ethyl 10-(2-iodophenyl)undecanoate

• ChemBase ID: 1058
• Molecular Formular: C19H29IO2
• Molecular Mass: 416.33683
• Monoisotopic Mass: 416.12122817
• SMILES: Ic1c(C(CCCCCCCCC(=O)OCC)C)cccc1
• Canonical SMILES: CCOC(=O)CCCCCCCCC(c1ccccc1I)C
• 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
• InChIKey: IWRUDYQZPTVTPA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 10-(2-iodophenyl)undecanoate
• IUPAC Traditional name: myodil
• Brand Name: Pantopaque
• Synonyms: Iophendylate

Database IDs

• CAS Number: 99-79-6
• PubChem SID: 160964521; 46508391
• PubChem CID: 3037234

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 6.886209
• LogD (pH = 7.4): 6.886209
• Log P: 6.886209
• Molar Refractivity: 101.6024 cm^3
• Polarizability: 39.936523 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 6.79
• LOG S: -7.22
• Solubility (Water): 2.52e-05 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 7.7

DETAILS

DrugBank - DB01187

• Drug 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".
• Indication: Iophendylate is used as a contrast agent to locate spinal tumors.
• Pharmacology: 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.
• Affected Organisms: Humans and other mammals