cerebrospinal fluid (CSF). Less than 20% binds to plasma proteins. Metronidazole is metabolized by oxidation and glucuronide formation in the liver and is primarily excreted by the kidneys, although small amounts can be found in saliva and breast milk. Dose reduction is generally unnecessary in renal failure.

Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenic data. Moderately toxic by ingestion, intraperitoneal, and subcutaneous routes. Human systemic effects by ingestion: paresthesia, nerve or sheath structural changes, eye changes, tremors, fever, jaundice and other liver changes, hearingacuity changes, somnolence, and ataxia. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Synthesis

Metronidazole, 2-methyl-5-nitroimidazol-1-ethanol (37.2.10), is made by nitrating 2-methylimidazole to make 2-methyl-5-nitroimidazole (37.2.9), which is then reacted with 2-chloroethanol or ethylenoxide, which is easily transformed to the desired metronidazole.

Potential Exposure

Metronidazole is an orally administered drug for the treatment of infections due to entamoeba histolytica; trichomonas vaginalis; giardia lamblia, and has also been used for treating Vincent’s infection. It can be used as a trichomonacide in veterinary medicine. One firm has petitioned EPA to use metronidazole as a disinfectant for cooling tower water.

Veterinary Drugs and Treatments

Although there are no veterinary-approved metronidazole products, the drug has been used extensively in the treatment of Giardia in both dogs and cats. It is also used clinically in small animals for the treatment of other parasites (Trichomonas and Balantidium coli) as well as treating both enteric and systemic anaerobic infections. In horses, metronidazole has been used clinically for the treatment of anaerobic infections.

Drug interactions

Potentially hazardous interactions with other drugs Alcohol: disulfiram-like reaction. Anticoagulants: effects of coumarins enhanced. Antiepileptics: metabolism of phenytoin inhibited; concentration reduced by phenobarbital. Busulfan: concentration of busulfan increased - risk of toxicity. Ciclosporin: raised blood level of ciclosporin. Cytotoxics: busulfan concentration increased; metabolism of fluorouracil inhibited.

Carcinogenicity

Metronidazole is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.

Environmental Fate

Due to metronidazole’s use as a pesticide, it may have been directly released into the environment. It lacks an adequate chromophore for absorbing light and undergoing photolytic degradation. In addition, in vitro assays demonstrated the compound’s robust stability in the atmosphere or aqueous environments. Metronidazole exhibited a soil half-life between 10 and 27 days.

Metabolism

Metronidazole is available in a variety of dosage forms, including IV, oral, rectal, and vaginal suppositories. The bioavailability of metronidazole is nearly 100% when administered orally but is significantly less when administered via the rectal route (67–82%) or the vaginal route (19–56%). The drug is not bound to plasma protein. Distribution of the drug is fairly uniform through out the body, including mother's milk. Liver metabolism of metronidazole leads to two major metabolites: hydroxylation of the 2-methyl group to 2-hydroxymethylmetronidazole (HM), and oxidation to metronidazole acetic acid. Both compounds possess biological activity. Additionally, HM is found in the urine as glucuronide and sulfate conjugates. In addition, a small amount of metronidazole is oxidized to acetamide, a known carcinogen in rats but not in humans.

Shipping

UN3249 Medicine, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.

Waste Disposal

Dispose of contents and container to an approved waste disposal plant. All federal, state, and local environmental regulations must be observed. It is inappropriate and possibly dangerous to the environment to dispose of expired or waste drugs and pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, doublebagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged, and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

Who Evaluation

Evaluation year: 1989

InChI:InChI=1/C6H9N3O3/c1-5-7-6(9(11)12)4-8(5)2-3-10/h4,10H,2-3H2,1H3

443-48-1 Relevant articles

SYNTHESIS OF METRONIDAZOLE FROM ETHYLENEDIAMINE

Kraft, M. Ya.,Kochergin, P. M.,Tsyganova, A. M.,Shlikhunova, V. S.

, p. 861 - 863 (1989)

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Method for synthesizing metronidazole under catalysis of solid acid

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Paragraph 0029-0058, (2019/09/05)

The invention discloses a method for syn...

Synthetic method for producing metronidazole raw medicinal material

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Paragraph 0013-0014, (2018/07/30)

The invention discloses a synthetic meth...

Tritiated metronidazole and preparation method thereof

-

Paragraph 0044; 0045, (2017/08/28)

The invention belongs to the field of ra...

Environment-friendly method for metronidazole synthesis

-

Paragraph 0040; 0041; 0047; 0048, (2016/10/07)

The invention discloses an environment-f...

443-48-1 Process route

metronidazole palmitate
13182-85-9

metronidazole palmitate

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

metronidazole
443-48-1

metronidazole

Conditions
Conditions Yield
With hydrogenchloride; citrate-phosphate-borate buffer; In ethanol; at 60 ℃; pH=3; Further Variations:; pH-values; Kinetics;
 
leucine ester of metronidaxole hydrochloride

leucine ester of metronidaxole hydrochloride

L-leucine
61-90-5,21675-61-6,25248-98-0,70-45-1

L-leucine

metronidazole
443-48-1

metronidazole

Conditions
Conditions Yield
With sodium chloride; at 25 ℃; Rate constant; rate constant of hydrolysis; pH 4.5; other pH, buffers;
 
With water; at 37 ℃; Rate constant; rate constant of hydrolysis;
 

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    C27H18N6O12

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