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SML0632

Sigma-Aldrich

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:
69123-98-4
Molecular Weight:
372.09
MDL number:
MFCD00866922
UNSPSC Code:
12352200
PubChem Substance ID:
329825571
NACRES:
NA.77

product name

Fialuridine, ≥98% (HPLC)

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Yun-Hee Kim et al.
Cancer letters, 344(2), 223-231 (2013-11-06)
The soluble protein pancreatic adenocarcinoma up-regulated factor (PAUF) plays an important role in pancreatic tumor progression and has begun to attract attention as a therapeutic target for pancreatic cancer. We herein present PAUF RNA-targeting gene therapy strategies with both targeting
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
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)
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)
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
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