Human Metabolome Database Version 3.5

Showing metabocard for Metronidazole (HMDB15052)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:51 -0600
Update Date 2013-02-08 17:32:52 -0700
HMDB ID HMDB15052
Secondary Accession Numbers None
Metabolite Identification
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 Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Methronidazole
  2. Metronidazol
  3. Metronidazole Benzoate
  4. Metronidazole in Plastic Container
  5. Metronidazolo
Chemical Formula C6H9N3O3
Average Molecular Weight 171.154
Monoisotopic Molecular Weight 171.064391169
IUPAC Name 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol
Traditional IUPAC 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
Kingdom Organic Compounds
Super Class Aromatic Heteromonocyclic Compounds
Class Azoles
Sub Class Imidazoles
Other Descriptors
  • Imidazoles
  • imidazoles(ChEBI)
Substituents
  • Nitro Compound
  • Organic Oxoazanium
  • Primary Alcohol
Direct Parent Nitroimidazoles
Ontology
Status Expected and 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
State Solid
Experimental Properties
Property Value Reference
Melting Point 160 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 5.92e+00 g/L Not Available
LogP -0.1 Not Available
Predicted Properties
Property Value Source
Water Solubility 5.92 g/L ALOGPS
LogP -0.15 ALOGPS
LogP -0.46 ChemAxon
LogS -1.46 ALOGPS
pKa (strongest acidic) 15.44 ChemAxon
pKa (strongest basic) 3.09 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 83.87 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 41.22 ChemAxon
Polarizability 15.82 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00916
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00916
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB00916 Link_out
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 Link_out
KEGG Compound ID C07203 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Metronidazole Link_out
NuGOwiki Link HMDB15052 Link_out
Metagene Link HMDB15052 Link_out
METLIN ID Not Available
PubChem Compound 4173 Link_out
PDB ID 2MN Link_out
ChEBI ID 6909 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. 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 Link_out
  2. 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 Link_out
  3. Lamont RF: Can antibiotics prevent preterm birth--the pro and con debate. BJOG. 2005 Mar;112 Suppl 1:67-73. Pubmed: 15715599 Link_out
  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 Link_out

Enzymes
Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C9
Reactions: Not Available
Gene Name: CYP2C9
Uniprot ID: P11712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C8
Reactions: Not Available
Gene Name: CYP2C8
Uniprot ID: P10632 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA