Page last updated: 2024-12-04

metrizoate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Metrizoate is an organic compound used as a contrast agent in medical imaging, particularly in X-ray procedures. It is synthesized through a multi-step process involving the reaction of 2,4,6-triiodobenzoic acid with the appropriate amine. Metrizoate is a non-ionic compound, meaning it does not dissociate into charged ions in solution. This property contributes to its safety and effectiveness as a contrast agent, reducing the risk of adverse reactions. The presence of iodine atoms in its structure allows it to absorb X-rays, making specific organs and tissues visible on radiographic images. This enhances the contrast between different structures and helps diagnose various medical conditions. Metrizoate is studied extensively due to its importance in medical imaging, allowing for accurate diagnosis and treatment planning. Research focuses on its pharmacokinetics, safety profile, and potential applications in various imaging procedures. It has also been investigated for its potential in drug delivery systems and other medical applications.'

Metrizoic Acid: A diagnostic radiopaque that usually occurs as the sodium salt. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID2528
CHEMBL ID1736
CHEBI ID34847
SCHEMBL ID37641
MeSH IDM0013692

Synonyms (55)

Synonym
3-(acetylamino)-5-[acetyl(methyl)amino]-2,4,6-triiodobenzoic acid
metrizoic acid
1949-45-7
benzoic acid, 3-(acetylamino)-5-(acetylmethylamino)-2,4,6-triiodo-
benzoic acid, 3-acetamido-2,4,6-triiodo-5-(n-methylacetamido)-
einecs 217-761-1
brn 2822724
metrizoic acid [jan]
acidum metrizoicum
acide metrizoique
3-acetamido-2,4,6-triiodo-5-n-methylacetamidobenzoic acid
metrizoate
sodium 3-acetamido-2,4, 6-triiodo-5-(n-methylacetamido)benzoate
3-acetamido-5-[acetyl(methyl)amino]-2,4,6-triiodo-benzoic acid
3-(acetylamino)-5-(acetyl(methyl)amino)-2,4,6-triiodobenzoic acid
sodium metrizoate (usan)
benzoic acid, 3-(acetylamino)-5-(acetylmethylamino)-2,4, 6-triiodo-, monosodium salt
benzoic acid, 3-acetamido-2,4, 6-triiodo-5-(n-methylacetamido)-, monosodium salt
3-acetamido-2,4, 6-triiodo-5-(n-methylacetamido)benzoate-
CHEBI:34847 ,
3-(acetylamino)-5-(acetylmethylamino)-2,4,6-triiodobenzoic acid
3-acetamido-2,4,6-triiodo-5-(n-methylacetamido)benzoic acid
CHEMBL1736
v08aa02
M1363
3-acetamido-5-(n-methylacetamido)-2,4,6-triiodobenzoic acid
3-acetamido-5-[acetyl(methyl)amino]-2,4,6-triiodobenzoic acid
unii-cm1n99qr1m
cm1n99qr1m ,
metrizoic acid, metrizoic acid 610.4mg
smr001550298
MLS004773979
FT-0672392
metrizoic acid [who-dd]
3-acetamido-2,4,6-tri-iodo-5-(n-methylacetamido)benzoic acid
metrizoic acid [mart.]
metrizoic acid [mi]
metrizoic acid [orange book]
MLS006010899
SCHEMBL37641
AKOS016846123
DTXSID6023311
DB09346
mfcd00867964
sr-01000939781
SR-01000939781-2
AS-70791
J-012629
HY-B1699
CS-0013692
Q6824400
metrizoic-acid
D91491
EN300-6731075
Z2417556930

Research Excerpts

Toxicity

Mglumine metrizoate was far more toxic to the endothelium than the nonionic media, metrizamide and iohexol. No complications were seen, and the adverse effects, usually a feeling of warmth, were very minor with both contrast media.

