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
- 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
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
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source boiling point (°C) 196-198 U.S. Patent 2,348,231. logP 7.7 Not Available - Predicted Properties
Property Value Source Water Solubility 2.52e-05 mg/mL 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 Å2 ChemAxon Rotatable Bond Count 12 ChemAxon Refractivity 101.6 m3·mol-1 ChemAxon Polarizability 41.29 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - 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 inhibitor Non-inhibitor 0.7188 CYP450 2D6 inhibitor Non-inhibitor 0.8414 CYP450 2C19 inhibitor Non-inhibitor 0.6081 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not 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 November 02, 2018 04:57