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Metronidazole

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  • Metronidazole
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  • 2018-12-29
  • CAS:443-48-1
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  • Metronidazole
  • US $10.00 / KG
  • 2018-09-06
  • CAS: 443-48-1
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Metronidazole Basic information
Brand Name(s) Indications and Usage Mechanisms of Action Warnings and Precautions Methods of production Pharmacology and mechanism of action Indications Side effects Contraindications and precautions Interactions Preparations References
Product Name:Metronidazole
Synonyms:metronidazole Solution, 100ppm;Metronidazole solution ;METRONIDAZOLE BIOXTRA;2-Methyl-5-nitroimidazole-1-ethanol 2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol;MNZ;skype:lila@tuskei.com;2-Met-h;2-Methyl-5-nitro-1H-imidazole-1-ethanol
CAS:443-48-1
MF:C6H9N3O3
MW:171.15
EINECS:207-136-1
Product Categories:Pharmaceutical intermediates;pharmaceutical intermediate;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
Melting point 159-161 °C(lit.)
Boiling point 301.12°C (rough estimate)
density 1.3994 (rough estimate)
refractive index 1.5800 (estimate)
Fp 9℃
storage temp. 2-8°C
solubility acetic acid: 0.1 M, clear, faintly yellow
form crystalline
pkapKa 2.62(H2O,t =25±0.2,Iundefined) (Uncertain)
color white to light yellow
Water Solubility <0.1 g/100 mL at 20 ºC
Merck 14,6157
BRN 611683
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
RIDADR UN1230 - class 3 - PG 2 - Methanol
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
Brand Name(s)Flagyl and generic
Indications and UsageMetronidazole 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 ActionMetronidazole 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 PrecautionsInteractions 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 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.
Pharmacology and mechanism of actionMetronidazole is a 5-nitroimidazole derivative which was originally introduced against Trichomonas vaginalis in 1960. Soon it was shown to possess a broad spectrum of activity against other protozoal infections such as amoebiasis and giardiasis, and more recently against infections due to anaerobic bacteria [1]. The mechanism of action of metronidazole is not well understood. In the parasite, the 5-nitro group of the drug undergoes reductive transformation to a cytotoxic intermediate which binds to the helical structure of the DNA leading to strand breakage and eventual cell death [2].
IndicationsAgainst 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.
Side effectsSide effects with doses used to treat protozoal infections are usually mild, reversible and self-limiting and may affect 4% to 5% of treated patients. The most common are gastrointestinal disturbances (nausea, vomiting, epigastric pain, metallic taste, furring of the tongue), intolerance to alcohol (disulfiram-like effect) and central nervous system effects (headache, dizziness and sleepiness) [3]. Other side effects reported include urticaria, darkening of the urine with a reddish-brown discoloration and transient neutropenia [4]. During prolonged high doses, the drug may cause severe neurotoxic side effects such as peripheral neuropathy, paraesthesia and epileptiform seizures [3,4]. Few case reports of bone marrow depression [5], gynecomastia [6] and acute pancreatitis [7] have been reported. Although metronidazole is mutagenic in bacteria and carcinogenic in rodents, no association with human cancer has been proven .
Contraindications and precautionsDosage 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).
InteractionsMetronidazole 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].
PreparationsMany 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® (Rhône-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® (Rhône-Poulenc Rorer). Oral solution 40 mg metronidazole base/ml.
References1. Scully BE (1988). Metronidazole. Med Clin North Amer, 72, 613–621.
2. Muller M (1983). Mode of action of metronidazole on anaerobic bacteria and protozoa. Surgery, 93, 165–171.
3. Lau AH, Lam NP, Piscitelli SS (1992). Clinical pharmacokinetics of metronidazole and other nitroimidazole anti-infectives. Clin Pharmacokinet, 23, 328–364.
4. Roe FJC (1985). Safety of nitroimidazoles. Scand J Infect Dis, 46, 72–81.
5. Heisterberg L, Branebjerg PE (1983). Blood and milk concentrations of metronidazole in mothers and infants. J Perinat Med, 11, 114–120.
6. Fagan TC, Johnson DG, Grosso DS (1985). Metronidazole-induced gynecomastia. J Am Med Ass, 254, 3217.
7. Poltkin BH, Cohen I, Tsang T, Cullinane T (1985). Metronidazole-induced pancreatitis. Ann Intern Med, 103, 891–892.
8. Rothstein E, Clancy DD (1969). Toxicity of disulfiram combined with metronidazole. N Engl J Med, 280, 1006–1007.
9. O’Reilly RA (1976). The stereoselective interaction of warfarin and metronidazole in man. N Engl J Med, 295, 354–357.
10. Gupte S (1983). Phenobarbital and metabolism of metronidazole. N Engl J Med, 308, 529. 11. Eradiri D, Jamali R, Thomson ABR (1988). Interaction of metronidazole with phenobarbital, cimetidine, prednisone, and sulphasalzine in Crohn’s disease. Biopharmaceut Drug Disp, 9, 219– 227.
