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Metronidazole

July 24, 2017
Common Name

Metronidazole 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). Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 1-(2-Hydroxy-1-ethyl)-2-methyl-5-nitroimidazoleChEBI 1-(2-Hydroxyethyl)-2-methyl-5-nitroimidazoleChEBI 1-(beta-Ethylol)-2-methyl-5-nitro-3-azapyrroleChEBI 1-(beta-Hydroxyethyl)-2-methyl-5-nitroimidazoleChEBI 1-(beta-Oxyethyl)-2-methyl-5-nitroimidazoleChEBI 2-Methyl-1-(2-hydroxyethyl)-5-nitroimidazoleChEBI 2-Methyl-3-(2-hydroxyethyl)-4-nitroimidazoleChEBI 2-Methyl-5-nitroimidazole-1-ethanolChEBI MetronidazolChEBI MetronidazolumChEBI 1-(b-Ethylol)-2-methyl-5-nitro-3-azapyrroleGenerator 1-(β-ethylol)-2-methyl-5-nitro-3-azapyrroleGenerator 1-(b-Hydroxyethyl)-2-methyl-5-nitroimidazoleGenerator 1-(β-hydroxyethyl)-2-methyl-5-nitroimidazoleGenerator 1-(b-Oxyethyl)-2-methyl-5-nitroimidazoleGenerator 1-(β-oxyethyl)-2-methyl-5-nitroimidazoleGenerator MethronidazoleHMDB Metronidazole benzoateHMDB Metronidazole in plastic containerHMDB MetronidazoloHMDB DanizolMeSH FlagylMeSH GineflavirMeSH MetricMeSH MetrodzhilMeSH MetrogylMeSH Metronidazole phosphoesterMeSH Metronidazole hydrochlorideMeSH Phosphoester, metronidazoleMeSH 2 Methyl 5 nitroimidazole 1 ethanolMeSH ClontMeSH Metronidazole phosphateMeSH Phosphate, metronidazoleMeSH TrivazolMeSH Bayer 5360MeSH Hydrochloride, metronidazoleMeSH MetroGelMeSH Metronidazole monohydrochlorideMeSH Monohydrochloride, metronidazoleMeSH SatricMeSH TrichazolMeSH TrichopolMeSH VagilenMeSH

Chemical Formlia

C6H9N3O3 Average Molecliar Weight

171.154 Monoisotopic Molecliar Weight

171.064391169 IUPAC Name

2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol Traditional Name

metronidazole CAS Registry Number

443-48-1 SMILES

CC1=NC=C(N1CCO)[N+]([O-])=O

InChI Identifier

InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3

InChI Key

VAOCPAMSLUNLGC-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as nitroimidazoles. These are compounds containing an imidazole ring which bears a nitro group. Kingdom

Organic compounds Super Class

Organoheterocyclic compounds Class

Azoles Sub Class

Imidazoles Direct Parent

Nitroimidazoles Alternative Parents

  • Nitroaromatic compounds
  • 1,2,5-trisubstituted imidazoles
  • N-substituted imidazoles
  • Heteroaromatic compounds
  • Propargyl-type 1,3-dipolar organic compounds
  • Organic oxoazanium compounds
  • Azacyclic compounds
  • Alkanolamines
  • Primary alcohols
  • Organopnictogen compounds
  • Organic zwitterions
  • Organic oxides
  • Hydrocarbon derivatives

    • 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

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

  • C-nitro compound (CHEBI:6909 )
  • imidazoles (CHEBI:6909 )
  • primary alcohol (CHEBI:6909 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Infective Agents
  • Anti-Infectives
  • Antiprotozoal Agents
  • Antiprotozoals
  • Radiation-Sensitizing Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point160 °CNot Available Boiling PointNot AvailableNot Available Water Solubility5.92e+00 g/LNot Available LogP-0.1Not Available

    Predicted Properties

    Property Value Source Water Solubility5.92 mg/mLALOGPS logP-0.15ALOGPS logP-0.46ChemAxon logS-1.5ALOGPS pKa (Strongest Acidic)15.44ChemAxon pKa (Strongest Basic)3.09ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area83.87 Å2ChemAxon Rotatable Bond Count3ChemAxon Refractivity41.22 m3·mol-1ChemAxon Polarizability15.82 Å3ChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-004i-1900000000-659f2bbb83f8ef5a85d1View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-004i-0900000000-50c7cfe79eb17c4440a8View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-00di-0900000000-b06d808767cc01c0d494View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-00fr-0900000000-e9c07cc448b8fb519022View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-004i-0900000000-8ad03b44aa7557127e34View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-004i-0900000000-ed7ba5c872a6309a31d4View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-004i-2900000000-e0ead4b0eec72b9c44b6View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-004i-5900000000-2da8a7b45537f9063220View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-00di-0900000000-24d94f1704e577b05eb7View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-00fr-0900000000-fbb1c4e8457cd3d799b9View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-004i-0900000000-fd6166313a17f944f530View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-004i-0900000000-5ebb32a580e1f5d00170View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-004i-2900000000-811a6e7e45b7ea1a6184View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-004i-5900000000-082e6de6c0fa3f382d84View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-004i-0900000000-baf9e195c01d875e77b5View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-00di-0900000000-ec181c008a10dac8040bView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-004i-1900000000-2a218e19a8fadb9c66d6View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-003r-9500000000-ed02acd36b190c189cc9View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-001i-9000000000-71ea79659ccd75c64befView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available MS

    Mass Spectrum (Electron Ionization)splash10-0li0-9300000000-2268b08f47fed3f6d263View in MoNA 1D NMR

    1H NMR SpectrumNot Available 1D NMR

    13C NMR SpectrumNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00916

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00916

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Predicted Concentrations

    Biofluid Value Original age Original sex Original condition Comments Blood0-6 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-3 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00916 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    4029 KEGG Compound ID

    C07203 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Metronidazole NuGOwiki Link

    HMDB15052 Metagene Link

    HMDB15052 METLIN ID

    Not Available PubChem Compound

    4173 PDB ID

    2MN ChEBI ID

    6909

    Product: TTNPB

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Download (PDF) General References
    1. 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. [PubMed:12022894 ]
    2. Williams CS, Woodcock KR: Do ethanol and metronidazole interact to produce a disulfiram-like reaction? Ann Pharmacother. 2000 Feb;34(2):255-7. [PubMed:10676835 ]
    3. Lamont RF: Can antibiotics prevent preterm birth–the pro and con debate. BJOG. 2005 Mar;112 Suppl 1:67-73. [PubMed:15715599 ]
    4. 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. [PubMed:16398774 ]

    Enzymes

    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
    Gene Name:
    CYP3A4
    Uniprot ID:
    P08684
    Molecular weight:
    57255.585
    References
    1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
    Gene Name:
    CYP2C9
    Uniprot ID:
    P11712
    Molecular weight:
    55627.365
    References
    1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
    Gene Name:
    CYP2C8
    Uniprot ID:
    P10632
    Molecular weight:
    55824.275
    References
    1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

    PMID: 19845676

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