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| {{drugbox | | | {{Details0|Metronidazole (oral)}} |
| | width=200
| | {{Details0|Metronidazole (injection)}} |
| | IUPAC_name = 2-(2-methyl-5-nitro-1''H''-imidazol-1-yl)ethanol
| | {{Details0|Metronidazole (topical)}} |
| | CAS_number = 443-48-1
| | {{Details0|Metronidazole (vaginal)}} |
| | ATC_prefix=A01
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| | ATC_suffix=AB17
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| | ATC_supplemental={{ATC|D06|BX01}}, {{ATC|G01|AF01}}, {{ATC|J01|XD01}}, {{ATC|P01|AB01}}
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| | PubChem=4173
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| | DrugBank=APRD00631
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| | C=6|H=9|N=3|O=3
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| | molecular_weight = 171.15 g/mol
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| | bioavailability = 100% (oral)<br />59–94% (rectal)
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| | metabolism = [[Hepatic]]
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| | elimination_half-life = 6–7 hours
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| | excretion = [[Renal]] (60-80%), [[biliary]] (6–15%)
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| | pregnancy_category = B2 <small>([[Australia|Au]])</small>
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| | legal_AU = S4
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| | legal_UK = POM
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| | routes_of_administration = Oral, [[topical]], [[suppository|rectal]], [[intravenous|IV]], [[vaginal]]
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| }} | |
| {{SI}} | |
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| '''Metronidazole''' ([[International Nonproprietary Name|INN]]) ([[International Phonetic Alphabet|IPA]]: {{IPA|[mɛtrəˈnaɪdəzoʊl]}}) is a [[nitroimidazole]] [[antibiotic|anti-infective]] drug used mainly in the treatment of infections caused by susceptible organisms, particularly [[anaerobe|anaerobic]] [[bacterium|bacteria]] and [[protozoa]]. It is marketed by [[Pfizer]] under the trade name '''Flagyl''', and also by various generic manufacturers, who sell it at a cheaper price.
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| Metronidazole is also used in the treatment of the [[dermatology|dermatological]] condition [[rosacea]], where it is marketed by [[Galderma]] under the trade names '''Rozex''' and '''MetroGel'''.
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| Metronidazole is a [[prodrug]]. It is converted in [[anaerobic organism]]s by the [[redox]] [[enzyme]] [[pyruvate]]-[[ferredoxin]] [[oxidoreductase]]. The nitro group of metronidazole is chemically reduced by ferredoxin (or a ferredoxin-linked metabolic process) and the products are responsible for disrupting the [[DNA]] helical structure, thus inhibiting [[nucleic acid]] synthesis. | |
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| Metronidazole is selectively taken up by [[anaerobic bacteria]] and sensitive [[protozoa|protozoal]] organisms because of the ability of these organisms to reduce metronidazole to its active form intracellularly.
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| ==Indications==
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| Systemic metronidazole is indicated for the treatment of:
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| *[[Vaginitis]] due to ''[[Trichomonas vaginalis]]'' (protozoal) infection in both symptomatic patients as well as their asymptomatic sexual contacts; and due to bacterial ''[[Gardnerella]]'' or ''[[Mycoplasma hominis]]'' infection in symptomatic patients
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| *[[Pelvic inflammatory disease]] in conjunction with other antibiotics such as [[ofloxacin]], [[levofloxacin]], or [[ceftriaxone]]
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| *[[Protozoa]]l infections due to ''[[Entamoeba histolytica]]'' ([[dysentery|Amoebic dysentery]] or [[abscess|Hepatic abscess]]es), and ''[[Giardia lamblia]]'' ([[Giardiasis]]) should be treated alone or in conjunction with [[iodoquinol]] or [[diloxanide furoate]]
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| *Anaerobic bacterial infections such as ''[[Bacteroides|Bacteroides fragilis, spp]]'', ''[[Fusobacterium|Fusobacterium spp]]'', ''[[Clostridium|Clostridium spp]]'', ''[[Peptostreptococcus|Peptostreptococcus spp]]'', ''[[Prevotella|Prevotella spp]]'', or any other anaerobes in [[intraabdominal abscess]], [[peritonitis]], [[empyema]], [[pneumonia]], [[aspiration pneumonia]], [[lung abscess]], diabetic foot ulcer, meningitis and [[brain abscess]], bone and joint infections, septicemia, [[endometritis]], [[tubo-ovarian abscess]], or [[endocarditis]]
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| *[[Pseudomembranous colitis]] due to ''[[Clostridium difficile]]''
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| *''[[Helicobacter pylori]]'' eradication therapy, as part of a multi-drug regimen in [[peptic ulcer disease]]
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| *Prophylaxis for those undergoing potentially contaminated colorectal surgery and may be combined with [[neomycin]]
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| *Acute [[gingivitis]] and other dental infections ([[Therapeutic Goods Administration|TGA]] approved, non-[[Food and Drug Administration]] (FDA) approved)
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| *[[Crohn's disease]] with colonic or perianal involvement (non-FDA approved)
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| Topical metronidazole is indicated for the treatment of [[rosacea]], and has been used in the treatment of malodorous [[neoplasia|fungating]] wounds.<ref name="AMH2006">Rossi S, editor. [[Australian Medicines Handbook]] 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3</ref>
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| ===Prevention of preterm births===
