Acetrizoic acid
Identification
- Generic Name
- Acetrizoic acid
- DrugBank Accession Number
- DB09347
- Background
Acetrizoic acid presents the molecular formula of 3-acetamidol-2,4,6-triiodobenzoic acid5 and it is the first monomeric ionic compound used as an X-ray contrast agent.1 It was first synthesized by Wallingford in 19532 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
- Type
- Small Molecule
- Groups
- Withdrawn
- Structure
- Weight
- Average: 556.864
Monoisotopic: 556.74818 - Chemical Formula
- C9H6I3NO3
- Synonyms
- Acide acetrizoique
- Urokonic acid
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
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- 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
- Adverse Effects
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- Toxicity
In preclinical studies performed in rodents, the LD50 after oral or intravenous administration was 2 g/kg and 8 g/kg respectively.8
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Acetrizoate sodium 5GF4B2I1DD 129-63-5 UCPVOMHRDXMAIZ-UHFFFAOYSA-M
Categories
- ATC Codes
- V08AA07 — Acetrizoic acid
- Drug Categories
- Acids, Carbocyclic
- Aminobenzoates
- Benzene Derivatives
- Benzoates
- Compounds used in a research, industrial, or household setting
- Contrast Media
- Diagnostic Uses of Chemicals
- Iodobenzoates
- meta-Aminobenzoates
- Triiodobenzoic Acids
- Watersoluble, Nephrotropic, High Osmolar X-Ray Contrast Media
- X-Ray Contrast Media, Iodinated
- Chemical TaxonomyProvided by Classyfire
- 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
- 1-carboxy-2-haloaromatic compound / 2-halobenzoic acid / 2-halobenzoic acid or derivatives / 4-halobenzoic acid / 4-halobenzoic acid or derivatives / Acetamide / Acetanilide / Acylaminobenzoic acid or derivatives / Anilide / Aromatic homomonocyclic compound show 29 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- aminobenzoic acid (CHEBI:34521)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 24256BQV7M
- CAS number
- 85-36-9
- 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
References
- General References
- Cheng KT: N,N -Bis(2,3-dihydroxypropyl)-5-[N-(2-hydroxyethyl)-glycolamidol]-2,4,6-triiodoisopht halamide . [Article]
- 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. [Article]
- Swanson D., et al. (1990). Pharmaceuticals in medical imaging. McGraw-Hill Professional.
- Dawson P. (1999). Textbook of contrast media. Oxford.
- Acetrizoic acid [Link]
- FDA Records [Link]
- Cilag [Link]
- ChemSrc [Link]
- Radiographic constrat agents [Link]
- 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
- ZINC
- ZINC000003830175
- Wikipedia
- Acetrizoic_acid
- MSDS
- Download (155 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source boiling point (°C) 547.1 at 760 mmHg 'MSDS' water solubility Soluble Cheng K. MICAD. (2008) logP 1.04 'MSDS' - Predicted Properties
Property Value Source Water Solubility 0.0559 mg/mL ALOGPS logP 3.03 ALOGPS logP 3.66 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 2.33 Chemaxon pKa (Strongest Basic) -4.5 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 66.4 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 88.26 m3·mol-1 Chemaxon Polarizability 33.43 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 174.18279 predictedDeepCCS 1.0 (2019) [M+H]+ 176.54079 predictedDeepCCS 1.0 (2019) [M+Na]+ 182.63393 predictedDeepCCS 1.0 (2019)
Carriers
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
Drug created at November 27, 2015 21:42 / Updated at February 02, 2024 22:54