Record Information |
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Version | 2.0 |
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Creation Date | 2014-09-11 02:05:41 UTC |
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Update Date | 2014-12-24 20:26:55 UTC |
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Accession Number | T3D4703 |
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Identification |
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Common Name | Metronidazole |
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Class | Small Molecule |
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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) this substance may reasonably be anticipated to be a carcinogen. |
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Compound Type | - Amine
- Anti-Infective Agent
- Antiprotozoal Agent
- Drug
- Household Toxin
- Metabolite
- Organic Compound
- Radiation-Sensitizing Agent
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Synonym | 1-(2-hydroxy-1-ethyl)-2-methyl-5-nitroimidazole | 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole | 1-(beta-Ethylol)-2-methyl-5-nitro-3-azapyrrole | 1-(beta-Hydroxyethyl)-2-methyl-5-nitroimidazole | 1-(beta-Oxyethyl)-2-methyl-5-nitroimidazole | 1-(β-ethylol)-2-methyl-5-nitro-3-azapyrrole | 1-(β-hydroxyethyl)-2-methyl-5-nitroimidazole | 1-(β-oxyethyl)-2-methyl-5-nitroimidazole | 2-methyl-1-(2-hydroxyethyl)-5-nitroimidazole | 2-methyl-3-(2-hydroxyethyl)-4-nitroimidazole | 2-methyl-5-nitroimidazole-1-ethanol | Acromona | Anabact | Arilin | Clont | Deflamon | Efloran | Elyzol | Entizol | Flagyl | Fossyol | Klion | Klont | Methronidazole | MetroCream | Metrogel | Metrogel-Vaginal | MetroLotion | Metrolyl | Metronidazol | Metronidazole Benzoate | Metronidazole in Plastic Container | Metronidazolo | Metronidazolum | Metrotop | Nalox | Nidagel | Noritate | Novonidazol | Orvagil | Protostat | Rosadan | Takimetol | Trichazole | Trichex | Trichopol | Tricowas B | Trikacide | Trikozol | Vagilen | Vagimid | Vandazole | Vertisal | Zadstat |
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Chemical Formula | C6H9N3O3 |
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Average Molecular Mass | 171.154 g/mol |
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Monoisotopic Mass | 171.064 g/mol |
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CAS Registry Number | 443-48-1 |
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IUPAC Name | 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol |
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Traditional Name | metronidazole |
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SMILES | CC1=NC=C(N1CCO)N(=O)=O |
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InChI Identifier | InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3 |
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InChI Key | InChIKey=VAOCPAMSLUNLGC-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as nitroimidazoles. Nitroimidazoles are compounds containing an imidazole ring which bears a nitro group. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Azoles |
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Sub Class | Imidazoles |
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Direct Parent | Nitroimidazoles |
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Alternative Parents | |
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Substituents | - 1,2,5-trisubstituted-imidazole
- Nitroaromatic compound
- Nitroimidazole
- Trisubstituted imidazole
- N-substituted imidazole
- Heteroaromatic compound
- Organic nitro compound
- C-nitro compound
- Alkanolamine
- Azacycle
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Allyl-type 1,3-dipolar organic compound
- Organic oxoazanium
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Organopnictogen compound
- Organic zwitterion
- Organic oxygen compound
- Organic nitrogen compound
- Alcohol
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 160.5°C | Boiling Point | Not Available | Solubility | 9500 mg/L (at 25°C) | LogP | -0.02 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0udl-9700000000-f1b60dcdd221dbdf9eaa | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0fmi-9410000000-3cec2097481329b98054 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-004i-1900000000-659f2bbb83f8ef5a85d1 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-004i-0900000000-50c7cfe79eb17c4440a8 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-00di-0900000000-b06d808767cc01c0d494 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-00fr-0900000000-e9c07cc448b8fb519022 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-004i-0900000000-8ad03b44aa7557127e34 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-004i-0900000000-ed7ba5c872a6309a31d4 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-004i-2900000000-e0ead4b0eec72b9c44b6 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-004i-5900000000-2da8a7b45537f9063220 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-00di-0900000000-24d94f1704e577b05eb7 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-00fr-0900000000-fbb1c4e8457cd3d799b9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-004i-0900000000-fd6166313a17f944f530 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-004i-0900000000-5ebb32a580e1f5d00170 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-004i-2900000000-811a6e7e45b7ea1a6184 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-004i-5900000000-082e6de6c0fa3f382d84 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-004i-0900000000-baf9e195c01d875e77b5 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-00di-0900000000-ec181c008a10dac8040b | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-004i-1900000000-2a218e19a8fadb9c66d6 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-003r-9500000000-ed02acd36b190c189cc9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-001i-9000000000-71ea79659ccd75c64bef | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0900000000-b28839ace139ee8a385b | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01ox-0900000000-94e5ccc473c03e521e89 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01po-9500000000-64f688b22d9371ed56c1 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0900000000-5f65f2637682eccd62a2 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-05fu-3900000000-dbc213039f9c3a43948e | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0007-9300000000-935f6b6b00b1b6b723b5 | JSpectraViewer | MS | Mass Spectrum (Electron Ionization) | splash10-0ul0-9300000000-2268b08f47fed3f6d263 | JSpectraViewer | MoNA | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer |
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Toxicity Profile |
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Route of Exposure | Well absorbed (at least 80%) with peak plasma concentrations achieved in 1-3 hours following oral administration of therapeutic doses of immediate release formulation. |
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Mechanism of Toxicity | 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. |
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Metabolism | Hepatic metabolism by hydroxylation, oxidation, and glucuronidation.
Half Life: 6-8 hours |
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Toxicity Values | LD50=500 mg/kg/day (orally in rat). |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | 2B, possibly carcinogenic to humans. (5) |
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Uses/Sources | 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. |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | 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). |
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Treatment | Not Available |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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External Links |
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DrugBank ID | DB00916 |
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HMDB ID | HMDB15052 |
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PubChem Compound ID | 4173 |
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ChEMBL ID | CHEMBL137 |
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ChemSpider ID | 4029 |
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KEGG ID | C07203 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 6909 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Not Available |
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PDB ID | 2MN |
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ACToR ID | Not Available |
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Wikipedia Link | Metronidazole |
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References |
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Synthesis Reference | DrugSyn.org |
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MSDS | Link |
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General References | - Shennan A, Crawshaw S, Briley A, Hawken J, Seed P, Jones G, Poston L: A randomised controlled trial of metronidazole for the prevention of preterm birth in women positive for cervicovaginal fetal fibronectin: the PREMET Study. BJOG. 2006 Jan;113(1):65-74. [16398774 ]
- Lamont RF: Can antibiotics prevent preterm birth--the pro and con debate. BJOG. 2005 Mar;112 Suppl 1:67-73. [15715599 ]
- Williams CS, Woodcock KR: Do ethanol and metronidazole interact to produce a disulfiram-like reaction? Ann Pharmacother. 2000 Feb;34(2):255-7. [10676835 ]
- Visapaa JP, Tillonen JS, Kaihovaara PS, Salaspuro MP: Lack of disulfiram-like reaction with metronidazole and ethanol. Ann Pharmacother. 2002 Jun;36(6):971-4. [12022894 ]
- International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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