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Record Information
Version2.0
Creation Date2014-09-11 02:05:41 UTC
Update Date2014-12-24 20:26:55 UTC
Accession NumberT3D4703
Identification
Common NameMetronidazole
ClassSmall Molecule
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) this substance may reasonably be anticipated to be a carcinogen.
Compound Type
  • Amine
  • Anti-Infective Agent
  • Antiprotozoal Agent
  • Drug
  • Household Toxin
  • Metabolite
  • Organic Compound
  • Radiation-Sensitizing Agent
  • Synthetic Compound
Chemical Structure
Thumb
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
Chemical FormulaC6H9N3O3
Average Molecular Mass171.154 g/mol
Monoisotopic Mass171.064 g/mol
CAS Registry Number443-48-1
IUPAC Name2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol
Traditional Namemetronidazole
SMILESCC1=NC=C(N1CCO)N(=O)=O
InChI IdentifierInChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3
InChI KeyInChIKey=VAOCPAMSLUNLGC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nitroimidazoles. Nitroimidazoles 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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point160.5°C
Boiling PointNot Available
Solubility9500 mg/L (at 25°C)
LogP-0.02
Predicted Properties
PropertyValueSource
Water Solubility5.92 g/LALOGPS
logP-0.15ALOGPS
logP-0.46ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)15.42ChemAxon
pKa (Strongest Basic)2.57ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area81.19 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity40.22 m³·mol⁻¹ChemAxon
Polarizability15.87 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udl-9700000000-f1b60dcdd221dbdf9eaaJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fmi-9410000000-3cec2097481329b98054JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-1900000000-659f2bbb83f8ef5a85d1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-50c7cfe79eb17c4440a8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0900000000-b06d808767cc01c0d494JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00fr-0900000000-e9c07cc448b8fb519022JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-8ad03b44aa7557127e34JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-ed7ba5c872a6309a31d4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-2900000000-e0ead4b0eec72b9c44b6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-5900000000-2da8a7b45537f9063220JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0900000000-24d94f1704e577b05eb7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00fr-0900000000-fbb1c4e8457cd3d799b9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-fd6166313a17f944f530JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-5ebb32a580e1f5d00170JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-2900000000-811a6e7e45b7ea1a6184JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-5900000000-082e6de6c0fa3f382d84JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-baf9e195c01d875e77b5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-ec181c008a10dac8040bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-1900000000-2a218e19a8fadb9c66d6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-003r-9500000000-ed02acd36b190c189cc9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-71ea79659ccd75c64befJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-b28839ace139ee8a385bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-0900000000-94e5ccc473c03e521e89JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01po-9500000000-64f688b22d9371ed56c1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-5f65f2637682eccd62a2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fu-3900000000-dbc213039f9c3a43948eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-9300000000-935f6b6b00b1b6b723b5JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0ul0-9300000000-2268b08f47fed3f6d263JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Toxicity Profile
Route of ExposureWell absorbed (at least 80%) with peak plasma concentrations achieved in 1-3 hours following oral administration of therapeutic doses of immediate release formulation.
Mechanism of ToxicityMetronidazole 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.
MetabolismHepatic metabolism by hydroxylation, oxidation, and glucuronidation. Half Life: 6-8 hours
Toxicity ValuesLD50=500 mg/kg/day (orally in rat).
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (5)
Uses/SourcesFor 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.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsAdverse 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).
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00916
HMDB IDHMDB15052
PubChem Compound ID4173
ChEMBL IDCHEMBL137
ChemSpider ID4029
KEGG IDC07203
UniProt IDNot Available
OMIM ID
ChEBI ID6909
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB ID2MN
ACToR IDNot Available
Wikipedia LinkMetronidazole
References
Synthesis Reference

DrugSyn.org

MSDSLink
General References
  1. 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 ]
  2. Lamont RF: Can antibiotics prevent preterm birth--the pro and con debate. BJOG. 2005 Mar;112 Suppl 1:67-73. [15715599 ]
  3. Williams CS, Woodcock KR: Do ethanol and metronidazole interact to produce a disulfiram-like reaction? Ann Pharmacother. 2000 Feb;34(2):255-7. [10676835 ]
  4. 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 ]
  5. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

1. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Salles JM, Salles MJ, Moraes LA, Silva MC: Invasive amebiasis: an update on diagnosis and management. Expert Rev Anti Infect Ther. 2007 Oct;5(5):893-901. [17914922 ]
  4. Li AQ, Dai N, Yan J, Zhu YL: [Screening for metronidazole-resistance associated gene fragments of Helicobacter pylori by suppression subtractive hybridization]. Zhejiang Da Xue Xue Bao Yi Xue Ban. 2007 Sep;36(5):465-9. [17924465 ]
  5. Edwards DI: Nitroimidazole drugs--action and resistance mechanisms. I. Mechanisms of action. J Antimicrob Chemother. 1993 Jan;31(1):9-20. [8444678 ]