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SML0632

Sigma-Aldrich

Fialuridine

≥98% (HPLC), powder, nucleoside analog

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C9H10FIN2O5
Numéro CAS:
69123-98-4
Poids moléculaire :
372.09
Numéro MDL:
MFCD00866922
Code UNSPSC :
12352200
ID de substance PubChem :
329825571
Nomenclature NACRES :
NA.77

product name

Fialuridine, ≥98% (HPLC)

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 5 mg/mL, clear (warmed)

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

IPVFGAYTKQKGBM-BYPJNBLXSA-N

Description générale

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.

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Sigma-Aldrich

Sigma-Aldrich

SRE0027

Héparine sodium salt from porcine intestinal mucosa

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)
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
Kristin L Peterson et al.
Nuclear medicine and biology, 40(5), 638-642 (2013-04-02)
Currently available infectious disease imaging techniques cannot differentiate between infection and sterile inflammation or between different types of infections. Recently, radiolabeled FIAU was found to be a substrate for the thymidine kinase (TK) enzyme of multiple pathogenic bacteria, leading to
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