Ioxaglic acid

Ioxaglic acid
Clinical data
Trade namesHexabrix
AHFS/Drugs.comFDA Professional Drug Information
Routes of
administration		Intravascular, intraarticular, by mouth
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding14%
MetabolismNone
Elimination half-life92 min
ExcretionUnchanged via kidneys
Identifiers
IUPAC name
  • 3-[(2-hydroxyethyl)carbamoyl]-2,4,6-triiodo-5-(2-{[2,4,6-triiodo-3-(methylcarbamoyl)-5-(N-methylacetamido)phenyl]formamido}acetamido)benzoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.055.945 Edit this at Wikidata
Chemical and physical data
FormulaC24H21I6N5O8
Molar mass1268.886 g·mol−1
3D model (JSmol)
SMILES
  • CC(=O)N(C)C1=C(C(=C(C(=C1I)C(=O)NCC(=O)NC2=C(C(=C(C(=C2I)C(=O)O)I)C(=O)NCCO)I)I)C(=O)NC)I
InChI
  • InChI=1S/C24H21I6N5O8/c1-7(37)35(3)20-17(29)10(21(39)31-2)13(25)11(18(20)30)23(41)33-6-8(38)34-19-15(27)9(22(40)32-4-5-36)14(26)12(16(19)28)24(42)43/h36H,4-6H2,1-3H3,(H,31,39)(H,32,40)(H,33,41)(H,34,38)(H,42,43)
  • Key:TYYBFXNZMFNZJT-UHFFFAOYSA-N

Ioxaglic acid (trade name Hexabrix) is pharmaceutical drug used as an iodinated contrast medium for X-ray imaging. It has low osmolality (relatively few molecules per volume), typically resulting in fewer side effects than high-osmolality media.[1] It is manufactured by Guerbet, but marketing in the US has been discontinued.[2] As of 2021, it may still be available in some European countries.[3]

It is applied in form of its salts, ioxaglate meglumine and ioxaglate sodium.[2]

Medical uses

Uses include angiography (imaging of blood vessels, including those of the brain and heart), arthrography (imaging of joints), urography (imaging of the urinary system), hysterosalpingography (imaging of the uterus and Fallopian tubes), imaging of the gastrointestinal tract, and endoscopic retrograde cholangiopancreatography (ERCP; imaging of the biliary and pancreatic ducts).[4]

Contraindications

Ioxaglic acid is contraindicated in people with hyperthyreosis because of the drug's iodine content. It must not be used for myelography (spinal cord imaging), for hysterosalpingography in women who are pregnant or have an acute inflammation in the pelvic region, or for arthrography if the joint is infected.[2][4]

Adverse effects

Adverse effects include reactions at the injection site, such as a hot or painful feeling as well as general reactions such as nausea and vomiting. All of these are usually mild and transient. Allergy-like effects such as itching, sneezing, coughing and yawning can be the first sign of severe adverse reactions, especially a shock.[4]

Accidental intrathecal administration (into the spinal canal) can result in life-threatening reactions such as convulsions, cerebral (brain) edema or cerebral bleed.[2]

Interactions

Iodine-131, a radioactive isotope used for thyroid imaging (scintigraphy) and therapy of thyroid cancers, can be less effective when used within two to six weeks after application of ioxaglic acid because of residual iodine in the body.[4]

Pharmacology

Chemistry and mechanism of action

Contrast CT of a patient with brain metastases from breast cancer, before (left) and after (right) injection of an iodine-containing contrast agent

Ioxaglic acid is an iodine-containing, water-soluble radiocontrast agent. The iodine atoms readily absorb X-rays, resulting in a higher contrast of X-ray images. It has a low osmolality of 600 mosm/kg water at 37 °C (99 °F), meaning that the solution has a relatively low concentration of molecules; this is usually associated with fewer adverse effects than high-osmolality contrast agents.[2][4]

Pharmacokinetics

After injection into a vein, 14% of the circulating ioxaglic acid is bound to blood plasma proteins, which is unusually high for a water-soluble iodinated contrast agent.[5] The substance is distributed in the body with a half-life of 12 minutes (range 4 to 17 minutes) and eliminated in unmetabolized (unchanged) form via the kidneys with a half-life of 92 minutes (range 61 to 140 minutes).[2] In people with kidney failure, it is eliminated via the bile duct, saliva or sweat.[4]

References

  1. ↑ Meijenhorst GC, de Bruin JN (August 1980). "Hexabrix (ioxaglate), a new low osmolality contrast agent for lumbar epidural double-catheter venography". Neuroradiology. 20 (1): 29–32. doi:10.1007/bf00346858. PMID 6999377. S2CID 39778683.
  2. 1 2 3 4 5 6 Hexabrix FDA Professional Drug Information. Accessed 2021-03-26.
  3. ↑ "Ioxaglic acid: List of nationally authorised medicinal products" (PDF). European Medicines Agency. 31 October 2018.
  4. 1 2 3 4 5 6 Haberfeld H, ed. (2020). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Hexabrix 320 mg Jod/ml-Ampullen.
  5. ↑ Krause W, Niehues D (1996). "Biochemical characterization of x-ray contrast media". Invest. Radiol. 31 (1): 30–42. doi:10.1097/00004424-199601000-00006. PMID 8850363.
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