Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H10FIN2O5 |
Molecular Weight | 369.0907 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H]1O[C@H]([C@@H](F)[C@@H]1O)N2C=C([124I])C(=O)NC2=O
InChI
InChIKey=IPVFGAYTKQKGBM-GDBQBOEPSA-N
InChI=1S/C9H10FIN2O5/c10-5-6(15)4(2-14)18-8(5)13-1-3(11)7(16)12-9(13)17/h1,4-6,8,14-15H,2H2,(H,12,16,17)/t4-,5+,6-,8-/m1/s1/i11-3
Molecular Formula | C9H10FIN2O5 |
Molecular Weight | 369.0907 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Fialuridine I-124 is an isotope-labeled form of fialuridine, or 1-(2-deoxy-2-fluoro-1-D-arabinofuranosyl)-5-iodouracil (FIAU), a thymidine nucleoside analog with activity against various herpesviruses and hepatitis B virus (HBV) in vitro and in vivo. Bacterial or herpes virus thymidine kinase (TK) considered to be a target of FIAU. Fialuridine I-124 is a positron emission tomography/computed tomography (PET/CT) tracer that was developed for imaging of cells transfected with the herpes simplex virus 1 (HSV1) thymidine kinase reporter gene. This enzyme transfers a γ phosphate group fom ATP to the 5’ hydroxyl group of pyrimidine deoxynucleosides. The lipophilic tracer diffuses into the cell and is trapped in the cell with HSV1-TK activity, because the phosphorylated tracer cannot pass the plasma membrane. TK gene of bacteria was sufficiently similar to that of the viral TK of HSV1 and fialuridine I-124 could also be phosphorylated by the endogenous bacterial TK. Once phosphorylated by TK, fialuridine I-124 becomes trapped within bacteria and can be detected with positron emission tomography/computed tomography (PET/CT).
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11337525
Curator's Comment: Fialuridine I124 (FIAU) does not penetrate the intact blood-brain barrier significantly
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1795127 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23133817 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27150029
To assess biodistribution and dosimetry, six subjects with suspected hip or knee prosthetic joint infections (PJI) and six healthy subjects underwent serial PET/CT after being dosed with 74MBq (2mCi) [(124)I]FIAU intravenously (IV). Estimated radiation doses were calculated with the OLINDA/EXM software. To determine accuracy of [(124)I]FIAU, 22 subjects with suspected hip or knee PJI were scanned at 2-6 and 24-30h post IV injection of 185MBq (5mCi) [(124)I]FIAU.
Route of Administration:
Intravenous
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:46:46 GMT 2023
by
admin
on
Fri Dec 15 15:46:46 GMT 2023
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Record UNII |
726X882183
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Record Status |
Validated (UNII)
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Record Version |
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183293-72-3
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726X882183
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