Ioxitalamic acid

Identification

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Name
Ioxitalamic acid
Accession Number
DB13444
Type
Small Molecule
Groups
Approved, Experimental
Description

Ioxitalamate is an ionic iodinated contrast medium.1 It is a first-generation contrast media formed by an ionic monomer with a high osmolarity of 1500-1800 mOsm/kg.2 Ioxitalamic acid in the salt forms of sodium and meglumine was developed by Liebel-Flarshem Canada Inc and approved by Health Canada in 1995. Until the last review in 2015, this drug is still available in the market.7

Structure
Thumb
Synonyms
  • acido ioxitalamico
  • Ioxitalamic acid
External IDs
AG-58107
Product Ingredients
IngredientUNIICASInChI Key
Meglumine ioxitalamate5791GC9HSW29288-99-1IFTFXKNYTWAOGK-WZTVWXICSA-N
Sodium ioxitalamate8P8Y8ZXJ8Y33954-26-6PZTAFRMXSAAHMQ-UHFFFAOYSA-M
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Telebrix 38 OralSodium ioxitalamate (255 mg) + Meglumine ioxitalamate (513 mg)SolutionOralLiebel Flarsheim Company Llc1995-12-31Not applicableCanada
Telebrix 38 OralSodium ioxitalamate (255 mg) + Meglumine ioxitalamate (513 mg)SolutionOralLiebel Flarsheim Company Llc1995-12-31Not applicableCanada
Categories
UNII
967RDI7Z6K
CAS number
28179-44-4
Weight
Average: 643.942
Monoisotopic: 643.78021
Chemical Formula
C12H11I3N2O5
InChI Key
OLAOYPRJVHUHCF-UHFFFAOYSA-N
InChI
InChI=1S/C12H11I3N2O5/c1-4(19)17-10-8(14)5(11(20)16-2-3-18)7(13)6(9(10)15)12(21)22/h18H,2-3H2,1H3,(H,16,20)(H,17,19)(H,21,22)
IUPAC Name
3-[(2-hydroxyethyl)-C-hydroxycarbonimidoyl]-5-[(1-hydroxyethylidene)amino]-2,4,6-triiodobenzoic acid
SMILES
CC(O)=NC1=C(I)C(C(O)=NCCO)=C(I)C(C(O)=O)=C1I

Pharmacology

Indication

Ioxitalamate in both of its available forms is indicated for exploration of the digestive tract by tomodensitometry or by regular gastroduodenal radiography. Its use is restrained to the cases in which the administration of barium sulfate is not recommended or contraindicated.9 The intravascular administration of ioxitalamate is contraindicated as it may present significant side effects.8

Pharmacodynamics

Ioxitalamate presents a very large osmolality which is related to the presence of renal toxicity, vasodilatation, bradycardia and pulmonary hypertension. This large osmolality allows ioxitalamate to move slowly in the bowel allowing for analysis for later follow excretion in the feces.3

Mechanism of action

Ioxitalamate acts as a bowel opacifier which facilitates the interpretation of the anatomy and differentiation of bowel loops from soft tissue masses.8

Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

When administered ioxitalamate is not absorbed in the GI tract. In the case of presence of an intestinal perforation, ioxitalamate is completely absorbed.9 When administered intravascularly, ioxitalamate is rapidly distributed in the interstitial space and intravascular compartment.10

Volume of distribution

The volume of distribution of ioxitalamate is 194 ml/kg.10

Protein binding

Iodinated monomeric contrast agents are rarely bound to plasma proteins and when they bind, usually the association is very weak.4 When bound, it only represents from 0 to 27% of the ioxitalamate administered dose.5

Metabolism

The rapid clearance suggests that ioxitalamate is not metabolized in the body.6

Route of elimination

As ioxitalamate is not absorbed in the normal intestine, the elimination route of this compound is entirely performed by the feces. When absorbed due to the presence of an intestinal perforation, ioxitalamate presents a rapid renal elimination.9 when ioxitalamate is administered intravascularly, it is eliminated unchanged mainly via renal excretion through glomerular filtration without reabsorption or tubular secretion. In the cases of renal failure, the elimination is mainly performed in the biliary, salivary, sudoral and colic route.10

Half life

The elimination half-life of ioxitalamate is 1.1 hours.[T56]