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| Metronidazole has also been used in women to prevent preterm birth associated with [[bacterial vaginosis]], amongst other risk factors including the presence of cervicovaginal fetal fibronectin (fFN). A [[randomised controlled trial]] demonstrated that metronidazole was ineffective in preventing preterm delivery in high-risk pregnant women and, conversely, the incidence of preterm delivery was actually higher in women treated with metronidazole.<ref name="Shennan2006">Shennan A, Crawshaw S, Briley A, Hawken J, Seed P, Jones G, et al. A randomised controlled trial of metronidazole for the prevention of preterm birth in women positive for cervicovaginal fetal fibronectin: the PREMET Study. BJOG 2006;113(1):65-74. PMID 16398774</ref>
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| Lamont has argued that Metronidazole is not the right antibiotic to administer in these circumstances and was often administered too late to be of use. [[Clindamycin]] administered early in the second trimester to women who test positive for [[bacterial vaginosis]] seems to be more effective. <ref name="Lamont2005"> Lamont RF. Can antibiotics prevent preterm birth--the pro and con debate. BJOG 2005;112(suppl):67-73. PMID 15715599</ref>
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| ==Adverse effects==
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| Common [[adverse drug reaction]]s (≥1% of patients) associated with [[systemic]] metronidazole therapy include: [[nausea]], [[diarrhea]], and/or metallic taste in the mouth. [[Intravenous]] administration is commonly associated with [[thrombophlebitis]]. Infrequent adverse effects include: [[hypersensitivity]] reactions (rash, itch, flushing, fever), headache, dizziness, [[vomiting]], [[glossitis]], [[stomatitis]], dark urine, and/or [[paraesthesia]].<ref name="AMH2006" />
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| High doses and/or long-term systemic treatment with metronidazole is associated with the development of [[black hairy tongue]], [[leukopenia]], [[neutropenia]], increased risk of [[peripheral neuropathy]] and/or [[central nervous system|CNS]] toxicity.<ref name="AMH2006" />
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| Metronidazole is listed by the [[International Agency for Research on Cancer]] (IARC) as a potential human [[carcinogen]]. Although some of the testing methods have been questioned, it has been shown to cause cancer in experimental animals.<ref>National Toxicology Program. Metronidazole. In: Report on carcinogens. 11th ed. Research Triangle Park (NC): U.S. Department of Health and Human Services. [updated 2005 Aug 26; cited 2006 Jun 20]. Available from: [http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s112metr.pdf http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s112metr.pdf]</ref> Nevertheless, it appears to have a fairly low potential for cancer risk and under most circumstances the benefits of treatment outweighs the risk.
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| Common adverse drug reactions associated with topical metronidazole therapy include local redness, dryness, and/or skin irritation; and eye watering (if applied near eyes).<ref name="AMH2006" />
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| ===Interaction with alcohol===
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| Co-administration of metronidazole and [[ethanol]] (alcohol) results, rarely, in a [[disulfiram]]-like reaction (nausea, vomiting, flushing, [[tachycardia]]). Consumption of alcohol should be avoided by patients during systemic metronidazole therapy and for at least 24 hours after completion of treatment.<ref name="AMH2006" /> However, the occurrence of this reaction in the clinical setting has recently been questioned by some authors.<ref name="Williams2000">Williams CS, Woodcock KR. Do ethanol and metronidazole interact to produce a disulfiram-like reaction? Ann Pharmacother 2000;34(2):255-7. PMID 10676835</ref><ref name="Visapaa2002">Visapaa JP, Tillonen JS, Kaihovaara PS, Salaspuro MP. Lack of disulfiram-like reaction with metronidazole and ethanol. Ann Pharmacother 2002;36(6):971-4. PMID 12022894</ref>
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| ==References==
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| <div class="references-small">{{reflist|2}}</div>
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| ==External links==
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| * [http://www.merck.com/mmpe/lexicomp/metronidazole.html Merck manuals]
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| {{Stomatological preparations}}
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| {{Antibiotics and chemotherapeutics for dermatological use}}
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| {{Gynecological anti-infectives and antiseptics}}
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| {{Other antibacterials}}
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| {{Agents against amoebiasis and other protozoal diseases}}
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| [[Category:Nitroimidazole antibiotics]]
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| [[Category:Antiprotozoal agents]]
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| [[Category:Dermatological preparations]]
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| [[de:Metronidazol]]
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| [[es:Metronidazol]]
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| [[fr:Métronidazole]]
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| [[it:Metronidazolo]]
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| [[hu:Metronidazol]]
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| [[pl:Metronidazol]]
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| [[pt:Metronidazol]]
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| [[ro:Metronidazol]]
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| [[fi:Metronidatsoli]]
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| {{WikiDoc Sources}}
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