Diatrizoate

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Diatrizoate
Diatrizoic acid.svg
Diatrizoic-acid-3D-spacefill.png
Clinical data
Trade names Hypaque, Gastrografin, Iothalmate, others
Other namesamidotrizoic acid, diatrizoic acid, 3,5-diacetamido-2,4,6-triiodobenzoic acid
AHFS/Drugs.com Micromedex Detailed Consumer Information
ATC code
Identifiers
  • 3,5-Bis(acetylamino)-2,4,6-triiodobenzoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.003.840 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C11H9I3N2O4
Molar mass 613.916 g·mol−1
3D model (JSmol)
  • CC(=O)NC1=C(C(=C(C(=C1I)C(=O)O)I)NC(=O)C)I
  • InChI=1S/C11H9I3N2O4/c1-3(17)15-9-6(12)5(11(19)20)7(13)10(8(9)14)16-4(2)18/h1-2H3,(H,15,17)(H,16,18)(H,19,20)
  • Key:YVPYQUNUQOZFHG-UHFFFAOYSA-N

Diatrizoate, also known as amidotrizoate, Gastrografin, is a contrast agent used during X-ray imaging. [1] This includes visualizing veins, the urinary system, spleen, and joints, as well as computer tomography (CT scan). [1] It is given by mouth, injection into a vein, injection into the bladder, through a nasogastric tube, or rectally. [2] [3]

Contents

Relatively common side effects include vomiting, diarrhea, and skin redness. [4] Other side effects include itchiness, kidney problems, low blood pressure, and allergic reactions. [1] It is not recommended in people who have an iodine allergy. [1] Diatrizoate is an iodinated ionic radiocontrast agent with high osmolality. [2]

Diatrizoate was approved for medical use in the United States in 1954. [4] It is on the World Health Organization's List of Essential Medicines. [5]

Medical uses

Diatrizoic acid may be used as an alternative to barium sulfate for medical imaging of the gastrointestinal tract, such as upper gastrointestinal series and small bowel series. It is indicated for use in patients who are allergic to barium, or in cases where the barium might leak into the abdominal cavity. It does not coat the stomach/bowel lining as well as barium, so it is not used commonly for this purpose.[ citation needed ]

It is also used to treat Ascaris lumbricoides (roundworms). [6] [7] Diatrizoate may not actually kill Ascaris, but instead it promotes shifting of fluid in the bowel lumen due to its osmotic properties[ clarify ], so may relieve intestinal obstruction caused by impacted Ascaris. [8]

Diatrizoate is used in suspected intestinal perforation, meconium ileus, and to identify bowel-lumen communication. It should not be used to investigate tracheo-oesophageal fistula because it can cause pulmonary oedema when aspirated into respiratory system. Diatrizoate can dislodge sticky meconium by drawing water into intestines. [9] Diatrizoate is minimally absorbed from the intestines and excreted into urinary bladder. [10] Because of its high osmolarity it can draw water from the surrounding tissues into the intestines, thus cause dehydration in people with already small plasma volume such as infants. Because of the additives and flavouring agents, diatrizoate formulated as Gastrografin must not be used intravascularly, though other formulations of diatrizoate are indicated for intravascular use. This chemical must be kept away from sunlight during storage. [11]

Administration

It is given orally on computed tomography of the abdomen and pelvis as 30 ml solution with 3% concentration to visualise the bowel lumen and any communications with the bowel lumen. [12] In principle, diatrizoic acid is administered by the route most appropriate and sensible to image the structure/-s of interest (e.g., IV for blood vessels through which it is distributed and kidney–ureters–bladder that excrete it; orally or per rectally as an enema for the gastrointestinal tract).[ citation needed ]

Contraindications

A history of sensitivity to iodine is not a contraindication to using diatrizoate, although it suggests caution in use of the agent. In this case, a regimen of oral or intravenous corticosteroids may be given as prophylaxis, or an alternative such as barium sulfate may be preferable.[ citation needed ]

Gastrografin is contraindicated to use along with certain medications that can cause lactic acidosis, such as metformin. Concurrent use may lead to kidney failure and lactic acidosis, and a clinician may need to space the agents apart over a number of days to prevent an interaction. [13]

Gastrografin is a hypertonic solution, and therefore it should be avoided in imaging studies of the upper gastrointestinal tract in patients who are at risk of aspiration, as it will cause prompt pulmonary edema if accidentally introduced into the tracheobronchial tree. [14] [15]

Urografin is not to be used for myelography, ventriculography or cisternography, since it is likely to provoke neurotoxic symptoms in these examinations. [16]

Chemistry

Diatrizoate is considered a high-osmolality contrast agent. Its osmolality ranges from approximately 1500 mOsm/kg (50% solution) [17] to over 2000 mOsm/kg (76% solution). [18]

Synthesis

3,5-Dinitrobenzoic acid is reduced to 3,5-diaminobenzoic acid using Raney nickel or palladium on carbon. This is then reacted with potassium iodochloride or iodine monochloride to produce 3,5-diamino-2,4,6-triidobenzoic acid, which is finally acylated using acetic anhydride and acidified with sulfuric acid to produce diatrizoate. [19]

Another synthesis pathway iodates 3,5-diacetamidobenzoic acid using iodine monochloride. [19]

Brand names

Brand names include Hypaque, Gastrografin, MD-Gastroview, Iothalmate, and Urografin. Urografin is a combination of the sodium and meglumine salts.[ citation needed ]

Related Research Articles

<span class="mw-page-title-main">Small intestine</span> Organ in the gastrointestinal tract

The small intestine or small bowel is an organ in the gastrointestinal tract where most of the absorption of nutrients from food takes place. It lies between the stomach and large intestine, and receives bile and pancreatic juice through the pancreatic duct to aid in digestion. The small intestine is about 5.5 metres long and folds many times to fit in the abdomen. Although it is longer than the large intestine, it is called the small intestine because it is narrower in diameter.

<span class="mw-page-title-main">Lower gastrointestinal series</span> Radiographs used to examine abnormalities of the colon

A lower gastrointestinal series is a medical procedure used to examine and diagnose problems with the human colon of the large intestine. Radiographs are taken while barium sulfate, a radiocontrast agent, fills the colon via an enema through the rectum.

<span class="mw-page-title-main">Upper gastrointestinal series</span> Radiographs used to examine abnormalities of the digestive system excluding the colon

An upper gastrointestinal series, also called a barium swallow, barium study, or barium meal, is a series of radiographs used to examine the gastrointestinal tract for abnormalities. A contrast medium, usually a radiocontrast agent such as barium sulfate mixed with water, is ingested or instilled into the gastrointestinal tract, and X-rays are used to create radiographs of the regions of interest. The barium enhances the visibility of the relevant parts of the gastrointestinal tract by coating the inside wall of the tract and appearing white on the film. This in combination with other plain radiographs allows for the imaging of parts of the upper gastrointestinal tract such as the pharynx, larynx, esophagus, stomach, and small intestine such that the inside wall lining, size, shape, contour, and patency are visible to the examiner. With fluoroscopy, it is also possible to visualize the functional movement of examined organs such as swallowing, peristalsis, or sphincter closure. Depending on the organs to be examined, barium radiographs can be classified into "barium swallow", "barium meal", "barium follow-through", and "enteroclysis". To further enhance the quality of images, air or gas is sometimes introduced into the gastrointestinal tract in addition to barium, and this procedure is called double-contrast imaging. In this case the gas is referred to as the negative contrast medium. Traditionally the images produced with barium contrast are made with plain-film radiography, but computed tomography is also used in combination with barium contrast, in which case the procedure is called "CT enterography".

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">Diverticulum</span> Medical or biological term for an outpouching of a hollow (or a fluid-filled) structure in the body

In medicine or biology, a diverticulum is an outpouching of a hollow structure in the body. Depending upon which layers of the structure are involved, diverticula are described as being either true or false.

<span class="mw-page-title-main">Dumping syndrome</span> Medical condition

Dumping syndrome occurs when food, especially sugar, moves too quickly from the stomach to the duodenum—the first part of the small intestine—in the upper gastrointestinal (GI) tract. This condition is also called rapid gastric emptying. It is mostly associated with conditions following gastric or esophageal surgery, though it can also arise secondary to diabetes or to the use of certain medications; it is caused by an absent or insufficiently functioning pyloric sphincter, the valve between the stomach and the duodenum.

<span class="mw-page-title-main">Volvulus</span> Twisting of part of the intestine, causing a bowel obstruction

A volvulus is when a loop of intestine twists around itself and the mesentery that supports it, resulting in a bowel obstruction. Symptoms include abdominal pain, abdominal bloating, vomiting, constipation, and bloody stool. Onset of symptoms may be rapid or more gradual. The mesentery may become so tightly twisted that blood flow to part of the intestine is cut off, resulting in ischemic bowel. In this situation there may be fever or significant pain when the abdomen is touched.

A contrast agent is a substance used to increase the contrast of structures or fluids within the body in medical imaging. Contrast agents absorb or alter external electromagnetism or ultrasound, which is different from radiopharmaceuticals, which emit radiation themselves. In X-ray imaging, contrast agents enhance the radiodensity in a target tissue or structure. In magnetic resonance imaging (MRI), contrast agents shorten the relaxation times of nuclei within body tissues in order to alter the contrast in the image.

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.

<span class="mw-page-title-main">Abdominal x-ray</span>

An abdominal x-ray is an x-ray of the abdomen. It is sometimes abbreviated to AXR, or KUB.

<span class="mw-page-title-main">Retrograde urethrogram</span> Medical imaging of the urethra

A retrograde urethrography is a routine radiologic procedure used to image the integrity of the urethra. Hence a retrograde urethrogram is essential for diagnosis of urethral injury, or urethral stricture.

<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">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.

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

Ioxaglic acid is pharmaceutical drug used as an iodinated contrast medium for X-ray imaging. It has low osmolality, typically resulting in fewer side effects than high-osmolality media. It is manufactured by Guerbet, but marketing in the US has been discontinued. As of 2021, it may still be available in some European countries.

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.

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

Gadoteric acid, sold under the brand name Dotarem among others, is a macrocycle-structured gadolinium-based MRI contrast agent (GBCA). It consists of the organic acid DOTA as a chelating agent, and gadolinium (Gd3+), and is used in form of the meglumine salt (gadoterate meglumine). The paramagnetic property of gadoteric acid reduces the T1 relaxation time (and to some extent the T2 and T2* relaxation times) in MRI, which is the source of its clinical utility. Because it has magnetic properties, gadoteric acid develops a magnetic moment when put under a magnetic field, which increases the signal intensity (brightness) of tissues during MRI imaging.

Magnetic resonance enterography is a magnetic resonance imaging technique used to evaluate bowel wall features of both upper and lower gastro-intestinal tract, although it is usually used for small bowel evaluation. It is a less invasive technique with the advantages of no ionizing radiation exposure, multiplanarity and high contrast resolution for soft tissue.

Computed tomography enterography is a medical imaging technique which uses computed tomography scanner and contrast media to examine the small bowel. It was first introduced by Raptopoulos et al. in 1997. CT Enterography can be used to assess a variety of problems involving the small bowel, however it is mainly used to diagnose and assess severity of Crohn's disease.

References

  1. 1 2 3 4 World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 316. hdl: 10665/44053 . ISBN   9789241547659.
  2. 1 2 Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 171. ISBN   9781284057560.
  3. ↑ Pollack HM (2012). "History of Iodinated Contrast Media". In Thomsen H, Muller RN, Mattrey RF (eds.). Trends in Contrast Media. Springer Science & Business Media. p. 13. ISBN   9783642598142. Archived from the original on 1 January 2017.
  4. 1 2 "Diatrizoate Side Effects in Detail". Drugs.com. Archived from the original on 1 January 2017. Retrieved 31 December 2016.
  5. ↑ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl: 10665/325771 . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  6. ↑ Sood S, Krishna A (1996). Surgical Diseases in Tropical Countries. Jaypee Brothers Publishers. pp. 72–. ISBN   978-81-7179-444-7 . Retrieved 11 August 2010.[ permanent dead link ]
  7. ↑ Kaushik R (2010). "Asia". In Schein M, Rogers P, Assalia A (eds.). Schein's Common Sense Emergency Abdominal Surgery. Springer. pp. 391–. ISBN   978-3-540-74820-5. Archived from the original on 29 March 2017. Retrieved 11 August 2010.
  8. ↑ Choi HK, Chu KW, Law WL (July 2002). "Therapeutic value of gastrografin in adhesive small bowel obstruction after unsuccessful conservative treatment: a prospective randomized trial". Annals of Surgery. 236 (1): 1–6. doi:10.1097/00000658-200207000-00002. PMC   1422541 . PMID   12131078.
  9. ↑ Nick W, Hefin J (2018). "Introduction to contrast media". Chapman & Nakielny's Guide to Radiological procedures (7th ed.). London: Elsevier. p. 44, 49, 69. ISBN   9780702071669.
  10. ↑ Poole CA, Rowe MI (January 1976). "Clinical evidence of intestinal absorption of Gastrografin". Radiology. 118 (1): 151–153. doi:10.1148/118.1.151. PMID   1244649.
  11. ↑ "Professional information: gastrografin aqueous solution" (PDF). Bayer. 2 September 2018. Archived from the original (PDF) on 2 February 2022. Retrieved 2 February 2022.
  12. ↑ Watson N, Jones H (2018). Chapman and Nakielny's Guide to Radiological Procedures. Elsevier. p. 44. ISBN   9780702071669.
  13. ↑ Micromedex Healthcare Series (November 2010). "DIATRIZOATE MEGLUMINE/DIATRIZOATE SODIUM". DRUGDEX. Thomson Reuters (Healthcare) Inc. Retrieved 10 November 2010.[ permanent dead link ]
  14. ↑ Blanzieri S (2012). "Pulmonary edema by aspiration of gastrografin: a case report and literature review". European Congress of Radiology-ECR: 985 words. doi:10.1594/ECR2012/C-0607.
  15. ↑ Mohajer P, Annan E, Ahuja J, Sharif M, Sung A (October 2012). "Acute Respiratory Failure From Aspiration Pneumonitis: A Complication of Gastrografin Contrast Media". Chest. 142 (4): 1017A. doi:10.1378/chest.1390596.
  16. ↑ Bayer New Zealand Limited (September 2007). "UROGRAFIN Urografin Corporate Core Text" (PDF). Archived (PDF) from the original on 4 March 2016. Retrieved 2 April 2012.
  17. ↑ Amersham Health (April 2006). "Hypaque sodium (Diatrizoate Sodium) injection, solution. Product label". DailyMed. U.S. National Library of Medicine. Archived from the original on 23 May 2011. Retrieved 29 March 2007.
  18. ↑ Amersham Health (April 2006). "Hypaque (Diatrizoate Meglumine and Diatrizoate Sodium) injection, solution. Product label". DailyMed. U.S. National Library of Medicine. Archived from the original on 23 May 2011. Retrieved 29 March 2007.
  19. 1 2 Lerner HH (1975). "Diatrizoic Acid". Analytical Profiles of Drug Substances. Vol. 4. Elsevier. p. 137–167. doi:10.1016/s0099-5428(08)60011-8. ISBN   978-0-12-260804-9.
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