Iophendylate

Identification

Generic Name
Iophendylate
DrugBank Accession Number
DB01187
Background

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".

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 416.3368
Monoisotopic: 416.121223592
Chemical Formula
C19H29IO2
Synonyms
  • Ethyl 10-(p-iodophenyl)-undecanoate
  • Ethyl 10-(p-iodophenyl)hendecanoate
  • Ethyl 10-(p-iodophenyl)undecylate
  • Iofendylate

Pharmacology

Indication

Iophendylate is used as a contrast agent to locate spinal tumors.

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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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International/Other Brands
Ethiodan / Pantopaque

Categories

ATC Codes
V08AD04 — Iofendylate
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aromatic homomonocyclic compound / Aryl halide / Aryl iodide / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Fatty acid ester / Fatty acyl / Hydrocarbon derivative / Iodobenzene
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
5153M06QEA
CAS number
99-79-6
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

References

Synthesis Reference

U.S. Patent 2,348,231.

General References
Not Available
Human Metabolome Database
HMDB0015318
PubChem Compound
3037234
PubChem Substance
46508391
ChemSpider
2301035
RxNav
5968
ChEMBL
CHEMBL951
PharmGKB
PA164743143
Wikipedia
Iofendylate

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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-MSsplash10-001i-2393000000-c63b6b1c060a30fc786c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01bj-3937200000-52534d239c20abf43e4a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0135900000-e3d42a9d6c055733231d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00or-2916000000-2e6ebe791054a5a4a165
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0079-2921000000-bb08106026d6727ac017
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00ko-1495000000-1cbf9b5343efd185063b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-5970000000-0d02e6c8fdf07ac31917
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-203.5463153
predicted
DarkChem Lite v0.1.0
[M-H]-182.60248
predicted
DeepCCS 1.0 (2019)
[M+H]+204.2849153
predicted
DarkChem Lite v0.1.0
[M+H]+184.96046
predicted
DeepCCS 1.0 (2019)
[M+Na]+203.7823153
predicted
DarkChem Lite v0.1.0
[M+Na]+191.12912
predicted
DeepCCS 1.0 (2019)

Drug created at June 13, 2005 13:24 / Updated at May 07, 2021 21:26