Chemical Propertieswhite to slightly yellow crystalline powder
Chemical PropertiesMetronidazole is an odorless, white, yellow, or cream-colored crystalline solid. Darkens on exposure to light. Bitter, salty taste (do not test).
UsesUsed as an antibacterial in the treatment of rosacea. Antiprotozoal (trichomonas). A potential human carcinogen.
DefinitionChEBI: 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.
Brand nameFlagyl (Searle); Metrogel (Galderma); Metrogel (3M Pharmaceuticals); Noritate(Sanofi Aventis); Vandazole (Teva).
Antimicrobial activityIt is a potent inhibitor of obligate anaerobic bacteria and protozoa, but not of any organism that is aerobic or incapable of anaerobic metabolism. Susceptible protozoa include T. vaginalis, G. lamblia, E. histolytica, Balantidium coli and Blastocystis hominis, which are inhibited by concentrations of 0.2–0.25 mg/L. Clostridium spp. (including C. difficile) are inhibited at concentrations of 0.5–8 mg/L. It is also active against the microaerophilic H. pylori (MIC for susceptible strains <8 mg/L). The 2-methoxy metabolite of metronidazole is more active (MIC about 0.3 mg/L), but the acid metabolite shows less activity than the parent drug (MIC about 3 mg/L). G. vaginalis shows similar susceptibility (MIC 1–8 mg/L); the methoxy metabolite is more active (MIC 0.02–2 mg/L).
Acquired resistanceAlthough 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.
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.
Pharmaceutical ApplicationsA 5-nitroimidazole available for oral administration or as a suppository; also formulated as the hydrochloride for intravenous use, and as the benzoate in an oral suspension and a dental gel. Aqueous solubility: 10 g/L at 20°C. Soluble in dilute acids. It is photolabile and preparations should be protected from light. Metronidazole hydrochloride has a low pH (0.5–2.0) when reconstituted, and reacts with aluminum in equipment, including needles, to produce a reddish-brown discoloration. It is incompatible with several agents and other drugs should not be added to intravenous solutions.
Contact allergensMetronidazole 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??????????????????????????????????????????????????????????
PharmacokineticsOral absorption :>90%
Cmax 400 mg oral :c. 10 mg/L after 3–5 h
Plasma half-life: 6–11 h
Volume of distribution:0.6–1.1 L/kg
Plasma protein binding:<20%
absorption
Peak plasma concentrations after oral administration are proportional to the dose. Plasma levels are usually lower in men because of weight differences. In patients treated intravenously with a loading dose of 15 mg/kg followed by 7.5 mg/kg every 6 h, peak steady state plasma concentrations averaged 25 mg/L with minimum trough concentrations averaging 18 mg/L.
The bioavailability of metronidazole in rectal suppositories is around 60%. Effective blood concentrations occur 5–12 h after the first suppository and are maintained by an 8 h regimen.
There are conflicting data on the effects of age on absorption. One study, which did not distinguish between metronidazole and its metabolites, indicated that the area under the curve (AUC) for plasma was almost doubled in the elderly. However, the general consensus is that there is no requirement for a decreased dosage for the elderly, unless there is significant renal impairment.
Distribution
It is widely distributed in body tissues after oral or intravenous administration.It appears about 90 min after an oral dose in brain tissue, cerebrospinal fluid (CSF), saliva and breast milk in concentrations similar to those found in plasma: and in :vaginal secretions, pleural and prostatic fluid at levels about 40% of those of the plasma. In patients receiving 500 mg every 12 h or 1 g every 6 h, CSF levels of up to 2 and 8 mg/L, respectively, have been found. Bactericidal concentrations of metronidazole are achieved in pus from hepatic abscesses. Concentrations in placenta and fetal tissue are related to the corresponding maternal plasma levels: concentrations of 3.5 mg/kg (placenta) and 9 mg/kg (fetus) when the plasma concentration was 13.5 mg/L.
Metabolism
It is metabolized in the liver to a glucuronide conjugate and to acid and hydroxy derivatives. The acid metabolite, produced by oxidation of the N-1 ethanol side-chain, is microbiologically inactive and appears in the urine because of its high water solubility. The hydroxy derivative, which is as active as the parent drug against G. vaginalis, is formed by oxidation of the methyl group on C-2 of the imidazole ring, first to the hydroxymethyl derivative and subsequently to the carboxylic acid. Hydroxymetronidazole has a half-life of 10–13 h. Both metronidazole itself and the hydroxymethyl metabolite can form sulfate or glucuronide conjugates: the acid metabolite may be excreted as the glycine conjugate. Traces of metabolites derived from reduction of the nitro group are found in urine and are assumed to be formed by the intestinal flora.
excretion
About 60–80% of the dose appears in the urine and 6–15% in the feces. The hydroxy and acid metabolites are also excreted in the urine. Glucuronide conjugates account for approximately 20% of the total. Renal clearance is approximately 10 mL/min per 1.73 m2. Decreased renal function does not alter the single-dose kinetics and dose adjustment is not normally required in patients with renal impairment. However, the hydroxy metabolite may accumulate in patients with end-stage disease and dose reduction may be necessary. Elimination is prolonged in patients with impaired liver function necessitating dose reduction. Hemodialysis increases the clearance of metronidazole, shortening the half-life to 2–3 h.
