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ONTOLOGY REPORT - ANNOTATIONS


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 "Beilstein";   CAS:443-48-1 "ChemIDplus";   CAS:443-48-1 "NIST Chemistry WebBook";   DrugBank:DB00916;   Drug_Central:1790 "DrugCentral";   HMDB:HMDB0015052;   KEGG:D00409;   LINCS:LSM-5628
 xref_mesh: MESH:D008795
 xref: PDBeChem:2MN;   PMID:11906111 "Europe PMC";   PMID:14702395 "Europe PMC";   PMID:15739364 "Europe PMC";   PMID:16304169 "Europe PMC";   PMID:16901452 "Europe PMC";   PMID:18397330 "Europe PMC";   PMID:19485831 "Europe PMC";   PMID:22226009 "Europe PMC";   PMID:22252819 "Europe PMC";   Patent:US2944061;   Reaxys:611683 "Reaxys";   VSDB:1826;   Wikipedia:Metronidazole
 cyclic_relationship: is_conjugate_base_of CHEBI:64682


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metronidazole term browser
Symbol Object Name JBrowse Chr Start Stop Reference
G Abcc2 ATP binding cassette subfamily C member 2 JBrowse link 1 263,554,426 263,612,556 RGD:6480464
G Abcc3 ATP binding cassette subfamily C member 3 JBrowse link 10 82,047,308 82,116,928 RGD:6480464
G Abcg8 ATP binding cassette subfamily G member 8 JBrowse link 6 7,961,413 7,980,708 RGD:6480464
G Acat2 acetyl-CoA acetyltransferase 2 JBrowse link 1 47,972,399 47,992,654 RGD:6480464
G Acat2l1 acetyl-CoA acetyltransferase 2-like 1 JBrowse link 1 48,008,574 48,025,730 RGD:6480464
G Ace2 angiotensin I converting enzyme 2 JBrowse link X 32,050,734 32,095,860 RGD:6480464
G Ahsg alpha-2-HS-glycoprotein JBrowse link 11 81,711,269 81,717,594 RGD:6480464
G Aldoa aldolase, fructose-bisphosphate A JBrowse link 1 198,228,387 198,233,988 RGD:6480464
G Aldob aldolase, fructose-bisphosphate B JBrowse link 5 64,805,772 64,818,813 RGD:6480464
G Arg2 arginase 2 JBrowse link 6 102,311,097 102,338,406 RGD:6480464
G Arpc3 actin related protein 2/3 complex, subunit 3 JBrowse link 12 39,653,951 39,667,817 RGD:6480464
G Asah1 N-acylsphingosine amidohydrolase 1 JBrowse link 16 53,998,604 54,030,006 RGD:6480464
G Atp1a1 ATPase Na+/K+ transporting subunit alpha 1 JBrowse link 2 204,003,742 204,032,023 RGD:6480464
G Atp2a3 ATPase sarcoplasmic/endoplasmic reticulum Ca2+ transporting 3 JBrowse link 10 59,528,849 59,560,440 RGD:6480464
G Atp5mf ATP synthase membrane subunit f JBrowse link 12 11,191,799 11,198,369 RGD:6480464
G Atp5pd ATP synthase peripheral stalk subunit d JBrowse link 10 103,967,340 103,972,552 RGD:6480464
G Atp5pf ATP synthase peripheral stalk subunit F6 JBrowse link 11 24,286,806 24,294,419 RGD:6480464
G B3galt5 Beta-1,3-galactosyltransferase 5 JBrowse link 11 36,638,067 36,683,915 RGD:6480464
G Clca4 chloride channel accessory 4 JBrowse link 2 250,842,939 250,864,060 RGD:6480464
G Cldn7 claudin 7 JBrowse link 10 56,576,326 56,578,632 RGD:6480464
G Cmbl carboxymethylenebutenolidase homolog JBrowse link 2 84,645,084 84,666,836 RGD:6480464
G Cndp2 carnosine dipeptidase 2 JBrowse link 18 81,521,966 81,539,065 RGD:6480464
G Cox5a cytochrome c oxidase subunit 5A JBrowse link 8 62,298,358 62,309,765 RGD:6480464
G Cox6b1 cytochrome c oxidase subunit 6B1 JBrowse link 1 89,075,987 89,084,834 RGD:6480464
G Cox7a2 cytochrome c oxidase subunit 7A2 JBrowse link 8 87,209,529 87,213,627 RGD:6480464
G Ctsa cathepsin A JBrowse link 3 161,298,750 161,304,627 RGD:6480464
G Cyp1a2 cytochrome P450, family 1, subfamily a, polypeptide 2 JBrowse link 8 62,451,360 62,458,244 RGD:6480464
G Cyp2c11 cytochrome P450, subfamily 2, polypeptide 11 JBrowse link 1 257,676,172 258,004,428 RGD:6480464
G Cyp2d2 cytochrome P450, family 2, subfamily d, polypeptide 2 JBrowse link 7 123,651,827 123,655,896 RGD:6480464
G Cyp2e1 cytochrome P450, family 2, subfamily e, polypeptide 1 JBrowse link 1 213,511,892 213,522,195 RGD:6480464
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 JBrowse link 12 11,641,500 11,677,818 RGD:6480464
G Epcam epithelial cell adhesion molecule JBrowse link 6 11,282,194 11,308,870 RGD:6480464
G Etfa electron transfer flavoprotein subunit alpha JBrowse link 8 60,028,786 60,086,352 RGD:6480464
G Ezr ezrin JBrowse link 1 47,287,872 47,331,412 RGD:6480464
G Gfpt2 glutamine-fructose-6-phosphate transaminase 2 JBrowse link 10 35,279,237 35,325,506 RGD:6480464
G Gipc2 GIPC PDZ domain containing family, member 2 JBrowse link 2 257,293,161 257,377,982 RGD:6480464
G Gng12 G protein subunit gamma 12 JBrowse link 4 97,634,925 97,763,478 RGD:6480464
G Gpx1 glutathione peroxidase 1 JBrowse link 8 117,117,430 117,118,528 RGD:6480464
G Gsta3 glutathione S-transferase alpha 3 JBrowse link 9 27,357,490 27,417,023 RGD:6480464
G Gstm2 glutathione S-transferase mu 2 JBrowse link 2 210,778,041 210,782,807 RGD:6480464
G Hexb hexosaminidase subunit beta JBrowse link 2 27,983,925 28,003,260 RGD:6480464
G Hnrnph2 heterogeneous nuclear ribonucleoprotein H2 JBrowse link X 105,417,603 105,423,531 RGD:6480464
G Hp haptoglobin JBrowse link 19 42,096,255 42,100,805 RGD:6480464
G Kng2 kininogen 2 JBrowse link 11 81,509,185 81,516,759 RGD:6480464
G Krt16 keratin 16 JBrowse link 10 88,149,210 88,152,167 RGD:6480464
G Lyz2 lysozyme 2 JBrowse link 7 60,335,968 60,341,264 RGD:6480464
G Mapk3 mitogen activated protein kinase 3 JBrowse link 1 198,192,773 198,198,975 RGD:6480464
G Myh14 myosin heavy chain 14 JBrowse link 1 100,608,975 100,671,086 RGD:6480464
G Ndufa13 NADH:ubiquinone oxidoreductase subunit A13 JBrowse link 16 21,275,311 21,282,246 RGD:6480464
G Ndufab1 NADH:ubiquinone oxidoreductase subunit AB1 JBrowse link 1 192,044,209 192,057,644 RGD:6480464
G Nos2 nitric oxide synthase 2 JBrowse link 10 66,188,290 66,221,621 RGD:6480464
G Npc2 NPC intracellular cholesterol transporter 2 JBrowse link 6 108,467,410 108,488,330 RGD:6480464
G Pdxk pyridoxal kinase JBrowse link 20 10,930,651 10,952,194 RGD:6480464
G Pfn1 profilin 1 JBrowse link 10 57,273,003 57,275,708 RGD:6480464
G Pgam1 phosphoglycerate mutase 1 JBrowse link 1 261,158,204 261,165,814 RGD:6480464
G Pmm2 phosphomannomutase 2 JBrowse link 10 7,056,258 7,077,443 RGD:6480464
G Ppp1ca protein phosphatase 1 catalytic subunit alpha JBrowse link 1 219,439,953 219,443,570 RGD:6480464
G Ppp1cb protein phosphatase 1 catalytic subunit beta JBrowse link 6 23,548,507 23,581,136 RGD:6480464
G Ppp1cc protein phosphatase 1 catalytic subunit gamma JBrowse link 12 39,864,302 39,882,030 RGD:6480464
G Psma3 proteasome 20S subunit alpha 3 JBrowse link 6 93,423,029 93,444,223 RGD:6480464
G Ralb RAS like proto-oncogene B JBrowse link 13 35,494,716 35,531,503 RGD:6480464
G Ran RAN, member RAS oncogene family JBrowse link 12 31,319,556 31,324,105 RGD:6480464
G Rida reactive intermediate imine deaminase A homolog JBrowse link 7 73,256,506 73,270,308 RGD:6480464
G Rpl30 ribosomal protein L30 JBrowse link 7 73,213,538 73,216,431 RGD:6480464
G Rpn2 ribophorin II JBrowse link 3 153,398,373 153,445,633 RGD:6480464
G Rps23 ribosomal protein S23 JBrowse link 2 19,823,234 19,824,804 RGD:6480464