ExcerptReferenceRelevance
" Amipaque had a significantly higher LD50 than Isopaque Coronar (17."( Studies on the acute toxicity of ionic and non-ionic contrast media following rapid intravenous injection. An experimental study in mice.
Almén, T; Aspelin, P,
)
0.13
"Selective left vertebral angiography was carried out in 21 rabbits comparing the toxic effects of meglumine iothalamate (Conray meglumine), meglumine metrizoate (Isopaque Cerebral) and metrizamide (Amipaque)."( The toxicity of the non-ionic watersoluble contrast medium metrizamide (Amipaque) in selective vertebral angiography. An experimental study in rabbits.
Skalpe, IO, 1977
)
0.46
" Adverse effects of contrast media on kidney function include diuresis, changes in renal blood flow, osmotic nephroses, albuminuria, enzymuria and, most important, glomerular filtration rate."( Contrast media-induced nephrotoxicity. Survey and present state.
Almén, T; Golman, K,
)
0.13
" No complications were seen, and the adverse effects, usually a feeling of warmth, were very minor with both contrast media, but iohexol caused less discomfort than sodium metrizoate."( Comparison of side effects during cerebral computed tomography with a nonionic (iohexol) and an ionic (metrizoate) contrast medium.
Hordvik, M; Skalpe, IO,
)
0.54
" The hyperosmolar, ionic contrast medium, meglumine metrizoate, was far more toxic to the endothelium than the nonionic media, metrizamide and iohexol, which are far less hyperosmolar."( Human endothelial cell culture as an evaluation system for the toxicity of intravascular contrast media.
Börsum, T; Laerum, F; Reisvaag, A,
)
0.38
" Serious adverse events did not occur in either group."( Image quality and safety in pediatric urography using an ionic and a non-ionic iodinated contrast agent.
Brekke, O; Kristofferssen, DT; Mortensson, W; Nybonde, T; Wahlgren, H, 1994
)
0.29

Pharmacokinetics

ExcerptReferenceRelevance
" The pharmacokinetic properties of iohexol, in combination with its low toxicity, make it a suitable agent for determination of glomerular filtration rate in clinical practice."( Contrast media and glomerular filtration: dose dependence of clearance for three agents.
Bäck, SE; Krutzén, E; Nilsson-Ehle, P, 1988
)
0.27
" pharmacokinetic data on 670 drugs representing, to our knowledge, the largest publicly available set of human clinical pharmacokinetic data."( Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
Lombardo, F; Obach, RS; Waters, NJ, 2008
)
0.35

Bioavailability

ExcerptReferenceRelevance
" It is not likely, that such a low dose of poorly absorbed drug would cause any adverse effects in the infant, unless it is hypersensitive to the drug already."( Excretion of iohexol and metrizoate in human breast milk.
Andrew, E; Hafsahl, G; Matheson, I; Nielsen, ST; Rasmussen, JN; Skinnemoen, K,
)
0.43

Dosage Studied

ExcerptRelevanceReference
" The incidence of eosinophilia was irrespective of dosage or type of RCM."( Eosinophilia caused by iodinated radiographic contrast media.
Kuzmanić, D; Plavsić, B; Rotkvić, I, 1983
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
radioopaque mediumA substance having the property of absorbing, and therefore being opaque to, electromagnetic radiation, particularly X-rays.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
monocarboxylic acidAn oxoacid containing a single carboxy group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency1.58490.035520.977089.1251AID504332
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID540213Half life in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID425652Total body clearance in human2009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
Physicochemical determinants of human renal clearance.
AID540210Clearance in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID540209Volume of distribution at steady state in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID425653Renal clearance in human2009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
Physicochemical determinants of human renal clearance.
AID540211Fraction unbound in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID588220Literature-mined public compounds from Kruhlak et al phospholipidosis modelling dataset2008Toxicology mechanisms and methods, , Volume: 18, Issue:2-3
Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.
AID540212Mean residence time in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (217)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990184 (84.79)18.7374
1990's23 (10.60)18.2507
2000's7 (3.23)29.6817
2010's2 (0.92)24.3611
2020's1 (0.46)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.89

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index23.89 (24.57)
Research Supply Index5.82 (2.92)
Research Growth Index3.91 (4.65)
Search Engine Demand Index25.99 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.89)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials67 (24.81%)5.53%
Reviews3 (1.11%)6.00%
Case Studies8 (2.96%)4.05%
Observational0 (0.00%)0.25%
Other192 (71.11%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]