SML0632
Fialuridine
≥98% (HPLC), powder, nucleoside analog
Synonym(s):
1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodo-2,4(1H,3H)-Pyrimidinedione, FIAU
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About This Item
Empirical Formula (Hill Notation):
C9H10FIN2O5
CAS Number:
Molecular Weight:
372.09
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
Fialuridine, ≥98% (HPLC)
Quality Level
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 5 mg/mL, clear (warmed)
storage temp.
−20°C
SMILES string
F[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N2C(NC(C(I)=C2)=O)=O
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
InChI key
IPVFGAYTKQKGBM-BYPJNBLXSA-N
General description
Fialuridine (1-(2-deoxy-2-fluoro-β-d-arabinofuranosyl)-5-iodouracil, or FIAU) is an antiviral agent. It is a thymidine-based nucleoside analogue.
Application
Fialuridine has been used in the selection of clones.
Biochem/physiol Actions
Fialuridine is a nucleoside analog antiviral agent.
Fialuridine is a nucleoside analog antiviral agent. The compound displays significant mitochondrial toxicity.
Fialuridine (1-(2-deoxy-2-fluoro-β-d-arabinofuranosyl)-5-iodouracil, or FIAU) and its metabolites blocks DNA polymerase at sites of multiple adjacent analog incorporation, reduces the presence of mtDNA (mitochondrial DNA) and results in mitochondrial structural defects in cultured hepatoblasts. It is considered as an efficient drug against hepatitis B virus (HBV) infection.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Fialuridine and its metabolites inhibit DNA polymerase gamma at sites of multiple adjacent analog incorporation, decrease mtDNA abundance, and cause mitochondrial structural defects in cultured hepatoblasts.
Lewis W, et al.
Proceedings of the National Academy of Sciences of the USA, 93(8), 3592-3597 (1996)
Kurt M Lin et al.
Molecular imaging and biology : MIB : the official publication of the Academy of Molecular Imaging, 10(5), 253-263 (2008-06-19)
Human ZR75-1 cells were among the first few characterized estrogen-dependent mammary gland carcinoma cell lines and had been utilized in various studies for the pro- or antitumor effect of xenoestrogens and antiestrogens. The objective of this study was to establish
De-Xue Fu et al.
Nature medicine, 14(10), 1118-1122 (2008-09-09)
We investigated the possibility of using a pharmacologic agent to modulate viral gene expression to target radiotherapy to tumor tissue. In a mouse xenograft model, we had previously shown targeting of [(125)I]2'-fluoro-2'-deoxy-beta-D-5-iodouracil-arabinofuranoside ([(125)I]FIAU) to tumors engineered to express the Epstein-Barr