Acetrizoic acid

Identification

Name
Acetrizoic acid
Accession Number
DB09347
Type
Small Molecule
Groups
Withdrawn
Description

Acetrizoic acid presents the molecular formula of 3-acetamidol-2,4,6-triiodobenzoic acid[5] and it is the first monomeric ionic compound used as an X-ray contrast agent.[1] It was first synthesized by Wallingford in 1953[2] and it was filled in the FDA by the Johnson & Johnson subsidiary, Cilag Chemie AG, on February 8th, 1978.[7] Acetrizoic acid presents, in the FDA records, a category of drug substance with an inactive status.[6]

Structure
Thumb
Synonyms
  • Acide acetrizoique
  • Urokonic acid
Product Ingredients
IngredientUNIICASInChI Key
Acetrizoate sodium5GF4B2I1DD129-63-5UCPVOMHRDXMAIZ-UHFFFAOYSA-M
Categories
UNII
24256BQV7M
CAS number
85-36-9
Weight
Average: 556.864
Monoisotopic: 556.74818
Chemical Formula
C9H6I3NO3
InChI Key
GNOGSFBXBWBTIG-UHFFFAOYSA-N
InChI
InChI=1S/C9H6I3NO3/c1-3(14)13-8-5(11)2-4(10)6(7(8)12)9(15)16/h2H,1H3,(H,13,14)(H,15,16)
IUPAC Name
3-acetamido-2,4,6-triiodobenzoic acid
SMILES
CC(=O)NC1=C(I)C(C(O)=O)=C(I)C=C1I

Pharmacology

Indication

Acetrizoic acid indication was to be used as a contrast agent for X-ray. Some information indicates its nephrotropic property as one of the characteristics for the utilization of acetrizoic acid.[1] The X-ray imaging depends on the difference in tissue density which is provided by an X-ray attenuation between the area of interest and the surrounding tissue. The use of contrast agents will provoke a contrast enhancement or opacification and it will improve the differentiation of pathological processes from normal tissue.[3]

Pharmacodynamics
Not Available
Mechanism of action

Iodine, a big component in acetrizoic acid, is an element with a high atomic density. This property causes attenuation of X-rays within the diagnostic energy spectrum. Thus, acetrizoic acid is a water-soluble and reasonably safe iodinated contrast agent that can be intravenously administered for clinical applications.[2]

Absorption

After intravenous administration, acetrizoic acid gets largely distributed in the extracellular fluid space.[4] Radiographic agents like acetrizoic agents present variations in the plasma concentration depending on the dose and injection rate. After 5 minutes of administration, about 80% of the administered dose will stay outside of the intravascular compartment. There are some exceptions to the diffusion, such as the brain, neural tissue and testes where the tight junctions do not allow extravascularization.[9]

Volume of distribution
Not Available
Protein binding

The radiographic agents such as acetrizoic acid are carried free in plasma in which less than 5% of the injected dose is protein bound.[9]

Metabolism

The majority of the administered dose of acetrizoic acid remains unchanged.[4]

Route of elimination

After intravenous administration, acetrizoic acid is mainly excreted unchanged by the kidney.[4] The elimination pathway is handled by a glomerular filtration and concentration by tubular resorption of water. The excreted dose is of about 83% of the administered dose after 3 hours and of about 100% at 24 hours.[9]

Half life

When water-soluble contrast agents, such as acetrizoic acid, are administered, it is reported a half-life of approximate 4 hours.[10]

Clearance
Not Available
Toxicity

In preclinical studies performed in rodents, the LD50 after oral or intravenous administration was 2 g/kg and 8 g/kg respectively.[8]

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Cheng KT: N,N -Bis(2,3-dihydroxypropyl)-5-[N-(2-hydroxyethyl)-glycolamidol]-2,4,6-triiodoisopht halamide . [PubMed:20641970]
  2. WALLINGFORD VH: The development of organic iodine compounds as x-ray contrast media. J Am Pharm Assoc Am Pharm Assoc. 1953 Dec;42(12):721-8. [PubMed:13108780]
  3. Swanson D., et al. (1990). Pharmaceuticals in medical imaging. McGraw-Hill Professional.
  4. Dawson P. (1999). Textbook of contrast media. Oxford.
  5. Acetrizoic acid [Link]
  6. FDA Records [Link]
  7. Cilag [Link]
  8. ChemSrc [Link]
  9. Radiographic constrat agents [Link]
  10. Water soluble contrast media [Link]
External Links
KEGG Drug
D02457
KEGG Compound
C14164
PubChem Compound
6806
PubChem Substance
310265221
ChemSpider
6547
ChEBI
34521
ChEMBL
CHEMBL1201327
Wikipedia
Acetrizoic_acid
ATC Codes
V08AA07 — Acetrizoic acid
MSDS
Download (155 KB)

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
PropertyValueSource
boiling point (°C)547.1 at 760 mmHg'MSDS'
water solubilitySolubleCheng K. MICAD. (2008)
logP1.04'MSDS'
Predicted Properties
PropertyValueSource
Water Solubility0.0559 mg/mLALOGPS
logP3.03ALOGPS
logP3.66ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)2.33ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity88.26 m3·mol-1ChemAxon
Polarizability33.43 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 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 10 more
Substituents
Acylaminobenzoic acid or derivatives / O-haloacetanilide / P-haloacetanilide / Haloacetanilide / Acetanilide / 2-halobenzoic acid or derivatives / 4-halobenzoic acid or derivatives / Halobenzoic acid or derivatives / 2-halobenzoic acid / 4-halobenzoic acid
show 29 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
aminobenzoic acid (CHEBI:34521)

Carriers

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Pinckard RN, Hawkins D, Farr RS: The influence of acetylsalicyclic acid on the binding of acetrizoate to human albumin. Ann N Y Acad Sci. 1973 Nov 26;226:341-54. [PubMed:4520401]

Drug created on November 27, 2015 14:42 / Updated on November 02, 2018 08:51