Clearance

The total clearance rate of ioxitalamate is 120 ml/min.10

Toxicity

Ioxitalamate is reported to induce acute kidney injury.2 Preclinical studies showed that it does not present a teratogenic potential as well as a lack of effect on fertility.9 Ioxitalamate overdose may increase the risk of nephropathy and cardiovascular disorders.8

Affected organisms
  • Humans and other mammals
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

References

General References
  1. Kim KH, Kim YS, Kuh SU, Park HS, Park JY, Chin DK, Kim KS, Cho YE: Time- and dose-dependent cytotoxicities of ioxitalamate and indigocarmine in human nucleus pulposus cells. Spine J. 2013 May;13(5):564-71. doi: 10.1016/j.spinee.2013.01.019. Epub 2013 Feb 11. [PubMed:23406968]
  2. Hsu SP, Tsai TJ, Chien CT: Ioxitalamate induces renal tubular apoptosis via activation of renal efferent nerve-mediated adrenergic signaling, renin activity, and reactive oxygen species production in rats. Toxicol Sci. 2010 Mar;114(1):149-58. doi: 10.1093/toxsci/kfp290. Epub 2009 Nov 26. [PubMed:19945959]
  3. Lusic H, Grinstaff MW: X-ray-computed tomography contrast agents. Chem Rev. 2013 Mar 13;113(3):1641-66. doi: 10.1021/cr200358s. Epub 2012 Dec 5. [PubMed:23210836]
  4. Buthiau D. and Khayat D. (1995). CT and MRI in oncology. Springer-Verlag. [ISBN:978-3-642-46844-5]
  5. Seyffart G. (1992). Drug dosage in renal insufficiency (2nd ed.). Springer Science+Business Media Dordrecht.
  6. Coyne C. (2006). Comparative diagnostics pharmacology. Blackwell publishing. [ISBN:978-0-8138-1753-8]
  7. Health Canada [Link]
  8. Health Canada label [File]
  9. Telebrix Gastro monograph [File]
  10. Telebrix summary of product [File]
External Links
ChemSpider
31782
ChEBI
83517
ChEMBL
CHEMBL2107239
Wikipedia
Ioxitalamic_acid
ATC Codes
V08AA05 — Ioxitalamic acid
MSDS
Download (127 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

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

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)349 ºC'MSDS'
water solubilitySolubleProduct Characteristics
Predicted Properties
PropertyValueSource
Water Solubility0.0525 mg/mLALOGPS
logP1.64ALOGPS
logP3.23ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)2.87ChemAxon
pKa (Strongest Basic)1.91ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area122.71 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity109.81 m3·mol-1ChemAxon
Polarizability41.94 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
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0000290000-bea113afa507d4f83832
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0560-0030892000-be529b9a08f8ec10951a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0069500000-5cf1940320c530eb1e63
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0019000000-95d4fdffc3e831a916f0
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0279000000-d3d29cce5fe216a78e8c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0kmj-0592000000-c952e97f08d9e00a87c7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a59-2940000000-1cba0b7e9f97e41f9238
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0560-0030971000-6f60254e136f17e3c7b3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0069600000-97414d2d7897ddd2088d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0019000000-afc026d3c384eece14d6
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0279000000-a9562bb10633969544f8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0zn9-0693000000-c7be2a986262c009581b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a59-2960000000-f8600c7dcbad916b1faf
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0000290000-d74c380fe3cfa9ff6047

Taxonomy

Description
This compound belongs to the class of organic compounds known as halobenzoic acids. These are benzoic acids carrying a halogen atom on the benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Halobenzoic acids
Alternative Parents
2-halobenzoic acids / 4-halobenzoic acids / Benzoic acids / 1-carboxy-2-haloaromatic compounds / Benzoyl derivatives / Iodobenzenes / Aryl iodides / Vinylogous halides / Propargyl-type 1,3-dipolar organic compounds / Alkanolamines
show 7 more
Substituents
Halobenzoic acid / 4-halobenzoic acid / 2-halobenzoic acid / 4-halobenzoic acid or derivatives / 2-halobenzoic acid or derivatives / Benzoic acid / Benzoyl / 1-carboxy-2-haloaromatic compound / Halobenzene / Iodobenzene
show 23 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
organoiodine compound, dicarboxylic acid monoamide, acetamides, benzoic acids (CHEBI:83517)

Drug created on June 23, 2017 14:42 / Updated on September 02, 2019 22:07