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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:00 UTC
HMDB IDHMDB0015518
Secondary Accession Numbers
  • HMDB15518
Metabolite Identification
Common NameMetrizamide
DescriptionMetrizamide 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 intravascular 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
Thumb
Synonyms
ValueSource
AmipaqueKegg
AmipakHMDB
3-[(1-Hydroxyethylidene)amino]-2,4,6-triiodo-5-(N-methylacetamido)-N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]benzene-1-carboximidateHMDB
Chemical FormulaC18H22I3N3O8
Average Molecular Weight789.096
Monoisotopic Molecular Weight788.854094955
IUPAC Name3-acetamido-2,4,6-triiodo-5-(N-methylacetamido)-N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]benzamide
Traditional Namemetrizamide
CAS Registry Number31112-62-6
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 KeyBAQCROVBDNBEEB-UBYUBLNFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
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
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point223 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.64 g/LNot Available
LogP-1.89HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01578 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01578 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID391998
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMetrizamide
METLIN IDNot Available
PubChem Compound443944
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot 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 ]