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Identification
NameIophendylate
Accession NumberDB01187  (APRD01312)
TypeSmall Molecule
GroupsApproved
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
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
EthiodanNot Available
PantopaqueNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number99-79-6
WeightAverage: 416.3368
Monoisotopic: 416.121223592
Chemical FormulaC19H29IO2
InChI KeyIWRUDYQZPTVTPA-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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentIodobenzenes
Alternative Parents
Substituents
  • Iodobenzene
  • Fatty acid ester
  • Fatty acyl
  • Aryl iodide
  • Aryl halide
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organoiodide
  • Organohalogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationIophendylate is used as a contrast agent to locate spinal tumors.
PharmacodynamicsIophendylate 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 actionIophendylate 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.7188
CYP450 2D6 substrateNon-inhibitor0.8414
CYP450 2C19 substrateNon-inhibitor0.6081
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateLiquid
Experimental Properties
PropertyValueSource
boiling point196-198U.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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

U.S. Patent 2,348,231.

General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on June 13, 2005 07:24 / Updated on May 02, 2014 13:25