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Tinidazole

July 24, 2017
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 reslit 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

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source TimidazoleChEBI Pierre fabre brand OF tinidazoleMeSH SimplotanMeSH Teofarma brand OF tinidazoleMeSH Farmasierra brand OF tinidazoleMeSH FasigyneMeSH Pfizer brand OF tinidazoleMeSH BioshikMeSH FasiginMeSH FasyginMeSH TricolamMeSH FasigynMeSH

Chemical Formlia

C8H13N3O4S Average Molecliar Weight

247.272 Monoisotopic Molecliar Weight

247.062676609 IUPAC Name

1-[2-(ethaneslifonyl)ethyl]-2-methyl-5-nitro-1H-imidazole Traditional 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 Description

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

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Azoles Direct Parent

Nitroimidazoles Alternative Parents

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

    • Substituents

  • 1,2,5-trisubstituted-imidazole
  • Nitroaromatic compound
  • Nitroimidazole
  • Trisubstituted imidazole
  • N-substituted imidazole
  • Slifone
  • Heteroaromatic compound
  • Slifonyl
  • C-nitro compound
  • Organic nitro compound
  • Organic oxoazanium
  • Azacycle
  • Organic 1,3-dipolar compound
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organoslifur compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

  • imidazoles (CHEBI:63627 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Alkylating Agents
  • Anti-Infectives
  • Antiprotozoals
  • Antitrichomonal Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point127 – 128 °CNot Available Boiling PointNot AvailableNot Available Water Solubility3.03e+00 g/LNot Available LogP0.7Not Available

    Predicted Properties

    Property Value Source Water Solubility3.03 mg/mLALOGPS logP-0.41ALOGPS logP-0.58ChemAxon logS-1.9ALOGPS pKa (Strongest Basic)3.1ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area97.78 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity57.66 m3·mol-1ChemAxon Polarizability23.27 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 – , positivesplash10-0002-0290000000-6e567c97c2cf4ca3fd01View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-004i-4910000000-8c46b903514b344ac47cView 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

    Biological Properties Cellliar Locations

  • Cytoplasm
  • 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 DB00911

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00911

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00911 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 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Tinidazole NuGOwiki Link

    HMDB15047 Metagene Link

    HMDB15047 METLIN ID

    Not Available PubChem Compound

    5479 PDB ID

    Not Available ChEBI ID

    63627

    Product: WZ4004

    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 ]
    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 ]
    3. MedlinePlus [Link]

    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 ]

    PMID: 2837278

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