Iofendylate

Iofendylate is a molecule that was used as a radiocontrast agent, typically for performing myelography studies. It was marketed under the trade names Pantopaque (in North America) and Myodil (rest of the world).

Iophendylate
Clinical data
Trade namesMyodil, Pantopaque
ATC code
Identifiers
IUPAC name
  • ethyl 10-(4-iodophenyl)undecanoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.002.534
Chemical and physical data
FormulaC19H29IO2
Molar mass416.33683 g·mol−1
3D model (JSmol)
SMILES
  • CCOC(=O)CCCCCCCCC(C)C1=CC=C(C=C1)I
InChI
  • InChI=1S/C19H29IO2/c1-3-22-19(21)11-9-7-5-4-6-8-10-16(2)17-12-14-18(20)15-13-17/h12-16H,3-11H2,1-2H3 N
  • Key:LAYLQVBQIBQVLL-UHFFFAOYSA-N N
 NY (what is this?)  (verify)

Iofendylate is a highly lipophilic (oily) substance and as such it was recommended that the physician remove it from the patient at the end of the myelography study, which was a difficult and painful part of the procedure. Moreover, because complete removal could not always be achieved (or even attempted by some physicians), iofendylate's persistence in the body might sometimes lead to arachnoiditis, a potentially painful and debilitating lifelong disorder of the spine.[1][2] As a result, the substance, which was used extensively for over three decades, became the subject of multiple lawsuits filed around the world.[3]

Iofendylate's use ceased when water-soluble agents suitable for spinal imaging (such as metrizamide) became available in the late 1970s. With those substances it was no longer necessary to manually remove the contrast agent as it would eventually be removed by the body.[4] Also, with the advent of MRI, myelography studies are nowadays much less-frequently performed.

References
  1. Dunlevy S (10 December 2016). "Australians crippled and in chronic pain from dye used in toxic X-rays". The Daily Telegraph. Retrieved 27 October 2017.
  2. Dillon WP, Dowd CF (2014). "Chapter 53 – Neurologic Complications of Imaging Procedures". Aminoff's Neurology and General Medicine (5th ed.). Elsevier Academic Press. pp. 1089–1105. ISBN 978-0-12-407710-2.
  3. Myodil litigation
  4. Leeds NE, Kieffer SA (November 2000). "Evolution of diagnostic neuroradiology from 1904 to 1999" (PDF). Radiology. 217 (2): 309–18. doi:10.1148/radiology.217.2.r00nv45309. PMID 11058623. S2CID 14639546. Archived from the original (PDF) on 2018-06-17.
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