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Fialuridine I-124

HCID 656409
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Basic informationOverviewNames & identifiersPropertiesRelated reactionsCompound notes
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Basic information

CAS
183293-72-3
Standard SMILES
O=c1[nH]c(=O)n([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2F)cc1[124I]
InChIKey
IPVFGAYTKQKGBM-GDBQBOEPSA-N
Molecular formula
C9H10FIN2O5
Average molar mass
369.09 g/mol
Monoisotopic mass
368.96358

Overview

Iodine I-124 FIAU is a radioconjugate containing the nucleoside analog 2'-fluoro-2'-deoxy-1beta-D-arabinofuranosyl-5-iodouracil (FIAU) labeled with the radioisotope iodine I 124 with positron-emitting activity. Chemotherapeutic agents such as bortezomib may induce viral thymidine kinase expression in EBV- and Kaposi's sarcoma herpesvirus (KSHV)-associated tumors. Subsequent to chemotherapy induction of viral TK in these tumors, administered iodine I 124 FIAU is phosphorylated by expressed viral TK, becoming selectively trapped within TK-expressing tumor cells; these cells can then be visualized with positron emission tomography (PET). Viral TK is either not expressed or is expressed at very low levels in EBV- and Kaposi's sarcoma herpesvirus (KSHV)-associated tumors and may be activated by certain chemotherapeutic agents.

Names & identifiers

Preferred name
Fialuridine I-124
IUPAC
1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(124I)iodopyrimidine-2,4-dione

Names & synonyms

Fialuridine I-124124I-FIAU124I-Labeled FIAU(124I)FIAUUNII-726X882183183293-72-3726X8821832,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)-5-(iodo-(sup 124)i)-[124I]FIAUSCHEMBL30178161DTXSID00171406Q27266040
Show more names
2'-Fluoro-2'-deoxy-5'-[124I]iodo-1 -D-arabinofuranosyluracil1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-(~124~I)iodopyrimidine-2,4(1H,3H)-dione2,4(1H,3H)-PYRIMIDINEDIONE, 1-(2-DEOXY-2-FLUORO-.BETA.-D-ARABINOFURANOSYL)-5-(IODO-(SUP 124)I)-

Database identifiers

CAS
183293-72-3
PubChem CID
656409
DTXSID
DTXSID00171406
UNII
726X882183

Properties

Computed structural properties

XLogP
-0.9
Topological polar surface area
99.1 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
6
Rotatable bonds
2
Heavy atoms
18
Formal charge
0
Complexity
418

Related reactions

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Compound notes

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