Iophendylate
Grundinformationen
- CAS
99-79-6- Standard-SMILES
CCOC(=O)CCCCCCCCC(C)c1ccc(I)cc1- InChIKey
LAYLQVBQIBQVLL-UHFFFAOYSA-N- Summenformel
- C19H29IO2
- Durchschnittliche Molmasse
- 416,3 g/mol
- Monoisotopische Masse
- 416,12123
Überblick
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".
Namen und Bezeichner
- Bevorzugter Name
- Iophendylate
- IUPAC
- ethyl 10-(4-iodophenyl)undecanoate
Namen und Synonyme
IofendylateIOPHENDYLATEethyl 10-(4-iodophenyl)undecanoate99-79-6MulsopaqueNeurotrastPantopaqueMyodilMyodylIofendylatumIofendilatoEthyl 10-(p-iodophenyl)undecylate
Weitere Namen anzeigen
Ethyl iodophenylundecylateEthyl 10-(p-iodophenyl)hendecanoateEthyl 10-(p-iodophenyl)undecanoate6V3I57K9ULUndecanoic acid, 10-(p-iodophenyl)-, ethyl esterBenzenedecanoic acid, 4-iodo-iota-methyl-, ethyl esterEthyl 10-(iodophenyl)undecanoateiophendylatum
Datenbank-Bezeichner
- CAS
99-79-6- PubChem CID
- 7458
- DTXSID
DTXSID2052869- ChEMBL
CHEMBL951- UNII
- 6V3I57K9UL
- EC Number
- 202-787-8
- Nikkaji
- J11.622J
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 7
- Polarare Oberfläche (TPSA)
- 26,3 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 12
- Schwere Atome
- 22
- Formalladung
- 0
- Komplexität
- 285
Experimentelle und physikochemische Eigenschaften
OdorODORLESS OR FAINTLY ETHEREAL ODOR
Density1.240-1.263 @ 20 DEG/20 °C
ViscosityLOW
Color/FormCOLORLESS TO PALE YELLOW, VISCOUS LIQUID
SolubilityFREELY SOL IN ALCOHOL, BENZENE, CHLOROFORM, ETHER; VERY SLIGHTLY SOL IN WATER
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point196-198
Refractive IndexINDEX OF REFRACTION: 1.5230-1.5280 @ 25 °C/D
Stability/Shelf LifeDARKENS SLOWLY IN AIR
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Toxikologische Informationen
Human Toxicity Excerpts
BULLOUS ERUPTIONS OCCURRED AFTER IOPHENDYLATE MYELOGRAPHY.
A 56-YR-OLD MAN DEVELOPED EOSINOPHILIC MENINGITIS FOLLOWING MYELOGRAPHY WITH IOPHENDYLATE.
A 30-YR-OLD WOMAN WITH HISTORY OF CERVICAL MYELOGRAM USING IOPHENDYLATE DEVELOPED FOCAL EPILEPTIC SEIZURES 4 MO LATER. RADIOLOGY & COMPUTERIZED TOMOGRAPHY REVEALED PRESENCE OF RETAINED CONTRAST MEDIA.
TWO UNUSUAL CASES OF CONSTRICTIVE ARACHNOIDITIS LOCALIZED TO THORACIC LEVELS AFTER PANTOPAQUE MYELOGRAPHY ARE PRESENTED.
For more Human Toxicity Excerpts (Complete) data for IOPHENDYLATE (7 total), please visit the HSDB record page.
Non-Human Toxicity Excerpts
ARACHNOIDITIS RESULTING FROM ADMIN OF INTRATHECAL IOPHENDYLATE WAS COMPARED WITH THAT FROM METRIZAMIDE IN 16 MONKEYS. FOUR ANIMALS INITIALLY UNDERWENT METRIZAMIDE MYELOGRAPHY, EIGHT UNDERWENT IOPHENDYLATE MYELOGRAPHY, & FOUR CONTROL ANIMALS RECEIVED ONLY CEREBROSPINAL FLUID. TWELVE WEEKS LATER, ALL 16 ANIMALS UNDERWENT METRIZAMIDE MYELOGRAPHY & THEN HISTOLOGIC STUDIES. ANIMALS RECEIVING IOPHENDYLATE FOR THE FIRST MYELOGRAM DIFFERED SIGNIFICANTLY FROM THE OTHER 2 GROUPS ON INFLAMMATION, FIBROSIS, & MYELOGRAPHIC EVIDENCE OF ARACHNOIDITIS. THE ARACHNOIDITIS PRODUCED BY IOPHENDYLATE WAS MORE SEVERE THAN THAT PRODUCED BY METRIZAMIDE. IOPHENDYLATE ALSO PRODUCED A MORE CELLULAR REACTION THAT WAS QUALITATIVELY DIFFERENT FROM THE REACTION TO METRIZAMIDE.
Chemie und Industrie
Pharmakologische Informationen
ATC Code
V - Various
QV - Various
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.
MeSH Pharmacological ClassificationSubstances used to allow enhanced visualization of tissues.
Absorption, Distribution and ExcretionWHEN EXAM IS COMPLETED, COMPD SHOULD BE REMOVED BY ASPIRATION. WHEN BULK OF MATERIAL IS REMOVED, REMAINDER IS ABSORBED WITHIN FEW MONTHS...
Verwendung und Herstellung
Uses
MEDICATION (VET)
MEDICATION
Methods of Manufacturing
STRAIN ET AL, J AM CHEM SOC 64, 1436 (1942); US PATENT 2,348,231 (1944 TO NONED CORP & KODAK); BAKER ET AL, J SOC CHEM IND 63, 223 (1944).
BENZENE IS REACTED WITH UNDECYLENIC ACID FORMING A MIXTURE OF ISOMERS OF PHENYLUNDECYCLIC ACID. THE MIXTURE IS IODINATED & FINALLY ESTERIFIED WITH ETHYL ALCOHOL. AFTER DECOLORIZATION, THE DESIRED FRACTION IS SEPARATED BY DISTILLATION.
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