Newborn infants possess a decreased capacity to eliminate metronidazole. In one study, the elimination half-life measured during the first 3 days of life was inversely related to gestational age. In premature newborns and infants whose gestational ages were between 28 and 40 weeks, the corresponding half-life elimination rates ranged from 10.9 to 22.5 h.
Clinical UseIt is also used in acne rosacea, balantidiasis and Guinea worm infection. T. vaginalis infections resistant to the usual dosage require special treatment.
Side effectsprecautions
Alcohol should not be taken during and for 48 h after therapy because of a possible disulfiram-like reaction, nor should it be combined with formulations containing alcohol. It should not be given in cases of known hypersensitivity to nitroimidazoles.
It enhances the anticoagulant effect of warfarin and may impair the clearance of phenytoin and lithium. Phenytoin may increase the metabolism of metronidazole. Plasma concentrations are decreased by the concomitant administration of phenobarbital (phenobarbitone). The drug may also mask the immunological response of untreated early syphilis cases because of its antitreponemal activity.
It should be used with care in patients with blood dyscrasias or with any central nervous system (CNS) disease.
The drug should be avoided in pregnancy, especially during the first trimester and particularly if high doses are being administered. Use during the second and third trimesters may be acceptable if alternative therapies for trichomoniasis have failed, but single-dose (2 g oral) therapy should be avoided. The drug may cause the breast milk to taste bitter. Breast feeding should be discontinued until 24 h after the last dose to allow excretion of the drug. It appears safe when given to nursing mothers at doses of up to 400 mg every 8 h.
adverse effects
An unpleasant sharp, metallic taste is not unusual. Furry tongue, glossitis and stomatitis have occurred; stomatitis may be associated with overgrowth of Candida spp. during treatment. Gastrointestinal disturbances include nausea, vomiting, abdominal discomfort and diarrhea, and occur with intravenous and oral preparations. Pseudomembranous colitis has also been reported.
Nervous system effects associated with intravenous and oral preparations include convulsive seizures, peripheral neuropathy, dizziness, vertigo, incoordination, ataxia, confusion, irritability, depression, weakness and insomnia. Peripheral neuropathy was found in 11 of 13 patients aged 12–22 years treated for Crohn’s disease. The symptoms disappeared when the dose was discontinued or markedly reduced. Peripheral neuropathy or CNS toxicity is more likely in patients treated for 10 days or more and treatment should be discontinued. The co-administration of cimetidine increases plasma levels of metronidazole and may increase the risk of neurological side effects.
Reversible neutropenia has been reported after administration of both intravenous and oral preparations. Bone marrow aplasia and thrombocytopenia are rare. Hemolytic uremic syndrome was reported in six children who had been given metronidazole for non-specific diarrhea or for prophylaxis after bowel surgery.
Erythematous rash and pruritus have been reported after use of the intravenous preparation. The risk of thrombophlebitis can be minimized by avoiding prolonged indwelling catheters for intravenous infusion.
Rarely, flattening of the T wave may be seen in electrocardiographic tracings. A number of cases of deafness have been reported. Myopia related to 11 days’ oral treatment for trichomoniasis disappeared 4 days after treatment was stopped, but returned when treatment was resumed. There have been isolated reports of pancreatitis and gynecomastia.
Safety ProfileConfirmed 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.
Potential ExposureMetronidazole 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.
First aidSkin Contact: Flood all areas of body that have contacted the substance with water. Don’t wait to remove contaminated clothing; do it under the water stream. Use soap to help assure removal. Isolate contaminated clothing when removed to prevent contact by others. Eye Contact: Remove any contact lenses at once. Flush eyes well with copious quantities of water or normal saline for at least 20 30 minutes. Seek medical attention. Inhalation: Leave area immediately; breathe fresh air. Proper respiratory protection must be supplied to any rescuers. If coughing, difficult breathing or any other symptoms develop, seek medical attention at once, even if symptoms develop many hours after exposure. Ingestion: If convulsions are not present, give a glass or two of water or milk to dilute the substance. Assure that the person’s airway is unobstructed and contact a hospital or poison center immediately for advice on whether or not to induce vomiting.
ShippingUN3249 Medicine, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
IncompatibilitiesIncompatible 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 DisposalDispose 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.
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