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Diatrizoate

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Diatrizoate
Skeletal formula
Space-filling model
Clinical data
Trade namesHypaque, Gastrografin, Iothalmate, Urografin, others
Other namesamidotrizoic acid, diatrizoic acid, 3,5-diacetamido-2,4,6-triiodobenzoic acid
AHFS/Drugs.comMicromedex Detailed Consumer Information
Identifiers
  • 3,5-Bis(acetylamino)-2,4,6-triiodobenzoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
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) checkY
  • Key:YVPYQUNUQOZFHG-UHFFFAOYSA-N

Diatrizoate, also known as amidotrizoate, is a contrast agent used during X-rays.[1] This includes when visualizing veins, the urinary system, spleen, and joints, as well as during computer tomography (CT scan).[1] It is given by mouth, injection into a vein, injection into the bladder, 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, the most effective and safe medicines needed in a health system.[5] The wholesale cost in the developing world is about 5.49 USD per 20 ml vial.[6] In the United States a dose costs less than 25 USD.[2]

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.

It is used for intravenous pyelography.

It is also used to treat Ascaris lumbricoides (roundworms).[7][8] Diatrizoate may not actually kill Ascaris, but instead it promotes shifting of fluid in the bowel lumen, so may relieve intestinal obstruction caused by impacted Ascaris.[9]

Administration

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.

Gastrografin is contraindicated to use along with certain medications that can cause lactic acidosis, such as metformin. Concurrent use may lead to renal failure and lactic acidosis, and a clinician may need to space the agents apart over a number of days to prevent an interaction.[10]

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.

Urografin is not to be used for myelography, ventriculography or cisternography, since it is likely to provoke neurotoxic symptoms in these examinations. [11]

Chemistry

Diatrizoate is considered a high-osmolality contrast agent. Its osmolality ranges from approximately 1500 mOsm/kg (50% solution)[12] to over 2000 mOsm/kg (76% solution).[13]

Brand names

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

See also

The core structure is a popular one and numerous analogues exist.

Mono-compounds
Bis-compounds

References

  1. ^ a b c d WHO Model Formulary 2008 (PDF). World Health Organization. 2009. p. 316. ISBN 9789241547659. Archived from the original (PDF) on 13 December 2016. Retrieved 8 December 2016. {{cite book}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  2. ^ a b c Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 171. ISBN 9781284057560.
  3. ^ Thomsen, Henrik; Muller, Robert N.; Mattrey, Robert F. (2012). Trends in Contrast Media. Springer Science & Business Media. p. 13. ISBN 9783642598142. Archived from the original on 2017-01-01. {{cite book}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  4. ^ a b "Diatrizoate Side Effects in Detail - Drugs.com". www.drugs.com. Archived from the original on 1 January 2017. Retrieved 31 December 2016. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  5. ^ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived from the original (PDF) on 13 December 2016. Retrieved 8 December 2016. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  6. ^ "Amidotrizoate". International Drug Price Indicator Guide. Retrieved 8 December 2016.
  7. ^ Sood. Surgical Diseases in Tropical Countries. Jaypee Brothers Publishers. pp. 72–. ISBN 978-81-7179-444-7. Retrieved 11 August 2010.
  8. ^ Moshe Schein; Paul Rogers; Ahmad Assalia (2010). 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. {{cite book}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  9. ^ "Archived copy". Archived from the original on 2016-06-18. Retrieved 2016-07-28. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)CS1 maint: archived copy as title (link)
  10. ^ Micromedex Healthcare Series (November 2010). "DIATRIZOATE MEGLUMINE/DIATRIZOATE SODIUM". DRUGDEX. Thomson Reuters (Healthcare) Inc. Retrieved 2010-11-10.
  11. ^ Bayer New Zealand Limited (September 2007). "UROGRAFIN Urografin Corporate Core Text" (PDF). Archived from the original (PDF) on 2016-03-04. Retrieved 2012-04-02. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  12. ^ Amersham Health (April 2006). "Hypaque sodium (Diatrizoate Sodium) injection, solution. Product label". DailyMed. U.S. National Library of Medicine. Archived from the original on 2011-05-23. Retrieved 2007-03-29. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  13. ^ 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 2011-05-23. Retrieved 2007-03-29. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
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