Iophendylate

Identification

Name
Iophendylate
Accession Number
DB01187  (APRD01312, DB13498)
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
3D
Similar Structures
Synonyms
  • Ethyl 10-(p-iodophenyl)-undecanoate
  • Ethyl 10-(p-iodophenyl)hendecanoate
  • Ethyl 10-(p-iodophenyl)undecylate
  • Iofendylate
International/Other Brands
Ethiodan / Pantopaque
Categories
UNII
6V3I57K9UL
CAS number
99-79-6
Weight
Average: 416.3368
Monoisotopic: 416.121223592
Chemical Formula
C19H29IO2
InChI Key
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
IUPAC Name
ethyl 10-(2-iodophenyl)undecanoate
SMILES
CCOC(=O)CCCCCCCCC(C)C1=CC=CC=C1I

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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

U.S. Patent 2,348,231.

General References
Not Available
External Links
Human Metabolome Database
HMDB0015318
PubChem Compound
3037234
PubChem Substance
46508391
ChemSpider
2301035
ChEMBL
CHEMBL951
PharmGKB
PA164743143
Wikipedia
Iophendylate
ATC Codes
V08AD04 — Iofendylate

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
boiling point (°C)196-198U.S. Patent 2,348,231.
logP7.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.52e-05 mg/mLALOGPS
logP6.79ALOGPS
logP6.89ChemAxon
logS-7.2ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity101.6 m3·mol-1ChemAxon
Polarizability41.29 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.988
Blood Brain Barrier+0.9833
Caco-2 permeable+0.7406
P-glycoprotein substrateNon-substrate0.6152
P-glycoprotein inhibitor INon-inhibitor0.8451
P-glycoprotein inhibitor IINon-inhibitor0.9207
Renal organic cation transporterNon-inhibitor0.8298
CYP450 2C9 substrateNon-substrate0.863
CYP450 2D6 substrateNon-substrate0.8373
CYP450 3A4 substrateNon-substrate0.553
CYP450 1A2 substrateInhibitor0.7452
CYP450 2C9 inhibitorNon-inhibitor0.7188
CYP450 2D6 inhibitorNon-inhibitor0.8414
CYP450 2C19 inhibitorNon-inhibitor0.6081
CYP450 3A4 inhibitorNon-inhibitor0.8839
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5831
Ames testNon AMES toxic0.9126
CarcinogenicityNon-carcinogens0.7268
BiodegradationNot ready biodegradable0.8676
Rat acute toxicity2.4999 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8919
hERG inhibition (predictor II)Non-inhibitor0.6457
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as iodobenzenes. These are aromatic compounds containing one or more iodine atoms attached to a benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Halobenzenes
Direct Parent
Iodobenzenes
Alternative Parents
Fatty acid esters / Aryl iodides / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organoiodides / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Fatty acid ester / Iodobenzene / Aryl halide / Aryl iodide / Fatty acyl / Carboxylic acid ester / Carboxylic acid derivative / Monocarboxylic acid or derivatives / Organoiodide / Organooxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on June 13, 2005 07:24 / Updated on July 02, 2018 17:30