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Metronidazole, marketed under the brand name Flagyl among others, is an antibiotic and antiprotozoal medication.
Common side effects include nausea, a metallic taste, loss of appetite, and headaches.
Metronidazole began to be commercially used in 1960 in France.
Contents
1 Medical uses
1.1 Bacterial vaginosis
1.2 Trichomoniasis
1.3 Giardiasis
1.4 Dracunculus
1.5 C. difficile colitis
1.6 E. histolytica
1.7 Preterm births
2 Adverse effects
2.1 Mutagenesis and carcinogenesis
2.2 Stevens–Johnson syndrome
3 Drug interactions
3.1 Alcohol
3.2 Other drug interactions
4 Mechanism of action
5 Synthesis
6 Veterinary use
7 References
8 External links
Medical uses
A tube of metronidazole
Metronidazole is primarily used to treat: bacterial vaginosis, pelvic inflammatory disease (along with other antibacterials like ceftriaxone ), pseudomembranous colitis, aspiration pneumonia, rosacea (topical), fungating wounds (topical), intra-abdominal infections, lung abscess, periodontitis, amoebiasis, oral infections, giardiasis, trichomoniasis, and infections caused by susceptible anaerobic organisms such as Bacteroides, Fusobacterium, Clostridium, Peptostreptococcus, and Prevotella species.
Metronidazole is bitter and so the liquid suspension contains metronidazole benzoate. This requires hydrolysis in the stomach and so maybe unsuitable in people with diarrhea or feeding-tubes in the duodenum or jejunum.
Bacterial vaginosis
Drugs of choice for the treatment of bacterial vaginosis include metronidazole and clindamycin. The treatment of choice for bacterial vaginosis in nonpregnant women include metronidazole oral twice daily for seven days, or metronidazole gel intravaginally once daily for five days, or clindamycin intravaginally at bedtime for seven days. For pregnant women, the treatment of choice is metronidazole oral three times a day for seven days. Data does not report routine treatment of male sexual partners.
Trichomoniasis
The 5- nitroimidazole drugs (metronidazole and tinidazole ) are the mainstay of treatment for infection with Trichomonas vaginalis. Treatment for both the infected patient and the patient’s sexual partner is recommended, even if asymptomatic. Therapy other than 5-nitroimidazole drugs is also an option, but cure rates are much lower.
Giardiasis
Oral metronidazole is a treatment option for giardiasis, however, the increasing incidence of nitroimidazole resistance is leading to the increased use of other compound classes.
Dracunculus
In the case of Dracunculus (guinea worm), metronidazole just eases worm extraction rather than killing the worm.
C. difficile colitis
Initial antibiotic therapy for less-severe Clostridium difficile colitis ( pseudomembranous colitis ) consists of metronidazole, vancomycin, or fidaxomicin by mouth.
E. histolytica
Entamoeba histolytica invasive amebiasis is treated with metronidazole for eradication, in combination with diloxanide to prevent recurrence.
Preterm births
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). Metronidazole was ineffective in preventing preterm delivery in high-risk pregnant women (selected by history and a positive fFN test) and, conversely, the incidence of preterm delivery was found to be higher in women treated with metronidazole.
Adverse effects
Common adverse drug reactions (≥1% of those treated with the drug) associated with systemic metronidazole therapy include: nausea, diarrhea, weight loss, abdominal pain, vomiting, headache, dizziness, and 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 paraesthesia.
Some evidence from studies in rats indicates the possibility it may contribute to serotonin syndrome, although no case reports documenting this have been published to date.
Mutagenesis and carcinogenesis
Metronidazole is listed by the US National Toxicology Program (NTP) as reasonably anticipated to be a human carcinogen.
Metronidazole is listed as a possible carcinogen according to the WHO International Agency for Research on Cancer.
Stevens–Johnson syndrome
Metronidazole alone rarely causes Stevens–Johnson syndrome, but is reported to occur at high rates when combined with mebendazole.
Drug interactions
Alcohol
See also: Disulfiram-like drug
Consuming alcohol while taking metronidazole has long been thought to have a disulfiram -like reaction with effects that can include nausea, vomiting, flushing of the skin, tachycardia, and shortness of breath.
and a possible central toxic serotonin reaction for the alcohol intolerance is suggested.
Other drug interactions
It also inhibits CYP2C9, so may interact with medications metabolised by these enzymes (e.g. lomitapide, warfarin ).
Mechanism of action
Metronidazole is of the nitroimidazole class. It inhibits nucleic acid synthesis by disrupting the DNA of microbial cells.
Synthesis
2-Methylimidazole ( 1 ) may be prepared via the Debus-Radziszewski imidazole synthesis, or from ethylenediamine and acetic acid, followed by treatment with lime, then Raney nickel. 2-Methylimidazole is nitrated to give 2-methyl-4(5)-nitroimidazole ( 2 ), which is in turn alkylated with ethylene oxide or 2-chloroethanol to give metronidazole ( 3 ):
Veterinary use
Metronidazole is widely used to treat infections of Giardia in dogs, cats, and other companion animals, although it does not reliably clear infection with this organism and is being supplanted by fenbendazole for this purpose in dogs and cats.

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