Posted inUncategorized

Metrizamide

July 24, 2017
Common Name

Metrizamide Description

Metrizamide is only found in individuals that have used or taken this drug. It is a solute for density gradient centrifugation offering higher maximum solution density without the problems of increased viscosity. It is also used as a resorbable, non-ionic contrast medium.Organic iodine compounds such as metrizamide block x-rays as they pass through the body, thereby allowing body structures containing iodine to be delineated in contrast to those structures that do not contain iodine. The degree of opacity produced by these compounds is directly proportional to the total amount (concentration and volume) of the iodinated contrast agent in the path of the x-rays. After intrathecal administration into the subarachnoid space, diffusion of metrizamide in the CSF allows the visualization of the subarachnoid spaces of the head and spinal canal. After intravascliar administration, metrizamide makes opaque those vessels in its path of flow, allowing visualization of the internal structures until significant hemodilution occurs. Metrazamide also has some toxic effects which are thought to be due to its ability to inhibit glucose metabolism. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source AmipaqueKegg AmipakMeSH

Chemical Formlia

C18H22I3N3O8 Average Molecliar Weight

789.096 Monoisotopic Molecliar Weight

788.854094955 IUPAC Name

3-acetamido-2,4,6-triiodo-5-(N-methylacetamido)-N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]benzamide Traditional Name

metrizamide CAS Registry Number

31112-62-6 SMILES

CN(C(C)=O)C1=C(I)C(C(=O)N[C@H]2C(O)O[C@H](CO)[C@@H](O)[C@@H]2O)=C(I)C(NC(C)=O)=C1I

InChI Identifier

InChI=1S/C18H22I3N3O8/c1-5(26)22-12-9(19)8(10(20)14(11(12)21)24(3)6(2)27)17(30)23-13-16(29)15(28)7(4-25)32-18(13)31/h7,13,15-16,18,25,28-29,31H,4H2,1-3H3,(H,22,26)(H,23,30)/t7-,13-,15-,16-,18?/m1/s1

InChI Key

BAQCROVBDNBEEB-UBYUBLNFSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic oxygen compounds Sub Class

Organooxygen compounds Direct Parent

Acylaminosugars Alternative Parents

  • N-acyl-alpha-hexosamines
  • Acylaminobenzoic acid and derivatives
  • Hexoses
  • P-haloacetanilides
  • O-haloacetanilides
  • 2-halobenzoic acids and derivatives
  • 4-halobenzoic acids and derivatives
  • Benzamides
  • N-acetylarylamines
  • Benzoyl derivatives
  • Iodobenzenes
  • Aryl iodides
  • Oxanes
  • Tertiary carboxylic acid amides
  • Acetamides
  • Vinylogous halides
  • Secondary carboxylic acid amides
  • Secondary alcohols
  • Hemiacetals
  • Polyols
  • Oxacyclic compounds
  • Carbonyl compounds
  • Organoiodides
  • Organopnictogen compounds
  • Organic oxides
  • Primary alcohols
  • Hydrocarbon derivatives

    • Substituents

  • Acylaminosugar
  • N-acyl-alpha-hexosamine
  • Acylaminobenzoic acid or derivatives
  • Hexose monosaccharide
  • O-haloacetanilide
  • P-haloacetanilide
  • Haloacetanilide
  • Acetanilide
  • 2-halobenzoic acid or derivatives
  • 4-halobenzoic acid or derivatives
  • Halobenzoic acid or derivatives
  • N-acetylarylamine
  • Benzamide
  • Anilide
  • Benzoic acid or derivatives
  • Benzoyl
  • N-arylamide
  • Halobenzene
  • Iodobenzene
  • Monocyclic benzene moiety
  • Aryl halide
  • Oxane
  • Aryl iodide
  • Monosaccharide
  • Benzenoid
  • Vinylogous halide
  • Tertiary carboxylic acid amide
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Carbonyl group
  • Organopnictogen compound
  • Primary alcohol
  • Alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organonitrogen compound
  • Organoiodide
  • Organohalogen compound
  • Aromatic heteromonocyclic compound

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Contrast Media

    • Application

  • Pharmaceutical

    • Cellliar locations

    Not Available Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point223 °CNot Available Boiling PointNot AvailableNot Available Water Solubility6.35e-01 g/LNot Available LogP-1.89HANSCH,C ET AL. (1995)

    Predicted Properties

    Property Value Source Water Solubility0.64 mg/mLALOGPS logP-1.2ALOGPS logP-0.24ChemAxon logS-3.1ALOGPS pKa (Strongest Acidic)11.44ChemAxon pKa (Strongest Basic)-1.5ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count8ChemAxon Hydrogen Donor Count6ChemAxon Polar Surface Area168.66 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity140.62 m3·mol-1ChemAxon Polarizability56.3 Å3ChemAxon Number of Rings2ChemAxon Bioavailability0ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-004i-1359511000-9fdee9e746613feb3df0View 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

    Not Available 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 DB01578

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01578

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01578 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

    391998 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB15518 Metagene Link

    HMDB15518 METLIN ID

    Not Available PubChem Compound

    443944 PDB ID

    Not Available ChEBI ID

    Not Available

    Product: Cabergoline

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Azuma H, Nomura S, Ikoma Y, Yokoyama M, Oshino N: A possible mechanism for the neural adverse reactions caused by metrizamide. Fortschr Geb Rontgenstrahlen Nuklearmed Erganzungsbd. 1989;128:134-42. [PubMed:2568781 ]
    2. Ekholm SE, Reece K, Coleman JR, Kido DK, Fischer HW: Metrizamide–a potential in vivo inhibitor of glucose metabolism. Radiology. 1983 Apr;147(1):119-21. [PubMed:6828715 ]

    PMID: 24116873

    Last updated on