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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-03-02 21:33:38 UTC
HMDB IDHMDB15052
Secondary Accession NumbersNone
Metabolite Identification
Common NameMetronidazole
DescriptionA 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
Thumb
Synonyms
ValueSource
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 FormulaC6H9N3O3
Average Molecular Weight171.154
Monoisotopic Molecular Weight171.064391169
IUPAC Name2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol
Traditional Namemetronidazole
CAS Registry Number443-48-1
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 KeyVAOCPAMSLUNLGC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as nitroimidazoles. These are compounds containing an imidazole ring which bears a nitro group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentNitroimidazoles
Alternative Parents
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
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-Infective Agents
  • Anti-Infectives
  • Antiprotozoal Agents
  • Antiprotozoals
  • Radiation-Sensitizing Agents
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point160 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.92e+00 g/LNot Available
LogP-0.1Not Available
Predicted Properties
PropertyValueSource
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-1900000000-659f2bbb83f8ef5a85d1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-50c7cfe79eb17c4440a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0900000000-b06d808767cc01c0d494View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00fr-0900000000-e9c07cc448b8fb519022View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-8ad03b44aa7557127e34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-ed7ba5c872a6309a31d4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-2900000000-e0ead4b0eec72b9c44b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-5900000000-2da8a7b45537f9063220View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0900000000-24d94f1704e577b05eb7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00fr-0900000000-fbb1c4e8457cd3d799b9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-fd6166313a17f944f530View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-5ebb32a580e1f5d00170View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-2900000000-811a6e7e45b7ea1a6184View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-5900000000-082e6de6c0fa3f382d84View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-baf9e195c01d875e77b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-ec181c008a10dac8040bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-1900000000-2a218e19a8fadb9c66d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-003r-9500000000-ed02acd36b190c189cc9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-71ea79659ccd75c64befView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0ul0-9300000000-2268b08f47fed3f6d263View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00916 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00916 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-6 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-3 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00916
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4029
KEGG Compound IDC07203
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMetronidazole
NuGOwiki LinkHMDB15052
Metagene LinkHMDB15052
METLIN IDNot Available
PubChem Compound4173
PDB ID2MN
ChEBI ID6909
References
Synthesis ReferenceNot 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 ]