| Candidate ID: | R0265 |
| Source ID: | DB00916 |
| Source Type: | approved |
| Compound Type: |
small molecule
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| Compound Name: |
Metronidazole
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| Synonyms: |
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| Molecular Formula: |
C6H9N3O3
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| SMILES: |
CC1=NC=C(N1CCO)[N+]([O-])=O
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| Structure: |
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| DrugBank Description: |
Metronidazole is a commonly used antibiotic, belonging to the nitroimidazole class of antibiotics.[L3754] It is frequently used to treat gastrointestinal infections as well as trichomoniasis and giardiasis, and amebiasis which are parasitic infections.[A181036,A18039] Metronidazole has been used as an antibiotic for several decades[L7429], with added antiparasitic properties that set it apart from many other antibacterial drugs, allowing it to treat a wide variety of infections. It is available in capsule form, tablet form, and topical form, and suppository preparations for the treatment of various infections.
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| CAS Number: |
443-48-1
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| Molecular Weight: |
171.154
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| DrugBank Indication: |
Metronidazole is indicated for the treatment of confirmed trichomoniasis caused by Trichomonas vaginalis (except for in the first trimester of pregnancy) and the patient's sexual partners, bacterial vaginosis[L7432], certain types of amebiasis, and various anaerobic infections.[A181057] The above anaerobic infections may occur on the skin and skin structures, the abdomen, the heart, reproductive organs, central nervous system, and the respiratory system. Some may also be present in the bloodstream in cases of septicemia. Common infections treated by metronidazole are Bacteroides species infections, Clostridium infections, and Fusobacterium infections, as well as Peptococcus and Peptostreptococcus infections.[L3754]
It is also used off-label in the treatment of Crohn's disease and rosacea, as a prophylactic agent after surgery[A181039], and in the treatment of Helicobacter pylori infection.[A181045] It has also been studied in the prevention of preterm births and to treat periodontal disease.[A1391,A181078]
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| DrugBank Pharmacology: |
Metronidazole treats amebiasis, trichomoniasis, and giardiasis, exerting both antibacterial and antiprotozoal activities.[L7432] Metronidazole is an effective treatment for some anaerobic bacterial infections.[A181057] Metronidazole has shown antibacterial activity against the majority of obligate anaerobes, however, during in vitro studies, it does not demonstrate significant action against facultative anaerobes or obligate aerobes.[L3754] The nitro group reduction of metronidazole by anaerobic organisms is likely responsible for the drug's antimicrobial cytotoxic effects, causing DNA strand damage to microbes.[A181039,A181045]
A note on convulsions and neuropathy and carcinogenesis
It is important to be aware of the risk of peripheral neuropathy and convulsions associated with metronidazole, especially at higher doses. If convulsions or numbness of an extremity occur, discontinue the drug immediately.[L3754] Metronidazole has been found to be carcinogenic in mice and rats. The relevance to this effect in humans is unknown. It is advisable to only administer metronidazole when clinically necessary and only for its approved indications.[L7474]
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| DrugBank MoA: |
The exact mechanism of action of metronidazole has not been fully established, however, it is possible that an intermediate in the reduction of metronidazole which is only made by anaerobic bacteria and protozoa, binds deoxyribonucleic acid and electron-transport proteins of organisms, blocking nucleic acid synthesis.[L3754]
After administration, metronidazole enters cells by passive diffusion. Following this, ferredoxin or flavodoxin reduce its nitro group to nitro radicals.
The redox potential of the electron transport portions of anaerobic or microaerophilic microorganisms renders metronidazole selective to these organisms, which cause nitro group reduction, leading to the production of toxic metabolites. These include N-(2-hydroxyethyl) oxamic acid and acetamide, which may damage DNA of replicating organisms.[A181039]
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| Targets: |
Oxygen-insensitive NADPH nitroreductase; Anaerobic bacterial DNA; Protozoal DNA
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| Inclusion Criteria: |
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