G Rps27l ribosomal protein S27-like JBrowse link 8 72,741,155 72,746,090 RGD:6480464
G RT1-Bb RT1 class II, locus Bb JBrowse link 20 4,043,726 4,049,367 RGD:6480464
G RT1-Db1 RT1 class II, locus Db1 JBrowse link 20 4,087,621 4,097,190 RGD:6480464
G RT1-DMb RT1 class II, locus DMb JBrowse link 20 3,945,383 3,952,838 RGD:6480464
G S100a10 S100 calcium binding protein A10 JBrowse link 2 193,892,589 193,901,236 RGD:6480464
G S100a11 S100 calcium binding protein A11 JBrowse link 2 193,863,185 193,868,646 RGD:6480464
G Scarb2 scavenger receptor class B, member 2 JBrowse link 14 17,064,173 17,115,620 RGD:6480464
G Serpinb6a serpin family B member 6A JBrowse link 17 32,154,747 32,209,598 RGD:6480464
G Shmt2 serine hydroxymethyltransferase 2 JBrowse link 7 70,824,718 70,829,822 RGD:6480464
G Slc3a1 solute carrier family 3 member 1 JBrowse link 6 8,284,937 8,318,649 RGD:6480464
G Slc51b solute carrier family 51, beta subunit JBrowse link 8 70,930,196 70,938,559 RGD:6480464
G Slco2b1 solute carrier organic anion transporter family, member 2b1 JBrowse link 1 164,623,313 164,671,612 RGD:6480464
G Smpd2 sphingomyelin phosphodiesterase 2 JBrowse link 20 46,212,070 46,215,183 RGD:6480464
G Tars1 threonyl-tRNA synthetase 1 JBrowse link 2 61,394,632 61,414,115 RGD:6480464
G Tm9sf2 transmembrane 9 superfamily member 2 JBrowse link 15 108,526,341 108,579,268 RGD:6480464
G Tmed10 transmembrane p24 trafficking protein 10 JBrowse link 6 109,169,739 109,205,004 RGD:6480464
G Tubal3 tubulin, alpha-like 3 JBrowse link 17 69,974,272 69,982,957 RGD:6480464
G Twf1 twinfilin actin-binding protein 1 JBrowse link 7 135,838,647 135,850,542 RGD:6480464
G Txndc5 thioredoxin domain containing 5 JBrowse link 17 26,925,828 26,953,981 RGD:6480464
G Uqcrc1 ubiquinol-cytochrome c reductase core protein 1 JBrowse link 8 117,679,328 117,691,073 RGD:6480464
G Uqcrfs1 ubiquinol-cytochrome c reductase, Rieske iron-sulfur polypeptide 1 JBrowse link 17 35,677,984 35,682,262 RGD:6480464
G Uqcrh ubiquinol-cytochrome c reductase hinge protein JBrowse link 5 134,919,040 134,927,235 RGD:6480464

Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19654
    role 19598
      biological role 19596
        antimicrobial agent 17143
          metronidazole 8
            metronidazole benzoate 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19654
    subatomic particle 19650
      composite particle 19650
        hadron 19650
          baryon 19650
            nucleon 19650
              atomic nucleus 19650
                atom 19650
                  main group element atom 19531
                    p-block element atom 19531
                      carbon group element atom 19413
                        carbon atom 19405
                          organic molecular entity 19405
                            organic molecule 19327
                              organic cyclic compound 19076
                                organic heterocyclic compound 18151
                                  heteroarene 15151
                                    monocyclic heteroarene 11614
                                      azole 10473
                                        diazole 8041
                                          imidazoles 7591
                                            metronidazole 8
                                              metronidazole benzoate 0
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.