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Iophendylate

HCID 7458
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
99-79-6
標準SMILES
CCOC(=O)CCCCCCCCC(C)c1ccc(I)cc1
InChIKey
LAYLQVBQIBQVLL-UHFFFAOYSA-N
分子式
C19H29IO2
平均分子量
416.3 g/mol
単同位体質量
416.12123

概要

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".

名称と識別子

優先名称
Iophendylate
IUPAC
ethyl 10-(4-iodophenyl)undecanoate

名称と別名

IofendylateIOPHENDYLATEethyl 10-(4-iodophenyl)undecanoate99-79-6MulsopaqueNeurotrastPantopaqueMyodilMyodylIofendylatumIofendilatoEthyl 10-(p-iodophenyl)undecylate
名称をさらに表示
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

データベース識別子

CAS
99-79-6
PubChem CID
7458
DTXSID
DTXSID2052869
ChEMBL
CHEMBL951
UNII
6V3I57K9UL
EC Number
202-787-8
Nikkaji
J11.622J

物性

構造計算による物性

XLogP
7
極性表面積
26.3 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
12
重原子数
22
形式電荷
0
複雑度
285

実験および物理化学的性質

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 · 2 件

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
Other Experimental PropertiesSAPONIFICATION EQUIV 395-420

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

毒性情報

Human Toxicity Excerpts · 5 件

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 · 1 件

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.

化学と産業

薬理情報

ATC Code · 2 件

V - Various

QV - Various

Pharmacodynamics · 1 件

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 · 1 件

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...

用途と製造

Uses · 2 件

MEDICATION (VET)

MEDICATION

Methods of Manufacturing · 2 件

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.

Formulations/Preparations

関連反応

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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
· 2 件

IOPHENDYLATE INJECTION, USP (PANTOPAQUE) IS MIXTURE OF ISOMERS OF ETHYL IODOPHENYLUNDECANOATE, CONSISTING OF ETHYL 10-(IODOPHENYL)UNDECANOATE. DOSAGE FORMS: INJECTION (STERILE IOPHENDYLATE): 1, 3, 6, & 12 ML.

VET: CONTAINS 30.5% IODINE.

General Manufacturing InformationIT WAS SUGGESTED THAT A 0.22 UM MILLIPORE FILTER BE USED TO SCREEN OFF THE GLASS PARTICLES THAT FALL INTO THE OILY MEDIUM WHEN GLASS AMPULS OF IOPHENDYLATE (PANTOPAQUE) ARE OPENED.