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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.
Term:metronidazole
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Accession:CHEBI:6909 term browser browse the term
Definition:A member of the class of imidazoles substituted at C-1, -2 and -5 with 2-hydroxyethyl, nitro and methyl groups respectively. It has activity against anaerobic bacteria and protozoa, and has a radiosensitising effect on hypoxic tumour cells. It may be given by mouth in tablets, or as the benzoate in an oral suspension. The hydrochloride salt can be used in intravenous infusions. Metronidazole is a prodrug and is selective for anaerobic bacteria due to their ability to intracellularly reduce the nitro group of metronidazole to give nitroso-containing intermediates. These can covalently bind to DNA, disrupting its helical structure, inducing DNA strand breaks and inhibiting bacterial nucleic acid synthesis, ultimately resulting in bacterial cell death.
Synonyms:exact_synonym: 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol
 related_synonym: 1-(2-hydroxy-1-ethyl)-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;   2-methyl-1-(2-hydroxyethyl)-5-nitroimidazole;   2-methyl-3-(2-hydroxyethyl)-4-nitroimidazole;   2-methyl-5-nitroimidazole-1-ethanol;   Formula=C6H9N3O3;   InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3;   InChIKey=VAOCPAMSLUNLGC-UHFFFAOYSA-N;   SMILES=Cc1ncc(n1CCO)[N+]([O-])=O;   metronidazol;   metronidazolum
 alt_id: CHEBI:39845;   CHEBI:63636
 xref: Beilstein:611683;   CAS:443-48-1;   DrugBank:DB00916;   Drug_Central:1790;   HMDB:HMDB0015052;   KEGG:D00409;   LINCS:LSM-5628
 xref_mesh: MESH:D008795
 xref: PDBeChem:2MN;   PMID:11906111;   PMID:14702395;   PMID:15739364;   PMID:16304169;   PMID:16901452;   PMID:18397330;   PMID:19485831;   PMID:22226009;   PMID:22252819;   Patent:US2944061;   Reaxys:611683;   VSDB:1826;   Wikipedia:Metronidazole
 cyclic_relationship: is_conjugate_base_of CHEBI:64682


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Path 1
Term Annotations click to browse term
  CHEBI ontology 499
    role 499
      biological role 499
        antimicrobial agent 125
          metronidazole 0
            metronidazole benzoate 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 499
    subatomic particle 499
      composite particle 499
        hadron 499
          baryon 499
            nucleon 499
              atomic nucleus 499
                atom 499
                  main group element atom 492
                    p-block element atom 492
                      carbon group element atom 481
                        carbon atom 480
                          organic molecular entity 480
                            organic molecule 471
                              organic cyclic compound 454
                                organic heterocyclic compound 417
                                  heteroarene 199
                                    monocyclic heteroarene 173
                                      azole 173
                                        diazole 13
                                          imidazoles 9
                                            metronidazole 0
                                              metronidazole benzoate 0
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