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SML0632

Sigma-Aldrich

Fialuridine

≥98% (HPLC), powder, nucleoside analog

Sinónimos:

1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodo-2,4(1H,3H)-Pyrimidinedione, FIAU

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About This Item

Fórmula empírica (notación de Hill):
C9H10FIN2O5
Número de CAS:
69123-98-4
Peso molecular:
372.09
MDL number:
MFCD00866922
UNSPSC Code:
12352200
PubChem Substance ID:
329825571
NACRES:
NA.77

product name

Fialuridine, ≥98% (HPLC)

Quality Level

100

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 (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.
Fialuridine is a nucleoside analog antiviral agent. The compound displays significant mitochondrial toxicity.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Fialuridine accumulates in DNA of dogs, monkeys, and rats following long-term oral administration.
Richardson FC, et al.
Proceedings of the National Academy of Sciences of the USA, 91(25), 12003-12007 (1994)
Hepatic failure and lactic acidosis due to fialuridine (FIAU), an investigational nucleoside analogue for chronic hepatitis B.
McKenzie R, et al.
The New England Journal of Medicine, 333(17), 1099-1105 (1995)
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
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)
P Honkoop et al.
Drug safety, 17(1), 1-7 (1997-07-01)
Fialuridine is an antiviral agent with potent activity against hepatitis B virus replication in vitro and in vivo. In a phase II study, 7 of 15 patients experienced severe toxicity due to the drug after 9 to 13 weeks of
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