Human Metabolome Database Version 3.5

Showing metabocard for Tinidazole (HMDB15047)

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 HMDB15047
Secondary Accession Numbers None
Metabolite Identification
Common Name Tinidazole
Description Tinidazole is only found in individuals that have used or taken this drug. It is a nitroimidazole antitrichomonal agent effective against Trichomonas vaginalis, Entamoeba histolytica, and Giardia lamblia infections. [PubChem]Tinidazole is a prodrug and antiprotozoal agent. The nitro group of tinidazole is reduced in Trichomonas by a ferredoxin-mediated electron transport system. The free nitro radical generated as a result of this reduction is believed to be responsible for the antiprotozoal activity. It is suggested that the toxic free radicals covalently bind to DNA, causing DNA damage and leading to cell death. The mechanism by which tinidazole exhibits activity against Giardia and Entamoeba species is not known, though it is probably similar.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Chemical Formula C8H13N3O4S
Average Molecular Weight 247.272
Monoisotopic Molecular Weight 247.062676609
IUPAC Name 1-[2-(ethanesulfonyl)ethyl]-2-methyl-5-nitro-1H-imidazole
Traditional IUPAC Name tinidazole
CAS Registry Number 19387-91-8
SMILES CCS(=O)(=O)CCN1C(C)=NC=C1[N+]([O-])=O
InChI Identifier InChI=1S/C8H13N3O4S/c1-3-16(14,15)5-4-10-7(2)9-6-8(10)11(12)13/h6H,3-5H2,1-2H3
InChI Key HJLSLZFTEKNLFI-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
  • Sulfone
  • Sulfonyl
  • Sulfoxide
Direct Parent Nitroimidazoles
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction
  • Alkylating Agents
  • Anti-Infectives
  • Antiprotozoals
  • Antitrichomonal Agents
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 127 - 128 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 3.03e+00 g/L Not Available
LogP 0.7 Not Available
Predicted Properties
Property Value Source
LogP -0.41 ALOGPS
LogP -0.58 ChemAxon
LogS -1.91 ALOGPS
pKa (strongest basic) 3.1 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 97.78 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 57.66 ChemAxon
Polarizability 23.27 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 DB00911
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00911
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB00911 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 5279 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Tinidazole Link_out
NuGOwiki Link HMDB15047 Link_out
Metagene Link HMDB15047 Link_out
METLIN ID Not Available
PubChem Compound 5479 Link_out
PDB ID Not Available
ChEBI ID 63627 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Fung HB, Doan TL: Tinidazole: a nitroimidazole antiprotozoal agent. Clin Ther. 2005 Dec;27(12):1859-84. Pubmed: 16507373 Link_out
  2. Lopez Nigro MM, Carballo MA: Genotoxicity and cell death induced by tinidazole (TNZ). Toxicol Lett. 2008 Jul 30;180(1):46-52. doi: 10.1016/j.toxlet.2008.05.017. Epub 2008 Jun 5. Pubmed: 18582545 Link_out
  3. MedlinePlus Link_out
Enzymes
Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA