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Details

Stereochemistry ACHIRAL
Molecular Formula C29H53INO4P
Molecular Weight 634.6154
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IOPOFOSINE I-124

SMILES

C[N+](C)(C)CCOP([O-])(=O)OCCCCCCCCCCCCCCCCCCC1=CC=C([124I])C=C1

InChI

InChIKey=ZOAIEFWMQLYMTF-PEHXSSJGSA-N
InChI=1S/C29H53INO4P/c1-31(2,3)25-27-35-36(32,33)34-26-19-17-15-13-11-9-7-5-4-6-8-10-12-14-16-18-20-28-21-23-29(30)24-22-28/h21-24H,4-20,25-27H2,1-3H3/i30-3

HIDE SMILES / InChI

Molecular Formula C29H53INO4P
Molecular Weight 634.6154
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

NM-404 I-124 ([124I]CLR-1404, LIGHT ) is a phospholipid ether analog labeled with iodine I 124, with a potential imaging property upon positron emission tomography (PET). Upon administration, NM-404 I-124 selectively accumulates in and is retained within tumor cells for a prolonged period of time due to the decreased activity of a phospholipase D (PLD), most likely isoform 1 of PLD, in tumor cells compared to normal cells. As tumor cells are unable to metabolize and eliminate MN404, tumor cells can be visualized upon PET imaging. In addition, NM-404 I-124 may provide a more accurate image of the tumor than imaging with the current standard. PLD is an enzyme found in the cell membrane of normal cells that degrades phospholipids. NM-404 I-124 enters cells predominately via lipid rafts, specialized microdomains of plasma membranes enriched in cholesterol and glycosphingolipids, which are found to be overexpressed 6-10 fold in malignant cells compared to normal cells. Although blood pool uptake in major vascular structures demonstrates high uptake initially, there is no significant CLR1404 uptake in normal brain tissue. Therefore, avid brain tumor uptake results in high tumor to back-ground signal and thus clear identification of viable tumor cells on PET scans. NM-404 I-124 selectively illuminated malignant tumors in 52 of 54 animal models of cancer, demonstrating evidence of broad-spectrum, cancer-selective uptake and retention. FDA granted orphan drug designation in the United States for NM-404 I-124 as a diagnostic for the management of glioma.

Approval Year

PubMed

PubMed

TitleDatePubMed
PET/CT imaging of the diapeutic alkylphosphocholine analog (124)I-CLR1404 in high and low-grade brain tumors.
2017
Impact of PET and MRI threshold-based tumor volume segmentation on patient-specific targeted radionuclide therapy dosimetry using CLR1404.
2017 Jul 6
Targeted Molecular Radiotherapy of Pediatric Solid Tumors Using a Radioiodinated Alkyl-Phospholipid Ether Analog.
2018 Feb
Patents

Patents

Sample Use Guides

Brain cancer patients were injected with 185 MBq ± 10% of NM-404 I-124 (124I-CLR1404) followed by PET/CT imaging at 6-, 24-, and 48-hour.
Route of Administration: Intravenous
Substance Class Chemical
Created
by admin
on Sat Dec 16 02:52:46 GMT 2023
Edited
by admin
on Sat Dec 16 02:52:46 GMT 2023
Record UNII
08W354EC17
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IOPOFOSINE I-124
Common Name English
18-(P-(124I )-IODOPHENYL)OCTADECYL PHOSPHOCHOLINE
Systematic Name English
I-124-CLR1404
Code English
(124I)-CLR1404
Code English
NM-404 I-124
Code English
ETHANAMINIUM, 2-((HYDROXY((18-(4-(IODO-124I)PHENYL)OCTADECYL)OXY)PHOSPHINYL)OXY)-N,N,N-TRIMETHYL-, INNER SALT
Systematic Name English
124I-CLR1404
Code English
CLR-1404 I-124
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 429514
Created by admin on Sat Dec 16 02:52:46 GMT 2023 , Edited by admin on Sat Dec 16 02:52:46 GMT 2023
Code System Code Type Description
PUBCHEM
11570943
Created by admin on Sat Dec 16 02:52:46 GMT 2023 , Edited by admin on Sat Dec 16 02:52:46 GMT 2023
PRIMARY
NCI_THESAURUS
C99636
Created by admin on Sat Dec 16 02:52:46 GMT 2023 , Edited by admin on Sat Dec 16 02:52:46 GMT 2023
PRIMARY
CAS
873438-87-0
Created by admin on Sat Dec 16 02:52:46 GMT 2023 , Edited by admin on Sat Dec 16 02:52:46 GMT 2023
PRIMARY
SMS_ID
100000183685
Created by admin on Sat Dec 16 02:52:46 GMT 2023 , Edited by admin on Sat Dec 16 02:52:46 GMT 2023
PRIMARY
FDA UNII
08W354EC17
Created by admin on Sat Dec 16 02:52:46 GMT 2023 , Edited by admin on Sat Dec 16 02:52:46 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY