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Diatrizoate

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Diatrizoate
Skeletal formula
Space-filling model
Clinical data
Trade namesHypaque, Gastrografin, Iothalmate, others
Other namesamidotrizoic acid, diatrizoic acid, 3,5-diacetamido-2,4,6-triiodobenzoic acid
AHFS/Drugs.comMicromedex 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 InfoCard100.003.840 Edit this at Wikidata
Chemical and physical data
FormulaC11H9I3N2O4
Molar mass613.916 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]

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

[edit]

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

[edit]

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

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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

[edit]

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

[edit]

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

[edit]

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

References

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  1. ^ a b c d 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. ^ a b 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. ^ a b "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. ^ a b 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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