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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
Structure of FIALURIDINE I-124

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

HIDE SMILES / InChI

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

Curator's Comment: Fialuridine I124 (FIAU) does not penetrate the intact blood-brain barrier significantly

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Quantitative kinetics of [124I]FIAU in cat and man.
2001 Mar
FIAU: From reporter gene imaging to imaging of bacterial proliferation.
2012
[(124)I]FIAU: Human dosimetry and infection imaging in patients with suspected prosthetic joint infection.
2016 May

Sample Use Guides

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
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:46:46 GMT 2023
Edited
by admin
on Fri Dec 15 15:46:46 GMT 2023
Record UNII
726X882183
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FIALURIDINE I-124
Common Name English
2,4(1H,3H)-PYRIMIDINEDIONE, 1-(2-DEOXY-2-FLUORO-.BETA.-D-ARABINOFURANOSYL)-5-(IODO-(SUP 124)I)-
Common Name English
124I-FIAU
Common Name English
Code System Code Type Description
NCI_THESAURUS
C88284
Created by admin on Fri Dec 15 15:46:46 GMT 2023 , Edited by admin on Fri Dec 15 15:46:46 GMT 2023
PRIMARY
CAS
183293-72-3
Created by admin on Fri Dec 15 15:46:46 GMT 2023 , Edited by admin on Fri Dec 15 15:46:46 GMT 2023
PRIMARY
EPA CompTox
DTXSID00171406
Created by admin on Fri Dec 15 15:46:46 GMT 2023 , Edited by admin on Fri Dec 15 15:46:46 GMT 2023
PRIMARY
PUBCHEM
656409
Created by admin on Fri Dec 15 15:46:46 GMT 2023 , Edited by admin on Fri Dec 15 15:46:46 GMT 2023
PRIMARY
FDA UNII
726X882183
Created by admin on Fri Dec 15 15:46:46 GMT 2023 , Edited by admin on Fri Dec 15 15:46:46 GMT 2023
PRIMARY