Metrizoic acid

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Metrizoic acid
Accession Number
DB09346
Type
Small Molecule
Groups
Approved
Description

Metrizoic acid is a molecule used as a contrast medium. Owing to its high osmolality, metrizoic acid has a risk of inducing allergic reactions compared to lower osmolar contrast media. Its approval has been discontinued by the FDA. One study in 1976 demonstrated that metrizoic acid, when used for cardiac angiography, was well tolerated. A total of 10, 000 injections were administered to 2,028 patients undergoing angiocardiographic procedures over a three-year period. With two exceptions, all complications occurred during injection of the right coronary artery. Seven cases of ventricular fibrillation, and 5 of significant bradycardia/asystole, were associated with metrizoic acid injection. In general, the drug was well tolerated by patients during cardiac examinations [A32901].

Structure
Thumb
Synonyms
Not Available
External IDs
V08AA02
Product Ingredients
IngredientUNIICASInChI Key
Calcium metrizoate1I3Z5LHR6P20828-80-2PPUUBZDQNSSJDN-UHFFFAOYSA-L
Meglumine metrizoateRJY6JR42WQ7241-11-4TXKOGNLDVKUFSI-WZTVWXICSA-N
Metrizoate magnesiumV717MS5D5B20968-37-0QGZYHVVYXBFUSE-UHFFFAOYSA-L
Metrizoate sodiumO65Q227UIC7225-61-8UKIYDXCFKFLIMU-UHFFFAOYSA-M
Categories
UNII
CM1N99QR1M
CAS number
1949-45-7
Weight
Average: 627.943
Monoisotopic: 627.78529
Chemical Formula
C12H11I3N2O4
InChI Key
GGGDNPWHMNJRFN-UHFFFAOYSA-N
InChI
InChI=1S/C12H11I3N2O4/c1-4(18)16-10-7(13)6(12(20)21)8(14)11(9(10)15)17(3)5(2)19/h1-3H3,(H,16,18)(H,20,21)
IUPAC Name
3-acetamido-2,4,6-triiodo-5-(N-methylacetamido)benzoic acid
SMILES
CN(C(C)=O)C1=C(I)C(C(O)=O)=C(I)C(NC(C)=O)=C1I

Pharmacology

Indication

For use as a contrast medium [2].

Pharmacodynamics
Not Available
Mechanism of action

The mechanism of action of metrizoic acid is as an X-Ray contrast activity [2].

Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Nitter-Hauge S, Enge I: Metrizoic acid (Isopaque coronar) used in man for cardiac angiography. Radiology. 1976 Dec;121(3 Pt. 1):537-40. doi: 10.1148/121.3.537. [PubMed:790454]
  2. Metrizoic Acid [Link]
  3. Metrizoic Acid [Link]
External Links
KEGG Compound
C14165
PubChem Compound
2528
PubChem Substance
310265220
ChemSpider
2433
ChEBI
34847
ChEMBL
CHEMBL1736
Wikipedia
Metrizoic_acid
ATC Codes
V08AA02 — Metrizoic acid

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0877 mg/mLALOGPS
logP2.18ALOGPS
logP2.76ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)2.16ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.71 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity106.24 m3·mol-1ChemAxon
Polarizability39.93 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Acylaminobenzoic acid and derivatives
Alternative Parents
P-haloacetanilides / O-haloacetanilides / 2-halobenzoic acids / 4-halobenzoic acids / Halobenzoic acids / Benzoic acids / N-acetylarylamines / 1-carboxy-2-haloaromatic compounds / Benzoyl derivatives / Iodobenzenes
show 11 more
Substituents
Acylaminobenzoic acid or derivatives / O-haloacetanilide / P-haloacetanilide / Haloacetanilide / Acetanilide / 2-halobenzoic acid / 4-halobenzoic acid / Halobenzoic acid / Halobenzoic acid or derivatives / 2-halobenzoic acid or derivatives
show 30 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monocarboxylic acid (CHEBI:34847)

Drug created on November 27, 2015 14:08 / Updated on November 02, 2018 08:50