{{Short description|Chemical compound}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 461935493 | IUPAC_name = ethyl 10-(4-iodophenyl)undecanoate | image = Iofendylate.png | image_class = skin-invert-image | drug_name = Iophendylate <!--Clinical data--> | tradename = Myodil, Pantopaque | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> | legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_status = | routes_of_administration = <!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = <!--Identifiers--> | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 99-79-6 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 2990I809YH | ATC_prefix = V08 | ATC_suffix = AD04 | PubChem = 7458 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB01187 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 7178 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 951 <!--Chemical data--> | chemical_formula = | C=19 | H=29 | I=1 | O=2 | smiles = CCOC(=O)CCCCCCCCC(C)C1=CC=C(C=C1)I | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = LAYLQVBQIBQVLL-UHFFFAOYSA-N }} '''Iofendylate''' is a molecule that was used yesteryear 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).
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 procedure, which was a difficult and painful part of the said 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 backbone.<ref>{{cite news| vauthors = Dunlevy S |title=Australians crippled and in chronic pain from dye used in toxic X-rays|url=http://www.dailytelegraph.com.au/lifestyle/health/australians-crippled-and-in-chronic-pain-from-dye-used-in-toxic-xrays/news-story/e35f258d50c2508c214809896673da88|access-date=27 October 2017|work=The Daily Telegraph|date=10 December 2016}}</ref><ref>{{cite book| vauthors = Dillon WP, Dowd CF |title=Aminoff's Neurology and General Medicine |pages=1089–1105 |edition=5th |chapter=Chapter 53 – Neurologic Complications of Imaging Procedures |date=2014 |publisher=Elsevier Academic Press |isbn=978-0-12-407710-2 }}</ref> As a result, the substance, which was used extensively for over three decades, became the subject of multiple lawsuits filed around the world.<ref>[https://books.google.com/books?id=wBqGbBvcOpsC&dq=source=bl&pg=PA119 Myodil litigation]</ref>
Iofendylate's use ended 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 normally be cleared by the body on its own.<ref name="radioNeuroHist">{{cite journal | vauthors = Leeds NE, Kieffer SA | title = Evolution of diagnostic neuroradiology from 1904 to 1999 | journal = Radiology | volume = 217 | issue = 2 | pages = 309–318 | date = November 2000 | pmid = 11058623 | doi = 10.1148/radiology.217.2.r00nv45309 | url = https://pdfs.semanticscholar.org/8bfc/17f6ff7c70706ad0ad25b382558088463a2c.pdf | url-status = dead | s2cid = 14639546 | archive-url = https://web.archive.org/web/20180617220005/https://pdfs.semanticscholar.org/8bfc/17f6ff7c70706ad0ad25b382558088463a2c.pdf | archive-date = 2018-06-17 }}</ref> Also, with the advent of MRI, myelography studies are nowadays much less-frequently performed.
== References == {{Reflist}}
== External links == *[https://youtube.com/watch?v=YUHl9IhEPE4 Report from FOX News about the repercussions of Pantopaque use] (video segment from the 1990s)
{{Contrast media}} Category:Radiocontrast agents Category:4-Iodophenyl compounds
{{pharmacology-stub}}