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Identification
Name Iophendylate
Accession Number DB01187 (APRD01312)
Type small molecule
Groups approved
Description

Iophendylate is a mixture of isomers used as contrast medium, mainly for brain and spinal cord visualization. Iophendylate is a myelographic oil-ester (U.S. Patent 2,348,231). Iophendylate, which was never shown to be safe, was initially introduced for use in small amounts (1-2cc) for locating spinal tumors. It next appeared on the world scene for high volume (12-15cc), routine use, in diagnosing disc herniations. A number of clinicians have published on the dangers of oil myelography. In 1942 Van Wagenen (a neurosurgical colleague of Warrens, at the University of Rochester) identified Iophendylate as causing chemical meningitis in 30 patients where “space-displacing masses within the spinal canal were suspected”.
Structure Thumb
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Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Pantopaque
Brand mixtures Not Available
Categories
  • Contrast Media
CAS number 99-79-6
Weight Average: 416.3368
Monoisotopic: 416.121223592
Chemical Formula C19H29IO2
InChI Key InChIKey=IWRUDYQZPTVTPA-UHFFFAOYSA-N
InChI
InChI=1S/C19H29IO2/c1-3-22-19(21)15-9-7-5-4-6-8-12-16(2)17-13-10-11-14-18(17)20/h10-11,13-14,16H,3-9,12,15H2,1-2H3
Plain Text
IUPAC Name
ethyl 10-(2-iodophenyl)undecanoate
SMILES
CCOC(=O)CCCCCCCCC(C)C1=CC=CC=C1I
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Cumenes and Derivatives
Substructures
  • Carboxylic Acids and Derivatives
  • Acetates
  • Ethers
  • Benzene and Derivatives
  • Cumenes and Derivatives
  • Aryl Halides
  • Aromatic compounds
  • Halobenzenes
Pharmacology
Indication Iophendylate is used as a contrast agent to locate spinal tumors.
Pharmacodynamics Iophendylate is a myelographic oil-ester initially introduced for use in small amounts (1-2cc) for locating spinal tumors. Later, it was found to cause adhesive arachnoiditis. Because these substances are hyperbaric once they were placed in the subarachnoid space they would migrate to the distal portion, where they remained, producing progressive scarring.
Mechanism of action Iophendylate has been shown to be both a radiographic and magnetic resonance (MR) contrast agent in patients with suspected cord abnormalities who underwent MR examination following myelography. The iophendylate appears as a linear band of high signal intensity along the dependent portion of the spinal canal on MR images obtained with a repetition time of 500 msec and an echo time of 30 msec.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Alcon laboratories inc
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State liquid
Experimental Properties
Property Value Source
melting point < 25 °C PhysProp
logP 7.7 Not Available
Predicted Properties
Property Value Source
water solubility 2.52e-05 g/l ALOGPS
logP 6.79 ALOGPS
logP 6.89 ChemAxon
logS -7.2 ALOGPS
pKa (strongest basic) -7 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 1 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 26.3 ChemAxon
rotatable bond count 12 ChemAxon
refractivity 101.6 ChemAxon
polarizability 41.29 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
PubChem Compound 3037234 Link_out
PubChem Substance 46508391 Link_out
ChemSpider 2301035 Link_out
PharmGKB PA164743143 Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19