ContaminantDB: Metrizamide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:43:39 UTC

Update Date

2016-11-09 01:15:28 UTC

Accession Number

CHEM016785

Identification

Common Name

Metrizamide

Class

Small Molecule

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 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.

Contaminant Sources

HMDB Contaminants - Urine
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Amipaque	Kegg
Amipak	HMDB
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-carboximidate	HMDB

Chemical Formula

C₁₈H₂₂I₃N₃O₈

Average Molecular Mass

789.096 g/mol

Monoisotopic Mass

788.854 g/mol

CAS Registry Number

31112-62-6

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

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

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Acylaminosugars

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.64 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-0.24	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	11.44	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	168.66 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	140.62 m³·mol⁻¹	ChemAxon
Polarizability	56.3 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dj-5000012900-4646ef3069fd298336cb	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-004i-1359511000-9fdee9e746613feb3df0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-004i-1359511000-9fdee9e746613feb3df0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-007a-0100000900-edf7e801c24feddefea3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004j-0100001900-9afd2e16c8f2e838e39c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004l-9300055700-94197b0e135f1654dff5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000005600-4b8d36bc606dab8c46b2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0axr-9000007700-a765f169e9e5078515cc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-9000014000-1ff138852d0e3ccd989c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dr-0000000900-96c917681df077d479a2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ot-0000006900-d1093a8d175523192a3f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0300-2000069200-4b21b2eafd27a829ff3b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-016r-0000009100-7665b8eb45f82ceb4a57	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002b-1100009300-e91c7a52f7331c06f5d1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0059-7300098400-1cec50ae438b423f57d8	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0015518

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Metrizamide

Chemspider ID

391998

ChEBI ID

Not Available

PubChem Compound ID

443944

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

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.

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.

Metrizamide (CHEM016785)

Structure for CHEM016785: Metrizamide