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PubChem
Name: Metronidazole
PubChem Compound ID: 11607826
Description: A nitroimidazole used to treat AMEBIASIS; VAGINITIS; TRICHOMONAS INFECTIONS; GIARDIASIS; ANAEROBIC BACTERIA; and TREPONEMAL INFECTIONS. It has also been proposed as a radiation sensitizer for hypoxic cells. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985, p133), this substance may reasonably be anticipated to be a carcinogen (Merck, 11th ed).
Molecular formula: C40H43BiK3N5O25
Molecular weight: 1320.06 g/mol
DrugBank
Identification
Name: Metronidazole
Name (isomeric): DB00916
Drug Type: small molecule
Description: A nitroimidazole used to treat AMEBIASIS; VAGINITIS; TRICHOMONAS INFECTIONS; GIARDIASIS; ANAEROBIC BACTERIA; and TREPONEMAL INFECTIONS. It has also been proposed as a radiation sensitizer for hypoxic cells. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985, p133), this substance may reasonably be anticipated to be a carcinogen (Merck, 11th ed).
Synonyms:
Metronidazole Hcl; Metronidazol; Metronidazole Benzoate; Methronidazole; Metronidazolo; Metronidazole in Plastic Container
Brand: Vagilen, Apo-Metronidazole, Deflamon-Wirkstoff, Cont, Novonidazol, Flegyl, Flagyl ER, Monasin, Tricho Cordes, Flagemona, Eumin, Danizol, Nalox, Entizol, Bexon, Metro I.V., Bayer 5360, Gineflavir, Takimetol, Trichopal, Noritate, Klont, Orvagil, Metrolyl, Atrivyl, Metro Cream, Tricowas B, Wagitran, Flagyl I.V., Trikozol, Vertisal, Nidagel, Neo-Tric, Nida, Giatricol, Tricom, Trikacide, Vagimid, Flagil, Metro I.V. In Plastic Container, Klion, Flagesol, Clont, Deflamon, Trikojol, Metromidol, Satric, Sanatrichom, Acromona, Anagiardil, Trikamon, Metrocream, Metronidaz, Trimeks, Trichomol, Monagyl, Trichopol, Flagyl, Metrolotion, Rathimed, Elyzol, Mexibol, Trichex, Arilin, Metrogel, Tricocet, Metrolag, Trichocide, Metric 21, Trivazol, Metrotop, Meronidal, Zadstat, Protostat, Metrogel-Vaginal, Fossyol, Trichazol, Tricho-Gynaedron, Efloran
Brand name mixture: Helidac(Metronidazole + Bismuth subsalicylate + tetracycline hydrochloride)
Category: Anti-Infective Agents, Antiprotozoal Agents, Radiation-Sensitizing Agents, Antiprotozoals, Anti-Infectives
CAS number: 443-48-1
Pharmacology
Indication: For the treatment of anaerobic infections and mixed infections, surgical prophylaxis requiring anaerobic coverage, Clostridium difficile-associated diarrhea and colitis, Helicobacter pylori infection and duodenal ulcer disease, bacterial vaginosis, Giardia lamblia gastro-enteritis, amebiasis caused by Entamoeba histolytica, acne rosacea (topical treatment), and Trichomonas infections.
Pharmacology: Metronidazole, a synthetic antibacterial and antiprotozoal agent of the nitroimidazole class, is used against protozoa such as Trichomonas vaginalis, amebiasis, and giardiasis. Metronidazole is extremely effective against anaerobic bacterial infections and is also used to treat Crohn's disease, antibiotic-associated diarrhea, and rosacea.
Mechanism of Action: Metronidazole is a prodrug. Unionized metronidazole is selective for anaerobic bacteria due to their ability to intracellularly reduce metronidazole to its active form. This reduced metronidazole then covalently binds to DNA, disrupt its helical structure, inhibiting bacterial nucleic acid synthesis and resulting in bacterial cell death.
Absorption: Well absorbed (at least 80%) with peak plasma concentrations achieved in 1-3 hours following oral administration of therapeutic doses of immediate release formulation.
Protein binding: Less than 20% bound to plasma proteins.
Biotransformation: Hepatic metabolism by hydroxylation, oxidation, and glucuronidation.
Half Life: 6-8 hours
Toxicity: LD50=500 mg/kg/day (orally in rat). Adverse effects include reversible peripheral neuropathy with prolonged therapy, CNS toxicity, disulfiram effect with alcohol, dark red-brown urine, metallic taste, nausea, epigastric distress, dizziness, vertigo and paresthesias associated with high doses, and neutropenia (reversible and mild).
Affected organisms: Bacteria and protozoa
Interactions
Food interaction:
Avoid alcohol.
Take with food to reduce irritation.
Drug interaction:
TolterodineMetronidazole may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
Quinidine barbiturateThe barbiturate, quinidine barbiturate, decreases the effect of metronidazole.
AcenocoumarolMetronidazole may increase the anticoagulant effect of acenocoumarol.
WarfarinMetronidazole may increase the serum concentration of warfarin by decreasing its metabolism. Consider alternate therapy or a dose reduction in warfarin. Monitor for changes in prothrombin time and therapeutic and adverse effects of warfarin if metronidazole is initiated, discontinued or dose changed.
TrazodoneThe CYP3A4 inhibitor, Metronidazole, may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Metronidazole is initiated, discontinued or dose changed.
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