Ioxaglic acid

Last updated
Ioxaglic acid
Ioxaglic acid.png
Clinical data
Trade names Hexabrix
AHFS/Drugs.com FDA Professional Drug Information
Routes of
administration
Intravascular, intraarticular, by mouth
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding 14%
Metabolism None
Elimination half-life 92 min
Excretion Unchanged via kidneys
Identifiers
  • 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 InfoCard 100.055.945 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C24H21I6N5O8
Molar mass 1268.886 g·mol−1
3D model (JSmol)
  • 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=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]

Contents

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 BrainMetastasisFromBreastCancer.jpg
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]

Related Research Articles

Radiocontrast agents are substances used to enhance the visibility of internal structures in X-ray-based imaging techniques such as computed tomography, projectional radiography, and fluoroscopy. Radiocontrast agents are typically iodine, or more rarely barium sulfate. The contrast agents absorb external X-rays, resulting in decreased exposure on the X-ray detector. This is different from radiopharmaceuticals used in nuclear medicine which emit radiation.

<span class="mw-page-title-main">Iodinated contrast</span> Substance to enhance X-ray imaging

Iodinated contrast is a form of water-soluble, intravenous radiocontrast agent containing iodine, which enhances the visibility of vascular structures and organs during radiographic procedures. Some pathologies, such as cancer, have particularly improved visibility with iodinated contrast.

<span class="mw-page-title-main">Iotrolan</span> Chemical compound

Iotrolan is an iodine-containing radiocontrast agent, a substance used to improve the visibility of body structures on images obtained by X-ray techniques.

<span class="mw-page-title-main">Arthrogram</span>

An arthrogram is a series of images of a joint after injection of a contrast medium, usually done by fluoroscopy or MRI. The injection is normally done under a local anesthetic such as Novocain or lidocaine. The radiologist or radiographer performs the study using fluoroscopy or x-ray to guide the placement of the needle into the joint and then injects around 10 ml of contrast based on age. There is some burning pain from the anesthetic and a painful bubbling feeling in the joint after the contrast is injected. This only lasts 20 – 30 hours until the Contrast is absorbed. During this time, while it is allowed, it is painful to use the limb for around 10 hours. After that the radiologist can more clearly see what is going on under your skin and can get results out within 24 to 48 hours.

<span class="mw-page-title-main">Diatrizoate</span> Chemical compound

Diatrizoate, also known as amidotrizoate, Gastrografin, is a contrast agent used during X-ray imaging. This includes visualizing veins, the urinary system, spleen, and joints, as well as computer tomography. It is given by mouth, injection into a vein, injection into the bladder, through a nasogastric tube, or rectally.

<span class="mw-page-title-main">Myelography</span> Medical Imaging Technique

Myelography is a type of radiographic examination that uses a contrast medium to detect pathology of the spinal cord, including the location of a spinal cord injury, cysts, and tumors. Historically the procedure involved the injection of a radiocontrast agent into the cervical or lumbar spine, followed by several X-ray projections. Today, myelography has largely been replaced by the use of MRI scans, although the technique is still sometimes used under certain circumstances – though now usually in conjunction with CT rather than X-ray projections.

<span class="mw-page-title-main">Sialography</span> Radiological technique

Sialography is the radiographic examination of the salivary glands. It usually involves the injection of a small amount of contrast medium into the salivary duct of a single gland, followed by routine X-ray projections.

Pyelogram is a form of imaging of the renal pelvis and ureter.

<span class="mw-page-title-main">Iohexol</span> Chemical compound

Iohexol, sold under the trade name Omnipaque among others, is a contrast agent used for X-ray imaging. This includes when visualizing arteries, veins, ventricles of the brain, the urinary system, and joints, as well as during computed tomography. It is given by mouth, injection into a vein, or into a body cavity.

Lymphography is a medical imaging technique in which a radiocontrast agent is injected, and then an X-ray picture is taken to visualise structures of the lymphatic system, including lymph nodes, lymph ducts, lymphatic tissues, lymph capillaries and lymph vessels. Lymphangiography is the same procedure, used only to visualize the lymph vessels. The x-ray film or image of the lymphatic vessels and lymph nodes is called a lymphogram or a lymphangiogram.

<span class="mw-page-title-main">Iopamidol</span> Contrast agent

Iopamidol (INN), sold under the brand name Isovue among others, is a nonionic, low-osmolar iodinated contrast agent, developed by Bracco Diagnostics.

<span class="mw-page-title-main">Metrizamide</span> Chemical compound

Metrizamide is a non-ionic iodine-based radiocontrast agent. It is also a density gradient medium for the centrifugation of biological particles.

<span class="mw-page-title-main">Iopentol</span> Chemical compound

Iopentol is a pharmaceutical drug that was used as a radiocontrast agent for X-ray imaging in Europe.

<span class="mw-page-title-main">Iobitridol</span> Pharmaceutical drug

Iobitridol is a pharmaceutical drug used as an iodine-based radiocontrast agent in X-ray imaging. It is injected into blood vessels, joints, or body cavities such as the uterus, and filtered out by the kidneys. Its most common adverse effect is nausea. Severe allergic reactions are rare.

<span class="mw-page-title-main">Metrizoic acid</span> Chemical compound

Metrizoic acid is a pharmaceutical drug that was used as an iodinated contrast medium for X-ray imaging. Its uses included angiography and urography, but it has been discontinued, at least in the US.

<span class="mw-page-title-main">Acetrizoic acid</span> Chemical compound

Acetrizoic acid is a pharmaceutical drug that was used as an iodinated contrast medium for X-ray imaging. It was applied in form of its salt, sodium acetrizoate, but is no longer in clinical use.

Iotroxic acid, used in the form of meglumine iotroxate, is a molecule used as a contrast medium during X-rays. It is specifically used during tests looking at the gallbladder and biliary tract. It is given by slow injection into a vein.

Organoiodine chemistry is the study of the synthesis and properties of organoiodine compounds, or organoiodides, organic compounds that contain one or more carbon–iodine bonds. They occur widely in organic chemistry, but are relatively rare in nature. The thyroxine hormones are organoiodine compounds that are required for health and the reason for government-mandated iodization of salt.

<span class="mw-page-title-main">Contrast CT</span> Medical imaging technique

Contrast CT, or contrast enhanced computed tomography (CECT), is X-ray computed tomography (CT) using radiocontrast. Radiocontrasts for X-ray CT are generally iodine-based types. This is useful to highlight structures such as blood vessels that otherwise would be difficult to delineate from their surroundings. Using contrast material can also help to obtain functional information about tissues. Often, images are taken both with and without radiocontrast. CT images are called precontrast or native-phase images before any radiocontrast has been administered, and postcontrast after radiocontrast administration.

<span class="mw-page-title-main">Carbon dioxide angiography</span> Diagnostic radiographic technique

Carbon dioxide angiography is a diagnostic radiographic technique in which a carbon dioxide (CO2) based contrast medium is used - unlike traditional angiography where the contrast medium normally used is iodine based – to see and study the body vessels. Since CO2 is a non-radio-opaque contrast medium, angiographic procedures need to be performed in digital subtraction angiography (DSA).

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.