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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
SaltsNot Available
Brand names
NameCompany
PantopaqueNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number99-79-6
WeightAverage: 416.3368
Monoisotopic: 416.121223592
Chemical FormulaC19H29IO2
InChI KeyInChIKey=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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassHalobenzenes
Direct parentIodobenzenes
Alternative parentsFatty Acid Esters; Aryl Iodides; Carboxylic Acid Esters; Ethers; Enolates; Polyamines; Organoiodides
Substituentsaryl halide; aryl iodide; carboxylic acid ester; ether; enolate; polyamine; carboxylic acid derivative; organoiodide; organohalogen
Classification descriptionThis compound belongs to the iodobenzenes. These are aromatic compounds containing one or more iodine atoms attached to a benzene.
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
Metabolism
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
Property Value Probability
Human Intestinal Absorption + 0.988
Blood Brain Barrier + 0.9833
Caco-2 permeable + 0.7406
P-glycoprotein substrate Non-substrate 0.6152
P-glycoprotein inhibitor I Non-inhibitor 0.8451
P-glycoprotein inhibitor II Non-inhibitor 0.9207
Renal organic cation transporter Non-inhibitor 0.8298
CYP450 2C9 substrate Non-substrate 0.863
CYP450 2D6 substrate Non-substrate 0.8373
CYP450 3A4 substrate Non-substrate 0.553
CYP450 1A2 substrate Inhibitor 0.7452
CYP450 2C9 substrate Non-inhibitor 0.7188
CYP450 2D6 substrate Non-inhibitor 0.8414
CYP450 2C19 substrate Non-inhibitor 0.6081
CYP450 3A4 substrate Non-inhibitor 0.8839
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5831
Ames test Non AMES toxic 0.9126
Carcinogenicity Non-carcinogens 0.7268
Biodegradation Not ready biodegradable 0.8676
Rat acute toxicity 2.4999 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8919
hERG inhibition (predictor II) Non-inhibitor 0.6457
Pharmacoeconomics
Manufacturers
  • Alcon laboratories inc
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Stateliquid
Experimental Properties
PropertyValueSource
melting point< 25 °CPhysProp
logP7.7Not Available
Predicted Properties
PropertyValueSource
water solubility2.52e-05 g/lALOGPS
logP6.79ALOGPS
logP6.89ChemAxon
logS-7.2ALOGPS
pKa (strongest basic)-7ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count0ChemAxon
polar surface area26.3ChemAxon
rotatable bond count12ChemAxon
refractivity101.6ChemAxon
polarizability41.29ChemAxon
number of rings1ChemAxon
bioavailability0ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound3037234
PubChem Substance46508391
ChemSpider2301035
PharmGKBPA164743143
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13